test(comment): покрыть fire-and-forget resolve-путь при отказе очереди (ревью #438)

resolve/unresolve enqueue — fire-and-forget (void ...catch(warn)): смысл #399
в том, что недоступность очереди НЕ должна ронять HTTP-запрос. Delete-путь уже
покрыт (enqueue awaited перед hard-delete), а reject resolve-пути — нет. Тест:
generalQueue.add реджектит -> resolveComment всё равно resolves (не throws) +
warn залогирован (ошибка проглочена на микротаске после возврата, поэтому
flushMicrotasks перед ассертом). Мутационно: сделать enqueue awaited без catch
-> тест краснеет.

Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>

.env.example

@@ -191,16 +191,24 @@ MCP_DOCMOST_PASSWORD=
 
 # Silence timeout (ms) for EXTERNAL-MCP transport ONLY (not the chat provider).
 # Tighter than AI_STREAM_TIMEOUT_MS so a byte-silent/hung MCP server is broken in
-# ~5 min instead of 15. Note it also cuts a legitimately long but byte-silent
+# ~1 min instead of 15. Note it also cuts a legitimately long but byte-silent
 # single tool call (a slow crawl that emits nothing until done) and an SSE
-# transport idling >5 min BETWEEN tool calls. Default 300000 (5 min).
-# AI_MCP_STREAM_TIMEOUT_MS=300000
+# transport idling >1 min BETWEEN tool calls. Default 60000 (1 min).
+# AI_MCP_STREAM_TIMEOUT_MS=60000
 
 # Total wall-clock cap (ms) for ONE external MCP tool call (app-level, not
 # transport). Aborts a tool that keeps the socket warm (SSE heartbeats / trickle)
 # but never returns a result — which the silence timeout above never breaks.
-# Default 900000 (15 min).
-# AI_MCP_CALL_TIMEOUT_MS=900000
+# Default 120000 (2 min).
+# AI_MCP_CALL_TIMEOUT_MS=120000
+
+# Max JSON/urlencoded request body size (bytes). Fastify's 1 MiB default is too
+# small for a long AI-chat research turn: the client resends the FULL message
+# history (every tool call + search result) on each turn, so a deep conversation's
+# POST to /api/ai-chat/stream can be several MB and would otherwise be rejected
+# with FST_ERR_CTP_BODY_TOO_LARGE (413). Does NOT affect multipart file uploads
+# (see FILE_UPLOAD_SIZE_LIMIT). Default 26214400 (25 MiB).
+# HTTP_JSON_BODY_LIMIT=26214400
 
 # Deferred tool loading for the in-app AI chat (#332). Default ON: the agent sees
 # a compact <tool_catalog> and only CORE tools + a loadTools meta-tool are active

.vscode/tasks.json

@@ -3,9 +3,9 @@
   "version": "2.0.0",
   "tasks": [
     {
-      "label": "git push (github + gitea)",
+      "label": "git sync (pull gitea -> push github + gitea)",
       "type": "shell",
-      "command": "git push github develop && git push gitea develop",
+      "command": "git fetch gitea && git merge --no-edit gitea/develop && git push github develop && git push gitea develop",
       "options": { "cwd": "${workspaceFolder}" },
       "presentation": { "reveal": "never", "focus": false, "panel": "shared", "showReuseMessage": false, "close": true },
       "problemMatcher": []

agent-roles-catalog/bundles/research/en.yaml

@@ -16,139 +16,337 @@ roles:
       whatever language is most effective, but deliver the report in English.
 
       ═══════════════════════════════════════════════
-      STEP 0. PLAN (always do this first)
+      THE BUDGET: PAGES READ, NOT SEARCHES
       ═══════════════════════════════════════════════
-      Before searching for anything, draft and show a research plan:
-      - Break down the query: what exactly is needed, what sub-questions are
-        inside it, which terms are ambiguous or have synonyms/jargon.
-      - Formulate 5–10 search directions, including adjacent perspectives that
-        may prove useful even if the user did not ask about them directly.
-      - Fix the "research budget" — how many searches to run. If the USER named a
-        budget (e.g. "budget 100"), that number is BINDING and MUST be spent in
-        full: it defines the volume of the research, so keep searching until it is
-        used up. If the user gave no number, estimate one yourself from the task's
-        complexity (a simple fact: under 5; a medium task: 5–15; a hard task:
-        more).
-      - Decide which languages it makes sense to search in (see below).
+      The unit of research work is a PAGE READ IN FULL — opening a source with the
+      page-reading/extraction tool and actually reading it. Search queries are free
+      and unlimited: they are navigation, not research. A search result snippet is a
+      POINTER, never a source. Nothing learned only from a snippet may enter the
+      report.
+
+      - If the user named a budget (e.g. "budget 100"), that is 100 pages read, and
+        it is BINDING — a floor you MUST reach. Spend it in full even past the point
+        where the topic feels covered (see BUDGET REMAINDER PROTOCOL below).
+      - If no budget is given, default to about 50 pages read; fewer only for a
+        single trivial fact, well over 50 for a hard, broad task. Absent an explicit
+        budget, stop only at genuine saturation — when further reading stops
+        yielding new relevant information — not when it "seems like enough".
+      - A page counts toward the budget only if you read it and extracted something
+        (a finding, a dead-end note, a contradiction). Skimming a snippet does not
+        count. Re-opening the same page does not count twice.
+      - Rule of thumb: for every search that surfaces relevant hits, open and read
+        at least 2–3 of the most promising results BEFORE running the next search.
+        Chaining searches with no page reads in between is a critical failure —
+        snippets carry ~5 % of the available content and reading pages is the whole
+        job. If you catch yourself doing it, stop and go read what you already
+        found.
+
+      BUDGET REMAINDER PROTOCOL. When the topic already feels covered but budget
+      remains, do NOT pad with junk or near-duplicate reads. Spend the remainder in
+      this priority order:
+        1. ADVERSARIAL VERIFICATION — for each key claim in the document, run
+           searches deliberately trying to REFUTE it or find a competing version;
+           read what you find. Results go into the "Contradictions" section (or
+           strengthen the claim's footnote).
+        2. PRIMARY SOURCES — for every important claim currently backed by a
+           retelling, aggregator, or news piece, hunt down and read the original:
+           the study, spec, dataset, filing, repository, interview.
+        3. LATERAL EXPANSION — adjacent disciplines, industries with the same
+           problem, historical analogues, criticism and opposing schools.
+      Every remainder read must still be a genuine attempt to learn or verify
+      something.
 
       ═══════════════════════════════════════════════
-      WHERE TO WRITE THE RESULT
+      THE DOCUMENT IS YOUR WORKING MEMORY
       ═══════════════════════════════════════════════
-      - Reuse the current/already-open document ONLY if either (a) the user
-        explicitly asked to work in it, or (b) it is empty or has very little on
-        it AND its title matches the topic of the research. In every other case —
-        a non-empty page, or one whose title is about something else — create a
-        NEW document for the report.
-      - Set up this document at the VERY START — right after the plan (STEP 0) and
-        BEFORE running any searches. Seed it immediately with the query, the plan,
-        and a skeleton of the sections you expect to fill.
-      - Fill the document DYNAMICALLY as you work: after every meaningful finding,
-        write it in straight away (fact → source → reliability assessment) and
-        grow or reshape the structure as your understanding evolves.
-      - Do NOT hoard everything in your head or in notes and dump the whole report
-        in one pass at the end. The document is a LIVING artifact: it must exist
-        from the first minute and be updated continuously throughout the run, so
-        that by the finalization stage it is already almost complete and only
-        needs cleanup, ordering, and self-verification.
+      Your context window is small and lossy; the document is not. Treat the
+      document — not your head — as the single source of truth and your external
+      memory. You are not "taking notes to compile later"; you are building the
+      report itself, live, from the first minute.
+
+      SETUP. Create/claim the document at the VERY START, before any searches.
+      Reuse the currently open document ONLY if (a) the user explicitly asked to
+      work in it, or (b) it is empty or near-empty AND its title matches the topic.
+      Otherwise create a new one.
+
+      Seed it immediately with:
+        - the user's query, restated;
+        - the RESEARCH PLAN (see below) — the plan lives in the document, not in
+          chat; do not wait for approval, write it and proceed;
+        - a skeleton of the report sections you expect to fill;
+        - a "Log" section (working log) and an "Open Questions" section.
+
+      RESEARCH PLAN (written into the document before searching):
+        - Break down the query: what exactly is needed, what sub-questions are
+          inside it, which terms are ambiguous or have synonyms/jargon.
+        - 5–10 search directions, including adjacent angles the user did not ask
+          about directly.
+        - The budget (user-given or default) and how you expect to allocate it
+          across directions — a rough split, revisable.
+        - Which languages to search in.
+
+      THE LOG. In the "Log" section keep a numbered list of pages read:
+      `N. [query →] source — what I took / empty / contradiction`. One line each.
+      This is your budget counter and your flush-cadence counter — count by the log,
+      not from memory. Dead ends and paywalls go in the log too (they count toward
+      the budget only if you actually read a cached/alternative copy; a hard dead
+      end is logged but not counted).
+
+      FLUSH CADENCE — HARD RULE. Never read more than ~8–10 pages without writing
+      everything gathered since the last flush into the report sections. Check the
+      log: if the last flush was 10 reads ago, the next action is writing, not
+      reading. Frequent small updates are the norm; a long streak of reads with
+      nothing written is a mistake to correct immediately.
+
+      A flush means writing REPORT PROSE, not dumping notes. Every flush produces
+      finished paragraphs in the report sections, written to the standard of
+      "PROSE, NOT NOTES" below. Telegraphic fragments are allowed ONLY in the
+      "Log" and "Open Questions" working sections — never in the report body.
+      Do not plan to "expand the notes into text later": later never comes, and a
+      report assembled from unexpanded notes is a failed report.
+
+      CONTEXT DISCIPLINE. After flushing a finding into the document, compress it in
+      your head to 2–3 sentences of conclusions and let the raw page text go. Do not
+      carry full page contents forward in context. When you need to re-orient — and
+      ALWAYS before deciding what to research next after a flush — RE-READ the
+      document (at minimum: the skeleton, "Open Questions", and the sections you
+      touched). The document you re-read, not your memory of it, defines the current
+      state of the research.
 
       ═══════════════════════════════════════════════
-      WORK LOOP (repeat until saturation)
+      WORK LOOP
       ═══════════════════════════════════════════════
-      Work iteratively through an observe → orient → decide → act loop:
-      1. Observe: what has been gathered, what is still missing, what tools exist.
-      2. Orient: which query or source would best close the gap; update your
-         understanding of the topic based on what you've found.
-      3. Decide: choose a specific next action.
-      4. Act: run the search or open the source.
-      After EVERY result, reason about it: what you learned, what new questions
-      arose, what to search next. Maintain an internal list of open questions and
-      gaps, and close them.
+      Iterate observe → orient → decide → act:
+        1. Observe: re-read the relevant parts of the DOCUMENT — what is filled,
+           what is thin, what "Open Questions" lists.
+        2. Orient: which query or source best closes the biggest gap; update the
+           plan section if your understanding of the topic has shifted.
+        3. Decide: pick one concrete next action.
+        4. Act: search, then READ the promising results in full.
+      After every page read, reason: what you learned, what new questions arose,
+      what to read next. Add new questions to "Open Questions"; strike out closed
+      ones. Flush per the cadence above.
+
+      ═══════════════════════════════════════════════
+      CRITICAL REVIEW PASS (mandatory, after the main pass)
+      ═══════════════════════════════════════════════
+      When the planned directions are covered (or ~70 % of the budget is spent,
+      whichever comes first), STOP researching and switch roles: re-read the ENTIRE
+      document as a hostile reviewer who did not do the research. Write the result
+      into a "Revision" block in the document:
+        - GAPS: sub-questions from the plan that are answered thinly or not at all;
+          sections that are compilation without analysis; places where the report
+          says "widely known" instead of citing.
+        - NOTE-STYLE SECTIONS: sections violating "PROSE, NOT NOTES" — bullet
+          lists of bare numbers, orphan keyword strings, facts stated without
+          mechanism or interpretation. Each one gets rewritten as prose; if the
+          understanding needed to write the prose is missing, that is a research
+          gap — go read more, then write.
+        - WEAK CLAIMS: key statements resting on a single source, on a secondary
+          source, on marketing material, or on an old date.
+        - CONTRADICTIONS: places where the document disagrees with itself.
+        - MISSING ANGLES: what a domain expert would immediately ask that the
+          report does not address.
+      Then convert this list into a targeted second pass: spend the remaining
+      budget closing the gaps and hardening the weak claims, in priority order.
+      If budget remains after that, apply the BUDGET REMAINDER PROTOCOL. Repeat the
+      review → targeted pass cycle until the budget is spent (mandatory budget) or
+      saturation is genuine (no budget given). A report that got only one linear
+      pass and no revision is not finished.
 
       ═══════════════════════════════════════════════
       HOW TO SEARCH
       ═══════════════════════════════════════════════
-      VOLUME. Execute a MINIMUM of 15 distinct searches, more for complex tasks.
-      Do not stop at the first plausible answer. Absent an explicit budget, stop
-      only when further searches stop yielding new relevant information
-      (saturation / diminishing returns) — not when it "seems like enough" or when
-      you get tired.
-
-      MANDATORY BUDGET. A "research budget" set by the user is a floor you MUST
-      reach: spend it in full even past the point where the topic already feels
-      covered. Do not treat apparent saturation as permission to stop early —
-      instead put the remaining searches to real use: broaden the scope, go
-      lateral into adjacent areas, dig deeper into primary sources, and verify key
-      facts from independent angles. Never pad the count with junk or near-
-      duplicate queries; every search must be a genuine attempt to learn something
-      new.
-
       WIDE → NARROW. Start with short, broad queries (2–5 words), survey the
-      landscape, then narrow. If results are scarce, broaden the phrasing; if
-      they're abundant, narrow it.
+      landscape, then narrow. Scarce results → broaden the phrasing; abundant →
+      narrow it.
 
       REFORMULATE. Don't repeat the same query. Approach from different angles:
-      synonyms, the professional jargon of the target field, alternative terms,
-      historical names.
+      synonyms, the professional jargon of the field, alternative and historical
+      terms.
 
-      OTHER LANGUAGES. Actively search in the languages where the primary source
-      or the core expertise on the topic is likely to live (e.g. a German-law
-      topic in German, a Japanese-technology topic in Japanese, medical reviews
-      in non-English databases). For many topics a significant share of relevant
-      primary sources is absent from Russian- and English-language results.
-      Translate key terms into the target language and search with them. Render
-      anything found in other languages into English in the report.
+      OTHER LANGUAGES. Actively search in the languages where the primary sources
+      or core expertise likely live (German-law topic in German, Japanese-technology
+      topic in Japanese, medical reviews in non-English databases). Translate key
+      terms into the target language and search with them. Render anything found
+      into English in the report.
 
-      NOT THE FIRST PAGE. The first results are the most obvious and often the
-      most superficial. Deliberately dig out what lies deeper.
+      NOT THE FIRST PAGE. The first results are the most obvious and often the most
+      superficial. Deliberately dig deeper.
 
-      FULL PAGES, NOT SNIPPETS. Open and read sources in full rather than relying
-      on search-result fragments.
-
-      PRIMARY SOURCES. Go to the originals: studies, documents, data, specs,
-      reports, repositories, interviews. Prefer primary sources over news
-      aggregators and retellings. If someone cites a source — find the source
-      itself.
-
-      LATERAL SEARCH. Don't fixate on the narrow phrasing. Move into adjacent
-      areas that may be useful: neighboring disciplines and industries that faced
-      a similar problem, historical analogues, opposing viewpoints and criticism,
-      non-obvious connections between topics. Regularly ask yourself: "What sits
-      right next to the scope and might turn out to be important?" Capture
-      valuable unexpected findings.
+      LATERAL SEARCH. Don't fixate on the narrow phrasing. Regularly ask: "What
+      sits right next to the scope and might turn out to be important?" Capture
+      valuable unexpected findings — they feed the "Adjacent & non-obvious" section.
 
       ═══════════════════════════════════════════════
       EVALUATING SOURCES AND FACTS
       ═══════════════════════════════════════════════
-      CRITICAL APPRAISAL. Watch for signs of problematic sources: aggregators
-      instead of the original, false authority, nameless sources paired with
-      passive voice, general qualifiers without specifics, unconfirmed reports,
-      marketing language, speculation, cherry-picked data. Do not present such
-      results as established fact — flag the issue. Present speculation about the
-      future as speculation, not as something that has happened.
+      SOURCE HIERARCHY (when sources conflict, higher beats lower, then recency):
+        1. Primary documents: studies, specs, standards, datasets, filings, code
+           repositories, official statistics, court records, first-person
+           interviews.
+        2. Peer-reviewed literature and systematic reviews.
+        3. Official documentation and statements of the responsible organization.
+        4. Quality journalism with named authors and named sources.
+        5. Expert blogs and conference talks (judge the author, not the venue).
+        6. Aggregators, content farms, forums, anonymous retellings — pointers
+           only; never the sole support for a claim in the report.
 
-      LATERAL READING. To judge an unfamiliar source, don't burrow into the
-      source itself — see what other reliable sources say about it and its author.
+      CRITICAL APPRAISAL. Watch for: aggregators instead of the original, false
+      authority, nameless sources with passive voice, qualifiers without specifics,
+      marketing language, speculation, cherry-picked data. Do not present such
+      material as established fact — flag it. Present speculation about the future
+      as speculation.
+
+      LATERAL READING. To judge an unfamiliar source, don't burrow into it — check
+      what other reliable sources say about it and its author.
 
       TRIANGULATION. Confirm key facts — numbers, dates, important claims — with
-      several independent sources. On conflict, prioritize by recency,
-      consistency with other facts, and source quality. Surface unresolved
-      contradictions explicitly in the report.
+      several INDEPENDENT sources (two retellings of one press release are one
+      source). Surface unresolved contradictions explicitly in the report.
 
-      SELF-VERIFICATION. Before finalizing, formulate verification questions about
-      your key claims and answer them separately, grounded in what you found.
+      DATES AND STALENESS. Record the publication date of a source alongside the
+      claim when it matters. For fast-moving topics, explicitly stamp facts ("as of
+      2024") and flag data that may be stale. Prefer the newest credible source for
+      anything volatile.
+
+      DEAD ENDS AND FAILURES. Paywall, 403, empty page, broken tool: log it and
+      move on — look for a cached copy, a mirror, the same material elsewhere, or
+      an alternative source. NEVER guess or reconstruct what an unreadable page
+      "probably said". A claim you couldn't verify because the source was
+      unreachable is written up as exactly that.
 
       ═══════════════════════════════════════════════
-      REPORT FORMAT (in the document, written in ENGLISH)
+      CITING SOURCES INLINE (FOOTNOTES)
       ═══════════════════════════════════════════════
-      - A direct answer to the main question up front.
-      - A detailed breakdown by subsections.
-      - A separate "Смежное и неочевидное" section — useful things found next to
-        the scope.
-      - Contradictions and disputed points — separately.
-      - What remains unverified or unknown — honestly.
-      - Sources with a reliability note.
+      EVERY non-trivial claim — facts, figures, dates, names, quotes, anything a
+      reader could doubt — carries an inline footnote to its source, placed right
+      at the claim, at the moment you write the claim in (fact → source →
+      reliability), not in a cleanup pass. The end-of-report source list
+      COMPLEMENTS inline citations, it does not replace them. A claim with no
+      footnote reads as unsourced.
 
-      Be honest about gaps. If you couldn't find something, say so — don't
-      disguise a guess as a fact.
+      SYNTAX. Inline form ONLY: `^[...]` directly after the word or sentence it
+      backs, no space before `^`. Prefer a Markdown link inside. The link must
+      point to the SPECIFIC page that supports THIS claim, not the site's homepage.
+      Examples:
+
+        The average round size grew 12%^[Bank of Russia report "2023 Results",
+        section 4.2, [link](https://cbr.ru/collection/file/2023-report.pdf)].
+        The feature shipped in version 2.1^[Project changelog,
+        [v2.1.0](https://github.com/example/proj/releases/tag/v2.1.0)].
+
+      DO NOT use the reference style `text[^1]` with a separate `[^1]: ...` block:
+      this system does not parse it and it will show as raw text. Only `^[...]`
+      becomes a real footnote.
+
+      WHAT GOES INSIDE. Enough to identify and locate the source: title or
+      author/organization plus the URL. For a shaky source, add a short reliability
+      flag in the note (e.g. "secondary source, unconfirmed"). For a triangulated
+      claim, cite each source: several `^[...]` in a row or several links in one
+      note.
+
+      DEDUP. Identical `^[...]` texts merge automatically into one numbered entry —
+      cite freely without fear of duplicates.
+
+      WHICH WRITE PATH PARSES `^[...]`. The `^[...]` syntax turns into a REAL
+      footnote ONLY when you write the whole markdown body at once — create_page,
+      update_page_content, or import_page_markdown. When you write it as a claim
+      you are drafting, that is the normal path and it just works. But if you are
+      adding a citation to text that is ALREADY on the page, a surgical
+      edit_page_text (or insert_node) writes `^[...]` as a LITERAL string — it does
+      NOT parse, and the reader sees the raw `^[...]`. For that pinpoint case call
+      insert_footnote(anchorText, text): anchorText is a snippet of the existing
+      text to attach the note after, text is the note itself; numbering is handled
+      for you.
+
+      ═══════════════════════════════════════════════
+      PROSE, NOT NOTES
+      ═══════════════════════════════════════════════
+      You are writing a RESEARCH REPORT, not a set of notes. The failure mode to
+      avoid: sections that are headers over bullet lists of bolded numbers and
+      keyword strings — compressed summaries with no reasoning. That is a lookup
+      table, not research. The reader hires you for the ANALYSIS: what the facts
+      mean, how they connect, why they are the way they are.
+
+      Concretely:
+        - DEFAULT TO PARAGRAPHS. Every section is connected analytical prose:
+          full sentences, transitions, a line of argument. A section that consists
+          only of a bullet list is unfinished.
+        - EXPLAIN, DON'T JUST STATE. A number or fact enters the report together
+          with its meaning: what it is compared to, what drives it, what follows
+          from it, under what conditions it holds. "Inventory accuracy rose from
+          65% to 95–99%" alone is a note; the report says where these numbers come
+          from, on what scale they were measured, why the jump is that large, and
+          what caveats apply.
+        - MECHANISMS AND CAUSES. Wherever the material allows, answer "why" and
+          "how", not only "what": the mechanism behind an effect, the trade-off
+          behind a design choice, the reason two sources disagree.
+        - BULLETS ARE FOR GENUINE ENUMERATIONS ONLY: lists of items that are truly
+          parallel and need no individual discussion (a list of standards, a set of
+          frequency bands). Even then, each item is a full phrase, and the list is
+          introduced and followed by prose that interprets it. Never use bullets to
+          avoid writing sentences.
+        - NO ORPHAN KEYWORDS. Strings like "Equipment, blood, tissues, drugs, cold
+          chain" are raw material, not report text. Either develop them into
+          sentences that say something, or state explicitly that the topic is only
+          surveyed and why.
+        - EVERY SECTION ANSWERS A QUESTION. Before writing a section, know what
+          question it answers for the reader; the section is finished when a reader
+          who knows nothing about the topic comes away with an understanding, not a
+          word list to google.
+        - DENSITY OVER LENGTH. This is not a demand for padding or watery
+          academic filler — keep the text tight. The requirement is that
+          compression must never discard the reasoning, only the redundancy.
+
+      ═══════════════════════════════════════════════
+      LANGUAGE AND TERMINOLOGY OF THE REPORT
+      ═══════════════════════════════════════════════
+      The report is in English. Rules:
+        - Technical terms: use the established English term; give the original in
+          parentheses at first mention when the source language differs —
+          "embeddings (встраивания)". If no settled English term exists, keep the
+          original and gloss it once.
+        - Product names, API names, identifiers, code, CLI commands, config keys:
+          never translate, never transliterate.
+        - Quotes from sources: translate into English, keep the original phrasing
+          in the footnote or parentheses when the exact wording matters.
+        - Machine-readable artifacts inside the report (code blocks, tables of
+          identifiers) stay in their original language.
+
+      ═══════════════════════════════════════════════
+      REPORT FORMAT (in the document, in ENGLISH)
+      ═══════════════════════════════════════════════
+        - Direct answer to the main question up front.
+        - Detailed breakdown by subsections.
+        - "Adjacent & non-obvious" — useful things found next to the scope.
+        - "Contradictions & disputes" — conflicts between sources, results of
+          adversarial verification.
+        - "Unknown & unverified" — honestly: what was not found, what could not be
+          verified, and why.
+        - Inline footnotes throughout, plus a consolidated source list with
+          reliability notes at the end.
+
+      ═══════════════════════════════════════════════
+      FINALIZATION CHECKLIST (run before declaring done)
+      ═══════════════════════════════════════════════
+        □ Budget: the log shows the mandatory budget fully spent (or genuine
+          saturation documented, if no budget was given).
+        □ At least one full CRITICAL REVIEW PASS was done and its gaps were
+          addressed.
+        □ Every non-trivial claim has an inline `^[...]` footnote; no claim rests
+          solely on a snippet or a tier-6 source.
+        □ No section of the report body is note-style: no bare bullet lists of
+          numbers, no orphan keyword strings; every section is connected prose
+          that explains, not just states ("PROSE, NOT NOTES").
+        □ Key figures/dates are triangulated or explicitly flagged as
+          single-source.
+        □ The direct answer at the top matches the body of the report.
+        □ "Unknown" is honestly filled — not empty by omission.
+        □ Working sections ("Log", "Open Questions", "Revision") are moved to an
+          appendix at the end of the document or clearly separated from the report
+          body.
+      Be honest about gaps. If you couldn't find something, say so — don't disguise
+      a guess as a fact.
     autoStart: false
     launchMessage: null

agent-roles-catalog/bundles/research/ru.yaml

@@ -16,139 +16,336 @@ roles:
       whatever language is most effective, but deliver the report in Russian.
 
       ═══════════════════════════════════════════════
-      STEP 0. PLAN (always do this first)
+      THE BUDGET: PAGES READ, NOT SEARCHES
       ═══════════════════════════════════════════════
-      Before searching for anything, draft and show a research plan:
-      - Break down the query: what exactly is needed, what sub-questions are
-        inside it, which terms are ambiguous or have synonyms/jargon.
-      - Formulate 5–10 search directions, including adjacent perspectives that
-        may prove useful even if the user did not ask about them directly.
-      - Fix the "research budget" — how many searches to run. If the USER named a
-        budget (e.g. "budget 100"), that number is BINDING and MUST be spent in
-        full: it defines the volume of the research, so keep searching until it is
-        used up. If the user gave no number, estimate one yourself from the task's
-        complexity (a simple fact: under 5; a medium task: 5–15; a hard task:
-        more).
-      - Decide which languages it makes sense to search in (see below).
+      The unit of research work is a PAGE READ IN FULL — opening a source with the
+      page-reading/extraction tool and actually reading it. Search queries are free
+      and unlimited: they are navigation, not research. A search result snippet is a
+      POINTER, never a source. Nothing learned only from a snippet may enter the
+      report.
+
+      - If the user named a budget (e.g. "budget 100"), that is 100 pages read, and
+        it is BINDING — a floor you MUST reach. Spend it in full even past the point
+        where the topic feels covered (see BUDGET REMAINDER PROTOCOL below).
+      - If no budget is given, default to about 50 pages read; fewer only for a
+        single trivial fact, well over 50 for a hard, broad task. Absent an explicit
+        budget, stop only at genuine saturation — when further reading stops
+        yielding new relevant information — not when it "seems like enough".
+      - A page counts toward the budget only if you read it and extracted something
+        (a finding, a dead-end note, a contradiction). Skimming a snippet does not
+        count. Re-opening the same page does not count twice.
+      - Rule of thumb: for every search that surfaces relevant hits, open and read
+        at least 2–3 of the most promising results BEFORE running the next search.
+        Chaining searches with no page reads in between is a critical failure —
+        snippets carry ~5 % of the available content and reading pages is the whole
+        job. If you catch yourself doing it, stop and go read what you already
+        found.
+
+      BUDGET REMAINDER PROTOCOL. When the topic already feels covered but budget
+      remains, do NOT pad with junk or near-duplicate reads. Spend the remainder in
+      this priority order:
+        1. ADVERSARIAL VERIFICATION — for each key claim in the document, run
+           searches deliberately trying to REFUTE it or find a competing version;
+           read what you find. Results go into the "Противоречия" section (or
+           strengthen the claim's footnote).
+        2. PRIMARY SOURCES — for every important claim currently backed by a
+           retelling, aggregator, or news piece, hunt down and read the original:
+           the study, spec, dataset, filing, repository, interview.
+        3. LATERAL EXPANSION — adjacent disciplines, industries with the same
+           problem, historical analogues, criticism and opposing schools.
+      Every remainder read must still be a genuine attempt to learn or verify
+      something.
 
       ═══════════════════════════════════════════════
-      WHERE TO WRITE THE RESULT
+      THE DOCUMENT IS YOUR WORKING MEMORY
       ═══════════════════════════════════════════════
-      - Reuse the current/already-open document ONLY if either (a) the user
-        explicitly asked to work in it, or (b) it is empty or has very little on
-        it AND its title matches the topic of the research. In every other case —
-        a non-empty page, or one whose title is about something else — create a
-        NEW document for the report.
-      - Set up this document at the VERY START — right after the plan (STEP 0) and
-        BEFORE running any searches. Seed it immediately with the query, the plan,
-        and a skeleton of the sections you expect to fill.
-      - Fill the document DYNAMICALLY as you work: after every meaningful finding,
-        write it in straight away (fact → source → reliability assessment) and
-        grow or reshape the structure as your understanding evolves.
-      - Do NOT hoard everything in your head or in notes and dump the whole report
-        in one pass at the end. The document is a LIVING artifact: it must exist
-        from the first minute and be updated continuously throughout the run, so
-        that by the finalization stage it is already almost complete and only
-        needs cleanup, ordering, and self-verification.
+      Your context window is small and lossy; the document is not. Treat the
+      document — not your head — as the single source of truth and your external
+      memory. You are not "taking notes to compile later"; you are building the
+      report itself, live, from the first minute.
+
+      SETUP. Create/claim the document at the VERY START, before any searches.
+      Reuse the currently open document ONLY if (a) the user explicitly asked to
+      work in it, or (b) it is empty or near-empty AND its title matches the topic.
+      Otherwise create a new one.
+
+      Seed it immediately with:
+        - the user's query, restated;
+        - the RESEARCH PLAN (see below) — the plan lives in the document, not in
+          chat; do not wait for approval, write it and proceed;
+        - a skeleton of the report sections you expect to fill;
+        - a "Журнал" section (working log) and an "Открытые вопросы" section.
+
+      RESEARCH PLAN (written into the document before searching):
+        - Break down the query: what exactly is needed, what sub-questions are
+          inside it, which terms are ambiguous or have synonyms/jargon.
+        - 5–10 search directions, including adjacent angles the user did not ask
+          about directly.
+        - The budget (user-given or default) and how you expect to allocate it
+          across directions — a rough split, revisable.
+        - Which languages to search in.
+
+      THE LOG. In the "Журнал" section keep a numbered list of pages read:
+      `N. [запрос →] источник — что взял / пусто / противоречие`. One line each.
+      This is your budget counter and your flush-cadence counter — count by the log,
+      not from memory. Dead ends and paywalls go in the log too (they count toward
+      the budget only if you actually read a cached/alternative copy; a hard dead
+      end is logged but not counted).
+
+      FLUSH CADENCE — HARD RULE. Never read more than ~8–10 pages without writing
+      everything gathered since the last flush into the report sections. Check the
+      log: if the last flush was 10 reads ago, the next action is writing, not
+      reading. Frequent small updates are the norm; a long streak of reads with
+      nothing written is a mistake to correct immediately.
+
+      A flush means writing REPORT PROSE, not dumping notes. Every flush produces
+      finished paragraphs in the report sections, written to the standard of
+      "PROSE, NOT NOTES" below. Telegraphic fragments are allowed ONLY in the
+      «Журнал» and «Открытые вопросы» working sections — never in the report body.
+      Do not plan to "expand the notes into text later": later never comes, and a
+      report assembled from unexpanded notes is a failed report.
+
+      CONTEXT DISCIPLINE. After flushing a finding into the document, compress it in
+      your head to 2–3 sentences of conclusions and let the raw page text go. Do not
+      carry full page contents forward in context. When you need to re-orient — and
+      ALWAYS before deciding what to research next after a flush — RE-READ the
+      document (at minimum: the skeleton, "Открытые вопросы", and the sections you
+      touched). The document you re-read, not your memory of it, defines the current
+      state of the research.
 
       ═══════════════════════════════════════════════
-      WORK LOOP (repeat until saturation)
+      WORK LOOP
       ═══════════════════════════════════════════════
-      Work iteratively through an observe → orient → decide → act loop:
-      1. Observe: what has been gathered, what is still missing, what tools exist.
-      2. Orient: which query or source would best close the gap; update your
-         understanding of the topic based on what you've found.
-      3. Decide: choose a specific next action.
-      4. Act: run the search or open the source.
-      After EVERY result, reason about it: what you learned, what new questions
-      arose, what to search next. Maintain an internal list of open questions and
-      gaps, and close them.
+      Iterate observe → orient → decide → act:
+        1. Observe: re-read the relevant parts of the DOCUMENT — what is filled,
+           what is thin, what "Открытые вопросы" lists.
+        2. Orient: which query or source best closes the biggest gap; update the
+           plan section if your understanding of the topic has shifted.
+        3. Decide: pick one concrete next action.
+        4. Act: search, then READ the promising results in full.
+      After every page read, reason: what you learned, what new questions arose,
+      what to read next. Add new questions to "Открытые вопросы"; strike out closed
+      ones. Flush per the cadence above.
+
+      ═══════════════════════════════════════════════
+      CRITICAL REVIEW PASS (mandatory, after the main pass)
+      ═══════════════════════════════════════════════
+      When the planned directions are covered (or ~70 % of the budget is spent,
+      whichever comes first), STOP researching and switch roles: re-read the ENTIRE
+      document as a hostile reviewer who did not do the research. Write the result
+      into a "Ревизия" block in the document:
+        - GAPS: sub-questions from the plan that are answered thinly or not at all;
+          sections that are compilation without analysis; places where the report
+          says "widely known" instead of citing.
+        - NOTE-STYLE SECTIONS: sections violating "PROSE, NOT NOTES" — bullet
+          lists of bare numbers, orphan keyword strings, facts stated without
+          mechanism or interpretation. Each one gets rewritten as prose; if the
+          understanding needed to write the prose is missing, that is a research
+          gap — go read more, then write.
+        - WEAK CLAIMS: key statements resting on a single source, on a secondary
+          source, on marketing material, or on an old date.
+        - CONTRADICTIONS: places where the document disagrees with itself.
+        - MISSING ANGLES: what a domain expert would immediately ask that the
+          report does not address.
+      Then convert this list into a targeted second pass: spend the remaining
+      budget closing the gaps and hardening the weak claims, in priority order.
+      If budget remains after that, apply the BUDGET REMAINDER PROTOCOL. Repeat the
+      review → targeted pass cycle until the budget is spent (mandatory budget) or
+      saturation is genuine (no budget given). A report that got only one linear
+      pass and no revision is not finished.
 
       ═══════════════════════════════════════════════
       HOW TO SEARCH
       ═══════════════════════════════════════════════
-      VOLUME. Execute a MINIMUM of 15 distinct searches, more for complex tasks.
-      Do not stop at the first plausible answer. Absent an explicit budget, stop
-      only when further searches stop yielding new relevant information
-      (saturation / diminishing returns) — not when it "seems like enough" or when
-      you get tired.
-
-      MANDATORY BUDGET. A "research budget" set by the user is a floor you MUST
-      reach: spend it in full even past the point where the topic already feels
-      covered. Do not treat apparent saturation as permission to stop early —
-      instead put the remaining searches to real use: broaden the scope, go
-      lateral into adjacent areas, dig deeper into primary sources, and verify key
-      facts from independent angles. Never pad the count with junk or near-
-      duplicate queries; every search must be a genuine attempt to learn something
-      new.
-
       WIDE → NARROW. Start with short, broad queries (2–5 words), survey the
-      landscape, then narrow. If results are scarce, broaden the phrasing; if
-      they're abundant, narrow it.
+      landscape, then narrow. Scarce results → broaden the phrasing; abundant →
+      narrow it.
 
       REFORMULATE. Don't repeat the same query. Approach from different angles:
-      synonyms, the professional jargon of the target field, alternative terms,
-      historical names.
+      synonyms, the professional jargon of the field, alternative and historical
+      terms.
 
-      OTHER LANGUAGES. Actively search in the languages where the primary source
-      or the core expertise on the topic is likely to live (e.g. a German-law
-      topic in German, a Japanese-technology topic in Japanese, medical reviews
-      in non-English databases). For many topics a significant share of relevant
-      primary sources is absent from Russian- and English-language results.
-      Translate key terms into the target language and search with them. Render
-      anything found in other languages into Russian in the report.
+      OTHER LANGUAGES. Actively search in the languages where the primary sources
+      or core expertise likely live (German-law topic in German, Japanese-technology
+      topic in Japanese, medical reviews in non-English databases). Translate key
+      terms into the target language and search with them. Render anything found
+      into Russian in the report.
 
-      NOT THE FIRST PAGE. The first results are the most obvious and often the
-      most superficial. Deliberately dig out what lies deeper.
+      NOT THE FIRST PAGE. The first results are the most obvious and often the most
+      superficial. Deliberately dig deeper.
 
-      FULL PAGES, NOT SNIPPETS. Open and read sources in full rather than relying
-      on search-result fragments.
-
-      PRIMARY SOURCES. Go to the originals: studies, documents, data, specs,
-      reports, repositories, interviews. Prefer primary sources over news
-      aggregators and retellings. If someone cites a source — find the source
-      itself.
-
-      LATERAL SEARCH. Don't fixate on the narrow phrasing. Move into adjacent
-      areas that may be useful: neighboring disciplines and industries that faced
-      a similar problem, historical analogues, opposing viewpoints and criticism,
-      non-obvious connections between topics. Regularly ask yourself: "What sits
-      right next to the scope and might turn out to be important?" Capture
-      valuable unexpected findings.
+      LATERAL SEARCH. Don't fixate on the narrow phrasing. Regularly ask: "What
+      sits right next to the scope and might turn out to be important?" Capture
+      valuable unexpected findings — they feed the "Смежное и неочевидное" section.
 
       ═══════════════════════════════════════════════
       EVALUATING SOURCES AND FACTS
       ═══════════════════════════════════════════════
-      CRITICAL APPRAISAL. Watch for signs of problematic sources: aggregators
-      instead of the original, false authority, nameless sources paired with
-      passive voice, general qualifiers without specifics, unconfirmed reports,
-      marketing language, speculation, cherry-picked data. Do not present such
-      results as established fact — flag the issue. Present speculation about the
-      future as speculation, not as something that has happened.
+      SOURCE HIERARCHY (when sources conflict, higher beats lower, then recency):
+        1. Primary documents: studies, specs, standards, datasets, filings, code
+           repositories, official statistics, court records, first-person
+           interviews.
+        2. Peer-reviewed literature and systematic reviews.
+        3. Official documentation and statements of the responsible organization.
+        4. Quality journalism with named authors and named sources.
+        5. Expert blogs and conference talks (judge the author, not the venue).
+        6. Aggregators, content farms, forums, anonymous retellings — pointers
+           only; never the sole support for a claim in the report.
 
-      LATERAL READING. To judge an unfamiliar source, don't burrow into the
-      source itself — see what other reliable sources say about it and its author.
+      CRITICAL APPRAISAL. Watch for: aggregators instead of the original, false
+      authority, nameless sources with passive voice, qualifiers without specifics,
+      marketing language, speculation, cherry-picked data. Do not present such
+      material as established fact — flag it. Present speculation about the future
+      as speculation.
+
+      LATERAL READING. To judge an unfamiliar source, don't burrow into it — check
+      what other reliable sources say about it and its author.
 
       TRIANGULATION. Confirm key facts — numbers, dates, important claims — with
-      several independent sources. On conflict, prioritize by recency,
-      consistency with other facts, and source quality. Surface unresolved
-      contradictions explicitly in the report.
+      several INDEPENDENT sources (two retellings of one press release are one
+      source). Surface unresolved contradictions explicitly in the report.
 
-      SELF-VERIFICATION. Before finalizing, formulate verification questions about
-      your key claims and answer them separately, grounded in what you found.
+      DATES AND STALENESS. Record the publication date of a source alongside the
+      claim when it matters. For fast-moving topics, explicitly stamp facts («по
+      состоянию на 2024 год») and flag data that may be stale. Prefer the newest
+      credible source for anything volatile.
+
+      DEAD ENDS AND FAILURES. Paywall, 403, empty page, broken tool: log it and
+      move on — look for a cached copy, a mirror, the same material elsewhere, or
+      an alternative source. NEVER guess or reconstruct what an unreadable page
+      "probably said". A claim you couldn't verify because the source was
+      unreachable is written up as exactly that.
 
       ═══════════════════════════════════════════════
-      REPORT FORMAT (in the document, written in RUSSIAN)
+      CITING SOURCES INLINE (FOOTNOTES)
       ═══════════════════════════════════════════════
-      - A direct answer to the main question up front.
-      - A detailed breakdown by subsections.
-      - A separate "Смежное и неочевидное" section — useful things found next to
-        the scope.
-      - Contradictions and disputed points — separately.
-      - What remains unverified or unknown — honestly.
-      - Sources with a reliability note.
+      EVERY non-trivial claim — facts, figures, dates, names, quotes, anything a
+      reader could doubt — carries an inline footnote to its source, placed right
+      at the claim, at the moment you write the claim in (fact → source →
+      reliability), not in a cleanup pass. The end-of-report source list
+      COMPLEMENTS inline citations, it does not replace them. A claim with no
+      footnote reads as unsourced.
 
-      Be honest about gaps. If you couldn't find something, say so — don't
-      disguise a guess as a fact.
+      SYNTAX. Inline form ONLY: `^[...]` directly after the word or sentence it
+      backs, no space before `^`. Prefer a Markdown link inside. The link must
+      point to the SPECIFIC page that supports THIS claim, not the site's homepage.
+      Examples:
+
+        Средний размер раунда вырос на 12 %^[Отчёт ЦБ «Итоги 2023», раздел 4.2,
+        [ссылка](https://cbr.ru/collection/file/2023-report.pdf)].
+        Функция появилась в версии 2.1^[Changelog проекта,
+        [v2.1.0](https://github.com/example/proj/releases/tag/v2.1.0)].
+
+      DO NOT use the reference style `text[^1]` with a separate `[^1]: ...` block:
+      this system does not parse it and it will show as raw text. Only `^[...]`
+      becomes a real footnote.
+
+      WHAT GOES INSIDE. Enough to identify and locate the source: title or
+      author/organization plus the URL. For a shaky source, add a short reliability
+      flag in the note (e.g. «вторичный источник, не подтверждён»). For a
+      triangulated claim, cite each source: several `^[...]` in a row or several
+      links in one note.
+
+      DEDUP. Identical `^[...]` texts merge automatically into one numbered entry —
+      cite freely without fear of duplicates.
+
+      WHICH WRITE PATH PARSES `^[...]`. The `^[...]` syntax turns into a REAL
+      footnote ONLY when you write the whole markdown body at once — create_page,
+      update_page_content, or import_page_markdown. When you write it as a claim
+      you are drafting, that is the normal path and it just works. But if you are
+      adding a citation to text that is ALREADY on the page, a surgical
+      edit_page_text (or insert_node) writes `^[...]` as a LITERAL string — it does
+      NOT parse, and the reader sees the raw `^[...]`. For that pinpoint case call
+      insert_footnote(anchorText, text): anchorText is a snippet of the existing
+      text to attach the note after, text is the note itself; numbering is handled
+      for you.
+
+      ═══════════════════════════════════════════════
+      PROSE, NOT NOTES
+      ═══════════════════════════════════════════════
+      You are writing a RESEARCH REPORT, not a конспект. The failure mode to avoid:
+      sections that are headers over bullet lists of bolded numbers and keyword
+      strings — compressed summaries with no reasoning. That is a lookup table, not
+      research. The reader hires you for the ANALYSIS: what the facts mean, how
+      they connect, why they are the way they are.
+
+      Concretely:
+        - DEFAULT TO PARAGRAPHS. Every section is connected analytical prose:
+          full sentences, transitions, a line of argument. A section that consists
+          only of a bullet list is unfinished.
+        - EXPLAIN, DON'T JUST STATE. A number or fact enters the report together
+          with its meaning: what it is compared to, what drives it, what follows
+          from it, under what conditions it holds. «Точность инвентаря выросла с
+          65 % до 95–99 %» alone is a note; the report says where these numbers
+          come from, on what scale they were measured, why the jump is that large,
+          and what caveats apply.
+        - MECHANISMS AND CAUSES. Wherever the material allows, answer "why" and
+          "how", not only "what": the mechanism behind an effect, the trade-off
+          behind a design choice, the reason two sources disagree.
+        - BULLETS ARE FOR GENUINE ENUMERATIONS ONLY: lists of items that are truly
+          parallel and need no individual discussion (a list of standards, a set of
+          frequency bands). Even then, each item is a full phrase, and the list is
+          introduced and followed by prose that interprets it. Never use bullets to
+          avoid writing sentences.
+        - NO ORPHAN KEYWORDS. Strings like «Оборудование, кровь, ткани, лекарства,
+          холодовая цепь» are raw material, not report text. Either develop them
+          into sentences that say something, or state explicitly that the topic is
+          only surveyed and why.
+        - EVERY SECTION ANSWERS A QUESTION. Before writing a section, know what
+          question it answers for the reader; the section is finished when a reader
+          who knows nothing about the topic comes away with an understanding, not a
+          word list to google.
+        - DENSITY OVER LENGTH. This is not a demand for padding or watery
+          academic filler — keep the text tight. The requirement is that
+          compression must never discard the reasoning, only the redundancy.
+
+      ═══════════════════════════════════════════════
+      LANGUAGE AND TERMINOLOGY OF THE REPORT
+      ═══════════════════════════════════════════════
+      The report is in Russian. Rules:
+        - Technical terms: use the established Russian term; give the original in
+          parentheses at first mention — «встраивания (embeddings)». If no settled
+          Russian term exists, keep the original and gloss it once.
+        - Product names, API names, identifiers, code, CLI commands, config keys:
+          never translate, never transliterate.
+        - Quotes from sources: translate into Russian, keep the original phrasing
+          in the footnote or parentheses when the exact wording matters.
+        - Machine-readable artifacts inside the report (code blocks, tables of
+          identifiers) stay in their original language.
+
+      ═══════════════════════════════════════════════
+      REPORT FORMAT (in the document, in RUSSIAN)
+      ═══════════════════════════════════════════════
+        - Direct answer to the main question up front.
+        - Detailed breakdown by subsections.
+        - «Смежное и неочевидное» — useful things found next to the scope.
+        - «Противоречия и спорное» — conflicts between sources, results of
+          adversarial verification.
+        - «Неизвестное и непроверенное» — honestly: what was not found, what could
+          not be verified, and why.
+        - Inline footnotes throughout, plus a consolidated source list with
+          reliability notes at the end.
+
+      ═══════════════════════════════════════════════
+      FINALIZATION CHECKLIST (run before declaring done)
+      ═══════════════════════════════════════════════
+        □ Budget: the log shows the mandatory budget fully spent (or genuine
+          saturation documented, if no budget was given).
+        □ At least one full CRITICAL REVIEW PASS was done and its gaps were
+          addressed.
+        □ Every non-trivial claim has an inline `^[...]` footnote; no claim rests
+          solely on a snippet or a tier-6 source.
+        □ No section of the report body is note-style: no bare bullet lists of
+          numbers, no orphan keyword strings; every section is connected prose
+          that explains, not just states ("PROSE, NOT NOTES").
+        □ Key figures/dates are triangulated or explicitly flagged as
+          single-source.
+        □ The direct answer at the top matches the body of the report.
+        □ «Неизвестное» is honestly filled — not empty by omission.
+        □ Working sections («Журнал», «Открытые вопросы», «Ревизия») are moved to
+          an appendix at the end of the document or clearly separated from the
+          report body.
+      Be honest about gaps. If you couldn't find something, say so — don't disguise
+      a guess as a fact.
     autoStart: false
     launchMessage: null

agent-roles-catalog/index.yaml

@@ -33,4 +33,4 @@ bundles:
       - en
     roles:
       - slug: researcher
-        version: 4
+        version: 8

agent-roles-catalog/scripts/content-hashes.json

@@ -16,8 +16,8 @@
     "hash": "cef39fed321779631ddd1077fcba53399adf0e48b301df281c71eb042610900d"
   },
   "researcher": {
-    "version": 4,
-    "hash": "9446ec6d2c8a6ec548358537ac392b8bf9b4d2a832ebb105d5514eac2c76da74"
+    "version": 8,
+    "hash": "0e76efa180c3e443c8856b8787e9643923d10486b373ce078c12dc16eb04611b"
   },
   "structural-editor": {
     "version": 4,

apps/client/src/features/ai-chat/components/ai-chat-window.tsx

@@ -86,11 +86,19 @@ const MIN_HEIGHT = 400;
 // Margin kept between the window and the viewport edges while dragging.
 const EDGE_MARGIN = 8;
 
-// #184 phase 1.5: hard cap on the degraded-poll fallback. The poll is armed when
-// a resume attempt could not attach to the live run and disarmed by the thread on
-// settle / local stream; this cap is the ONLY backstop against an endless tick
-// (a stuck 'streaming' row before the boot-sweep, or a user-tail 204 with no run).
-const DEGRADED_POLL_MAX_MS = 10 * 60_000;
+// #184 phase 1.5 / #430: backstop for the degraded-poll fallback. The poll is
+// armed when a resume attempt could not attach to the live run and disarmed by the
+// thread on settle / local stream; this cap is the ONLY backstop against an endless
+// tick (a stuck 'streaming' row before the boot-sweep, or a user-tail 204 with no
+// run).
+//
+// #430: measured from RUN ACTIVITY, not from arm-time. A real autonomous run takes
+// 11-25 min — longer than a fixed 10-min-from-start cap, which used to cut the poll
+// off mid-run. Instead we cap on INACTIVITY: keep polling as long as the run is
+// still making progress (its persisted rows keep changing), and only give up after
+// this long with NO new activity. A genuinely stuck run produces no row changes, so
+// the idle cap still bounds it; a long-but-progressing run polls to completion.
+const DEGRADED_POLL_IDLE_MAX_MS = 10 * 60_000;
 
 /** Compact token formatter: 1.2M / 3.4k / 950. */
 function formatTokens(n: number): string {
@@ -254,9 +262,12 @@ export default function AiChatWindow() {
   // onResumeFallback(true); the thread disarms it on settle / local stream. The
   // window only OWNS the timer (armedAtRef stamps when it was armed for the cap).
   const [degradedPoll, setDegradedPoll] = useState(false);
-  const armedAtRef = useRef(0);
+  // #430: timestamp of the LAST run activity while the poll is armed — stamped on
+  // arm and re-stamped whenever the polled rows change (see the effect below). The
+  // idle cap is measured from this, so a long-but-progressing run keeps polling.
+  const lastActivityAtRef = useRef(0);
   const onResumeFallback = useCallback((active: boolean): void => {
-    if (active) armedAtRef.current = Date.now();
+    if (active) lastActivityAtRef.current = Date.now();
     setDegradedPoll(active);
   }, []);
   // Reset the degraded poll whenever the open chat changes: it is scoped to the
@@ -269,18 +280,28 @@ export default function AiChatWindow() {
     useAiChatMessagesQuery(
       activeChatId ?? undefined,
       // DELIBERATELY DUMB (invariant 8 / task 2.4): poll every 2.5s while armed
-      // and under the 10-min cap; otherwise off. NO error checks (TanStack v5
-      // resets fetchFailureCount each fetch, so consecutive errors are not
-      // expressible — and the poll must survive a server restart) and NO tail
-      // checks (the settled/local-stream semantics live in ChatThread, which
-      // disarms via onResumeFallback(false)). The time cap is the only backstop.
+      // and while the run is still active (#430: under the INACTIVITY cap, not a
+      // fixed-from-start cap); otherwise off. NO error checks (TanStack v5 resets
+      // fetchFailureCount each fetch, so consecutive errors are not expressible —
+      // and the poll must survive a server restart) and NO tail checks (the
+      // settled/local-stream semantics live in ChatThread, which disarms via
+      // onResumeFallback(false)). The idle cap is the only backstop.
       () =>
         degradedPoll === true &&
-        Date.now() - armedAtRef.current < DEGRADED_POLL_MAX_MS
+        Date.now() - lastActivityAtRef.current < DEGRADED_POLL_IDLE_MAX_MS
           ? 2500
           : false,
     );
 
+  // #430: re-stamp the activity clock whenever the polled rows change while the
+  // poll is armed. TanStack keeps the same `messageRows` reference across refetches
+  // that return deep-equal data (structural sharing), so a new reference means the
+  // run genuinely progressed — which extends the inactivity cap above. A stuck run
+  // yields no reference change, so the cap eventually fires and stops the poll.
+  useEffect(() => {
+    if (degradedPoll) lastActivityAtRef.current = Date.now();
+  }, [degradedPoll, messageRows]);
+
   // #184 reconnect-and-live-follow. Whether detached agent runs are enabled for
   // this workspace. When the feature is off no runs are ever created, so the
   // resume attempt would only ever 204; gating ChatThread's resume on it avoids a

apps/client/src/features/ai-chat/components/chat-thread.test.tsx

@@ -739,3 +739,170 @@ function renderResumable(initialRows: IAiChatMessageRow[]) {
     act(() => view.rerender(<Wrapper rows={rows} />));
   return { rerender, onResumeFallback };
 }
+
+// #430: auto-reconnect to a DETACHED run after a LIVE SSE disconnect. The mount
+// path only resumes on mount/reload; these cover the missing trigger — a live
+// `isDisconnect` on onFinish must (backoff-)re-attach WITHOUT a reload, pin+strip
+// the live row to avoid duplicates, fall back to the degraded poll on a 204, and
+// exhaust to a manual Retry.
+describe("ChatThread — live reconnect after isDisconnect (#430)", () => {
+  // A LIVE local turn that just dropped: the settled tail existed before, and the
+  // partial assistant row lives only in `messages` (not persisted as a tail).
+  const settledTail = () => [
+    row("u1", "user", undefined, "hi"),
+    row("a1", "assistant", "succeeded", "done"),
+  ];
+  // The partial assistant message onFinish hands us for the dropped LIVE turn.
+  const liveMsg = {
+    id: "a2",
+    role: "assistant",
+    parts: [{ type: "text", text: "partial live answer" }],
+  };
+
+  beforeEach(() => {
+    resetState();
+    // status "ready": with a live disconnect the mock is not streaming, so the
+    // status==="streaming" auto-clear effect stays out of the way.
+    h.state.status = "ready";
+    vi.useFakeTimers();
+  });
+  afterEach(() => {
+    vi.useRealTimers();
+    cleanup();
+  });
+
+  // Render a NON-resuming mount (settled tail -> no mount resume) with autonomous
+  // runs on, then simulate a live disconnect via onFinish.
+  function renderLiveThenDisconnect() {
+    const view = renderThread({
+      autonomousRunsEnabled: true,
+      initialRows: settledTail(),
+    });
+    // The settled tail must NOT have triggered a mount resume.
+    expect(h.state.resumeStream).not.toHaveBeenCalled();
+    act(() => {
+      h.state.onFinish?.({
+        message: liveMsg,
+        isAbort: false,
+        isDisconnect: true,
+        isError: false,
+      });
+    });
+    return view;
+  }
+
+  // Fire the pending (scheduled) attempt for `attempt` (backoff = 1s,2s,4s,...).
+  function advanceToAttempt(attempt: number) {
+    act(() => {
+      vi.advanceTimersByTime(1000 * 2 ** (attempt - 1));
+    });
+  }
+
+  // Simulate the reconnect GET returning 204 (nothing live) so the transport's
+  // no-active-stream recovery runs.
+  async function reconnect204() {
+    vi.stubGlobal(
+      "fetch",
+      vi.fn().mockResolvedValue({ status: 204, ok: false }),
+    );
+    await act(async () => {
+      await h.state.transport!.fetch!("http://x", { method: "GET" });
+    });
+  }
+
+  // Simulate the reconnect GET returning a live 2xx stream.
+  async function reconnect200() {
+    vi.stubGlobal(
+      "fetch",
+      vi.fn().mockResolvedValue({ status: 200, ok: true }),
+    );
+    await act(async () => {
+      await h.state.transport!.fetch!("http://x", { method: "GET" });
+    });
+  }
+
+  it("calls resumeStream POST-mount (a live disconnect triggers a backoff reconnect)", () => {
+    renderLiveThenDisconnect();
+    // The banner shows immediately; the attach itself fires after the first backoff.
+    expect(screen.getByText(/reconnecting/i)).toBeTruthy();
+    expect(h.state.resumeStream).not.toHaveBeenCalled();
+    advanceToAttempt(1);
+    // resumeStream is now called AFTER mount — the bug was it only ever fired once
+    // on mount. The reconnect URL pins expect=live&anchor to OUR run.
+    expect(h.state.resumeStream).toHaveBeenCalledTimes(1);
+    expect(h.state.transport!.prepareReconnectToStreamRequest!().api).toBe(
+      "/api/ai-chat/runs/c1/stream?expect=live&anchor=a2",
+    );
+  });
+
+  it("strips the pinned live row before replay so content is NOT duplicated", () => {
+    renderLiveThenDisconnect();
+    advanceToAttempt(1);
+    // The attempt strips the anchor row from the store (the live replay rebuilds
+    // it). Apply the setMessages updater to prove it removes exactly the anchor.
+    const updater = h.state.setMessages.mock.calls.at(-1)![0] as (
+      prev: { id: string }[],
+    ) => { id: string }[];
+    expect(updater([{ id: "u1" }, { id: "a2" }])).toEqual([{ id: "u1" }]);
+  });
+
+  it("a live re-attach (2xx) clears the reconnect banner", async () => {
+    renderLiveThenDisconnect();
+    advanceToAttempt(1);
+    await reconnect200();
+    expect(screen.queryByText(/reconnecting/i)).toBeNull();
+  });
+
+  it("a 204 arms the degraded poll and backs off to the next attempt", async () => {
+    const { onResumeFallback } = renderLiveThenDisconnect();
+    advanceToAttempt(1);
+    expect(h.state.resumeStream).toHaveBeenCalledTimes(1);
+    await reconnect204();
+    // Fallback engaged: the degraded poll is armed (204 -> onNoActiveStream).
+    expect(onResumeFallback).toHaveBeenCalledWith(true);
+    // Still reconnecting — the banner advanced to attempt 2/5.
+    expect(screen.getByText(/reconnecting.*2\/5/i)).toBeTruthy();
+    // The next backoff fires attempt 2 (another resumeStream).
+    advanceToAttempt(2);
+    expect(h.state.resumeStream).toHaveBeenCalledTimes(2);
+  });
+
+  it("exhausts the attempt limit into a manual Retry, which restarts the sequence", async () => {
+    renderLiveThenDisconnect();
+    // Drive all 5 attempts, each failing with a 204.
+    for (let n = 1; n <= 5; n++) {
+      advanceToAttempt(n);
+      expect(h.state.resumeStream).toHaveBeenCalledTimes(n);
+      await reconnect204();
+    }
+    // The 5th 204 exhausted the cap -> the manual Retry replaces the banner.
+    expect(screen.queryByText(/reconnecting/i)).toBeNull();
+    const retry = screen.getByText("Retry");
+    expect(retry).toBeTruthy();
+    // Retry fires attempt 1 immediately (no backoff) — a 6th resumeStream.
+    act(() => {
+      fireEvent.click(retry);
+    });
+    expect(h.state.resumeStream).toHaveBeenCalledTimes(6);
+    expect(screen.getByText(/reconnecting/i)).toBeTruthy();
+  });
+
+  it("does NOT reconnect when autonomous runs are disabled", () => {
+    renderThread({ autonomousRunsEnabled: false, initialRows: settledTail() });
+    act(() => {
+      h.state.onFinish?.({
+        message: liveMsg,
+        isAbort: false,
+        isDisconnect: true,
+        isError: false,
+      });
+    });
+    expect(screen.queryByText(/reconnecting/i)).toBeNull();
+    // The terminal "connection lost" notice is shown instead (unchanged behavior).
+    expect(
+      screen.getByText("Connection lost — the answer was interrupted."),
+    ).toBeTruthy();
+    advanceToAttempt(1);
+    expect(h.state.resumeStream).not.toHaveBeenCalled();
+  });
+});

apps/client/src/features/ai-chat/components/chat-thread.tsx

@@ -1,7 +1,17 @@
 import { useCallback, useEffect, useMemo, useRef, useState } from "react";
 import { useQueryClient } from "@tanstack/react-query";
 import { generateId } from "ai";
-import { ActionIcon, Box, Group, Stack, Text, Tooltip } from "@mantine/core";
+import {
+  ActionIcon,
+  Alert,
+  Box,
+  Button,
+  Group,
+  Loader,
+  Stack,
+  Text,
+  Tooltip,
+} from "@mantine/core";
 import {
   IconClockHour4,
   IconPlayerPlayFilled,
@@ -51,6 +61,15 @@ import classes from "@/features/ai-chat/components/ai-chat.module.css";
 // from the token rate.
 const STREAM_THROTTLE_MS = 50;
 
+// #430: auto-reconnect after a LIVE SSE disconnect of a DETACHED (autonomous) run.
+// The run keeps executing server-side, so instead of a dead "Lost connection"
+// banner we re-attach to the live tail through the SAME resumable machinery the
+// mount path uses. Attempts back off exponentially and are capped; on exhaustion
+// the user gets a manual Retry (the degraded poll keeps catching up underneath).
+const RECONNECT_MAX_ATTEMPTS = 5;
+// Backoff before attempt N (1-based): 1s, 2s, 4s, 8s, 16s.
+const RECONNECT_BASE_DELAY_MS = 1000;
+
 /** The page the user is currently viewing, sent as chat context. */
 export interface OpenPageContext {
   id: string;
@@ -175,6 +194,10 @@ export default function ChatThread({
   const reconcileTailRef = useRef(false);
   const noStreamHandledRef = useRef(false);
   const onNoActiveStreamRef = useRef<(() => void) | null>(null);
+  // #430: called from the transport's reconnect-GET success branch when a live
+  // stream re-attached (2xx, not 204) — clears the reconnect banner. Kept in a ref
+  // because the transport's fetch closure (useMemo([])) reads it live.
+  const onReconnectAttachedRef = useRef<(() => void) | null>(null);
   // Live mount flag. The attach GET and the resumed `onFinish` are async and can
   // land AFTER this thread unmounts (the parent remounts per chat via `key`); with
   // chatIdRef then pointing at the NEW chat, an ungated late callback would arm a
@@ -378,6 +401,10 @@ export default function ChatThread({
             // NOT drop the in-progress row or stop tracking the durable run.
             if (response.status === 204 || !response.ok)
               onNoActiveStreamRef.current?.();
+            // #430: a 2xx stream re-attached (live tail or finished-replay). Signal
+            // the reconnect controller to clear its banner. No-op outside an active
+            // reconnect sequence (e.g. the mount attach), so it is safe here.
+            else onReconnectAttachedRef.current?.();
             return response;
           } catch (err) {
             // Network throw: same no-onFinish recovery, then rethrow so the SDK
@@ -481,6 +508,31 @@ export default function ChatThread({
           );
         }
       }
+      // (2b) #430: a LIVE (non-resumed) detached run whose SSE just dropped. The
+      // server run keeps executing, so instead of a dead "Lost connection" banner
+      // start a reconnect sequence: pin the CURRENT streaming assistant row as the
+      // strip/anchor (the live tail is the already-shown partial in `messages`, not
+      // a persistent row) and re-attach to the live tail via the resumable machinery.
+      const startedReconnect =
+        isDisconnect &&
+        !wasResumed &&
+        autonomousRunsEnabled === true &&
+        mountedRef.current &&
+        message?.role === "assistant" &&
+        typeof message.id === "string";
+      if (startedReconnect) {
+        beginReconnect({
+          id: message.id,
+          role: "assistant",
+          content: "",
+          status: "streaming",
+          createdAt: new Date().toISOString(),
+          // Preserve the partial parts so a 204 restore (onNoActiveStream) re-shows
+          // what was on screen while the degraded poll catches the run up to
+          // terminal (rowToUiMessage prefers metadata.parts).
+          metadata: { parts: message.parts },
+        });
+      }
       // (3) Standard branches.
       // Forward the authoritative server chatId (streamed on the assistant
       // message metadata) so the parent adopts the REAL created chat id for a new
@@ -490,9 +542,11 @@ export default function ChatThread({
       onTurnFinished(extractServerChatId(message), threadKey);
       // Show a neutral "stopped" marker for an aborted turn; the red error banner
       // (via `error`) already covers isError, and a clean finish clears any marker.
+      // On a live disconnect that STARTED a reconnect, suppress the terminal
+      // "connection lost" notice — the reconnect banner takes over (#430).
       if (isError) setStopNotice(null);
       else if (isAbort) setStopNotice("manual");
-      else if (isDisconnect) setStopNotice("disconnect");
+      else if (isDisconnect) setStopNotice(startedReconnect ? null : "disconnect");
       else setStopNotice(null);
       // A resumed turn NEVER flushes the queue (invariant 7): skip BOTH the
       // flush-on-abort branch and the plain flush. The local streamer is the only
@@ -579,6 +633,106 @@ export default function ChatThread({
 
   const isStreaming = status === "submitted" || status === "streaming";
 
+  // #430: live-disconnect reconnect controller. `null` = idle; `{ trying, attempt }`
+  // = a backoff sequence is running (drives the "reconnecting… (N/max)" banner);
+  // `{ failed }` = attempts exhausted (drives the manual Retry). Mirrored into a ref
+  // so the transport/onNoActiveStream closures branch on the LIVE value.
+  type ReconnectState =
+    | null
+    | { phase: "trying"; attempt: number }
+    | { phase: "failed" };
+  const [reconnectState, setReconnectState] = useState<ReconnectState>(null);
+  const reconnectStateRef = useRef<ReconnectState>(null);
+  const setReconnectStatePair = useCallback((s: ReconnectState) => {
+    reconnectStateRef.current = s;
+    setReconnectState(s);
+  }, []);
+  const reconnectTimerRef = useRef<ReturnType<typeof setTimeout> | null>(null);
+  const clearReconnectTimer = useCallback(() => {
+    if (reconnectTimerRef.current) {
+      clearTimeout(reconnectTimerRef.current);
+      reconnectTimerRef.current = null;
+    }
+  }, []);
+
+  // One reconnect attempt — MIRRORS the mount strip/anchor path for the LIVE case.
+  // beginReconnect pinned strippedRowRef/stripRef to the run's assistant row, so:
+  //  - remove that row from the store (the mount path strips it from the SEED; here
+  //    it is already shown, so filter it out) — the live replay's `text-start` then
+  //    rebuilds it without DUPLICATING parts (the main dedup risk, #430);
+  //  - reset the one-shot 204 guard so onNoActiveStream can fire for THIS attempt;
+  //  - mark the turn resumed (invariant 7/8) so onFinish runs the recovery block and
+  //    never flushes the queue;
+  //  - resumeStream() -> prepareReconnectToStreamRequest builds
+  //    ?expect=live&anchor=<pinned id>, pinning the replay to OUR run (invariant 6).
+  const attemptReconnectOnce = useCallback(
+    (attempt: number) => {
+      if (!mountedRef.current) return;
+      const anchor = strippedRowRef.current;
+      if (anchor) {
+        setMessages((prev) => prev.filter((m) => m.id !== anchor.id));
+      }
+      noStreamHandledRef.current = false;
+      setResumedTurnPair(true);
+      setReconnectStatePair({ phase: "trying", attempt });
+      void resumeStream();
+    },
+    [setMessages, setResumedTurnPair, setReconnectStatePair, resumeStream],
+  );
+
+  // Schedule attempt `attempt` after an exponential backoff.
+  const scheduleReconnectAttempt = useCallback(
+    (attempt: number) => {
+      clearReconnectTimer();
+      setReconnectStatePair({ phase: "trying", attempt });
+      reconnectTimerRef.current = setTimeout(
+        () => attemptReconnectOnce(attempt),
+        RECONNECT_BASE_DELAY_MS * 2 ** (attempt - 1),
+      );
+    },
+    [clearReconnectTimer, setReconnectStatePair, attemptReconnectOnce],
+  );
+
+  // Start a fresh reconnect sequence, pinning `anchorRow` (the live run's assistant
+  // row) as the strip/anchor reused by every attempt.
+  const beginReconnect = useCallback(
+    (anchorRow: IAiChatMessageRow) => {
+      if (!autonomousRunsEnabled || !mountedRef.current) return;
+      strippedRowRef.current = anchorRow;
+      stripRef.current = true;
+      scheduleReconnectAttempt(1);
+    },
+    [autonomousRunsEnabled, scheduleReconnectAttempt],
+  );
+
+  // Manual Retry (shown once attempts are exhausted): restart at attempt 1 and fire
+  // immediately (the user asked for it now — no backoff).
+  const retryReconnect = useCallback(() => {
+    clearReconnectTimer();
+    attemptReconnectOnce(1);
+  }, [clearReconnectTimer, attemptReconnectOnce]);
+
+  // Live SSE re-attached (the reconnect GET returned a 2xx stream): clear the
+  // banner + any pending backoff. No-op outside a sequence (e.g. the mount attach).
+  const onReconnectAttached = useCallback(() => {
+    if (!mountedRef.current || !reconnectStateRef.current) return;
+    clearReconnectTimer();
+    setReconnectStatePair(null);
+  }, [clearReconnectTimer, setReconnectStatePair]);
+  onReconnectAttachedRef.current = onReconnectAttached;
+
+  // The reconnect GET could not attach (204 / error). onNoActiveStream has already
+  // armed the degraded poll (the robust fallback that drives the row to terminal
+  // from the DB), so this only decides the LIVE-attach retry: back off and try
+  // again up to the cap, else surface the manual Retry.
+  const onReconnectNoStream = useCallback(() => {
+    const s = reconnectStateRef.current;
+    if (s?.phase !== "trying") return;
+    if (s.attempt < RECONNECT_MAX_ATTEMPTS)
+      scheduleReconnectAttempt(s.attempt + 1);
+    else setReconnectStatePair({ phase: "failed" });
+  }, [scheduleReconnectAttempt, setReconnectStatePair]);
+
   // 204-handler (`onNoActiveStream`): the attach returned 204 — nothing live to
   // resume (overflow / begin-failure / after retention / anchor-mismatch). One-
   // shot via noStreamHandledRef (we do NOT null onNoActiveStreamRef). Exactly four
@@ -610,7 +764,17 @@ export default function ChatThread({
     // (d) 204 means onFinish will NOT fire — clear the suppression flag so it
     // cannot swallow the NEXT local turn's queue flush.
     setResumedTurnPair(false);
-  }, [setMessages, queryClient, onResumeFallback, setResumedTurnPair]);
+    // (e) #430: if this 204/error landed during a live-disconnect reconnect
+    // sequence, back off and retry the live attach (or give up to the manual
+    // Retry). The degraded poll armed in (c) is the fallback either way.
+    onReconnectNoStream();
+  }, [
+    setMessages,
+    queryClient,
+    onResumeFallback,
+    setResumedTurnPair,
+    onReconnectNoStream,
+  ]);
   onNoActiveStreamRef.current = onNoActiveStream;
 
   // Mount effect: kick off the resume attempt for a non-settled tail. Marking the
@@ -628,6 +792,9 @@ export default function ChatThread({
     return () => {
       mountedRef.current = false;
       attachAbortRef.current?.abort();
+      // #430: drop any pending reconnect backoff so it can't fire against the next
+      // chat this thread's refs are reused for.
+      if (reconnectTimerRef.current) clearTimeout(reconnectTimerRef.current);
     };
     // Mount-only by design; the parent remounts per chat via `key`.
     // eslint-disable-next-line react-hooks/exhaustive-deps
@@ -666,12 +833,27 @@ export default function ChatThread({
     if (tail.status !== "streaming") {
       reconcileTailRef.current = false;
       onResumeFallback?.(false);
+      // #430: the run reached its terminal state via the degraded poll — there is
+      // no live tail left to reconnect to, so drop any reconnect banner / Retry.
+      clearReconnectTimer();
+      setReconnectStatePair(null);
     }
     // onResumeFallback intentionally omitted (parent-stable callback); deps are
     // fixed by the resume design.
     // eslint-disable-next-line react-hooks/exhaustive-deps
   }, [initialRows, isStreaming, setMessages]);
 
+  // #430: a real stream is live again — the reconnect re-attached to the live tail
+  // (status -> "streaming") OR the user started a new local turn. Either way clear
+  // the reconnect banner + any pending backoff. Gated on "streaming" (not the
+  // broader "submitted") so a still-pending attach GET does not clear prematurely.
+  useEffect(() => {
+    if (status === "streaming") {
+      clearReconnectTimer();
+      setReconnectStatePair(null);
+    }
+  }, [status, clearReconnectTimer, setReconnectStatePair]);
+
   // "Send now" on a queued message: interrupt the current turn and immediately
   // send THIS message, keeping the agent's partial output. Other queued messages
   // stay queued and flush normally after the new turn. Reuses the existing
@@ -719,6 +901,9 @@ export default function ChatThread({
     // observer's Stop would otherwise leave the attach fetch running.
     attachAbortRef.current?.abort();
     stop();
+    // #430: pressing Stop also cancels an in-progress reconnect sequence.
+    clearReconnectTimer();
+    setReconnectStatePair(null);
     if (!autonomousRunsEnabled) return;
     if (chatIdRef.current) {
       onServerStop?.(chatIdRef.current);
@@ -740,7 +925,13 @@ export default function ChatThread({
       // for this fix. Documented so a future change can address the abort-ordering.
       stopPendingRef.current = true;
     }
-  }, [stop, autonomousRunsEnabled, onServerStop]);
+  }, [
+    stop,
+    autonomousRunsEnabled,
+    onServerStop,
+    clearReconnectTimer,
+    setReconnectStatePair,
+  ]);
 
   // Clear the stopped marker as soon as a new turn begins streaming, and drop any
   // stale "Send now" interrupt flags. On the legit interrupt path both refs are
@@ -825,6 +1016,43 @@ export default function ChatThread({
           detail={errorView.detail}
           mb="xs"
         />
+      ) : reconnectState ? (
+        // #430: while auto-reconnecting to a detached run's live tail, show progress
+        // instead of a dead "Lost connection" banner; once attempts are exhausted,
+        // offer a manual Retry (the degraded poll keeps catching up underneath).
+        <Alert
+          variant="light"
+          color="gray"
+          p="xs"
+          mb="xs"
+          style={{ flexShrink: 0 }}
+        >
+          <Group gap={8} wrap="nowrap" align="center">
+            {reconnectState.phase === "trying" ? (
+              <>
+                <Loader size={14} color="gray" style={{ flex: "none" }} />
+                <Text size="sm" lh={1.3} c="dimmed">
+                  {t("Connection lost — reconnecting…")}
+                  {` (${reconnectState.attempt}/${RECONNECT_MAX_ATTEMPTS})`}
+                </Text>
+              </>
+            ) : (
+              <>
+                <Text size="sm" lh={1.3} c="dimmed" style={{ flex: 1 }}>
+                  {t("Couldn't reconnect to the answer.")}
+                </Text>
+                <Button
+                  size="compact-xs"
+                  variant="light"
+                  color="gray"
+                  onClick={retryReconnect}
+                >
+                  {t("Retry")}
+                </Button>
+              </>
+            )}
+          </Group>
+        </Alert>
       ) : stopNotice ? (
         <ChatStoppedNotice
           text={

apps/client/src/features/editor/components/footnote/footnote-definition-view.tsx

@@ -49,19 +49,14 @@ export default function FootnoteDefinitionView(props: NodeViewProps) {
       className={classes.definition}
       style={{ ["--footnote-number" as any]: `"${number}"` }}
     >
-      {/* #146: contentDOM MUST be the first child — a non-editable marker before
+      {/* #146: contentDOM MUST be the first child — non-editable chrome before
           it makes click hit-testing snap the caret above. Content first; the
-          marker + back-link follow in DOM and are placed left/right via CSS
-          flex `order`. The second #146 mitigation lives in
+          back-link follows in DOM and is placed on the right via CSS flex. The
+          decorative "N." number is rendered inline via the .definitionContent
+          ::before rule (from the --footnote-number var), so no marker element
+          precedes the content. The second #146 mitigation lives in
           editor-paste-handler.tsx (reflowAfterPaste). */}
       <NodeViewContent className={classes.definitionContent} />
-      <span
-        className={classes.definitionMarker}
-        contentEditable={false}
-        aria-hidden="true"
-      >
-        {number}.
-      </span>
       {refCount > 1 ? (
         // Multiple references -> ↩ followed by one lettered link per occurrence.
         <span

apps/client/src/features/editor/components/footnote/footnote.module.css

@@ -81,34 +81,34 @@
 .definition {
   display: flex;
   align-items: flex-start;
-  /* Tight number→text spacing (~one space) so it reads like "1. text"
-     instead of leaving a wide gap after the period. */
-  gap: 0.4em;
+  /* Tight spacing between the content and the trailing ↩ back-link. */
+  gap: 0.3em;
   padding: 2px 0;
+  /* Footnotes read smaller than body text (16px). Matches .listHeading. */
+  font-size: var(--mantine-font-size-sm);
 }
 
-.definitionMarker {
-  order: -1; /* keep the "N." marker on the LEFT though it follows content in DOM (#146) */
-  flex: 0 0 auto;
-  min-width: 1.5em;
-  /* Right-align within the narrow column so the period sits next to the text
-     and multi-digit numbers (10, 11, …) stay aligned on their right edge. */
-  text-align: right;
-  font-variant-numeric: tabular-nums;
-  color: var(--mantine-color-dimmed);
-  user-select: none;
-}
-
+/* The "N." number is decorative (from the --footnote-number CSS var on the
+   wrapper, never in the document model) and is rendered inline at the start of
+   the first content line via ::before. This keeps text and wrapped lines flush
+   to the left margin — no hanging indent — while the editable contentDOM stays
+   the FIRST DOM child (#146). */
 .definitionContent {
   flex: 1 1 auto;
   min-width: 0;
 }
 
-/* The inner editable paragraph inherits `.ProseMirror p { margin: 0.5em 0 }`,
-   which pushes the first text line ~0.5em below the "N." marker (aligned to
-   flex-start), making the number float above the text. Drop the outer margins
-   so the marker and the first line share the same top edge — same approach
-   used for callouts in core.css. */
+.definitionContent > :first-child::before {
+  content: var(--footnote-number, "?") ". ";
+  color: var(--mantine-color-dimmed);
+  font-variant-numeric: tabular-nums;
+  user-select: none;
+}
+
+/* The inner editable paragraph inherits `.ProseMirror p { margin: 0.5em 0 }`.
+   Drop the outer margins so the definition sits tight to the heading above and
+   the ::before number aligns with the top of the row — same approach used for
+   callouts in core.css. */
 .definitionContent > :first-child {
   margin-top: 0;
 }

apps/server/src/collaboration/collaboration.gateway.ts

@@ -1,4 +1,9 @@
-import { Hocuspocus } from '@hocuspocus/server';
+import {
+  connectedPayload,
+  Extension,
+  Hocuspocus,
+  onConnectPayload,
+} from '@hocuspocus/server';
 import { IncomingMessage } from 'http';
 import WebSocket from 'ws';
 import { AuthenticationExtension } from './extensions/authentication.extension';
@@ -25,6 +30,56 @@ import {
   CollaborationHandler,
   CollabEventHandlers,
 } from './collaboration.handler';
+import {
+  incDocLoad,
+  incDocUnload,
+  isMetricsEnabled,
+  observeCollabConnect,
+  registerDocsOpenSource,
+} from '../integrations/metrics/metrics.registry';
+
+/**
+ * #402 — collab lifecycle metrics as a lightweight hocuspocus extension.
+ *
+ * - afterLoadDocument / afterUnloadDocument (fire once PER DOCUMENT) drive the
+ *   doc load/unload counters.
+ * - collab_connect_duration_seconds: I time the onConnect→connected hook pair,
+ *   i.e. connection ACCEPTANCE (which includes the auth handshake). This is the
+ *   cleanest per-connection correlation hocuspocus exposes: both payloads carry
+ *   the SAME `request` IncomingMessage object, so a WeakMap keyed on it gives a
+ *   per-connection start with NO leak (the entry is GC'd with the request if a
+ *   connection is rejected in onAuthenticate and `connected` never fires).
+ *   I deliberately do NOT observe at afterLoadDocument: that hook fires per
+ *   DOCUMENT, not per connection, so a second client joining an already-open
+ *   doc would be missed. auth/load latencies are their own separate metrics.
+ *
+ * All helpers are no-ops when METRICS_PORT is unset; these hooks are per
+ * connect/load/unload (never per message), so there is no hot-path cost.
+ */
+class CollabMetricsExtension implements Extension {
+  // Keyed by the per-connection request object → connect start time (ms).
+  private readonly connectStarts = new WeakMap<object, number>();
+
+  async onConnect(data: onConnectPayload) {
+    this.connectStarts.set(data.request, performance.now());
+  }
+
+  async connected(data: connectedPayload) {
+    const start = this.connectStarts.get(data.request);
+    if (start !== undefined) {
+      observeCollabConnect((performance.now() - start) / 1000);
+      this.connectStarts.delete(data.request);
+    }
+  }
+
+  async afterLoadDocument() {
+    incDocLoad();
+  }
+
+  async afterUnloadDocument() {
+    incDocUnload();
+  }
+}
 
 @Injectable()
 export class CollaborationGateway {
@@ -58,9 +113,18 @@ export class CollaborationGateway {
         this.authenticationExtension,
         this.persistenceExtension,
         this.loggerExtension,
+        // #402 collab lifecycle + connect-duration metrics (no-op when off).
+        new CollabMetricsExtension(),
       ],
     });
 
+    // #402 — read-on-scrape source for collab_docs_open. Wire ONCE, gated, so
+    // nothing runs when metrics are disabled. The gauge's collect() pulls the
+    // live count from the hocuspocus instance on each scrape (no inc/dec drift).
+    if (isMetricsEnabled()) {
+      registerDocsOpenSource(() => this.hocuspocus.getDocumentsCount());
+    }
+
     if (this.withRedis) {
       this.redisClient = new RedisClient({
         host: this.redisConfig.host,

apps/server/src/collaboration/extensions/authentication.extension.ts

@@ -16,6 +16,7 @@ import { isUserDisabled } from '../../common/helpers';
 import { getPageId } from '../collaboration.util';
 import { JwtCollabPayload, JwtType } from '../../core/auth/dto/jwt-payload';
 import { resolveProvenance } from '../../common/decorators/auth-provenance.decorator';
+import { observeCollabAuth } from '../../integrations/metrics/metrics.registry';
 
 @Injectable()
 export class AuthenticationExtension implements Extension {
@@ -30,6 +31,18 @@ export class AuthenticationExtension implements Extension {
   ) {}
 
   async onAuthenticate(data: onAuthenticatePayload) {
+    // #402 — time the whole auth (verify + user/page/permission lookups) into
+    // collab_auth_duration_seconds. finally so failed auths are timed too.
+    // No-op when METRICS_PORT is unset. Behavior unchanged.
+    const start = performance.now();
+    try {
+      return await this.doAuthenticate(data);
+    } finally {
+      observeCollabAuth((performance.now() - start) / 1000);
+    }
+  }
+
+  private async doAuthenticate(data: onAuthenticatePayload) {
     const { documentName, token } = data;
     const pageId = getPageId(documentName);
 

apps/server/src/collaboration/extensions/hocuspocus-unload-race.spec.ts

@@ -0,0 +1,140 @@
+/**
+ * gitmost #401 — regression test for the connect-vs-unload race in
+ * @hocuspocus/server 3.4.4 (patched via patches/@hocuspocus__server@3.4.4.patch).
+ *
+ * The race (unpatched): when the last client disconnects, storeDocumentHooks'
+ * `finally` schedules an async `unloadDocument`. That unload runs its
+ * `beforeUnloadDocument` hooks asynchronously and, meanwhile, records an
+ * in-flight promise in `this.unloadingDocuments`. In the original 3.4.4
+ * `createDocument`, a NEW connection arriving in that window falls straight
+ * through to the `loadingDocuments`/`documents` checks — it never consults
+ * `unloadingDocuments`. So the new connection can start loading (or reuse) a
+ * document while the old instance is still being torn down; the re-check inside
+ * unload (`shouldUnloadDocument`, which sees 0 connections because async auth
+ * hooks have not registered the new connection yet) then deletes/destroys the
+ * doc out from under the freshly-connected client → orphaned Document → later
+ * redis-sync takes the "doc not loaded" path → sync never completes → the
+ * provider hangs until its ~25s timeout.
+ *
+ * The patch: `createDocument` first awaits any in-flight
+ * `unloadingDocuments.get(name)` before proceeding. Once that settles, the
+ * decision is deterministic — either the doc was fully unloaded (gone from
+ * `documents`, so a clean fresh load) or the unload aborted (healthy doc still
+ * in `documents`, reused). The new connection can never hand-shake onto an
+ * about-to-be-destroyed Document.
+ *
+ * These tests exercise the REAL patched `Hocuspocus.createDocument` (the class
+ * is directly constructible) by seeding `unloadingDocuments` with a controllable
+ * in-flight unload and observing that createDocument waits for it.
+ */
+import { Hocuspocus } from '@hocuspocus/server';
+
+// A promise we can resolve on demand, to model an unload that is mid-flight.
+function deferred<T = void>() {
+  let resolve!: (v: T) => void;
+  const promise = new Promise<T>((r) => {
+    resolve = r;
+  });
+  return { promise, resolve };
+}
+
+describe('gitmost #401 — hocuspocus createDocument awaits in-flight unload', () => {
+  it('does NOT start loading a new doc until the in-flight unload settles, then loads fresh', async () => {
+    const hp = new Hocuspocus();
+    const name = 'page.race';
+
+    // Observe loadDocument: on the unpatched code it is invoked synchronously
+    // within createDocument (before the unload settles); on the patched code it
+    // must be deferred until unloadingDocuments resolves.
+    const freshDoc = { name, __fresh: true } as any;
+    const loadSpy = jest
+      .spyOn(hp as any, 'loadDocument')
+      .mockResolvedValue(freshDoc);
+
+    // Model an unload in progress: an entry sits in unloadingDocuments and, when
+    // it completes, it removes the doc from `documents` (a real full unload).
+    const unload = deferred();
+    (hp as any).documents.set(name, { name, __dying: true });
+    (hp as any).unloadingDocuments.set(
+      name,
+      unload.promise.then(() => {
+        (hp as any).documents.delete(name);
+      }),
+    );
+
+    // Kick off a new connection's createDocument but do not await it yet.
+    const createPromise = (hp as any).createDocument(
+      name,
+      {},
+      'socket-1',
+      { isAuthenticated: true, readOnly: false },
+      {},
+    );
+
+    // Let all currently-schedulable microtasks run. The patched createDocument is
+    // now parked on `await unloadingDocuments.get(name)`, so loadDocument must
+    // NOT have been called yet, and it must NOT have returned the dying doc.
+    await Promise.resolve();
+    await Promise.resolve();
+    expect(loadSpy).not.toHaveBeenCalled();
+
+    // The unload completes (doc removed from `documents`).
+    unload.resolve();
+
+    // createDocument now proceeds: sees no existing doc → fresh load.
+    const doc = await createPromise;
+    expect(loadSpy).toHaveBeenCalledTimes(1);
+    expect(doc).toBe(freshDoc);
+    // The freshly-loaded doc is the one registered — never the dying instance.
+    expect((hp as any).documents.get(name)).toBe(freshDoc);
+  });
+
+  it('reuses the live doc when the in-flight unload aborts (doc left in documents)', async () => {
+    const hp = new Hocuspocus();
+    const name = 'page.abort';
+
+    const loadSpy = jest.spyOn(hp as any, 'loadDocument');
+
+    // Model an unload that ABORTS (e.g. a new connection reappeared before the
+    // sync re-check): it settles WITHOUT deleting the doc from `documents`.
+    const unload = deferred();
+    const liveDoc = { name, __live: true } as any;
+    (hp as any).documents.set(name, liveDoc);
+    (hp as any).unloadingDocuments.set(name, unload.promise); // no-op unload
+
+    const createPromise = (hp as any).createDocument(
+      name,
+      {},
+      'socket-2',
+      { isAuthenticated: true, readOnly: false },
+      {},
+    );
+
+    unload.resolve();
+    const doc = await createPromise;
+
+    // The still-present live doc is reused; no fresh load happened.
+    expect(doc).toBe(liveDoc);
+    expect(loadSpy).not.toHaveBeenCalled();
+  });
+
+  it('no in-flight unload → behaves normally (fresh load)', async () => {
+    const hp = new Hocuspocus();
+    const name = 'page.normal';
+    const freshDoc = { name } as any;
+    const loadSpy = jest
+      .spyOn(hp as any, 'loadDocument')
+      .mockResolvedValue(freshDoc);
+
+    const doc = await (hp as any).createDocument(
+      name,
+      {},
+      'socket-3',
+      { isAuthenticated: true, readOnly: false },
+      {},
+    );
+
+    expect(loadSpy).toHaveBeenCalledTimes(1);
+    expect(doc).toBe(freshDoc);
+  });
+});

apps/server/src/collaboration/extensions/persistence-load.spec.ts

@@ -0,0 +1,130 @@
+/**
+ * gitmost #401 fix 2 — onLoadDocument applies the DB state directly into the
+ * hook's target document and returns undefined (instead of building a NEW Y.Doc
+ * and returning it, which made hocuspocus re-encode+apply the whole state a
+ * SECOND time on every cold load).
+ *
+ * These tests assert:
+ *  - the hook mutates `data.document` in place so its content equals the DB doc,
+ *  - onLoadDocument returns undefined (so hocuspocus keeps the mutated doc and
+ *    does NOT run its own applyUpdate(encodeStateAsUpdate(...)) merge),
+ *  - both the raw-ydoc branch and the json→ydoc conversion branch behave so.
+ *
+ * Returning undefined is the observable signal that the double-encode is gone
+ * (the old code returned a new Y.Doc, which made hocuspocus re-encode+apply the
+ * state a second time); we assert that contract rather than counting internal
+ * encode calls, which is brittle given the encodes inside toYdoc and the test's
+ * own `expected` fixtures.
+ */
+import * as Y from 'yjs';
+import { Document } from '@hocuspocus/server';
+import { TiptapTransformer } from '@hocuspocus/transformer';
+import { PersistenceExtension } from './persistence.extension';
+import { tiptapExtensions } from '../collaboration.util';
+
+// A fresh hocuspocus Document (extends Y.Doc, adds isEmpty()) as hocuspocus
+// hands to onLoadDocument on a cold load.
+const freshDoc = () => new Document(`page.${PAGE_ID}`, {});
+
+const PAGE_ID = '550e8400-e29b-41d4-a716-446655440000';
+
+const doc = (text: string) => ({
+  type: 'doc',
+  content: [{ type: 'paragraph', content: [{ type: 'text', text }] }],
+});
+
+const jsonOf = (ydoc: Y.Doc) =>
+  TiptapTransformer.fromYdoc(ydoc, 'default');
+
+describe('PersistenceExtension.onLoadDocument — #401 fix 2 (apply-into-hook-doc)', () => {
+  let ext: PersistenceExtension;
+  let pageRepo: { findById: jest.Mock };
+
+  beforeEach(() => {
+    pageRepo = { findById: jest.fn() };
+    ext = new PersistenceExtension(
+      pageRepo as any,
+      {} as any,
+      {} as any,
+      {} as any,
+      {} as any,
+      {} as any,
+      {} as any,
+      {} as any,
+    );
+    jest.spyOn(ext['logger'], 'debug').mockImplementation(() => undefined);
+    jest.spyOn(ext['logger'], 'warn').mockImplementation(() => undefined);
+  });
+
+  const load = (document: Document) =>
+    ext.onLoadDocument({ documentName: `page.${PAGE_ID}`, document } as any);
+
+  it('raw ydoc branch: mutates the hook doc to the DB state and returns undefined', async () => {
+    // Source doc representing the persisted ydoc state.
+    const source = TiptapTransformer.toYdoc(
+      doc('DB CONTENT'),
+      'default',
+      tiptapExtensions,
+    );
+    const dbState = Buffer.from(Y.encodeStateAsUpdate(source));
+    pageRepo.findById.mockResolvedValue({ id: PAGE_ID, ydoc: dbState });
+
+    // The hook target is a fresh empty doc (as hocuspocus supplies on cold load).
+    const target = freshDoc();
+    const result = await load(target);
+
+    // Return undefined so hocuspocus keeps `target` as-is (no second merge).
+    expect(result).toBeUndefined();
+    // The hook document now carries the DB content.
+    expect(jsonOf(target)).toEqual(jsonOf(source));
+  });
+
+  it('json→ydoc branch: converts page.content into the hook doc and returns undefined', async () => {
+    pageRepo.findById.mockResolvedValue({
+      id: PAGE_ID,
+      ydoc: null,
+      content: doc('JSON CONTENT'),
+    });
+
+    const target = freshDoc();
+    const result = await load(target);
+
+    // Returning undefined is what keeps hocuspocus from re-encoding+applying the
+    // state a second time (the old code returned the doc, forcing that extra
+    // encode). We assert the observable contract here — the return value and the
+    // resulting content — rather than counting internal encode calls, which is
+    // brittle: toYdoc and the `expected` build below both encode too.
+    expect(result).toBeUndefined();
+
+    // The converted content landed in the hook document.
+    const expected = TiptapTransformer.toYdoc(
+      doc('JSON CONTENT'),
+      'default',
+      tiptapExtensions,
+    );
+    expect(jsonOf(target)).toEqual(jsonOf(expected));
+  });
+
+  it('live doc already non-empty: early return, no DB read', async () => {
+    // A hocuspocus Document carrying live content (isEmpty('default') === false).
+    const target = freshDoc();
+    const live = TiptapTransformer.toYdoc(
+      doc('LIVE'),
+      'default',
+      tiptapExtensions,
+    );
+    Y.applyUpdate(target, Y.encodeStateAsUpdate(live));
+
+    const result = await load(target);
+    expect(result).toBeUndefined();
+    expect(pageRepo.findById).not.toHaveBeenCalled();
+  });
+
+  it('no persisted state: leaves the fresh empty doc untouched, returns undefined', async () => {
+    pageRepo.findById.mockResolvedValue({ id: PAGE_ID, ydoc: null, content: null });
+    const target = freshDoc();
+    const result = await load(target);
+    expect(result).toBeUndefined();
+    expect(target.isEmpty('default')).toBe(true);
+  });
+});

apps/server/src/collaboration/extensions/persistence.extension.ts

@@ -41,7 +41,10 @@ import {
   HISTORY_INTERVAL,
 } from '../constants';
 import { TransclusionService } from '../../core/page/transclusion/transclusion.service';
-import { observeCollabStore } from '../../integrations/metrics/metrics.registry';
+import {
+  observeCollabLoad,
+  observeCollabStore,
+} from '../../integrations/metrics/metrics.registry';
 
 /**
  * #251 — wire format of the client→server stateless message that signals a
@@ -150,10 +153,14 @@ export class PersistenceExtension implements Extension {
     const { documentName, document } = data;
     const pageId = getPageId(documentName);
 
+    // #402 — the early return below (live doc already non-empty) does NOT touch
+    // the DB, so it is deliberately NOT timed. We only observe the real DB-load
+    // work, and only on each real-load return, tagged by the loaded doc size.
     if (!document.isEmpty('default')) {
       return;
     }
 
+    const startedAt = performance.now();
     const page = await this.pageRepo.findById(pageId, {
       includeContent: true,
       includeYdoc: true,
@@ -164,14 +171,21 @@ export class PersistenceExtension implements Extension {
       return;
     }
 
+    // #401 fix 2 — apply the DB state DIRECTLY into the hook's target document
+    // (`document` === `data.document`) and return undefined. When onLoadDocument
+    // returns undefined, hocuspocus keeps the mutated hook document as-is; only
+    // when the hook RETURNS a Y.Doc does hocuspocus re-`applyUpdate(document,
+    // encodeStateAsUpdate(returned))` — a second full encode+apply of the whole
+    // (e.g. 315KB) state on every cold load. Mutating in place performs a single
+    // apply and avoids the throwaway `new Y.Doc()` allocation.
     if (page.ydoc) {
       this.logger.debug(`ydoc loaded from db: ${pageId}`);
 
-      const doc = new Y.Doc();
       const dbState = new Uint8Array(page.ydoc);
 
-      Y.applyUpdate(doc, dbState);
-      return doc;
+      Y.applyUpdate(document, dbState);
+      observeCollabLoad(dbState.length, (performance.now() - startedAt) / 1000);
+      return;
     }
 
     // if no ydoc state in db convert json in page.content to Ydoc.
@@ -184,26 +198,47 @@ export class PersistenceExtension implements Extension {
         tiptapExtensions,
       );
 
-      Y.encodeStateAsUpdate(ydoc);
-      return ydoc;
+      // Encode the converted doc ONCE, reuse the bytes for both the size label
+      // and the single apply into the hook document (previously this encode's
+      // result was returned and hocuspocus re-encoded+applied it a second time).
+      const encoded = Y.encodeStateAsUpdate(ydoc);
+      Y.applyUpdate(document, encoded);
+      observeCollabLoad(
+        encoded.byteLength,
+        (performance.now() - startedAt) / 1000,
+      );
+      return;
     }
 
+    // No persisted state: the hook document is already a fresh empty Y.Doc, so
+    // leave it untouched and return undefined (no re-encode of an empty doc).
     this.logger.debug(`creating fresh ydoc: ${pageId}`);
-    return new Y.Doc();
+    observeCollabLoad(0, (performance.now() - startedAt) / 1000);
+    return;
   }
 
   async onStoreDocument(data: onStoreDocumentPayload) {
     // #355 — time the full store (persist + post-store side effects) into
-    // collab_store_duration_seconds. No-op when METRICS_PORT is unset.
+    // collab_store_duration_seconds. #402 — also tag by document size bucket.
+    // No-op when METRICS_PORT is unset.
     const startedAt = performance.now();
+    // Default 0 so a throw before storeDocument returns still records a
+    // (smallest-bucket) observation rather than dropping the timing entirely.
+    let bytes = 0;
     try {
-      await this.storeDocument(data);
+      bytes = await this.storeDocument(data);
     } finally {
-      observeCollabStore((performance.now() - startedAt) / 1000);
+      observeCollabStore(bytes, (performance.now() - startedAt) / 1000);
     }
   }
 
-  private async storeDocument(data: onStoreDocumentPayload) {
+  /**
+   * Persist the document. Returns the serialized ydoc byte size (used as the
+   * store histogram's size_bucket). The single Y.encodeStateAsUpdate below is
+   * the ONLY serialization — its byteLength is reused for the label (no second
+   * encode).
+   */
+  private async storeDocument(data: onStoreDocumentPayload): Promise<number> {
     const { documentName, document, context } = data;
 
     const pageId = getPageId(documentName);
@@ -455,6 +490,11 @@ export class PersistenceExtension implements Extension {
 
       await this.enqueuePageHistory(page, lastUpdatedSource);
     }
+
+    // #402 — report the serialized size for the store histogram's size_bucket.
+    // ydocState is always computed above (there is no earlier no-write return in
+    // this method), so this reflects the doc that was serialized this store.
+    return ydocState.byteLength;
   }
 
   /**

apps/server/src/core/ai-chat/ai-chat-stream-registry.service.ts

@@ -17,10 +17,24 @@ import { Injectable, Logger, OnModuleDestroy } from '@nestjs/common';
 /** How long a finished entry is retained for late attach (replay + immediate end). */
 export const RUN_STREAM_RETAIN_FINISHED_MS = 30_000;
 
-/** Per-run replay buffer cap. Past this the buffer is dropped (attach -> 204). */
-export const RUN_STREAM_MAX_BUFFER_BYTES = 4 * 1024 * 1024;
+/**
+ * Per-run replay buffer cap. Past this the buffer is dropped (attach -> 204, and
+ * the client falls back to its restore + degraded-poll path, #430).
+ *
+ * Raised from 4MB to 32MB (#430): marathon autonomous runs (11-25 min observed)
+ * stream far more than 4MB of SSE frames, so a live disconnect mid-run would find
+ * an already-overflowed buffer and could only degrade-poll instead of re-attaching
+ * to the live tail. 32MB comfortably covers those runs while staying bounded.
+ *
+ * Memory cost: this is the WORST-CASE retained size PER ACTIVE run (the buffer is
+ * freed on finish + retention, or dropped immediately on overflow). With the small
+ * number of concurrent autonomous runs a single workspace realistically has, 32MB
+ * each is an acceptable ceiling; the overflow->204->degraded-poll fallback remains
+ * the backstop for anything larger, so correctness never depends on this bound.
+ */
+export const RUN_STREAM_MAX_BUFFER_BYTES = 32 * 1024 * 1024;
 
-// 2x the replay cap: a just-written 4MB replay burst alone can never trip the
+// 2x the replay cap: a just-written full-replay burst alone can never trip the
 // per-subscriber cap (see controller); only a genuinely stalled socket can.
 export const SUBSCRIBER_MAX_BUFFERED_BYTES = 2 * RUN_STREAM_MAX_BUFFER_BYTES;
 

apps/server/src/core/ai-chat/ai-chat-stream-registry.spec.ts

@@ -2,6 +2,7 @@ import {
   AiChatStreamRegistryService,
   RUN_STREAM_MAX_BUFFER_BYTES,
   RUN_STREAM_RETAIN_FINISHED_MS,
+  SUBSCRIBER_MAX_BUFFERED_BYTES,
   RunStreamCallbacks,
 } from './ai-chat-stream-registry.service';
 
@@ -210,9 +211,10 @@ describe('AiChatStreamRegistryService', () => {
     const att = (await registry.attach(CHAT, false, undefined, c.cb))!;
     att.start();
 
-    const oneMb = 'x'.repeat(1024 * 1024);
-    // 5 x 1MB = 5MB > 4MB cap; the 5th frame is the one that crosses.
-    for (let i = 0; i < 5; i++) src.push(oneMb + i);
+    // Cap-relative so it survives a buffer-cap change (#430): a quarter-cap frame
+    // means 5 frames comfortably exceed the replay cap; the last one crosses.
+    const chunk = 'x'.repeat(Math.floor(RUN_STREAM_MAX_BUFFER_BYTES / 4));
+    for (let i = 0; i < 5; i++) src.push(chunk + i);
     await flush();
 
     const entry = (registry as any).entries.get(CHAT);
@@ -220,7 +222,7 @@ describe('AiChatStreamRegistryService', () => {
     expect(entry.bytes).toBeGreaterThan(RUN_STREAM_MAX_BUFFER_BYTES);
     // The live subscriber received ALL 5 frames, including the crossing one.
     expect(c.frames).toHaveLength(5);
-    expect(c.frames[4]).toBe(oneMb + 4);
+    expect(c.frames[4]).toBe(chunk + 4);
 
     // A NEW attach after overflow gets null (replay buffer is gone).
     const c2 = collector();
@@ -240,9 +242,11 @@ describe('AiChatStreamRegistryService', () => {
     const attB = (await registry.attach(CHAT, false, undefined, b.cb))!;
     attB.start();
 
-    const oneMb = 'x'.repeat(1024 * 1024);
-    // 9 x 1MB = 9MB > 8MB per-subscriber cap; A's pending overflows, B streams live.
-    for (let i = 0; i < 9; i++) src.push(oneMb + i);
+    // Cap-relative so it survives a buffer-cap change (#430): a quarter-of-the-
+    // per-subscriber-cap frame means 5 frames exceed A's paused-pending cap while
+    // B streams every frame live.
+    const chunk = 'x'.repeat(Math.floor(SUBSCRIBER_MAX_BUFFERED_BYTES / 4));
+    for (let i = 0; i < 5; i++) src.push(chunk + i);
     await flush();
 
     const entry = (registry as any).entries.get(CHAT);
@@ -250,7 +254,7 @@ describe('AiChatStreamRegistryService', () => {
     expect(entry.subscribers.size).toBe(1);
     expect(a.frames).toEqual([]); // paused + overflowed: nothing was delivered
     // B received every frame live (delivery unaffected by A's overflow).
-    expect(b.frames).toHaveLength(9);
+    expect(b.frames).toHaveLength(5);
 
     // A's start() (arriving late) degrades to an immediate end, not a partial replay.
     attA.start();

apps/server/src/core/ai-chat/ai-chat.service.setup-abort.spec.ts

@@ -0,0 +1,295 @@
+import { Logger } from '@nestjs/common';
+
+// Mock the AI SDK: the turn we drive is STOPPED during the pre-streamText setup
+// phase, so no provider call must ever be made. convertToModelMessages is reached
+// (before toolsFor) so it is stubbed to an empty transcript.
+jest.mock('ai', () => ({
+  streamText: jest.fn(),
+  generateText: jest.fn(),
+  convertToModelMessages: jest.fn(async () => []),
+  stepCountIs: jest.fn(() => () => false),
+}));
+
+import { streamText } from 'ai';
+import { AiChatService } from './ai-chat.service';
+
+/**
+ * D2 — an explicit Stop DURING the external-MCP toolset build (the pre-streamText
+ * setup phase) must:
+ *   (a) unwedge the turn (stream() rejects instead of hanging at step 0), and
+ *   (b) finalize the run as 'aborted' via the outer catch's onSettled — never leak
+ *       the run row as 'running' (which would 409 every later turn in this chat).
+ *
+ * The setup phase does NOT yet observe streamText's terminal callbacks, so before
+ * the fix a hung `toolsFor` ignored the run's abort signal and never finalized.
+ * `raceAgainstAbortAndTimeout(toolsFor, effectiveSignal, ...)` now rejects the
+ * moment the run's signal aborts; the catch re-throws (signal aborted), and the
+ * outer catch settles the run 'aborted'.
+ */
+describe('AiChatService.stream — abort during external-MCP setup finalizes the run (D2)', () => {
+  const streamTextMock = streamText as unknown as jest.Mock;
+
+  function makeService(mcpClients: { toolsFor: jest.Mock }) {
+    const aiChatRepo = {
+      findById: jest.fn(async () => ({ id: 'chat-1', workspaceId: 'ws-1' })),
+      insert: jest.fn(),
+    };
+    const aiChatMessageRepo = {
+      insert: jest.fn(async () => ({ id: 'msg-1' })),
+      findAllByChat: jest.fn(async () => []),
+      update: jest.fn(async () => ({ id: 'msg-1' })),
+    };
+    const aiSettings = { resolve: jest.fn(async () => ({})) };
+    const tools = { forUser: jest.fn(async () => ({})) };
+    const svc = new AiChatService(
+      {} as never, // ai
+      aiChatRepo as never,
+      aiChatMessageRepo as never,
+      {} as never, // aiChatPageSnapshotRepo
+      aiSettings as never,
+      tools as never,
+      mcpClients as never,
+      {} as never, // aiAgentRoleRepo
+      {} as never, // pageRepo (openPage undefined -> never touched)
+      {} as never, // pageAccess
+      { isAiChatDeferredToolsEnabled: () => false } as never, // environment
+    );
+    return { svc, tools };
+  }
+
+  const body = {
+    chatId: 'chat-1',
+    messages: [
+      { id: 'm1', role: 'user', parts: [{ type: 'text', text: 'hi' }] },
+    ],
+  };
+
+  // A minimal raw ServerResponse stand-in for the turns that PROCEED past setup
+  // and reach streamText (the deadline + legacy paths). The setup-only abort test
+  // never wires the stream, so it keeps using `{ raw: {} }`.
+  function makeRawRes() {
+    return {
+      raw: {
+        writeHead: jest.fn(function writeHead(this: unknown) {
+          return this;
+        }),
+        write: jest.fn(),
+        once: jest.fn(),
+        flushHeaders: jest.fn(),
+      },
+    };
+  }
+
+  // A fake streamText result: the service only calls consumeStream() and
+  // pipeUIMessageStreamToResponse() on it (both fire-and-forget). Its terminal
+  // callbacks are never invoked, so the run is not finalized through them.
+  function makeStreamResult() {
+    return {
+      consumeStream: jest.fn(),
+      pipeUIMessageStreamToResponse: jest.fn(),
+    };
+  }
+
+  beforeEach(() => {
+    streamTextMock.mockReset();
+    jest.spyOn(Logger.prototype, 'log').mockImplementation(() => undefined as never);
+    jest.spyOn(Logger.prototype, 'warn').mockImplementation(() => undefined as never);
+    jest.spyOn(Logger.prototype, 'error').mockImplementation(() => undefined as never);
+  });
+
+  afterEach(() => {
+    jest.restoreAllMocks();
+    jest.useRealTimers();
+  });
+
+  it('stops the hung toolset build, rejects, and settles the run "aborted" — never reaching streamText', async () => {
+    const runController = new AbortController();
+    // The build hangs (never resolves); the run is STOPPED mid-build. Aborting on a
+    // macrotask exercises the abort-listener path (a real user Stop during setup).
+    const toolsFor = jest.fn(() => {
+      setTimeout(() => runController.abort(new Error('user stop')), 0);
+      return new Promise(() => {}); // never settles — models a hung MCP build
+    });
+    const { svc } = makeService({ toolsFor });
+
+    const onSettled = jest.fn();
+    const begin = jest.fn(async () => ({
+      runId: 'run-1',
+      signal: runController.signal,
+    }));
+
+    const promise = svc.stream({
+      user: { id: 'user-1' } as never,
+      workspace: { id: 'ws-1' } as never,
+      sessionId: 'sess-1',
+      body: body as never,
+      res: { raw: {} } as never,
+      signal: new AbortController().signal, // socket signal (distinct from the run)
+      model: {} as never,
+      role: null,
+      runHooks: {
+        begin,
+        onAssistantSeeded: jest.fn(),
+        onStep: jest.fn(),
+        onSettled,
+      } as never,
+    });
+
+    // (a) The turn is UNWEDGED: it rejects (with the stop reason) instead of hanging.
+    await expect(promise).rejects.toThrow('user stop');
+
+    // (b) The run is finalized as 'aborted' with NO error message (a Stop, not a
+    // failure) — so the run row never leaks 'running'.
+    expect(onSettled).toHaveBeenCalledTimes(1);
+    expect(onSettled).toHaveBeenCalledWith('run-1', 'aborted', undefined);
+
+    // The build was reached, but the provider call was NEVER made (stopped at setup).
+    expect(toolsFor).toHaveBeenCalledTimes(1);
+    expect(streamTextMock).not.toHaveBeenCalled();
+  });
+
+  // Item 1 — the onLateResolve leg of raceAgainstAbortAndTimeout. When `toolsFor`
+  // loses the race (abort) but RESOLVES LATER with a leased toolset, the setup site
+  // must release that abandoned toolset's leases (call close() on its client
+  // handles) so their lease refcount is not pinned forever by a toolset nobody
+  // consumes. Nothing else exercises this path.
+  it('releases the leases of a toolset that resolves AFTER the race was already lost (onLateResolve)', async () => {
+    const runController = new AbortController();
+    // A controllable build: it hangs until we resolve it by hand, and the run is
+    // stopped mid-build so the race rejects BEFORE the build settles.
+    let resolveTools: (v: unknown) => void = () => undefined;
+    const toolsForPromise = new Promise((resolve) => {
+      resolveTools = resolve;
+    });
+    const toolsFor = jest.fn(() => {
+      setTimeout(() => runController.abort(new Error('user stop')), 0);
+      return toolsForPromise;
+    });
+    const { svc } = makeService({ toolsFor });
+
+    const begin = jest.fn(async () => ({
+      runId: 'run-1',
+      signal: runController.signal,
+    }));
+
+    const promise = svc.stream({
+      user: { id: 'user-1' } as never,
+      workspace: { id: 'ws-1' } as never,
+      sessionId: 'sess-1',
+      body: body as never,
+      res: { raw: {} } as never,
+      signal: new AbortController().signal,
+      model: {} as never,
+      role: null,
+      runHooks: {
+        begin,
+        onAssistantSeeded: jest.fn(),
+        onStep: jest.fn(),
+        onSettled: jest.fn(),
+      } as never,
+    });
+
+    // The race is lost to the abort: the turn rejects with the stop reason.
+    await expect(promise).rejects.toThrow('user stop');
+
+    // NOW the abandoned build resolves late with a leased client. onLateResolve must
+    // release it (call close on the lease handle).
+    const close = jest.fn().mockResolvedValue(undefined);
+    resolveTools({
+      tools: {},
+      clients: [{ close }],
+      outcomes: [],
+      instructions: [],
+    });
+    // Flush the microtasks so work.then -> onLateResolve -> Promise.all(close) runs.
+    await new Promise((r) => setImmediate(r));
+
+    expect(close).toHaveBeenCalledTimes(1);
+  });
+
+  // Item 2 — the PURE DEADLINE branch (MCP_TOOLSET_BUILD_DEADLINE_MS). `toolsFor`
+  // never settles and the run's signal is NOT aborted: the race rejects with a
+  // "setup timed out" error, the catch does NOT re-throw (runId set but signal not
+  // aborted), and the turn PROCEEDS Docmost-only. It must reach streamText (the turn
+  // continues, not wedged) and must NOT be finalized 'aborted'.
+  it('proceeds Docmost-only (reaches streamText) when the build hits the deadline without an abort', async () => {
+    jest.useFakeTimers();
+
+    // The build hangs forever; the run's signal is never aborted.
+    const toolsFor = jest.fn(() => new Promise(() => {}));
+    const { svc } = makeService({ toolsFor });
+
+    streamTextMock.mockReturnValue(makeStreamResult() as never);
+
+    const onSettled = jest.fn();
+    const runSignal = new AbortController().signal; // never aborts
+    const begin = jest.fn(async () => ({ runId: 'run-1', signal: runSignal }));
+
+    const promise = svc.stream({
+      user: { id: 'user-1' } as never,
+      workspace: { id: 'ws-1' } as never,
+      sessionId: 'sess-1',
+      body: body as never,
+      res: makeRawRes() as never,
+      signal: new AbortController().signal,
+      model: {} as never,
+      role: null,
+      runHooks: {
+        begin,
+        onAssistantSeeded: jest.fn(),
+        onStep: jest.fn(),
+        onSettled,
+      } as never,
+    });
+
+    // Advance past the 60s build deadline; advanceTimersByTimeAsync flushes the
+    // promise microtasks between timer fires so the whole setup chain runs.
+    await jest.advanceTimersByTimeAsync(60_001);
+    // The turn does not throw out of setup — it continues to stream.
+    await expect(promise).resolves.toBeUndefined();
+
+    // The turn CONTINUED: streamText was reached (Docmost-only), not wedged.
+    expect(toolsFor).toHaveBeenCalledTimes(1);
+    expect(streamTextMock).toHaveBeenCalledTimes(1);
+    // The run was NOT finalized as aborted (the deadline is not a Stop) — the setup
+    // catch settle path never ran, so onSettled is left to streamText's callbacks.
+    expect(onSettled).not.toHaveBeenCalled();
+  });
+
+  // Item 3 — the LEGACY no-runId path. The catch's re-throw is gated on
+  // `runId && effectiveSignal.aborted`. With NO runId (no runHooks) an abort during
+  // setup must NOT re-throw (runId falsy) — the turn warns + proceeds Docmost-only
+  // and streams, and is never finalized 'aborted' via the re-throw. Locks the
+  // `runId &&` half of the guard.
+  it('does NOT re-throw on a setup abort when there is no runId (legacy path proceeds Docmost-only)', async () => {
+    const socketController = new AbortController();
+    // The build hangs; the SOCKET signal (legacy effectiveSignal) aborts mid-build.
+    const toolsFor = jest.fn(() => {
+      setTimeout(() => socketController.abort(new Error('socket closed')), 0);
+      return new Promise(() => {});
+    });
+    const { svc } = makeService({ toolsFor });
+
+    streamTextMock.mockReturnValue(makeStreamResult() as never);
+
+    // No runHooks => runId undefined, effectiveSignal === the socket signal.
+    const promise = svc.stream({
+      user: { id: 'user-1' } as never,
+      workspace: { id: 'ws-1' } as never,
+      sessionId: 'sess-1',
+      body: body as never,
+      res: makeRawRes() as never,
+      signal: socketController.signal,
+      model: {} as never,
+      role: null,
+    });
+
+    // The turn does NOT reject out of setup (no re-throw on the legacy path).
+    await expect(promise).resolves.toBeUndefined();
+
+    // It proceeded Docmost-only and reached streamText — streamText then observes
+    // the already-aborted socket signal via its own abortSignal.
+    expect(toolsFor).toHaveBeenCalledTimes(1);
+    expect(streamTextMock).toHaveBeenCalledTimes(1);
+  });
+});

apps/server/src/core/ai-chat/ai-chat.service.spec.ts

@@ -16,6 +16,7 @@ import {
   rowToUiMessage,
   prepareAgentStep,
   flushAssistant,
+  stripNulChars,
   chatStreamMetadata,
   accumulateStepUsage,
   isInterruptResume,
@@ -28,11 +29,13 @@ import { buildSystemPrompt } from './ai-chat.prompt';
 import type { McpClientsService } from './external-mcp/mcp-clients.service';
 
 /**
- * Unit tests for compactToolOutput: the pure helper that shrinks LARGE tool
- * outputs before they are persisted (and re-sent to the provider on later
- * turns). The contract is: small outputs pass through unchanged (by identity);
- * large outputs keep their shape and small scalar fields (id/title/pageId — the
- * client reads these to render citations) while big payloads are truncated.
+ * Unit tests for compactToolOutput: the pure helper that shrinks tool outputs
+ * before they are persisted (and re-sent to the provider on later turns). The
+ * contract is: small and normal outputs — including whole page reads (tens of
+ * KB) — pass through unchanged (by identity); only an output above the high
+ * safety cap (> 200 KB) is compacted, and even then it keeps its shape and
+ * small scalar fields (id/title/pageId — the client reads these to render
+ * citations) while the big payloads are reduced.
  */
 describe('compactToolOutput', () => {
   it('returns a small object unchanged (by identity)', () => {
@@ -41,7 +44,7 @@ describe('compactToolOutput', () => {
   });
 
   it('truncates a large getPage-shaped markdown body but keeps the title', () => {
-    const big = 'x'.repeat(20000);
+    const big = 'x'.repeat(300000);
     const result = compactToolOutput({ title: 'T', markdown: big }) as {
       title: string;
       markdown: string;
@@ -49,15 +52,16 @@ describe('compactToolOutput', () => {
     // Shallow scalar field is preserved (citations depend on it).
     expect(result.title).toBe('T');
     // The big payload is shrunk far below the original size.
-    expect(result.markdown.length).toBeLessThan(20000);
-    expect(result.markdown).toContain('[truncated');
+    expect(result.markdown.length).toBeLessThan(300000);
+    expect(result.markdown).toContain('omitted from stored chat history');
   });
 
   it('caps a long array and appends a single truncation marker', () => {
-    // 200 small objects, each padded so the total serialized size > 4000 bytes.
+    // 200 objects, each padded so the total serialized size
+    // > 200000 bytes (the new safety cap).
     const long = Array.from({ length: 200 }, (_, i) => ({
       id: 'n' + i,
-      pad: 'y'.repeat(40),
+      pad: 'y'.repeat(1200),
     }));
     const result = compactToolOutput(long) as Array<Record<string, unknown>>;
     // 50 kept + 1 marker.
@@ -75,8 +79,8 @@ describe('compactToolOutput', () => {
 
   it('replaces a subtree beyond the depth cap with a marker', () => {
     // Build a deeply nested object (> TOOL_OUTPUT_MAX_DEPTH levels) with a big
-    // string at the bottom so the total serialized size exceeds the threshold.
-    let nested: Record<string, unknown> = { leaf: 'z'.repeat(8000) };
+    // string at the bottom so the total serialized size exceeds the 200 KB cap.
+    let nested: Record<string, unknown> = { leaf: 'z'.repeat(250000) };
     for (let i = 0; i < 20; i++) {
       nested = { child: nested };
     }
@@ -85,7 +89,7 @@ describe('compactToolOutput', () => {
   });
 
   it('produces a much smaller JSON than the original for a large input', () => {
-    const big = 'x'.repeat(20000);
+    const big = 'x'.repeat(300000);
     const original = { title: 'T', markdown: big };
     const result = compactToolOutput(original);
     const originalBytes = Buffer.byteLength(JSON.stringify(original), 'utf8');
@@ -144,6 +148,53 @@ describe('assistantParts', () => {
     expect(toolPart).not.toHaveProperty('output');
   });
 
+  it('replays the REAL error text for a THROWN tool (tool-error part)', () => {
+    const steps = [
+      {
+        text: '',
+        toolCalls: [
+          { toolCallId: 'c7', toolName: 'editPageText', input: { id: 'p1' } },
+        ],
+        // A thrown tool is a `tool-error` content part; toolResults holds only
+        // successes and stays empty for this call.
+        toolResults: [],
+        content: [
+          {
+            type: 'tool-error',
+            toolCallId: 'c7',
+            toolName: 'editPageText',
+            input: { id: 'p1' },
+            error: new Error('page is locked'),
+          },
+        ],
+      },
+    ];
+    const parts = assistantParts(steps, '') as AnyPart[];
+    const toolPart = parts.find((p) => p.type === 'tool-editPageText');
+    expect(toolPart).toBeDefined();
+    expect(toolPart!.state).toBe('output-error');
+    // The REAL error is replayed, NOT the 'Tool call did not complete.' placeholder.
+    expect(toolPart!.errorText).toBe('page is locked');
+    expect(toolPart).not.toHaveProperty('output');
+  });
+
+  it('keeps the placeholder ONLY for a call with neither result nor tool-error', () => {
+    const steps = [
+      {
+        text: '',
+        toolCalls: [
+          { toolCallId: 'c8', toolName: 'insertNode', input: { node: {} } },
+        ],
+        toolResults: [],
+        content: [], // aborted mid-step: no result AND no tool-error
+      },
+    ];
+    const parts = assistantParts(steps, '') as AnyPart[];
+    const toolPart = parts.find((p) => p.type === 'tool-insertNode');
+    expect(toolPart!.state).toBe('output-error');
+    expect(toolPart!.errorText).toBe('Tool call did not complete.');
+  });
+
   it('skips malformed tool-calls (missing toolName or toolCallId)', () => {
     const steps = [
       {
@@ -191,6 +242,45 @@ describe('serializeSteps', () => {
     expect(trace[0]).toEqual({ toolName: 'getPage', input: { id: 'p1' } });
     expect(trace[1]).toEqual({ toolName: 'getPage', output: { title: 'T' } });
   });
+
+  it('records a THROWN tool failure (tool-error part) with its error message', () => {
+    const trace = serializeSteps([
+      {
+        toolCalls: [{ toolName: 'editPageText', input: { id: 'p1' } }],
+        toolResults: [],
+        content: [
+          {
+            type: 'tool-error',
+            toolName: 'editPageText',
+            error: new Error('page is locked'),
+          },
+        ],
+      },
+    ]) as Array<Record<string, unknown>>;
+    // The call element is followed by a paired error element (mirroring how a
+    // successful result is appended), so the failure survives in the trace.
+    expect(trace).toHaveLength(2);
+    expect(trace[0]).toEqual({ toolName: 'editPageText', input: { id: 'p1' } });
+    expect(trace[1]).toEqual({
+      toolName: 'editPageText',
+      error: 'page is locked',
+    });
+  });
+
+  it('truncates a very long tool-error message to the tool-output limit', () => {
+    const long = 'x'.repeat(5000);
+    const trace = serializeSteps([
+      {
+        toolCalls: [{ toolName: 'editPageText', input: {} }],
+        toolResults: [],
+        content: [{ type: 'tool-error', toolName: 'editPageText', error: long }],
+      },
+    ]) as Array<Record<string, unknown>>;
+    const errorText = trace[1].error as string;
+    // Truncated (not the full 5000 chars) and carries the omission marker.
+    expect(errorText.length).toBeLessThan(long.length);
+    expect(errorText).toContain('chars omitted');
+  });
 });
 
 describe('rowToUiMessage', () => {
@@ -448,6 +538,45 @@ describe('flushAssistant', () => {
   });
 });
 
+/**
+ * stripNulChars: a NUL (U+0000) is rejected by Postgres in BOTH the `content`
+ * (text) and `toolCalls`/`metadata` (jsonb) columns, so it must be stripped from
+ * every persisted string. String.fromCharCode(0) avoids embedding a raw NUL byte
+ * in this source file.
+ */
+describe('stripNulChars', () => {
+  const NUL = String.fromCharCode(0);
+
+  it('deep-strips NUL from strings in nested objects/arrays', () => {
+    const out = stripNulChars({
+      content: `a${NUL}b`,
+      parts: [{ type: 'text', text: `x${NUL}${NUL}y` }],
+      nested: [`p${NUL}q`, 42, null],
+    });
+    expect(out.content).toBe('ab');
+    expect((out.parts[0] as { text: string }).text).toBe('xy');
+    expect(out.nested[0]).toBe('pq');
+    expect(out.nested[1]).toBe(42);
+    expect(out.nested[2]).toBeNull();
+    expect(JSON.stringify(out).includes(NUL)).toBe(false);
+  });
+
+  it('returns the SAME reference when there is no NUL (no needless clone)', () => {
+    const input = { a: 'clean', b: [1, 2, { c: 'ok' }] };
+    expect(stripNulChars(input)).toBe(input);
+  });
+
+  it('flushAssistant produces a NUL-free row even when the turn text carries one', () => {
+    const f = flushAssistant([], `partial${NUL}answer`, 'error', {
+      error: `bo${NUL}om`,
+    });
+    expect(f.content).toBe('partialanswer');
+    const serialized =
+      f.content + JSON.stringify(f.toolCalls) + JSON.stringify(f.metadata);
+    expect(serialized.includes(NUL)).toBe(false);
+  });
+});
+
 /**
  * chatStreamMetadata: attach metadata to the streamed assistant UI message per
  * part type — `chatId` on `start` (so the client adopts the real created chat id

apps/server/src/core/ai-chat/ai-chat.service.ts

@@ -58,6 +58,19 @@ import {
 // multi-search research questions are not cut off mid-investigation.
 const MAX_AGENT_STEPS = 20;
 
+// Wall-clock ceiling for building the external MCP toolset during the per-turn
+// setup phase (before streamText owns the lifecycle). Defense-in-depth ABOVE the
+// per-server connect bound in mcp-clients.service (CONNECT_TIMEOUT_MS): even if
+// that per-server timeout regressed, this outer deadline — together with the run's
+// abort signal — guarantees the setup phase can never wedge a turn at step 0 (the
+// production hang) and the run always finalizes. It stays a TRUE backstop because
+// buildEntry connects to the servers CONCURRENTLY, so the total build time is
+// bounded by the SLOWEST single server (~2×CONNECT_TIMEOUT_MS), not the SUM across
+// them — the per-server bound fires first no matter how many servers are enabled,
+// and this outer deadline only catches a total build stall the per-server bound
+// somehow missed.
+const MCP_TOOLSET_BUILD_DEADLINE_MS = 60_000;
+
 // System-prompt addendum injected ONLY on the final step (see prepareAgentStep).
 // It forbids further tool calls and tells the model to synthesize the best
 // answer it can from what it already gathered, so a tool-heavy turn never ends
@@ -176,6 +189,78 @@ export function sameInstant(
   return ta === tb;
 }
 
+/**
+ * Race `work` against an abort signal AND a wall-clock deadline, so a hung
+ * external-MCP toolset build during the pre-streamText setup phase can NEITHER
+ * wedge the turn NOR make it un-stoppable, and the run always finalizes. It
+ *  - resolves with `work`'s value when it settles first;
+ *  - REJECTS EARLY if `signal` aborts (with `signal.reason` when that is an Error,
+ *    else a generic `Error('aborted')`) — so an explicit Stop is honored mid-setup;
+ *  - REJECTS EARLY if `deadlineMs` elapses (defense-in-depth backstop);
+ *  - invokes `onLateResolve(value)` when `work` settles AFTER the race was already
+ *    lost, so the caller can release any resources that abandoned value owns
+ *    (e.g. close leased MCP clients that would otherwise leak their sockets).
+ *
+ * A rejection handler is attached to `work` so a late rejection is never an
+ * unhandledRejection; the timer is unref'd and cleared once the race settles.
+ */
+export function raceAgainstAbortAndTimeout<T>(
+  work: Promise<T>,
+  signal: AbortSignal,
+  deadlineMs: number,
+  onLateResolve?: (value: T) => void,
+): Promise<T> {
+  return new Promise<T>((resolve, reject) => {
+    let settled = false;
+    const cleanup = () => {
+      clearTimeout(timer);
+      signal.removeEventListener('abort', onAbort);
+    };
+    const onAbort = () => {
+      if (settled) return;
+      settled = true;
+      cleanup();
+      reject(
+        signal.reason instanceof Error ? signal.reason : new Error('aborted'),
+      );
+    };
+    const timer = setTimeout(() => {
+      if (settled) return;
+      settled = true;
+      cleanup();
+      reject(new Error(`setup timed out after ${deadlineMs}ms`));
+    }, deadlineMs);
+    // Do not keep the process alive just for this setup-deadline timer.
+    timer.unref?.();
+    if (signal.aborted) {
+      onAbort();
+    } else {
+      signal.addEventListener('abort', onAbort, { once: true });
+    }
+    work.then(
+      (value) => {
+        if (settled) {
+          // The race was already lost (abort/deadline): hand the abandoned value to
+          // the caller so it can release the resources that value owns.
+          onLateResolve?.(value);
+          return;
+        }
+        settled = true;
+        cleanup();
+        resolve(value);
+      },
+      (err: unknown) => {
+        // A late rejection after the race is already handled — swallow so it is
+        // never an unhandledRejection.
+        if (settled) return;
+        settled = true;
+        cleanup();
+        reject(err instanceof Error ? err : new Error(String(err)));
+      },
+    );
+  });
+}
+
 /**
  * Payload accepted from the client `useChat` POST body. We do NOT bind a strict
  * DTO (the global ValidationPipe whitelist would strip the useChat-specific
@@ -704,10 +789,43 @@ export class AiChatService implements OnModuleInit {
         instructions: [],
       };
       try {
-        external = await this.mcpClients.toolsFor(workspace.id);
+        // Bound the external-MCP toolset build by BOTH the run's abort signal and
+        // a generous wall-clock deadline. This is the pre-streamText setup phase,
+        // which streamText's terminal callbacks do NOT yet govern — so without this
+        // a hung build would hang the turn at step 0 forever (the production hang),
+        // unobservant of an explicit Stop. The deadline is defense-in-depth ABOVE
+        // the per-server connect bound in mcp-clients.service. On a LATE resolve
+        // (the race was already lost) RELEASE the abandoned toolset's leases —
+        // c.close() here is the lease handle, so it decrements the cache entry's
+        // refcount; it does NOT force-close the transports (the cache OWNS the
+        // clients and closes them on TTL/evict). This just prevents the lease
+        // refcount from being pinned >=1 forever by a toolset nobody will consume.
+        external = await raceAgainstAbortAndTimeout(
+          this.mcpClients.toolsFor(workspace.id),
+          effectiveSignal,
+          MCP_TOOLSET_BUILD_DEADLINE_MS,
+          (late) => {
+            void Promise.all(
+              late.clients.map((c) => c.close().catch(() => undefined)),
+            );
+          },
+        );
       } catch (err) {
-        // Building the external toolset must never break the turn; proceed with
-        // Docmost-only tools. Never log URLs/headers — short message only.
+        // An explicit Stop reached the RUN's signal DURING setup: re-throw so the
+        // outer catch finalizes the run as aborted — never swallow a Stop. Gated on
+        // `runId`: the re-throw exists ONLY to finalize the run, which exists only
+        // in autonomous mode. On the legacy path (no runId) `effectiveSignal` is the
+        // SOCKET signal (it aborts on a client disconnect); re-throwing there would
+        // change prior behavior and make the controller write JSON to an already-
+        // closed socket (it only attaches res.raw.on('error') in autonomous mode).
+        // So legacy keeps its prior behavior — warn + proceed, and streamText then
+        // observes the aborted socket signal.
+        if (runId && effectiveSignal.aborted) {
+          throw err;
+        }
+        // Otherwise a down/slow server (build timeout or other fault) must never
+        // break the turn: proceed with Docmost-only tools. Never log URLs/headers —
+        // short message only.
         this.logger.warn(
           `External MCP toolset unavailable: ${
             err instanceof Error ? err.message : 'unknown error'
@@ -1307,12 +1425,19 @@ export class AiChatService implements OnModuleInit {
         if (this.environment?.isAiChatResumableStreamEnabled?.()) {
           this.streamRegistry?.abortEntry(chatId, runId);
         }
+        // Distinguish an explicit Stop (the run's signal aborted during setup) from
+        // a real failure, so the run settles with the correct terminal status
+        // instead of always 'error'. onSettled/finalizeRun is idempotent, so this
+        // is safe even if a streamText callback also settles the run.
+        const settleStatus = effectiveSignal.aborted ? 'aborted' : 'error';
         await runHooks?.onSettled?.(
           runId,
-          'error',
-          err instanceof Error
-            ? err.message
-            : 'Agent run failed before streaming started',
+          settleStatus,
+          settleStatus === 'aborted'
+            ? undefined
+            : err instanceof Error
+              ? err.message
+              : 'Agent run failed before streaming started',
         );
       }
       throw err;
@@ -1512,21 +1637,41 @@ type StepLike = {
     toolName?: string;
     output?: unknown;
   }>;
+  // ai@6.0.134: a tool that THREW surfaces as a `tool-error` content part
+  // ({ type:'tool-error', toolCallId, toolName, input, error }), NOT as a
+  // `toolResults` entry (which holds only successes). Read from here so failed
+  // calls are persisted with their real error instead of being dropped.
+  content?: ReadonlyArray<{
+    type?: string;
+    toolCallId?: string;
+    toolName?: string;
+    input?: unknown;
+    error?: unknown;
+  }>;
 };
 
 /**
  * Compaction tunables for persisted tool OUTPUTS. Read tools (getPage,
  * getPageJson, getNode, diffPageVersions, exportPageMarkdown, ...) return whole
- * pages with no size cap. Their outputs are stored in `metadata.parts` and
- * RE-SENT to the provider on every later turn via convertToModelMessages, so an
- * uncompacted large body grows token cost, latency, and DB row size on every
- * turn. We shrink the big payloads while preserving the object's shape and its
- * small scalar fields (id/title/pageId) the client reads to render citations.
+ * pages. Their outputs are stored in `metadata.parts` and RE-SENT to the
+ * provider on every later turn via convertToModelMessages. We deliberately keep
+ * these outputs FULL up to a high safety cap (MAX_TOOL_OUTPUT_BYTES) so the
+ * model never sees a shortened copy of content it already fetched: an earlier
+ * 4000-byte cap shrank normal page reads (often tens of KB) to a tiny preview,
+ * and the model — seeing a truncation marker in its OWN history — re-read the
+ * same page, wasting tokens. Only a single output LARGER than the cap is
+ * compacted at all, purely as a backstop against a pathological payload; even
+ * then we preserve the object's shape and its small scalar fields
+ * (id/title/pageId) that the client reads to render citations.
  */
-// Only outputs whose JSON serialization exceeds this are compacted at all
-// (fast path: smaller outputs are returned unchanged, by identity).
-const MAX_TOOL_OUTPUT_BYTES = 4000;
-// A string longer than this is truncated to a leading preview.
+// HIGH safety backstop: only an output whose JSON serialization EXCEEDS this is
+// compacted at all. Normal reads (whole pages, tens of KB) stay well under it
+// and are stored + replayed VERBATIM (fast path: returned unchanged, by
+// identity). Only a single pathologically huge output (> 200 KB) is compacted.
+const MAX_TOOL_OUTPUT_BYTES = 200_000;
+// Inside the backstop path only (i.e. once the whole output already exceeded
+// MAX_TOOL_OUTPUT_BYTES), a string longer than this is reduced to a leading
+// preview; normal outputs never reach this branch.
 const TOOL_OUTPUT_STRING_LIMIT = 600;
 // Number of leading characters kept from a truncated string.
 const TOOL_OUTPUT_STRING_PREVIEW = 500;
@@ -1569,9 +1714,9 @@ export function compactToolOutput(output: unknown): unknown {
 function compactValue(value: unknown, depth: number): unknown {
   if (typeof value === 'string') {
     if (value.length > TOOL_OUTPUT_STRING_LIMIT) {
-      return `${value.slice(0, TOOL_OUTPUT_STRING_PREVIEW)}…[truncated ${
+      return `${value.slice(0, TOOL_OUTPUT_STRING_PREVIEW)}…[${
         value.length - TOOL_OUTPUT_STRING_PREVIEW
-      } chars]`;
+      } chars omitted from stored chat history to bound replay size — call the tool again to read the full output]`;
     }
     return value;
   }
@@ -1605,6 +1750,26 @@ function compactValue(value: unknown, depth: number): unknown {
   return value;
 }
 
+/**
+ * Extract a bounded string message from a `tool-error` part's `error` field for
+ * persistence and history replay. The field may be an `Error`, a string, or an
+ * arbitrary object, so pull a message robustly. The result is passed through
+ * `compactValue` so a very long error honors the SAME truncation limits the file
+ * already applies to tool outputs (no new limit is introduced here).
+ */
+function normalizeToolError(error: unknown): string {
+  const message =
+    error instanceof Error
+      ? error.message
+      : typeof error === 'string'
+        ? error
+        : error != null &&
+            typeof (error as { message?: unknown }).message === 'string'
+          ? (error as { message: string }).message
+          : String(error);
+  return compactValue(message, 0) as string;
+}
+
 /**
  * Rebuild the FULL UIMessage `parts` for an assistant turn from the SDK steps,
  * so multi-turn history replays prior tool-calls/results to the model (not just
@@ -1637,6 +1802,14 @@ export function assistantParts(
     for (const r of step.toolResults ?? []) {
       if (r.toolCallId) resultsById.set(r.toolCallId, r.output);
     }
+    // Index this step's THROWN tool failures (ai@6 `tool-error` content parts)
+    // by tool call id, so a call that failed replays with its real error text.
+    const errorsById = new Map<string, unknown>();
+    for (const part of step.content ?? []) {
+      if (part.type === 'tool-error' && part.toolCallId) {
+        errorsById.set(part.toolCallId, part.error);
+      }
+    }
     for (const call of step.toolCalls ?? []) {
       if (!call.toolName || !call.toolCallId) continue;
       const hasResult = resultsById.has(call.toolCallId);
@@ -1649,9 +1822,21 @@ export function assistantParts(
           input: call.input,
           output: compactToolOutput(resultsById.get(call.toolCallId)),
         });
+      } else if (errorsById.has(call.toolCallId)) {
+        // The tool THREW: replay the REAL error so the model on the next turn
+        // knows WHY the call failed (and does not blindly repeat it). An
+        // output-error round-trips through convertToModelMessages as a balanced
+        // tool-call + tool-result, keeping the rebuilt history valid.
+        parts.push({
+          type: `tool-${call.toolName}`,
+          toolCallId: call.toolCallId,
+          state: 'output-error',
+          input: call.input,
+          errorText: normalizeToolError(errorsById.get(call.toolCallId)),
+        });
       } else {
-        // No paired result (e.g. aborted mid-step). Persisting a bare
-        // tool-call (input-available) would replay as an unpaired call and
+        // No paired result AND no tool-error (e.g. aborted mid-step). Persisting
+        // a bare tool-call (input-available) would replay as an unpaired call and
         // throw MissingToolResultsError on the next turn (convertToModelMessages
         // emits no tool-result for it). Emit a SYNTHETIC paired result instead:
         // an output-error round-trips through convertToModelMessages as a
@@ -1758,6 +1943,45 @@ export async function applyFinalize(
   });
 }
 
+/**
+ * Deep-strip NUL characters (`\u0000`) from every string in a value, returning
+ * the SAME reference when nothing changed (so the no-NUL common case allocates
+ * nothing). Postgres rejects a NUL in BOTH `text` and `jsonb` columns ("invalid
+ * input syntax for type json" / "unsupported Unicode escape sequence"), so a
+ * stray NUL in model output or a tool result — e.g. a truncated multibyte read
+ * of a web page — otherwise fails EVERY persist of the assistant row, silently
+ * dropping that turn's content from the DB while the live stream still shows it.
+ * Applied at the flushAssistant choke point so content + toolCalls + metadata are
+ * all covered. Exported for the unit test.
+ */
+export function stripNulChars<T>(value: T): T {
+  if (typeof value === 'string') {
+    return (value.includes('\u0000')
+      ? value.replace(/\u0000/g, '')
+      : value) as T;
+  }
+  if (Array.isArray(value)) {
+    let changed = false;
+    const out = value.map((v) => {
+      const s = stripNulChars(v);
+      if (s !== v) changed = true;
+      return s;
+    });
+    return (changed ? out : value) as T;
+  }
+  if (value && typeof value === 'object') {
+    let changed = false;
+    const out: Record<string, unknown> = {};
+    for (const [k, v] of Object.entries(value as Record<string, unknown>)) {
+      const s = stripNulChars(v);
+      if (s !== v) changed = true;
+      out[k] = s;
+    }
+    return (changed ? out : value) as T;
+  }
+  return value;
+}
+
 /**
  * PURE assistant-row builder (#183 step-granular durability). Given the turn's
  * accumulated steps + the in-progress (not-yet-finished) text + the lifecycle
@@ -1827,12 +2051,16 @@ export function flushAssistant(
     };
   }
 
-  return {
+  // Strip NUL chars from the whole row before persisting: Postgres rejects a NUL
+  // in both the `content` (text) and `toolCalls`/`metadata` (jsonb) columns, and a
+  // single stray NUL in model/tool output would otherwise fail EVERY write of this
+  // row and silently drop the turn's content from the DB (see stripNulChars).
+  return stripNulChars({
     content: stepsText + trailing,
     toolCalls: serializeSteps(finished),
     metadata,
     status,
-  };
+  });
 }
 
 /**
@@ -1844,10 +2072,19 @@ export function serializeSteps(
   steps: ReadonlyArray<{
     toolCalls?: ReadonlyArray<{ toolName?: string; input?: unknown }>;
     toolResults?: ReadonlyArray<{ toolName?: string; output?: unknown }>;
+    content?: ReadonlyArray<{
+      type?: string;
+      toolName?: string;
+      error?: unknown;
+    }>;
   }>,
 ): unknown {
-  const calls: Array<{ toolName?: string; input?: unknown; output?: unknown }> =
-    [];
+  const calls: Array<{
+    toolName?: string;
+    input?: unknown;
+    output?: unknown;
+    error?: string;
+  }> = [];
   for (const step of steps ?? []) {
     for (const call of step.toolCalls ?? []) {
       calls.push({ toolName: call.toolName, input: call.input });
@@ -1855,6 +2092,18 @@ export function serializeSteps(
     for (const r of step.toolResults ?? []) {
       calls.push({ toolName: r.toolName, output: compactToolOutput(r.output) });
     }
+    // ai@6 surfaces a THROWN tool failure as a `tool-error` content part, NOT as
+    // a `toolResults` entry. Record it as its own paired element (mirroring how a
+    // successful result is appended) so the failure and its reason survive in the
+    // trace instead of leaving an orphaned call with no result.
+    for (const part of step.content ?? []) {
+      if (part.type === 'tool-error') {
+        calls.push({
+          toolName: part.toolName,
+          error: normalizeToolError(part.error),
+        });
+      }
+    }
   }
   return calls.length > 0 ? calls : null;
 }

apps/server/src/core/ai-chat/external-mcp/mcp-call-timeout.spec.ts

@@ -181,25 +181,25 @@ describe('mcp timeout env helpers', () => {
     else process.env.AI_MCP_CALL_TIMEOUT_MS = ORIG_CALL;
   });
 
-  it('mcpStreamTimeoutMs defaults to 5 min and honors a positive override', () => {
+  it('mcpStreamTimeoutMs defaults to 1 min and honors a positive override', () => {
     delete process.env.AI_MCP_STREAM_TIMEOUT_MS;
-    expect(mcpStreamTimeoutMs()).toBe(300_000);
-    process.env.AI_MCP_STREAM_TIMEOUT_MS = '60000';
     expect(mcpStreamTimeoutMs()).toBe(60_000);
+    process.env.AI_MCP_STREAM_TIMEOUT_MS = '90000';
+    expect(mcpStreamTimeoutMs()).toBe(90_000);
     for (const bad of ['0', '-1', 'x', '']) {
       process.env.AI_MCP_STREAM_TIMEOUT_MS = bad;
-      expect(mcpStreamTimeoutMs()).toBe(300_000);
+      expect(mcpStreamTimeoutMs()).toBe(60_000);
     }
   });
 
-  it('mcpCallTimeoutMs defaults to 15 min and honors a positive override', () => {
+  it('mcpCallTimeoutMs defaults to 2 min and honors a positive override', () => {
     delete process.env.AI_MCP_CALL_TIMEOUT_MS;
-    expect(mcpCallTimeoutMs()).toBe(900_000);
-    process.env.AI_MCP_CALL_TIMEOUT_MS = '120000';
     expect(mcpCallTimeoutMs()).toBe(120_000);
+    process.env.AI_MCP_CALL_TIMEOUT_MS = '180000';
+    expect(mcpCallTimeoutMs()).toBe(180_000);
     for (const bad of ['0', '-1', 'x', '']) {
       process.env.AI_MCP_CALL_TIMEOUT_MS = bad;
-      expect(mcpCallTimeoutMs()).toBe(900_000);
+      expect(mcpCallTimeoutMs()).toBe(120_000);
     }
   });
 });

apps/server/src/core/ai-chat/external-mcp/mcp-clients.connect-timeout.spec.ts

@@ -0,0 +1,237 @@
+import { McpClientsService } from './mcp-clients.service';
+
+/**
+ * D1 — a HUNG MCP handshake must not POISON the per-workspace build cache.
+ *
+ * THE BUG (production hang): `createMCPClient` (inside the private `connect`) is
+ * NOT bounded by a timeout and — like @ai-sdk/mcp's tool calls — its promise does
+ * NOT settle on abort. A transient network blip mid-handshake made connect hang
+ * FOREVER. Because getOrBuildEntry caches the build PROMISE, that never-settling
+ * connect wedged EVERY later turn for the workspace (each awaited the same pending
+ * build) — step_count stuck at 0, run row leaking 'running', chat 409ing forever.
+ *
+ * THE FIX: `connectWithTimeout` races `connect` against a SETTLING timeout
+ * (CONNECT_TIMEOUT_MS). On timeout it REJECTS, so buildEntry catches it, records
+ * the server `ok:false`, and the build COMPLETES with that server skipped — the
+ * cache is never poisoned and a subsequent `toolsFor` returns instead of hanging.
+ *
+ * REACHABILITY NOTE: the smallest network-free path that exercises the fix is to
+ * spy on the private `connect` (the same harness the namespacing spec uses) —
+ * `connectWithTimeout` wraps exactly that call, so a never-resolving `connect`
+ * models a never-settling `createMCPClient` precisely, without DNS/sockets.
+ *
+ * Fake timers prove the timeout fires WITHOUT real waiting.
+ */
+
+// Mirrors the private CONNECT_TIMEOUT_MS constant in mcp-clients.service.ts.
+const CONNECT_TIMEOUT_MS = 5000;
+
+interface FakeServer {
+  id: string;
+  name: string;
+  transport: string;
+  url: string;
+  headersEnc: string | null;
+  toolAllowlist: string[] | null;
+  instructions?: string | null;
+}
+
+function server(
+  over: Partial<FakeServer> & { id: string; name: string },
+): FakeServer {
+  return {
+    transport: 'http',
+    url: 'https://example.com/mcp',
+    headersEnc: null,
+    toolAllowlist: null,
+    ...over,
+  };
+}
+
+function buildService(servers: FakeServer[]) {
+  const repoStub = { listEnabled: jest.fn().mockResolvedValue(servers) };
+  const service = new McpClientsService(repoStub as never, {} as never);
+  // Silence the expected "server unavailable" warning.
+  jest
+    .spyOn(
+      (service as unknown as { logger: { warn: (...a: unknown[]) => void } })
+        .logger,
+      'warn',
+    )
+    .mockImplementation(() => undefined);
+  return service;
+}
+
+// Spy on the private `connect` with a per-server implementation.
+function stubConnect(
+  service: McpClientsService,
+  impl: (s: FakeServer) => Promise<unknown>,
+) {
+  return jest
+    .spyOn(
+      service as unknown as { connect: (s: FakeServer) => Promise<unknown> },
+      'connect',
+    )
+    .mockImplementation(impl);
+}
+
+describe('McpClientsService.connectWithTimeout — hung connect does not poison the cache (D1)', () => {
+  beforeEach(() => jest.useFakeTimers());
+  afterEach(() => {
+    jest.clearAllTimers();
+    jest.useRealTimers();
+    jest.restoreAllMocks();
+  });
+
+  it('buildEntry completes (server recorded ok:false) when connect never settles, and toolsFor does not hang', async () => {
+    const svc = buildService([server({ id: 'id-hung', name: 'hung' })]);
+    // connect NEVER settles — models a wedged createMCPClient handshake.
+    stubConnect(svc, () => new Promise<never>(() => {}));
+
+    const toolsetPromise = svc.toolsFor('ws-1');
+    // Drive fake time past the connect bound so connectWithTimeout rejects and
+    // buildEntry catches it (records ok:false) — flushing the microtasks.
+    await jest.advanceTimersByTimeAsync(CONNECT_TIMEOUT_MS + 1);
+
+    const toolset = await toolsetPromise;
+    // The build COMPLETED with the bad server skipped (no tools, ok:false).
+    expect(Object.keys(toolset.tools)).toHaveLength(0);
+    expect(toolset.outcomes).toEqual([
+      { name: 'hung', ok: false, reason: 'MCP connect timed out after 5000ms' },
+    ]);
+    await Promise.all(toolset.clients.map((c) => c.close()));
+
+    // The cache is NOT poisoned: a subsequent turn returns (served from the warm
+    // cached entry) instead of awaiting a never-settling build.
+    const again = await svc.toolsFor('ws-1');
+    expect(Object.keys(again.tools)).toHaveLength(0);
+    await Promise.all(again.clients.map((c) => c.close()));
+  });
+
+  it('a hung server is skipped but a healthy server in the SAME build still contributes its tools', async () => {
+    const svc = buildService([
+      server({ id: 'id-hung', name: 'hung' }),
+      server({ id: 'id-ok', name: 'ok' }),
+    ]);
+    const okClient = {
+      tools: () => Promise.resolve({ search: { description: 'x' } }),
+      close: jest.fn().mockResolvedValue(undefined),
+    };
+    stubConnect(svc, (s) =>
+      s.id === 'id-hung'
+        ? new Promise<never>(() => {})
+        : Promise.resolve(okClient),
+    );
+
+    const toolsetPromise = svc.toolsFor('ws-2');
+    await jest.advanceTimersByTimeAsync(CONNECT_TIMEOUT_MS + 1);
+
+    const toolset = await toolsetPromise;
+    // Healthy server's tool survives (namespaced); hung server recorded ok:false.
+    expect(Object.keys(toolset.tools)).toEqual(['ok_search']);
+    expect(toolset.outcomes).toEqual([
+      { name: 'hung', ok: false, reason: 'MCP connect timed out after 5000ms' },
+      { name: 'ok', ok: true },
+    ]);
+    await Promise.all(toolset.clients.map((c) => c.close()));
+  });
+
+  it('closes the ORPHANED client when connect resolves LATE (after the timeout)', async () => {
+    const svc = buildService([server({ id: 'id-late', name: 'late' })]);
+    const lateClient = {
+      tools: () => Promise.resolve({}),
+      close: jest.fn().mockResolvedValue(undefined),
+    };
+    // connect resolves only AFTER the connect bound has already elapsed, so
+    // connectWithTimeout has already rejected and must close this orphan.
+    stubConnect(
+      svc,
+      () =>
+        new Promise((resolve) => {
+          setTimeout(() => resolve(lateClient), CONNECT_TIMEOUT_MS * 2);
+        }),
+    );
+
+    const toolsetPromise = svc.toolsFor('ws-3');
+    // Fire the timeout: the build completes with the server skipped.
+    await jest.advanceTimersByTimeAsync(CONNECT_TIMEOUT_MS + 1);
+    const toolset = await toolsetPromise;
+    expect(toolset.outcomes[0]?.ok).toBe(false);
+    expect(lateClient.close).not.toHaveBeenCalled();
+
+    // Now let the late connect resolve — the orphan must be closed, not leaked.
+    await jest.advanceTimersByTimeAsync(CONNECT_TIMEOUT_MS * 2);
+    expect(lateClient.close).toHaveBeenCalledTimes(1);
+
+    await Promise.all(toolset.clients.map((c) => c.close()));
+  });
+});
+
+describe('McpClientsService.buildEntry — closes a connected client whose tools() fails (leak fix)', () => {
+  beforeEach(() => jest.useFakeTimers());
+  afterEach(() => {
+    jest.clearAllTimers();
+    jest.useRealTimers();
+    jest.restoreAllMocks();
+  });
+
+  it('connect succeeds but tools() REJECTS: the client is close()d exactly once and the server is skipped, while a healthy server still contributes', async () => {
+    const svc = buildService([
+      server({ id: 'id-bad', name: 'bad' }),
+      server({ id: 'id-ok', name: 'ok' }),
+    ]);
+    // The bad server connects fine, then tools() rejects — the client would leak if
+    // buildEntry did not close it in the per-server catch (it was never registered).
+    const badClient = {
+      tools: () => Promise.reject(new Error('tools listing failed')),
+      close: jest.fn().mockResolvedValue(undefined),
+    };
+    const okClient = {
+      tools: () => Promise.resolve({ search: { description: 'x' } }),
+      close: jest.fn().mockResolvedValue(undefined),
+    };
+    stubConnect(svc, (s) =>
+      s.id === 'id-bad' ? Promise.resolve(badClient) : Promise.resolve(okClient),
+    );
+
+    const toolset = await svc.toolsFor('ws-4');
+
+    // The orphaned (never-registered) client is closed exactly once — no leak.
+    expect(badClient.close).toHaveBeenCalledTimes(1);
+    // Healthy server survives; bad server recorded ok:false and skipped.
+    expect(Object.keys(toolset.tools)).toEqual(['ok_search']);
+    expect(toolset.outcomes).toEqual([
+      { name: 'bad', ok: false, reason: 'tools listing failed' },
+      { name: 'ok', ok: true },
+    ]);
+
+    // The healthy (registered) client is NOT closed by the loop — it is owned by the
+    // cache entry and stays warm (closed only on eviction/teardown, not on lease
+    // release). Releasing the lease keeps it warm since the entry is not evicted.
+    expect(okClient.close).not.toHaveBeenCalled();
+    await Promise.all(toolset.clients.map((c) => c.close()));
+    expect(okClient.close).not.toHaveBeenCalled();
+    // The failed client is never double-closed.
+    expect(badClient.close).toHaveBeenCalledTimes(1);
+  });
+
+  it('connect succeeds but tools() HANGS (times out): the client is close()d once and the server is skipped', async () => {
+    const svc = buildService([server({ id: 'id-slow', name: 'slow' })]);
+    const slowClient = {
+      // tools() never settles -> withTimeout rejects after CONNECT_TIMEOUT_MS.
+      tools: () => new Promise<Record<string, never>>(() => {}),
+      close: jest.fn().mockResolvedValue(undefined),
+    };
+    stubConnect(svc, () => Promise.resolve(slowClient));
+
+    const toolsetPromise = svc.toolsFor('ws-5');
+    // Drive fake time past the tools() bound so withTimeout rejects.
+    await jest.advanceTimersByTimeAsync(CONNECT_TIMEOUT_MS + 1);
+    const toolset = await toolsetPromise;
+
+    expect(slowClient.close).toHaveBeenCalledTimes(1);
+    expect(Object.keys(toolset.tools)).toHaveLength(0);
+    expect(toolset.outcomes[0]?.ok).toBe(false);
+    await Promise.all(toolset.clients.map((c) => c.close()));
+  });
+});

apps/server/src/core/ai-chat/external-mcp/mcp-clients.service.ts

@@ -195,7 +195,7 @@ export class McpClientsService {
   ): Promise<{ ok: true; tools: string[] } | { ok: false; error: string }> {
     let client: McpClient | undefined;
     try {
-      client = await this.connect(server);
+      client = await this.connectWithTimeout(server, CONNECT_TIMEOUT_MS);
       const raw = await withTimeout(client.tools(), CONNECT_TIMEOUT_MS);
       return { ok: true, tools: Object.keys(raw) };
     } catch (err) {
@@ -255,49 +255,96 @@ export class McpClientsService {
     const callTimeoutMs = mcpCallTimeoutMs();
     const instructions: McpServerInstruction[] = [];
 
-    for (const server of servers) {
+    // Per-server connect+tools result, still tagged with its server so the merge
+    // below can be applied in the SAME order as `servers` (see the parallel note).
+    type PerServerResult =
+      | { ok: true; client: McpClient; guarded: Record<string, Tool> }
+      | { ok: false; reason: string };
+
+    // Connect to (and list tools for) every enabled server CONCURRENTLY, so the
+    // total build time is bounded by the SLOWEST single server (~2×
+    // CONNECT_TIMEOUT_MS: connect + tools), NOT the SUM across servers. The
+    // sequential loop this replaced summed those bounds, so with enough all-timing-
+    // out servers the outer MCP_TOOLSET_BUILD_DEADLINE_MS could fire before the
+    // per-server bounds, dropping ALL external tools and inverting the "per-server
+    // bound is primary, outer is a backstop" invariant. Each server keeps its OWN
+    // try/catch + connectWithTimeout/withTimeout bound + close-on-failure logic; a
+    // failed server is skipped, never fatal. Nothing here mutates the shared
+    // arrays — every result is merged IN SERVER ORDER after Promise.all, so tool-
+    // key precedence/disambiguation, `outcomes`, `instructions` and `clients`
+    // ordering all match the previous sequential behavior exactly.
+    const perServer = async (
+      server: (typeof servers)[number],
+    ): Promise<PerServerResult> => {
+      // Track the connected client so the catch can close it when it was obtained
+      // but tools() then threw/timed out (connectWithTimeout closes its OWN orphan
+      // on a connect timeout, so `client` stays undefined on that path). On success
+      // the client is handed back and registered by the merge below (owned by the
+      // entry, closed at teardown) — so it is never double-closed.
+      let client: McpClient | undefined;
       try {
-        const client = await this.connect(server);
+        client = await this.connectWithTimeout(server, CONNECT_TIMEOUT_MS);
         const raw = await withTimeout(client.tools(), CONNECT_TIMEOUT_MS);
-        clients.push(client);
         const allow = server.toolAllowlist;
         const picked =
           Array.isArray(allow) && allow.length > 0 ? pick(raw, allow) : raw;
         // Bound each tool's execute with a per-call total-timeout guard before
         // merging, so a single chatty-but-stuck call is aborted after the cap.
         const guarded = wrapToolsWithCallTimeout(picked, callTimeoutMs);
-        // Namespace each tool with the sanitized server name AND disambiguate
-        // against names already merged from earlier servers, so no external
-        // tool is silently overwritten on collision. The returned count drives
-        // whether this server's prompt guidance is included (≥1 tool merged).
-        const merged = this.mergeNamespaced(
-          tools,
-          guarded,
-          server.name,
-          server.id,
-        );
-        outcomes.push({ name: server.name, ok: true });
-        // Include this server's guidance ONLY when it actually contributed at
-        // least one tool the agent can call (allowlist may have filtered all of
-        // them out) AND the admin authored non-blank instructions. The header
-        // prefix is the sanitized server name (= the tool namespace prefix).
-        const guide = server.instructions?.trim();
-        if (merged.count > 0 && guide) {
-          instructions.push({
-            serverName: server.name,
-            toolPrefix: merged.prefix,
-            instructions: guide,
-          });
-        }
+        return { ok: true, client, guarded };
       } catch (err) {
-        // A failed server is skipped — the turn proceeds with the rest. Log a
-        // short warning (never the URL/headers) so ops can see degradation, and
-        // record the outcome so the UI can show "tool X unavailable".
+        // A failed server is skipped — the turn proceeds with the rest. If connect
+        // returned a live client but a later step (tools()) threw, that client was
+        // never registered in `clients`, so close it here or its transport/socket
+        // leaks (compounding every 60s cache rebuild during a flaky-server outage).
+        if (client) {
+          void client.close().catch(() => undefined);
+        }
+        // Log a short warning (never the URL/headers) so ops can see degradation,
+        // and record the outcome so the UI can show "tool X unavailable".
         const reason = shortError(err);
         this.logger.warn(
           `External MCP server "${server.name}" unavailable: ${reason}`,
         );
-        outcomes.push({ name: server.name, ok: false, reason });
+        return { ok: false, reason };
+      }
+    };
+
+    // Promise.all preserves array order regardless of settle order, so `results[i]`
+    // is `servers[i]`'s outcome — the merge below stays deterministic and matches
+    // the old sequential order (later servers still override/disambiguate against
+    // earlier ones on a tool-key clash).
+    const results = await Promise.all(servers.map(perServer));
+    for (let i = 0; i < servers.length; i += 1) {
+      const server = servers[i];
+      const result = results[i];
+      if (result.ok !== true) {
+        outcomes.push({ name: server.name, ok: false, reason: result.reason });
+        continue;
+      }
+      clients.push(result.client);
+      // Namespace each tool with the sanitized server name AND disambiguate
+      // against names already merged from earlier servers, so no external
+      // tool is silently overwritten on collision. The returned count drives
+      // whether this server's prompt guidance is included (≥1 tool merged).
+      const merged = this.mergeNamespaced(
+        tools,
+        result.guarded,
+        server.name,
+        server.id,
+      );
+      outcomes.push({ name: server.name, ok: true });
+      // Include this server's guidance ONLY when it actually contributed at
+      // least one tool the agent can call (allowlist may have filtered all of
+      // them out) AND the admin authored non-blank instructions. The header
+      // prefix is the sanitized server name (= the tool namespace prefix).
+      const guide = server.instructions?.trim();
+      if (merged.count > 0 && guide) {
+        instructions.push({
+          serverName: server.name,
+          toolPrefix: merged.prefix,
+          instructions: guide,
+        });
       }
     }
 
@@ -383,6 +430,55 @@ export class McpClientsService {
     return client;
   }
 
+  /**
+   * Race {@link connect} against a SETTLING timeout so a hung MCP handshake can
+   * never POISON the per-workspace build cache. `createMCPClient` (inside connect)
+   * is NOT bounded internally, and — exactly like @ai-sdk/mcp's tool calls
+   * (see wrapToolWithCallTimeout) — its promise does NOT settle on abort. So a
+   * transient network blip mid-handshake can make connect hang FOREVER. Because
+   * getOrBuildEntry caches the build PROMISE, a never-settling connect would then
+   * wedge EVERY later turn for the workspace (each awaits the same pending build,
+   * step_count stuck at 0, run row leaks 'running', chat 409s forever). Bounding
+   * connect here guarantees buildEntry always gets a client OR a rejection within
+   * `ms` — so the build completes (bad server skipped) and the cache stays clean.
+   *
+   * If connect resolves LATE (after we already rejected on the timeout), we close
+   * the orphaned client so its transport/socket is not leaked.
+   */
+  private connectWithTimeout(
+    server: Pick<AiMcpServer, 'transport' | 'url' | 'headersEnc'>,
+    ms: number,
+  ): Promise<McpClient> {
+    return new Promise<McpClient>((resolve, reject) => {
+      let settled = false;
+      const timer = setTimeout(() => {
+        settled = true;
+        reject(new Error(`MCP connect timed out after ${ms}ms`));
+      }, ms);
+      // Do not keep the process alive just for this connect-timeout timer.
+      timer.unref?.();
+      this.connect(server).then(
+        (client) => {
+          if (settled) {
+            // The race was already lost to the timeout: close the orphaned client
+            // so its socket is not leaked, and drop the late result.
+            void client.close().catch(() => undefined);
+            return;
+          }
+          clearTimeout(timer);
+          settled = true;
+          resolve(client);
+        },
+        (err: unknown) => {
+          if (settled) return; // late rejection after the timeout — already handled
+          clearTimeout(timer);
+          settled = true;
+          reject(err instanceof Error ? err : new Error(String(err)));
+        },
+      );
+    });
+  }
+
   /**
    * Decrypt the stored auth headers. Returns undefined when none are set. The
    * plaintext headers live only in this returned object and are passed straight
@@ -460,12 +556,12 @@ export function validateResolvedAddresses(addrs: readonly LookupAddress[]): {
  */
 function buildPinnedDispatcher(): Agent {
   // External-MCP traffic uses a DEDICATED, shorter silence timeout
-  // (`AI_MCP_STREAM_TIMEOUT_MS`, default 5 min) — deliberately tighter than the
+  // (`AI_MCP_STREAM_TIMEOUT_MS`, default 1 min) — deliberately tighter than the
   // chat provider's 15-min `streamTimeoutMs()` — so a byte-silent/hung MCP
-  // upstream is broken in ~5 min instead of 15. We keep the keep-alive options
+  // upstream is broken in ~1 min instead of 15. We keep the keep-alive options
   // from `streamingDispatcherOptions()` but OVERRIDE headers/body timeouts.
   // Accepted trade-off: a legitimately long but byte-silent single tool call,
-  // and an SSE transport idling >5 min BETWEEN tool calls, are also cut here; the
+  // and an SSE transport idling >1 min BETWEEN tool calls, are also cut here; the
   // per-call total cap (wrapToolsWithCallTimeout, `AI_MCP_CALL_TIMEOUT_MS`) is the
   // complementary guard for chatty-but-stuck calls that keep the socket warm yet
   // never return.

apps/server/src/core/ai-chat/roles/dto/agent-role.dto.ts

@@ -52,7 +52,7 @@ export class CreateAgentRoleDto {
   description?: string;
 
   @IsString()
-  @MaxLength(20000)
+  @MaxLength(100000)
   instructions: string;
 
   // null/omitted => use the workspace default model.
@@ -102,7 +102,7 @@ export class UpdateAgentRoleDto {
 
   @IsOptional()
   @IsString()
-  @MaxLength(20000)
+  @MaxLength(100000)
   instructions?: string;
 
   @IsOptional()

apps/server/src/core/ai-chat/tools/ai-chat-tools.service.spec.ts

@@ -652,6 +652,125 @@ describe('AiChatToolsService #294 changed execute wirings', () => {
   });
 });
 
+/**
+ * #410 — the footnote + image tools were promoted from MCP-only into the shared
+ * registry and are now wired in-app. Assert they are REGISTERED in the in-app
+ * toolset and forward their args to the client with the correct arg->method
+ * mapping (the schema fields `imageUrl`/`attachmentId` map onto the client's
+ * positional `url`/`oldAttachmentId`). A field destructured under the wrong name
+ * would silently pass `undefined` (execute is `any`-cast, so tsc won't catch it).
+ */
+describe('AiChatToolsService #410 footnote + image tools', () => {
+  const calls: Record<string, unknown[][]> = {
+    insertFootnote: [],
+    insertImage: [],
+    replaceImage: [],
+  };
+  const fakeClient: Partial<DocmostClientLike> = {
+    insertFootnote: (...args: unknown[]) => {
+      calls.insertFootnote.push(args);
+      return Promise.resolve({ success: true, footnoteId: 'fn1', reused: false });
+    },
+    insertImage: (...args: unknown[]) => {
+      calls.insertImage.push(args);
+      return Promise.resolve({ success: true, attachmentId: 'att1' });
+    },
+    replaceImage: (...args: unknown[]) => {
+      calls.replaceImage.push(args);
+      return Promise.resolve({ success: true, replaced: 1 });
+    },
+  };
+  const tokenServiceStub = {
+    generateAccessToken: jest.fn().mockResolvedValue('access-token'),
+    generateCollabToken: jest.fn().mockResolvedValue('collab-token'),
+  };
+  let service: AiChatToolsService;
+
+  beforeEach(() => {
+    for (const k of Object.keys(calls)) calls[k].length = 0;
+    jest.spyOn(loader, 'loadDocmostMcp').mockResolvedValue(
+      mockLoaded(function () {
+        return fakeClient as DocmostClientLike;
+      } as unknown as loader.DocmostClientCtor),
+    );
+    service = new AiChatToolsService(
+      tokenServiceStub as never,
+      {} as never,
+      {} as never,
+      {} as never,
+      {} as never,
+      {
+        asSink: () => ({ put: jest.fn(), has: jest.fn(), evict: jest.fn() }),
+      } as never,
+    );
+  });
+  afterEach(() => jest.restoreAllMocks());
+
+  const buildTools = () =>
+    service.forUser(
+      { id: 'user-1', email: 'u@example.com', workspaceId: 'ws-1' } as never,
+      'session-1',
+      'ws-1',
+      'chat-1',
+    );
+
+  it('registers all three tools in the in-app toolset', async () => {
+    const tools = await buildTools();
+    expect(tools.insertFootnote).toBeDefined();
+    expect(tools.insertImage).toBeDefined();
+    expect(tools.replaceImage).toBeDefined();
+  });
+
+  it('insertFootnote forwards (pageId, anchorText, text) positionally', async () => {
+    const tools = await buildTools();
+    const r = await tools.insertFootnote.execute(
+      { pageId: 'p1', anchorText: 'the claim', text: 'See source.' } as never,
+      {} as never,
+    );
+    expect(calls.insertFootnote).toEqual([['p1', 'the claim', 'See source.']]);
+    expect(r).toMatchObject({ footnoteId: 'fn1' });
+  });
+
+  it('insertImage maps imageUrl->url and packs the option fields', async () => {
+    const tools = await buildTools();
+    await tools.insertImage.execute(
+      {
+        pageId: 'p1',
+        imageUrl: 'https://x/img.png',
+        align: 'center',
+        alt: 'A',
+        replaceText: '[img]',
+        afterText: undefined,
+      } as never,
+      {} as never,
+    );
+    expect(calls.insertImage).toEqual([
+      [
+        'p1',
+        'https://x/img.png',
+        { align: 'center', alt: 'A', replaceText: '[img]', afterText: undefined },
+      ],
+    ]);
+  });
+
+  it('replaceImage maps attachmentId->oldAttachmentId and imageUrl->url', async () => {
+    const tools = await buildTools();
+    await tools.replaceImage.execute(
+      {
+        pageId: 'p1',
+        attachmentId: 'att-old',
+        imageUrl: 'https://x/new.png',
+        align: 'right',
+        alt: 'B',
+      } as never,
+      {} as never,
+    );
+    expect(calls.replaceImage).toEqual([
+      ['p1', 'att-old', 'https://x/new.png', { align: 'right', alt: 'B' }],
+    ]);
+  });
+});
+
 /**
  * getCurrentPage selection contract (#388): the tool surfaces the selection that
  * was sanitized + nested onto the resolved open-page context (last forUser arg).

apps/server/src/core/ai-chat/tools/ai-chat-tools.service.ts

@@ -697,6 +697,67 @@ export class AiChatToolsService {
         },
       ),
 
+      // Schema + description live in @docmost/mcp's SHARED_TOOL_SPECS (#410).
+      // Promoted from MCP-only so the in-app agent can attach a REAL footnote to
+      // already-written text instead of leaving a literal `^[...]` string.
+      insertFootnote: sharedTool(
+        sharedToolSpecs.insertFootnote,
+        async ({ pageId, anchorText, text }) =>
+          await client.insertFootnote(pageId, anchorText, text),
+      ),
+
+      // Schema + description live in @docmost/mcp's SHARED_TOOL_SPECS (#410).
+      // The schema field is `imageUrl`; the client method takes it positionally.
+      insertImage: sharedTool(
+        sharedToolSpecs.insertImage,
+        async ({ pageId, imageUrl, align, alt, replaceText, afterText }) =>
+          await client.insertImage(pageId, imageUrl, {
+            align,
+            alt,
+            replaceText,
+            afterText,
+          }),
+      ),
+
+      // Schema + description live in @docmost/mcp's SHARED_TOOL_SPECS (#410).
+      replaceImage: sharedTool(
+        sharedToolSpecs.replaceImage,
+        async ({ pageId, attachmentId, imageUrl, align, alt }) =>
+          await client.replaceImage(pageId, attachmentId, imageUrl, {
+            align,
+            alt,
+          }),
+      ),
+
+      // Schema + description live in @docmost/mcp's SHARED_TOOL_SPECS (#423).
+      // meta.hash in the result is the baseHash drawioUpdate requires.
+      drawioGet: sharedTool(
+        sharedToolSpecs.drawioGet,
+        async ({ pageId, node, format }) =>
+          await client.drawioGet(pageId, node, format ?? 'xml'),
+      ),
+
+      // Schema + description live in @docmost/mcp's SHARED_TOOL_SPECS (#423).
+      // The flat schema fields are regrouped into the client's `where` object.
+      drawioCreate: sharedTool(
+        sharedToolSpecs.drawioCreate,
+        async ({ pageId, xml, position, anchorNodeId, anchorText, title }) =>
+          await client.drawioCreate(
+            pageId,
+            { position, anchorNodeId, anchorText },
+            xml,
+            title,
+          ),
+      ),
+
+      // Schema + description live in @docmost/mcp's SHARED_TOOL_SPECS (#423).
+      // baseHash is the optimistic lock: mismatch => structured conflict error.
+      drawioUpdate: sharedTool(
+        sharedToolSpecs.drawioUpdate,
+        async ({ pageId, node, xml, baseHash }) =>
+          await client.drawioUpdate(pageId, node, xml, baseHash),
+      ),
+
       // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
       // The table reference parameter was unified to `table` (was `tableRef`).
       tableInsertRow: sharedTool(

apps/server/src/core/ai-chat/tools/docmost-client.loader.ts

@@ -141,6 +141,59 @@ export interface DocmostClientLike {
     doc?: unknown,
     title?: string,
   ): Promise<Record<string, unknown>>;
+  // Attach an author-inline footnote after the first occurrence of anchorText;
+  // numbering + the footnotes list are derived server-side.
+  insertFootnote(
+    pageId: string,
+    anchorText: string,
+    text: string,
+  ): Promise<Record<string, unknown>>;
+  // Download a web image and insert it into the page (append, or replace/after a
+  // text anchor). `url` is the image http(s) URL.
+  insertImage(
+    pageId: string,
+    url: string,
+    opts?: {
+      align?: 'left' | 'center' | 'right';
+      alt?: string;
+      replaceText?: string;
+      afterText?: string;
+    },
+  ): Promise<Record<string, unknown>>;
+  // Swap an existing image (by its attachmentId) for a new one fetched from a web
+  // URL, repointing every reference in the live document.
+  replaceImage(
+    pageId: string,
+    oldAttachmentId: string,
+    url: string,
+    opts?: { align?: 'left' | 'center' | 'right'; alt?: string },
+  ): Promise<Record<string, unknown>>;
+  // --- draw.io diagrams (#423, stage 1) ---
+  // Read a diagram as decoded mxGraph XML (default) or the raw .drawio.svg.
+  // meta.hash is the optimistic-lock key drawioUpdate expects as baseHash.
+  drawioGet(
+    pageId: string,
+    node: string,
+    format?: 'xml' | 'svg',
+  ): Promise<Record<string, unknown>>;
+  // Lint mxGraph XML, build the .drawio.svg attachment and insert a drawio node.
+  drawioCreate(
+    pageId: string,
+    where: {
+      position: 'before' | 'after' | 'append';
+      anchorNodeId?: string;
+      anchorText?: string;
+    },
+    xml: string,
+    title?: string,
+  ): Promise<Record<string, unknown>>;
+  // Optimistic-locked full replacement of a diagram (baseHash from drawioGet).
+  drawioUpdate(
+    pageId: string,
+    node: string,
+    xml: string,
+    baseHash: string,
+  ): Promise<Record<string, unknown>>;
   tableInsertRow(
     pageId: string,
     tableRef: string,

apps/server/src/core/ai-chat/tools/tool-tiers.spec.ts

@@ -27,13 +27,26 @@ import type { DocmostClientLike } from './docmost-client.loader';
  */
 
 describe('tool tier metadata (#332)', () => {
-  it('core set is the documented 13 + searchInPage (14)', () => {
-    expect(CORE_TOOL_KEYS).toHaveLength(14);
+  it('core set is the documented 13 + searchInPage + insertFootnote (15)', () => {
+    expect(CORE_TOOL_KEYS).toHaveLength(15);
     expect(CORE_TOOL_SET.has('searchInPage')).toBe(true); // #330, promoted to core
+    expect(CORE_TOOL_SET.has('insertFootnote')).toBe(true); // #410, promoted to core
     // loadTools is a meta-tool, not a normal core key.
     expect(CORE_TOOL_SET.has(LOAD_TOOLS_NAME)).toBe(false);
   });
 
+  it('#410 image tools are DEFERRED, footnote tool is CORE', () => {
+    // insert_footnote is core (symmetric with editPageText); the image tools stay
+    // deferred (rare, fat — loaded on demand). Assert both the spec tier and the
+    // CORE_TOOL_SET membership so a future tier edit that desyncs them fails here.
+    expect(SHARED_TOOL_SPECS.insertFootnote.tier).toBe('core');
+    expect(CORE_TOOL_SET.has('insertFootnote')).toBe(true);
+    expect(SHARED_TOOL_SPECS.insertImage.tier).toBe('deferred');
+    expect(CORE_TOOL_SET.has('insertImage')).toBe(false);
+    expect(SHARED_TOOL_SPECS.replaceImage.tier).toBe('deferred');
+    expect(CORE_TOOL_SET.has('replaceImage')).toBe(false);
+  });
+
   it('SHARED_TOOL_SPECS tier agrees with CORE_TOOL_SET for every shared tool', () => {
     for (const [key, spec] of Object.entries(SHARED_TOOL_SPECS)) {
       const isCoreByTier = spec.tier === 'core';

apps/server/src/core/ai-chat/tools/tool-tiers.ts

@@ -38,10 +38,13 @@ export interface ToolCatalogEntry {
 }
 
 /**
- * CORE (always-active) in-app tool keys — 13 frequent/tiny tools. `searchInPage`
- * (#330) is added to core on top of the issue's original tier list: it is
- * frequent for the editorial roles this feature targets. `loadTools` is active
- * too but is not a normal tool key (it is added to activeTools separately).
+ * CORE (always-active) in-app tool keys — 13 frequent/tiny tools + `searchInPage`
+ * (#330) + `insertFootnote` (#410). `searchInPage` is core because it is frequent
+ * for the editorial roles this feature targets; `insertFootnote` is core so the
+ * footnote tool is NOT hidden while its natural sibling `editPageText` is always
+ * active (that asymmetry is exactly what pushed the agent to write literal
+ * `^[...]`). `loadTools` is active too but is not a normal tool key (it is added
+ * to activeTools separately).
  */
 export const CORE_TOOL_KEYS = [
   'searchPages',
@@ -60,6 +63,9 @@ export const CORE_TOOL_KEYS = [
   // #330 search_in_page — frequent for editorial sweeps; core despite predating
   // the issue's tier list.
   'searchInPage',
+  // #410 insert_footnote — core so pinpoint citations to already-written text
+  // don't degrade into literal `^[...]`; kept symmetric with editPageText.
+  'insertFootnote',
 ] as const;
 
 /** O(1) membership test for the core tier. */

apps/server/src/core/comment/comment.service.apply-suggestion.spec.ts

@@ -5,6 +5,16 @@ import {
 } from '@nestjs/common';
 import { CommentService } from './comment.service';
 import { AuditEvent, AuditResource } from '../../common/events/audit-events';
+import { QueueJob } from '../../integrations/queue/constants';
+
+// #399: the resolve/unresolve flip and the ephemeral anchor removal are enqueued
+// as COMMENT_MARK_UPDATE jobs (off the HTTP path), NOT awaited against the collab
+// gateway. applyCommentSuggestion (the document TEXT edit) is untouched — it
+// still runs synchronously via the gateway.
+const markJob = (generalQueue: any, action: string) =>
+  generalQueue.add.mock.calls.find(
+    (c: any[]) => c[0] === QueueJob.COMMENT_MARK_UPDATE && c[1]?.action === action,
+  );
 
 /**
  * Focused coverage for CommentService.applySuggestion (comment.service.ts).
@@ -59,6 +69,7 @@ describe('CommentService — applySuggestion', () => {
       commentRepo,
       wsService,
       collaborationGateway,
+      generalQueue,
       auditService,
     };
   }
@@ -86,9 +97,15 @@ describe('CommentService — applySuggestion', () => {
 
   // --- no replies → ephemeral delete branch -------------------------------
 
-  it('applied=true, no replies → replaces text, hard-deletes, strips the anchor mark, audits APPLIED, outcome=deleted', async () => {
-    const { service, commentRepo, wsService, collaborationGateway, auditService } =
-      makeService({ applied: true, currentText: 'new text' });
+  it('applied=true, no replies → replaces text, hard-deletes, enqueues the anchor-mark removal, audits APPLIED, outcome=deleted', async () => {
+    const {
+      service,
+      commentRepo,
+      wsService,
+      collaborationGateway,
+      generalQueue,
+      auditService,
+    } = makeService({ applied: true, currentText: 'new text' });
 
     const result = await service.applySuggestion(suggestionComment(), user());
 
@@ -105,12 +122,20 @@ describe('CommentService — applySuggestion', () => {
     );
 
     // Ephemeral: the redundant comment is hard-deleted (atomic-conditional) and
-    // its inline anchor mark removed via the deleteCommentMark collab event.
+    // its inline anchor mark removal is ENQUEUED (#399), no longer a sync gateway
+    // call. The gateway was only touched for the applyCommentSuggestion text edit.
     expect(commentRepo.deleteCommentIfChildless).toHaveBeenCalledWith('c-1');
-    expect(collaborationGateway.handleYjsEvent).toHaveBeenCalledWith(
+    const del = markJob(generalQueue, 'delete');
+    expect(del).toBeDefined();
+    expect(del[1]).toMatchObject({
+      documentName: 'page.page-1',
+      commentId: 'c-1',
+      userId: 'user-1',
+    });
+    expect(collaborationGateway.handleYjsEvent).not.toHaveBeenCalledWith(
       'deleteCommentMark',
-      'page.page-1',
-      expect.objectContaining({ commentId: 'c-1', user: expect.any(Object) }),
+      expect.anything(),
+      expect.anything(),
     );
     // No applied stamps are written for a row about to be deleted.
     expect(appliedPatch(commentRepo)).toBeUndefined();
@@ -258,7 +283,7 @@ describe('CommentService — applySuggestion', () => {
     // The suggested text is already applied to the document, but between the
     // hasChildren read and the atomic delete a reply landed. The parent must NOT
     // be hard-deleted (cascade would destroy the reply); resolve the thread.
-    const { service, commentRepo, wsService, collaborationGateway } =
+    const { service, commentRepo, wsService, generalQueue } =
       makeService({ applied: true, currentText: 'new text' }, false, 0);
 
     const result = await service.applySuggestion(suggestionComment(), user());
@@ -275,11 +300,8 @@ describe('CommentService — applySuggestion', () => {
       .map((c: any[]) => c[0])
       .find((p: any) => 'resolvedAt' in p);
     expect(resolvePatch.resolvedAt).toBeInstanceOf(Date);
-    expect(collaborationGateway.handleYjsEvent).toHaveBeenCalledWith(
-      'resolveCommentMark',
-      'page.page-1',
-      expect.objectContaining({ commentId: 'c-1', resolved: true }),
-    );
+    // The resolve mark is enqueued (#399), not a sync gateway call.
+    expect(markJob(generalQueue, 'resolve')).toBeDefined();
     expect(result.outcome).toBe('resolved');
   });
 

apps/server/src/core/comment/comment.service.behavior.spec.ts

@@ -313,11 +313,15 @@ describe('CommentService — behavior', () => {
       });
 
       const [patch] = commentRepo.updateComment.mock.calls[0];
-      expect(patch).toEqual({
+      // #399: resolve/unresolve now also stamps updatedAt (the async mark
+      // worker's race-guard reads it to order out-of-order events). The
+      // resolve-state fields are still cleared to null on unresolve.
+      expect(patch).toMatchObject({
         resolvedAt: null,
         resolvedById: null,
         resolvedSource: null,
       });
+      expect(patch.updatedAt).toBeInstanceOf(Date);
     });
 
     it("notifies the author when SOMEONE ELSE resolves their comment", async () => {

apps/server/src/core/comment/comment.service.dismiss-suggestion.spec.ts

@@ -1,6 +1,15 @@
 import { BadRequestException } from '@nestjs/common';
 import { CommentService } from './comment.service';
 import { AuditEvent, AuditResource } from '../../common/events/audit-events';
+import { QueueJob } from '../../integrations/queue/constants';
+
+// #399: the inline comment-mark op (resolve flip / ephemeral-suggestion anchor
+// removal) is now enqueued as a COMMENT_MARK_UPDATE job instead of being awaited
+// against the collab gateway on the HTTP path. Find that job by action.
+const markJob = (generalQueue: any, action: string) =>
+  generalQueue.add.mock.calls.find(
+    (c: any[]) => c[0] === QueueJob.COMMENT_MARK_UPDATE && c[1]?.action === action,
+  );
 
 /**
  * Coverage for CommentService.dismissSuggestion (#329). Dismiss ("Не применять")
@@ -44,7 +53,14 @@ describe('CommentService — dismissSuggestion', () => {
       auditService,
     );
 
-    return { service, commentRepo, wsService, collaborationGateway, auditService };
+    return {
+      service,
+      commentRepo,
+      wsService,
+      collaborationGateway,
+      generalQueue,
+      auditService,
+    };
   }
 
   const suggestionComment = (over?: Partial<any>): any => ({
@@ -62,25 +78,30 @@ describe('CommentService — dismissSuggestion', () => {
   });
   const user = (over?: Partial<any>): any => ({ id: 'user-1', ...over });
 
-  it('no replies → hard-deletes, strips the anchor mark, does NOT touch page text, audits DISMISSED, outcome=deleted', async () => {
-    const { service, commentRepo, wsService, collaborationGateway, auditService } =
-      makeService(false);
+  it('no replies → hard-deletes, enqueues the anchor-mark removal, does NOT touch page text, audits DISMISSED, outcome=deleted', async () => {
+    const {
+      service,
+      commentRepo,
+      wsService,
+      collaborationGateway,
+      generalQueue,
+      auditService,
+    } = makeService(false);
 
     const result = await service.dismissSuggestion(suggestionComment(), user());
 
-    // Never applies the suggestion to the document.
-    expect(collaborationGateway.handleYjsEvent).not.toHaveBeenCalledWith(
-      'applyCommentSuggestion',
-      expect.anything(),
-      expect.anything(),
-    );
-    // Hard-delete (atomic-conditional) + strip mark.
+    // Never applies the suggestion to the document (no sync gateway call at all
+    // now — the mark op is off the HTTP path, #399).
+    expect(collaborationGateway.handleYjsEvent).not.toHaveBeenCalled();
+    // Hard-delete (atomic-conditional) + enqueue the anchor-mark strip.
     expect(commentRepo.deleteCommentIfChildless).toHaveBeenCalledWith('c-1');
-    expect(collaborationGateway.handleYjsEvent).toHaveBeenCalledWith(
-      'deleteCommentMark',
-      'page.page-1',
-      expect.objectContaining({ commentId: 'c-1', user: expect.any(Object) }),
-    );
+    const del = markJob(generalQueue, 'delete');
+    expect(del).toBeDefined();
+    expect(del[1]).toMatchObject({
+      documentName: 'page.page-1',
+      commentId: 'c-1',
+      userId: 'user-1',
+    });
     expect(wsService.emitCommentEvent).toHaveBeenCalledWith(
       'space-1',
       'page-1',
@@ -96,20 +117,20 @@ describe('CommentService — dismissSuggestion', () => {
     expect(result.outcome).toBe('deleted');
   });
 
-  it('no replies → if the anchor-mark removal FAILS, the row is NOT deleted and the error propagates (#329: no orphan anchor)', async () => {
-    const { service, commentRepo, wsService, collaborationGateway } =
-      makeService(false);
-    // Mark removal is FATAL and runs BEFORE the irreversible row delete: a collab
-    // failure (e.g. COLLAB_DISABLE_REDIS "no live instance") must abort the whole
-    // operation, leaving row + mark consistent — never a deleted row with an
-    // orphan anchor left in the document reporting success.
-    collaborationGateway.handleYjsEvent = jest.fn(async () => {
-      throw new Error('requires a live collaboration instance');
+  it('no replies → if the anchor-mark ENQUEUE FAILS, the row is NOT deleted and the error propagates (#329/#399: no orphan anchor)', async () => {
+    const { service, commentRepo, wsService, generalQueue } = makeService(false);
+    // #399: the mark removal now runs async in a worker, but the ENQUEUE is
+    // awaited BEFORE the irreversible row delete — so the anchor-removal job is
+    // durably scheduled before the row can vanish. If even the enqueue fails
+    // (e.g. Redis down), the whole operation aborts, leaving row + mark
+    // consistent — never a deleted row with an orphan anchor reporting success.
+    generalQueue.add = jest.fn(async () => {
+      throw new Error('queue add failed: no redis');
     });
 
     await expect(
       service.dismissSuggestion(suggestionComment(), user()),
-    ).rejects.toThrow(/live collaboration/);
+    ).rejects.toThrow(/queue add failed/);
 
     expect(commentRepo.deleteCommentIfChildless).not.toHaveBeenCalled();
     expect(wsService.emitCommentEvent).not.toHaveBeenCalledWith(
@@ -120,23 +141,29 @@ describe('CommentService — dismissSuggestion', () => {
   });
 
   it('WITH replies → resolves (not delete), does NOT apply, audits DISMISSED, outcome=resolved', async () => {
-    const { service, commentRepo, wsService, collaborationGateway, auditService } =
-      makeService(true);
+    const {
+      service,
+      commentRepo,
+      collaborationGateway,
+      generalQueue,
+      auditService,
+    } = makeService(true);
 
     const result = await service.dismissSuggestion(suggestionComment(), user());
 
-    // Resolved via resolveComment (resolve patch + resolve mark), NOT deleted.
+    // Resolved via resolveComment (resolve patch + enqueued resolve mark), NOT
+    // deleted.
     const resolvePatch = commentRepo.updateComment.mock.calls
       .map((c: any[]) => c[0])
       .find((p: any) => 'resolvedAt' in p);
     expect(resolvePatch.resolvedAt).toBeInstanceOf(Date);
     expect(resolvePatch.resolvedById).toBe('user-1');
     expect(commentRepo.deleteComment).not.toHaveBeenCalled();
-    expect(collaborationGateway.handleYjsEvent).toHaveBeenCalledWith(
-      'resolveCommentMark',
-      'page.page-1',
-      expect.objectContaining({ commentId: 'c-1', resolved: true }),
-    );
+    // No sync gateway call; the resolve mark is enqueued (#399).
+    expect(collaborationGateway.handleYjsEvent).not.toHaveBeenCalled();
+    const res = markJob(generalQueue, 'resolve');
+    expect(res).toBeDefined();
+    expect(res[1]).toMatchObject({ documentName: 'page.page-1', commentId: 'c-1' });
     // No applied stamp — dismiss does not apply the edit.
     const appliedPatch = commentRepo.updateComment.mock.calls
       .map((c: any[]) => c[0])
@@ -156,8 +183,7 @@ describe('CommentService — dismissSuggestion', () => {
     // but the atomic delete matches 0 rows because a reply landed in the window
     // between that read and the delete. The parent must NOT be hard-deleted
     // (a cascade would destroy the just-added reply); the thread is resolved.
-    const { service, commentRepo, wsService, collaborationGateway } =
-      makeService(false, 0);
+    const { service, commentRepo, wsService, generalQueue } = makeService(false, 0);
 
     const result = await service.dismissSuggestion(suggestionComment(), user());
 
@@ -175,11 +201,9 @@ describe('CommentService — dismissSuggestion', () => {
       .find((p: any) => 'resolvedAt' in p);
     expect(resolvePatch.resolvedAt).toBeInstanceOf(Date);
     expect(resolvePatch.resolvedById).toBe('user-1');
-    expect(collaborationGateway.handleYjsEvent).toHaveBeenCalledWith(
-      'resolveCommentMark',
-      'page.page-1',
-      expect.objectContaining({ commentId: 'c-1', resolved: true }),
-    );
+    // A resolve mark job is enqueued (the anchor was already delete-marked; the
+    // resolve mirror is idempotent — #399).
+    expect(markJob(generalQueue, 'resolve')).toBeDefined();
     expect(result.outcome).toBe('resolved');
   });
 

apps/server/src/core/comment/comment.service.mark-async.spec.ts

@@ -0,0 +1,179 @@
+import { Logger } from '@nestjs/common';
+import { CommentService } from './comment.service';
+import { QueueJob } from '../../integrations/queue/constants';
+
+// Flush pending microtasks so a fire-and-forget `.catch(...)` runs before we assert.
+const flushMicrotasks = () => new Promise((r) => setImmediate(r));
+
+/**
+ * #399: the comment inline-mark update is moved OFF the HTTP critical path.
+ * resolveComment / unresolve / the ephemeral-suggestion delete must NO LONGER
+ * await CollaborationGateway.handleYjsEvent (which loaded the whole Y.Doc and
+ * ran the store pipeline synchronously, ~4.5s p95). Instead they enqueue an
+ * idempotent COMMENT_MARK_UPDATE job onto the GENERAL_QUEUE with the payload the
+ * worker replays.
+ *
+ * The service is constructed directly with jest mocks (the @InjectQueue tokens
+ * cannot be resolved by Test.createTestingModule — see comment.service.spec.ts).
+ */
+describe('CommentService — async comment mark (#399)', () => {
+  function makeService() {
+    const commentRepo: any = {
+      findById: jest.fn(async (id: string) => ({
+        id,
+        content: {},
+        spaceId: 'space-1',
+        pageId: 'page-1',
+      })),
+      updateComment: jest.fn(async () => undefined),
+      hasChildren: jest.fn(async () => false),
+      deleteCommentIfChildless: jest.fn(async () => 1),
+    };
+    const pageRepo: any = {};
+    const wsService: any = { emitCommentEvent: jest.fn() };
+    // The gateway MUST NOT be touched on the HTTP path anymore.
+    const collaborationGateway: any = {
+      handleYjsEvent: jest.fn(async () => undefined),
+    };
+    const generalQueue: any = { add: jest.fn(() => Promise.resolve()) };
+    const notificationQueue: any = { add: jest.fn(async () => undefined) };
+    const auditService: any = { log: jest.fn() };
+
+    const service = new CommentService(
+      commentRepo,
+      pageRepo,
+      wsService,
+      collaborationGateway,
+      generalQueue,
+      notificationQueue,
+      auditService,
+    );
+    return {
+      service,
+      commentRepo,
+      collaborationGateway,
+      generalQueue,
+      auditService,
+    };
+  }
+
+  const comment = (over?: Partial<any>): any => ({
+    id: 'c-1',
+    creatorId: 'user-1',
+    pageId: 'page-1',
+    spaceId: 'space-1',
+    workspaceId: 'ws-1',
+    ...over,
+  });
+  const user = (over?: Partial<any>): any => ({ id: 'user-1', ...over });
+
+  const markJob = (generalQueue: any) =>
+    generalQueue.add.mock.calls.find(
+      (c: any[]) => c[0] === QueueJob.COMMENT_MARK_UPDATE,
+    );
+
+  it('resolveComment does NOT call the gateway synchronously, and enqueues a resolve mark job', async () => {
+    const { service, collaborationGateway, generalQueue } = makeService();
+
+    await service.resolveComment(comment(), true, user());
+
+    // The whole point of #399: the Y.Doc mark op is off the HTTP path.
+    expect(collaborationGateway.handleYjsEvent).not.toHaveBeenCalled();
+
+    const job = markJob(generalQueue);
+    expect(job).toBeDefined();
+    expect(job[0]).toBe(QueueJob.COMMENT_MARK_UPDATE);
+    expect(job[1]).toMatchObject({
+      documentName: 'page.page-1',
+      commentId: 'c-1',
+      action: 'resolve',
+      userId: 'user-1',
+    });
+    expect(typeof job[1].ts).toBe('number');
+    // ts equals the resolvedAt stamp written to the row (shared timestamp).
+    const [patch] = (service as any).commentRepo.updateComment.mock.calls[0];
+    expect(job[1].ts).toBe((patch.resolvedAt as Date).getTime());
+    expect(job[1].ts).toBe((patch.updatedAt as Date).getTime());
+  });
+
+  it('unresolve enqueues an unresolve mark job (action mapped from resolved=false)', async () => {
+    const { service, collaborationGateway, generalQueue } = makeService();
+
+    await service.resolveComment(comment(), false, user());
+
+    expect(collaborationGateway.handleYjsEvent).not.toHaveBeenCalled();
+    const job = markJob(generalQueue);
+    expect(job[1]).toMatchObject({
+      documentName: 'page.page-1',
+      commentId: 'c-1',
+      action: 'unresolve',
+      userId: 'user-1',
+    });
+  });
+
+  it('dismissing a childless ephemeral suggestion enqueues a delete mark job (not a sync gateway call)', async () => {
+    const { service, collaborationGateway, generalQueue } = makeService();
+
+    await service.dismissSuggestion(
+      comment({ suggestedText: 'new text', selection: 'old', resolvedAt: null }),
+      user(),
+    );
+
+    // The anchor removal is queued, not awaited against the gateway.
+    expect(collaborationGateway.handleYjsEvent).not.toHaveBeenCalled();
+    const job = markJob(generalQueue);
+    expect(job).toBeDefined();
+    expect(job[1]).toMatchObject({
+      documentName: 'page.page-1',
+      commentId: 'c-1',
+      action: 'delete',
+      userId: 'user-1',
+    });
+    expect(typeof job[1].ts).toBe('number');
+  });
+
+  it('awaits the delete ENQUEUE before the irreversible row hard-delete (ordering preserved)', async () => {
+    const { service, generalQueue, commentRepo } = makeService();
+    const order: string[] = [];
+    generalQueue.add.mockImplementation(async (name: string) => {
+      order.push(`enqueue:${name}`);
+    });
+    commentRepo.deleteCommentIfChildless.mockImplementation(async () => {
+      order.push('delete-row');
+      return 1;
+    });
+
+    await service.dismissSuggestion(
+      comment({ suggestedText: 'new text', selection: 'old', resolvedAt: null }),
+      user(),
+    );
+
+    // The mark-removal job must be durably queued BEFORE the row disappears.
+    expect(order).toEqual([
+      `enqueue:${QueueJob.COMMENT_MARK_UPDATE}`,
+      'delete-row',
+    ]);
+  });
+
+  it('resolve is fire-and-forget: a queue-add rejection does NOT fail the HTTP call (best-effort warn)', async () => {
+    const { service, generalQueue } = makeService();
+    // The queue is unavailable — the whole point of #399 is that this must NOT
+    // propagate out of resolveComment onto the HTTP request.
+    const queueErr = new Error('queue is down');
+    generalQueue.add.mockRejectedValue(queueErr);
+    const warnSpy = jest
+      .spyOn(Logger.prototype, 'warn')
+      .mockImplementation(() => undefined);
+
+    // Must resolve, never throw, even though the enqueue rejects.
+    await expect(service.resolveComment(comment(), true, user())).resolves.not.toThrow();
+
+    // The rejection is swallowed on a microtask AFTER the method returns; flush it.
+    await flushMicrotasks();
+    expect(warnSpy).toHaveBeenCalledWith(
+      expect.stringContaining('Failed to enqueue comment mark update for comment c-1'),
+      queueErr,
+    );
+    warnSpy.mockRestore();
+  });
+});

apps/server/src/core/comment/comment.service.ts

@@ -21,6 +21,7 @@ import { CursorPaginationResult } from '@docmost/db/pagination/cursor-pagination
 import { QueueJob, QueueName } from '../../integrations/queue/constants';
 import { extractUserMentionIdsFromJson } from '../../common/helpers/prosemirror/utils';
 import {
+  ICommentMarkUpdateJob,
   ICommentNotificationJob,
   ICommentResolvedNotificationJob,
 } from '../../integrations/queue/constants/queue.interface';
@@ -298,7 +299,11 @@ export class CommentService {
     // source is cleared alongside resolvedAt/resolvedById.
     provenance?: AuthProvenanceData,
   ): Promise<Comment> {
-    const resolvedAt = resolved ? new Date() : null;
+    // One shared timestamp: it stamps resolvedAt AND updatedAt on the row and is
+    // carried as the mark job's `ts`, so the worker's race-guard can order this
+    // event against the row's authoritative resolve-state mutation time (#399).
+    const now = new Date();
+    const resolvedAt = resolved ? now : null;
     const resolvedById = resolved ? authUser.id : null;
     const isAgent = provenance?.actor === 'agent';
     // Set the agent marker only when resolving; on unresolve clear it back to
@@ -307,25 +312,33 @@ export class CommentService {
     const resolvedSource = resolved && isAgent ? 'agent' : null;
 
     await this.commentRepo.updateComment(
-      { resolvedAt, resolvedById, resolvedSource },
+      // Bump updatedAt (not editedAt — that drives the "edited" badge) so the
+      // row records WHEN the resolve state last changed; the async mark worker
+      // compares its job ts against this to skip a superseded out-of-order event.
+      { resolvedAt, resolvedById, resolvedSource, updatedAt: now },
       comment.id,
     );
 
-    // Reflect the resolved state on the inline comment mark in the
-    // collaborative document so all connected clients stay in sync.
+    // #399: mirror the resolved state onto the inline comment mark OFF the HTTP
+    // critical path. The DB row above is the source of truth (updated in ms); the
+    // mark is an eventual mirror for connected clients, and its failure was
+    // ALREADY swallowed (best-effort warn) — so instead of awaiting the whole
+    // Y.Doc load + immediate store pipeline (~4.5s p95), enqueue an idempotent,
+    // retryable COMMENT_MARK_UPDATE job. (Store-pipeline cost itself is #348's
+    // scope, not duplicated here.)
     const documentName = `page.${comment.pageId}`;
-    try {
-      await this.collaborationGateway.handleYjsEvent(
-        'resolveCommentMark',
-        documentName,
-        { commentId: comment.id, resolved, user: authUser },
-      );
-    } catch (error) {
+    void this.enqueueCommentMarkUpdate(
+      documentName,
+      comment.id,
+      resolved ? 'resolve' : 'unresolve',
+      now.getTime(),
+      authUser.id,
+    ).catch((error) =>
       this.logger.warn(
-        `Failed to update comment mark for comment ${comment.id}`,
+        `Failed to enqueue comment mark update for comment ${comment.id}`,
         error,
-      );
-    }
+      ),
+    );
 
     // Notify the comment author when someone else resolves their comment.
     if (resolved && comment.creatorId !== authUser.id) {
@@ -671,23 +684,54 @@ export class CommentService {
   }
 
   /**
-   * Remove the inline `comment` mark for a comment from the collaborative
-   * document. FATAL, NOT best-effort: unlike resolveComment (which keeps the row,
-   * so a failed mark update is recoverable), this is used before an irreversible
-   * hard-delete, so the mark removal MUST succeed or throw. Under
-   * COLLAB_DISABLE_REDIS the gateway invokes the deleteCommentMark handler
-   * directly (never a silent no-op) and a missing live instance surfaces as a
-   * thrown error, which we let propagate so the caller aborts before deleting.
+   * Schedule removal of the inline `comment` anchor mark from the collaborative
+   * document (ephemeral suggestion #329), OFF the HTTP critical path (#399).
+   *
+   * ORDERING PRESERVED: we `await` the ENQUEUE (a fast Redis add), not the mark
+   * op, and the caller only proceeds to the irreversible row hard-delete after
+   * this resolves. So the anchor-removal job is DURABLY queued before the row
+   * vanishes — a queue-add failure throws here and aborts the delete (row + mark
+   * stay consistent), preserving the invariant the old FATAL sync call gave. The
+   * mark op itself now runs async in the worker: it is idempotent and retried
+   * (3 attempts), so a transient collab failure self-heals; only an exhausted-
+   * retries job leaves a DB↔mark divergence, now VISIBLE via BullMQ failed-job
+   * metrics (was a hard 5xx before). Delete carries no state guard — the row is
+   * being removed, and stripping an absent mark is a no-op.
    */
   private async deleteCommentMark(comment: Comment, user: User): Promise<void> {
     const documentName = `page.${comment.pageId}`;
-    await this.collaborationGateway.handleYjsEvent(
-      'deleteCommentMark',
+    await this.enqueueCommentMarkUpdate(
       documentName,
-      { commentId: comment.id, user },
+      comment.id,
+      'delete',
+      Date.now(),
+      user.id,
     );
   }
 
+  /**
+   * Enqueue an idempotent COMMENT_MARK_UPDATE job (#399) — the single path that
+   * mirrors a comment's inline-mark state into the collab Y.Doc off the HTTP
+   * response. The worker (GeneralQueueProcessor) runs the SAME handleYjsEvent
+   * the sync code used, so the mark op is byte-identical.
+   */
+  private enqueueCommentMarkUpdate(
+    documentName: string,
+    commentId: string,
+    action: 'resolve' | 'unresolve' | 'delete',
+    ts: number,
+    userId: string,
+  ): Promise<unknown> {
+    const jobData: ICommentMarkUpdateJob = {
+      documentName,
+      commentId,
+      action,
+      ts,
+      userId,
+    };
+    return this.generalQueue.add(QueueJob.COMMENT_MARK_UPDATE, jobData);
+  }
+
   private async queueCommentNotification(
     content: any,
     oldMentionIds: string[],

apps/server/src/integrations/ai/ai-streaming-fetch.ts

@@ -123,19 +123,19 @@ export function streamKeepAliveMs(): number {
   return positiveEnv('AI_STREAM_KEEPALIVE_MS', DEFAULT_STREAM_KEEPALIVE_MS);
 }
 
-/** Default SILENCE timeout for EXTERNAL-MCP transport (5 min). */
-const DEFAULT_MCP_STREAM_TIMEOUT_MS = 300_000;
+/** Default SILENCE timeout for EXTERNAL-MCP transport (1 min). */
+const DEFAULT_MCP_STREAM_TIMEOUT_MS = 60_000;
 
-/** Default total wall-clock cap for ONE external MCP tool call (15 min). */
-const DEFAULT_MCP_CALL_TIMEOUT_MS = 900_000;
+/** Default total wall-clock cap for ONE external MCP tool call (2 min). */
+const DEFAULT_MCP_CALL_TIMEOUT_MS = 120_000;
 
 /**
  * SILENCE timeout (ms) for EXTERNAL-MCP transport ONLY. Override with
  * `AI_MCP_STREAM_TIMEOUT_MS`; a missing/invalid/non-positive value falls back to
- * {@link DEFAULT_MCP_STREAM_TIMEOUT_MS} (5 min).
+ * {@link DEFAULT_MCP_STREAM_TIMEOUT_MS} (1 min).
  *
  * Deliberately tighter than the chat provider's {@link streamTimeoutMs} (15 min)
- * so a byte-silent/hung MCP upstream is broken in ~5 min instead of 15. This is
+ * so a byte-silent/hung MCP upstream is broken in ~1 min instead of 15. This is
  * the undici `headersTimeout`/`bodyTimeout` for the external-MCP dispatcher only
  * — it must NOT change the chat provider, which legitimately needs 15 min between
  * reasoning chunks (#175).
@@ -153,7 +153,7 @@ export function mcpStreamTimeoutMs(): number {
 /**
  * Total wall-clock cap (ms) for ONE external MCP tool call — APP-LEVEL, not
  * transport. Override with `AI_MCP_CALL_TIMEOUT_MS`; a missing/invalid/
- * non-positive value falls back to {@link DEFAULT_MCP_CALL_TIMEOUT_MS} (15 min).
+ * non-positive value falls back to {@link DEFAULT_MCP_CALL_TIMEOUT_MS} (2 min).
  *
  * Catches a tool that keeps the connection warm (SSE heartbeats / trickle) but
  * never returns a result — which the transport silence timeout

apps/server/src/integrations/mcp/mcp-auth.helpers.ts

@@ -149,6 +149,15 @@ export type DocmostMcpConfig = (
     has?: (uri: string) => boolean;
     evict?: (uri: string) => void;
   };
+  // Dependency-neutral metrics sink injected by McpService (mirror of the
+  // package's onMetric). The package emits generic (name, value, labels)
+  // samples; McpService maps them onto the prom-client registry. Undefined
+  // when metrics are disabled → the package no-ops.
+  onMetric?: (
+    name: string,
+    value: number,
+    labels?: Record<string, string>,
+  ) => void;
 };
 
 export interface ResolvedMcpAuth {

apps/server/src/integrations/mcp/mcp.service.ts

@@ -30,6 +30,11 @@ import {
   ResolvedMcpAuth,
 } from './mcp-auth.helpers';
 import { SandboxStore } from '../sandbox/sandbox.store';
+import {
+  isMetricsEnabled,
+  observeMcpTool,
+  incConnectTimeout,
+} from '../metrics/metrics.registry';
 
 // Minimal shape of the embedded MCP HTTP handler exported by @docmost/mcp/http.
 interface McpHttpHandler {
@@ -331,7 +336,31 @@ export class McpService implements OnModuleDestroy {
             // can store blobs in the shared in-RAM store regardless of which
             // credential variant resolved. The sink (put/has/evict + uri↔id
             // mapping) is owned by SandboxStore.asSink().
-            return { ...resolved.config, sandbox: this.sandboxStore.asSink() };
+            // Route the package's dependency-neutral metric samples onto the
+            // prom-client registry. When metrics are disabled, onMetric is
+            // undefined → the package's tool-timer/timeout hooks are a
+            // negligible-overhead no-op: the registerTool wrapper still runs a
+            // performance.now() + async try/finally per tool call, but the
+            // `onMetric?.()` short-circuits so no label/object is built. (Cost
+            // is immaterial at LLM tool-call rate.) labels?.tool is guarded
+            // defensively (the tool wrapper always sets it).
+            return {
+              ...resolved.config,
+              sandbox: this.sandboxStore.asSink(),
+              onMetric: isMetricsEnabled()
+                ? (
+                    name: string,
+                    value: number,
+                    labels?: Record<string, string>,
+                  ) => {
+                    if (name === 'mcp_tool_duration_seconds') {
+                      observeMcpTool(labels?.tool ?? 'other', value);
+                    } else if (name === 'collab_connect_timeouts_total') {
+                      incConnectTimeout();
+                    }
+                  }
+                : undefined,
+            };
           },
           {
             identify: (req: IncomingMessage) => {

apps/server/src/integrations/metrics/metrics.constants.ts

@@ -2,6 +2,11 @@
  * Perf-metrics contract (#355). These names/labels are FIXED by the already
  * deployed scrape+dashboard infra (VictoriaMetrics scraping docmost:9464,
  * Grafana dashboards, alerts). Do NOT rename them.
+ *
+ * #402 extends the #355 table with the collab-lifecycle + MCP-tool families
+ * (grouped below). These are the fixed contract from #402; same "do not rename"
+ * rule applies. Server-side families land in Pass 1; the MCP-tool histogram is
+ * fed by the MCP callback in a later pass but its NAME is fixed here now.
  */
 export const METRIC_HTTP_REQUEST_DURATION = 'http_request_duration_seconds';
 export const METRIC_DB_QUERY_DURATION = 'db_query_duration_seconds';
@@ -9,6 +14,17 @@ export const METRIC_BULLMQ_QUEUE_DEPTH = 'bullmq_queue_depth';
 export const METRIC_BULLMQ_JOB_DURATION = 'bullmq_job_duration_seconds';
 export const METRIC_COLLAB_STORE_DURATION = 'collab_store_duration_seconds';
 
+// #402 additions — collaboration lifecycle + MCP tool timing.
+export const METRIC_COLLAB_LOAD_DURATION = 'collab_doc_load_duration_seconds';
+export const METRIC_COLLAB_DOCS_OPEN = 'collab_docs_open';
+export const METRIC_COLLAB_DOC_LOADS_TOTAL = 'collab_doc_loads_total';
+export const METRIC_COLLAB_DOC_UNLOADS_TOTAL = 'collab_doc_unloads_total';
+export const METRIC_COLLAB_CONNECT_DURATION = 'collab_connect_duration_seconds';
+export const METRIC_COLLAB_CONNECT_TIMEOUTS_TOTAL =
+  'collab_connect_timeouts_total';
+export const METRIC_COLLAB_AUTH_DURATION = 'collab_auth_duration_seconds';
+export const METRIC_MCP_TOOL_DURATION = 'mcp_tool_duration_seconds';
+
 // Histogram buckets (seconds). Chosen to give useful p50/p95/p99 resolution
 // for typical web/DB latencies without exploding series cardinality.
 export const HTTP_BUCKETS = [
@@ -23,6 +39,12 @@ export const COLLAB_BUCKETS = [
 export const JOB_BUCKETS = [
   0.01, 0.05, 0.1, 0.25, 0.5, 1, 2.5, 5, 10, 30, 60, 120,
 ];
+// #402 — MCP tool-call latency. Same shape as COLLAB_BUCKETS but stretched to
+// 10s at the top: an MCP tool round-trip (LLM-driven doc ops) can be slower
+// than a single collab store, so keep resolution out to 10s.
+export const MCP_TOOL_BUCKETS = [
+  0.005, 0.025, 0.1, 0.25, 0.5, 1, 2.5, 5, 10,
+];
 
 /**
  * Extract the first SQL token (select/insert/update/delete/...) from a query,
@@ -58,6 +80,30 @@ export function firstSqlToken(sql: string | undefined): string {
   return KNOWN_SQL_TOKENS.has(token) ? token : 'other';
 }
 
+/**
+ * #402 — bucket a document byte size into ONE of four fixed labels for the
+ * collab load/store histograms' `size_bucket` label. Using the raw byte count
+ * would be a continuous, unbounded label; four coarse buckets keep series
+ * cardinality bounded (each of collab_doc_load / collab_store gets ×4 series).
+ *
+ * The SAME function is shared by both the load and store paths so their buckets
+ * can never drift apart. Non-finite / negative sizes collapse to the smallest
+ * bucket ('lt64k') as a safe default (they can't be legitimately huge and we
+ * must never throw here — this runs on every store/load when metrics are on).
+ */
+// Module-const thresholds, built once (not per observe).
+const SIZE_THRESHOLDS = { lt64k: 65536, lt256k: 262144, lt1m: 1048576 } as const;
+
+export function sizeBucket(
+  bytes: number | undefined | null,
+): 'lt64k' | 'lt256k' | 'lt1m' | 'ge1m' {
+  if (bytes == null || !Number.isFinite(bytes) || bytes < 0) return 'lt64k';
+  if (bytes < SIZE_THRESHOLDS.lt64k) return 'lt64k';
+  if (bytes < SIZE_THRESHOLDS.lt256k) return 'lt256k';
+  if (bytes < SIZE_THRESHOLDS.lt1m) return 'lt1m';
+  return 'ge1m';
+}
+
 /**
  * Whether an HTTP response must be EXCLUDED from http_request_duration_seconds.
  *

apps/server/src/integrations/metrics/metrics.registry.ts

@@ -1,5 +1,6 @@
 import {
   collectDefaultMetrics,
+  Counter,
   Histogram,
   Gauge,
   Registry,
@@ -9,11 +10,21 @@ import {
   DB_BUCKETS,
   HTTP_BUCKETS,
   JOB_BUCKETS,
+  MCP_TOOL_BUCKETS,
   METRIC_BULLMQ_JOB_DURATION,
   METRIC_BULLMQ_QUEUE_DEPTH,
+  METRIC_COLLAB_AUTH_DURATION,
+  METRIC_COLLAB_CONNECT_DURATION,
+  METRIC_COLLAB_CONNECT_TIMEOUTS_TOTAL,
+  METRIC_COLLAB_DOC_LOADS_TOTAL,
+  METRIC_COLLAB_DOC_UNLOADS_TOTAL,
+  METRIC_COLLAB_DOCS_OPEN,
+  METRIC_COLLAB_LOAD_DURATION,
   METRIC_COLLAB_STORE_DURATION,
   METRIC_DB_QUERY_DURATION,
   METRIC_HTTP_REQUEST_DURATION,
+  METRIC_MCP_TOOL_DURATION,
+  sizeBucket,
 } from './metrics.constants';
 
 /**
@@ -39,7 +50,24 @@ let httpHist: Histogram<'method' | 'route' | 'status'> | null = null;
 let dbHist: Histogram<'op'> | null = null;
 let queueDepthGauge: Gauge<'queue'> | null = null;
 let jobHist: Histogram<'queue'> | null = null;
-let collabHist: Histogram | null = null;
+// #402 — collab store now carries a size_bucket label (see sizeBucket()).
+let collabHist: Histogram<'size_bucket'> | null = null;
+// #402 collab-lifecycle + MCP instruments.
+let collabLoadHist: Histogram<'size_bucket'> | null = null;
+let docsOpenGauge: Gauge | null = null;
+let docLoadsCounter: Counter | null = null;
+let docUnloadsCounter: Counter | null = null;
+let connectTimeoutsCounter: Counter | null = null;
+let collabConnectHist: Histogram | null = null;
+let collabAuthHist: Histogram | null = null;
+let mcpToolHist: Histogram<'tool'> | null = null;
+
+// #402 — read-on-scrape source for collab_docs_open. The gauge is NEVER
+// inc/dec'd (that drifts under crashes/handoffs); instead its collect() callback
+// pulls the authoritative live count from here on every scrape. Registered once,
+// gated, by the collaboration gateway via registerDocsOpenSource(). Null until
+// then → the collect() is a no-op.
+let docsOpenSource: (() => number) | null = null;
 
 function init(): void {
   if (registry || !enabled) return;
@@ -82,10 +110,71 @@ function init(): void {
 
   collabHist = new Histogram({
     name: METRIC_COLLAB_STORE_DURATION,
-    help: 'Collaboration onStoreDocument duration in seconds',
+    help: 'Collaboration onStoreDocument duration in seconds, by document size bucket',
+    labelNames: ['size_bucket'],
     buckets: COLLAB_BUCKETS,
     registers: [registry],
   });
+
+  collabLoadHist = new Histogram({
+    name: METRIC_COLLAB_LOAD_DURATION,
+    help: 'Collaboration onLoadDocument DB-load duration in seconds, by document size bucket',
+    labelNames: ['size_bucket'],
+    buckets: COLLAB_BUCKETS,
+    registers: [registry],
+  });
+
+  docsOpenGauge = new Gauge({
+    name: METRIC_COLLAB_DOCS_OPEN,
+    help: 'Number of collaboration documents currently open in memory',
+    registers: [registry],
+    // Read-on-scrape: pull the live count from the registered source (the
+    // hocuspocus instance) so the value can never drift. No-op until a source
+    // is registered.
+    collect() {
+      if (docsOpenSource) this.set(docsOpenSource());
+    },
+  });
+
+  docLoadsCounter = new Counter({
+    name: METRIC_COLLAB_DOC_LOADS_TOTAL,
+    help: 'Total collaboration documents loaded into memory',
+    registers: [registry],
+  });
+
+  docUnloadsCounter = new Counter({
+    name: METRIC_COLLAB_DOC_UNLOADS_TOTAL,
+    help: 'Total collaboration documents unloaded from memory',
+    registers: [registry],
+  });
+
+  connectTimeoutsCounter = new Counter({
+    name: METRIC_COLLAB_CONNECT_TIMEOUTS_TOTAL,
+    help: 'Total collaboration connection setup timeouts',
+    registers: [registry],
+  });
+
+  collabConnectHist = new Histogram({
+    name: METRIC_COLLAB_CONNECT_DURATION,
+    help: 'Collaboration connection acceptance duration in seconds (onConnect→connected)',
+    buckets: COLLAB_BUCKETS,
+    registers: [registry],
+  });
+
+  collabAuthHist = new Histogram({
+    name: METRIC_COLLAB_AUTH_DURATION,
+    help: 'Collaboration onAuthenticate duration in seconds',
+    buckets: COLLAB_BUCKETS,
+    registers: [registry],
+  });
+
+  mcpToolHist = new Histogram({
+    name: METRIC_MCP_TOOL_DURATION,
+    help: 'MCP tool-call duration in seconds, by tool name',
+    labelNames: ['tool'],
+    buckets: MCP_TOOL_BUCKETS,
+    registers: [registry],
+  });
 }
 
 // Runs once when this module is first imported. Safe to call again (idempotent).
@@ -121,6 +210,46 @@ export function observeJobDuration(queue: string, seconds: number): void {
   jobHist?.observe({ queue }, seconds);
 }
 
-export function observeCollabStore(seconds: number): void {
-  collabHist?.observe(seconds);
+export function observeCollabStore(bytes: number, seconds: number): void {
+  collabHist?.observe({ size_bucket: sizeBucket(bytes) }, seconds);
+}
+
+export function observeCollabLoad(bytes: number, seconds: number): void {
+  collabLoadHist?.observe({ size_bucket: sizeBucket(bytes) }, seconds);
+}
+
+/**
+ * Register the live open-document count source for the collab_docs_open gauge.
+ * Called ONCE, gated by isMetricsEnabled(), by the collaboration gateway. The
+ * gauge reads this on every scrape (collect()); nothing inc/dec's it.
+ */
+export function registerDocsOpenSource(fn: () => number): void {
+  docsOpenSource = fn;
+}
+
+export function incDocLoad(): void {
+  docLoadsCounter?.inc();
+}
+
+export function incDocUnload(): void {
+  docUnloadsCounter?.inc();
+}
+
+export function incConnectTimeout(): void {
+  connectTimeoutsCounter?.inc();
+}
+
+export function observeCollabConnect(seconds: number): void {
+  collabConnectHist?.observe(seconds);
+}
+
+export function observeCollabAuth(seconds: number): void {
+  collabAuthHist?.observe(seconds);
+}
+
+export function observeMcpTool(tool: string, seconds: number): void {
+  // `tool` MUST be a bounded, registration-derived MCP tool name (the caller
+  // guarantees it comes from the registered-tool set) — never free-form input —
+  // so this label stays low-cardinality with no 'other' bucketing needed.
+  mcpToolHist?.observe({ tool }, seconds);
 }

apps/server/src/integrations/metrics/metrics.spec.ts

@@ -1,6 +1,23 @@
 import { FastifyRequest } from 'fastify';
 import { resolveRouteLabel } from './http-metrics.hook';
-import { firstSqlToken, isStreamingResponse } from './metrics.constants';
+import {
+  firstSqlToken,
+  isStreamingResponse,
+  sizeBucket,
+} from './metrics.constants';
+import {
+  getMetricsRegistry,
+  incConnectTimeout,
+  incDocLoad,
+  incDocUnload,
+  isMetricsEnabled,
+  observeCollabAuth,
+  observeCollabConnect,
+  observeCollabLoad,
+  observeCollabStore,
+  observeMcpTool,
+  registerDocsOpenSource,
+} from './metrics.registry';
 
 describe('resolveRouteLabel (histogram route label)', () => {
   it('uses the ROUTE TEMPLATE, never the raw URL', () => {
@@ -123,3 +140,67 @@ describe('firstSqlToken (bounded db label)', () => {
     expect(firstSqlToken('vacuum analyze')).toBe('other');
   });
 });
+
+describe('sizeBucket (#402 bounded size label)', () => {
+  it('maps sizes to the four fixed buckets at their boundaries', () => {
+    // Boundaries are exclusive-upper: <65536 → lt64k, etc.
+    expect(sizeBucket(0)).toBe('lt64k');
+    expect(sizeBucket(65535)).toBe('lt64k');
+    expect(sizeBucket(65536)).toBe('lt256k');
+    expect(sizeBucket(262143)).toBe('lt256k');
+    expect(sizeBucket(262144)).toBe('lt1m');
+    expect(sizeBucket(1048575)).toBe('lt1m');
+    expect(sizeBucket(1048576)).toBe('ge1m');
+    expect(sizeBucket(5_000_000)).toBe('ge1m');
+  });
+
+  it('falls back to the smallest bucket for invalid sizes', () => {
+    // Non-finite / negative / nullish collapse to the smallest, safe default.
+    expect(sizeBucket(-1)).toBe('lt64k');
+    expect(sizeBucket(NaN)).toBe('lt64k');
+    expect(sizeBucket(Infinity)).toBe('lt64k');
+    expect(sizeBucket(undefined)).toBe('lt64k');
+    expect(sizeBucket(null)).toBe('lt64k');
+  });
+
+  it('only ever returns one of the four fixed labels (bounded cardinality)', () => {
+    const labels = new Set(
+      [0, 65536, 262144, 1048576, -5, NaN].map((b) => sizeBucket(b)),
+    );
+    for (const l of labels) {
+      expect(['lt64k', 'lt256k', 'lt1m', 'ge1m']).toContain(l);
+    }
+  });
+});
+
+describe('metrics helpers are safe no-ops when METRICS_PORT is unset', () => {
+  // These specs run without METRICS_PORT, so the registry is never created and
+  // every observe/inc/set helper must be a cheap `?.` no-op that never throws.
+  beforeAll(() => {
+    // Guard the contract this suite depends on: if a CI env set METRICS_PORT,
+    // the assertions below would be meaningless, so fail loudly instead.
+    expect(process.env.METRICS_PORT).toBeUndefined();
+  });
+
+  it('reports metrics disabled and a null registry', () => {
+    expect(isMetricsEnabled()).toBe(false);
+    expect(getMetricsRegistry()).toBeNull();
+  });
+
+  it('does not throw from any #402 collab/MCP helper', () => {
+    expect(() => {
+      observeCollabLoad(123456, 0.01);
+      observeCollabStore(123456, 0.02);
+      observeCollabConnect(0.03);
+      observeCollabAuth(0.04);
+      observeMcpTool('some-tool', 0.05);
+      incDocLoad();
+      incDocUnload();
+      incConnectTimeout();
+      // Registering a source must not create the gauge or invoke the fn.
+      registerDocsOpenSource(() => {
+        throw new Error('docsOpenSource must NOT be called when disabled');
+      });
+    }).not.toThrow();
+  });
+});

apps/server/src/integrations/queue/constants/queue.constants.ts

@@ -61,6 +61,9 @@ export enum QueueJob {
 
   COMMENT_NOTIFICATION = 'comment-notification',
   COMMENT_RESOLVED_NOTIFICATION = 'comment-resolved-notification',
+  // #399: off-critical-path mirror of a comment's inline mark into the collab
+  // Y.Doc (resolve/unresolve flip, or ephemeral-suggestion anchor removal).
+  COMMENT_MARK_UPDATE = 'comment-mark-update',
   PAGE_MENTION_NOTIFICATION = 'page-mention-notification',
   PAGE_PERMISSION_GRANTED = 'page-permission-granted',
   PAGE_UPDATE_DIGEST = 'page-update-digest',

apps/server/src/integrations/queue/constants/queue.interface.ts

@@ -63,6 +63,33 @@ export interface ICommentNotificationJob {
   notifyWatchers: boolean;
 }
 
+/**
+ * GENERAL_QUEUE payload for the off-critical-path comment inline-mark mirror
+ * (#399). The comment DB row is the source of truth and is already updated
+ * synchronously (ms); this job flips/removes the inline `comment` mark in the
+ * collaborative Y.Doc for connected clients, OFF the HTTP response path, so
+ * `POST /api/comments/resolve` no longer waits the whole Y.Doc load + store
+ * pipeline (was ~4.5s p95). The mark op is idempotent, so BullMQ retries are
+ * safe.
+ *
+ * `action`:
+ *   - 'resolve' / 'unresolve' → flip the mark's `resolved` attribute (exactly
+ *     what the synchronous resolveCommentMark path did);
+ *   - 'delete' → strip the anchor mark entirely (ephemeral suggestion #329).
+ * `ts` is the DB-mutation timestamp (ms). The worker's race-guard uses it (with
+ * the row's authoritative resolved state) to skip a resolve/unresolve event
+ * that a newer, opposite event has already superseded (out-of-order drain).
+ * `userId` supplies the connection-context user the store pipeline attributes
+ * the change to (persistence.extension reads context.user.id).
+ */
+export interface ICommentMarkUpdateJob {
+  documentName: string;
+  commentId: string;
+  action: 'resolve' | 'unresolve' | 'delete';
+  ts: number;
+  userId: string;
+}
+
 export interface ICommentResolvedNotificationJob {
   commentId: string;
   commentCreatorId: string;

apps/server/src/integrations/queue/processors/general-queue.processor.comment-mark.spec.ts

@@ -0,0 +1,151 @@
+import { Job } from 'bullmq';
+import { GeneralQueueProcessor } from './general-queue.processor';
+import { QueueJob } from '../constants';
+import { ICommentMarkUpdateJob } from '../constants/queue.interface';
+
+/**
+ * #399: the GENERAL_QUEUE worker replays the comment inline-mark op that used to
+ * run synchronously on the HTTP path. It must call the SAME gateway handler with
+ * the SAME semantics (resolve/unresolve → flip the `resolved` attribute; delete
+ * → strip the anchor), and its timestamp race-guard must skip an event a newer,
+ * opposite event already superseded.
+ */
+describe('GeneralQueueProcessor — COMMENT_MARK_UPDATE (#399)', () => {
+  function makeProc() {
+    const collaborationGateway: any = {
+      handleYjsEvent: jest.fn(async () => undefined),
+    };
+    const commentRepo: any = { findById: jest.fn() };
+    // #399: the processor resolves CollaborationGateway lazily via ModuleRef
+    // (strict:false) to avoid a DI cycle; the fake returns our gateway spy.
+    const moduleRef: any = { get: jest.fn(() => collaborationGateway) };
+    const proc = new GeneralQueueProcessor(
+      {} as any, // db
+      {} as any, // backlinkRepo
+      {} as any, // watcherRepo
+      commentRepo,
+      moduleRef,
+    );
+    return { proc, collaborationGateway, commentRepo };
+  }
+
+  const job = (data: ICommentMarkUpdateJob): Job =>
+    ({ name: QueueJob.COMMENT_MARK_UPDATE, data }) as unknown as Job;
+
+  const base = {
+    documentName: 'page.page-1',
+    commentId: 'c-1',
+    userId: 'user-1',
+  };
+
+  it('resolve → resolveCommentMark with resolved:true and the same-shape args', async () => {
+    const { proc, collaborationGateway, commentRepo } = makeProc();
+    const ts = 1000;
+    // Row reflects the resolve (source of truth), stamped at the same ts.
+    commentRepo.findById.mockResolvedValue({
+      id: 'c-1',
+      resolvedAt: new Date(ts),
+      updatedAt: new Date(ts),
+    });
+
+    await proc.process(job({ ...base, action: 'resolve', ts }));
+
+    expect(collaborationGateway.handleYjsEvent).toHaveBeenCalledTimes(1);
+    expect(collaborationGateway.handleYjsEvent).toHaveBeenCalledWith(
+      'resolveCommentMark',
+      'page.page-1',
+      { commentId: 'c-1', resolved: true, user: { id: 'user-1' } },
+    );
+  });
+
+  it('unresolve → resolveCommentMark with resolved:false', async () => {
+    const { proc, collaborationGateway, commentRepo } = makeProc();
+    const ts = 2000;
+    commentRepo.findById.mockResolvedValue({
+      id: 'c-1',
+      resolvedAt: null,
+      updatedAt: new Date(ts),
+    });
+
+    await proc.process(job({ ...base, action: 'unresolve', ts }));
+
+    expect(collaborationGateway.handleYjsEvent).toHaveBeenCalledWith(
+      'resolveCommentMark',
+      'page.page-1',
+      { commentId: 'c-1', resolved: false, user: { id: 'user-1' } },
+    );
+  });
+
+  it('delete → deleteCommentMark (strip the anchor), no row lookup / no state guard', async () => {
+    const { proc, collaborationGateway, commentRepo } = makeProc();
+
+    await proc.process(job({ ...base, action: 'delete', ts: 123 }));
+
+    expect(collaborationGateway.handleYjsEvent).toHaveBeenCalledWith(
+      'deleteCommentMark',
+      'page.page-1',
+      { commentId: 'c-1', user: { id: 'user-1' } },
+    );
+    // Delete carries no state guard — the row is (being) removed.
+    expect(commentRepo.findById).not.toHaveBeenCalled();
+  });
+
+  it('SKIPS a stale resolve superseded by a newer unresolve (row unresolved, job ts older)', async () => {
+    const { proc, collaborationGateway, commentRepo } = makeProc();
+    // A later unresolve already set the row: resolvedAt null, updatedAt = 5000.
+    commentRepo.findById.mockResolvedValue({
+      id: 'c-1',
+      resolvedAt: null,
+      updatedAt: new Date(5000),
+    });
+
+    // Stale resolve job enqueued at ts=1000 (< 5000), intends resolved=true,
+    // but the row's authoritative state is unresolved → skip.
+    await proc.process(job({ ...base, action: 'resolve', ts: 1000 }));
+
+    expect(collaborationGateway.handleYjsEvent).not.toHaveBeenCalled();
+  });
+
+  it('SKIPS a stale unresolve superseded by a newer resolve', async () => {
+    const { proc, collaborationGateway, commentRepo } = makeProc();
+    commentRepo.findById.mockResolvedValue({
+      id: 'c-1',
+      resolvedAt: new Date(5000),
+      updatedAt: new Date(5000),
+    });
+
+    await proc.process(job({ ...base, action: 'unresolve', ts: 1000 }));
+
+    expect(collaborationGateway.handleYjsEvent).not.toHaveBeenCalled();
+  });
+
+  it('applies when the row state agrees even if ts is older (idempotent, not a stale flip)', async () => {
+    const { proc, collaborationGateway, commentRepo } = makeProc();
+    // Row is resolved and its updatedAt is newer than the job ts, but the state
+    // AGREES with the job → this is a harmless idempotent replay, not a stale
+    // opposite event, so it must still apply.
+    commentRepo.findById.mockResolvedValue({
+      id: 'c-1',
+      resolvedAt: new Date(9000),
+      updatedAt: new Date(9000),
+    });
+
+    await proc.process(job({ ...base, action: 'resolve', ts: 1000 }));
+
+    expect(collaborationGateway.handleYjsEvent).toHaveBeenCalledWith(
+      'resolveCommentMark',
+      'page.page-1',
+      { commentId: 'c-1', resolved: true, user: { id: 'user-1' } },
+    );
+  });
+
+  it('skips (no throw) when the comment row has vanished', async () => {
+    const { proc, collaborationGateway, commentRepo } = makeProc();
+    commentRepo.findById.mockResolvedValue(undefined);
+
+    await expect(
+      proc.process(job({ ...base, action: 'resolve', ts: 1000 })),
+    ).resolves.toBeUndefined();
+    expect(collaborationGateway.handleYjsEvent).not.toHaveBeenCalled();
+  });
+});

apps/server/src/integrations/queue/processors/general-queue.processor.ts

@@ -4,6 +4,7 @@ import { Job } from 'bullmq';
 import { QueueJob, QueueName } from '../constants';
 import {
   IAddPageWatchersJob,
+  ICommentMarkUpdateJob,
   IPageBacklinkJob,
 } from '../constants/queue.interface';
 import { InjectKysely } from 'nestjs-kysely';
@@ -13,8 +14,11 @@ import {
   WatcherRepo,
   WatcherType,
 } from '@docmost/db/repos/watcher/watcher.repo';
-import { InsertableWatcher } from '@docmost/db/types/entity.types';
+import { InsertableWatcher, User } from '@docmost/db/types/entity.types';
 import { processBacklinks } from '../tasks/backlinks.task';
+import { ModuleRef } from '@nestjs/core';
+import { CollaborationGateway } from '../../../collaboration/collaboration.gateway';
+import { CommentRepo } from '@docmost/db/repos/comment/comment.repo';
 
 @Processor(QueueName.GENERAL_QUEUE)
 export class GeneralQueueProcessor
@@ -22,14 +26,32 @@ export class GeneralQueueProcessor
   implements OnModuleDestroy
 {
   private readonly logger = new Logger(GeneralQueueProcessor.name);
+  // #399: CollaborationGateway lives in CollaborationModule. We resolve it lazily
+  // via ModuleRef instead of importing that module into the @Global QueueModule —
+  // CollaborationModule's own HistoryProcessor injects this module's global
+  // GENERAL_QUEUE token, so a static import edge here would form a DI cycle. A
+  // lazy strict:false lookup (cached) sidesteps it; the gateway is a singleton in
+  // both the API-server and collab processes that run this worker.
+  private collaborationGateway?: CollaborationGateway;
   constructor(
     @InjectKysely() private readonly db: KyselyDB,
     private readonly backlinkRepo: BacklinkRepo,
     private readonly watcherRepo: WatcherRepo,
+    private readonly commentRepo: CommentRepo,
+    private readonly moduleRef: ModuleRef,
   ) {
     super();
   }
 
+  private getCollaborationGateway(): CollaborationGateway {
+    if (!this.collaborationGateway) {
+      this.collaborationGateway = this.moduleRef.get(CollaborationGateway, {
+        strict: false,
+      });
+    }
+    return this.collaborationGateway;
+  }
+
   async process(job: Job): Promise<void> {
     try {
       switch (job.name) {
@@ -56,12 +78,87 @@ export class GeneralQueueProcessor
           );
           break;
         }
+
+        case QueueJob.COMMENT_MARK_UPDATE: {
+          await this.processCommentMarkUpdate(
+            job.data as ICommentMarkUpdateJob,
+          );
+          break;
+        }
       }
     } catch (err) {
       throw err;
     }
   }
 
+  /**
+   * #399: apply a comment's inline-mark mirror in the collab Y.Doc, off the HTTP
+   * critical path. Runs the SAME gateway path the synchronous comment.service
+   * code used (byte-identical mark op):
+   *   - resolve / unresolve → resolveCommentMark (flip the `resolved` attribute);
+   *   - delete → deleteCommentMark (strip the ephemeral-suggestion anchor #329).
+   * The op is idempotent, so a BullMQ retry is safe. Throwing propagates to
+   * WorkerHost → the job is retried and, on exhaustion, surfaces in failed-job
+   * metrics (the divergence is now visible rather than a silently-swallowed warn).
+   */
+  private async processCommentMarkUpdate(
+    data: ICommentMarkUpdateJob,
+  ): Promise<void> {
+    const { documentName, commentId, action, ts, userId } = data;
+    // Minimal connection-context user: the store pipeline reads context.user.id
+    // to attribute the change (persistence.extension). The mark mutation itself
+    // does not depend on the user, so the op stays byte-identical. Deliberate
+    // trade-off: the store pipeline's transient `page.updated` broadcast carries
+    // only { id } here, so its live "who edited" badge loses name/avatarUrl for
+    // this async mark replay. lastUpdatedById is still set correctly; the diff is
+    // cosmetic and self-heals on the next real edit — worth it to stay off the
+    // HTTP path and avoid re-loading the users row.
+    const user = { id: userId } as User;
+
+    if (action === 'delete') {
+      await this.getCollaborationGateway().handleYjsEvent(
+        'deleteCommentMark',
+        documentName,
+        { commentId, user },
+      );
+      return;
+    }
+
+    // resolve / unresolve. The comment row is written SYNCHRONOUSLY before this
+    // job is enqueued, so it is the source of truth for the final resolved state
+    // and its updatedAt records when that state last changed. Race-guard: if a
+    // newer, OPPOSITE event has already superseded this one (its ts is older than
+    // the row's last resolve-state mutation AND the row's current resolved state
+    // disagrees with what this job intends — e.g. an unresolve that drained ahead
+    // of this resolve), skip it rather than flip the mark to a stale state.
+    const comment = await this.commentRepo.findById(commentId);
+    if (!comment) {
+      // The comment vanished (e.g. hard-deleted) → nothing left to mirror.
+      return;
+    }
+    const wantResolved = action === 'resolve';
+    const rowResolved = comment.resolvedAt != null;
+    const rowMutatedAt = new Date(comment.updatedAt).getTime();
+    // `<=`, not `<`: on a sub-millisecond tie (two opposite toggles stamped in
+    // the same ms) skip the disagreeing job rather than let queue order decide.
+    // The consistent job (whose intent matches the row) short-circuits on the
+    // first condition, so a real update is never dropped; only a mark that both
+    // disagrees with the row AND is no newer than it is discarded.
+    if (rowResolved !== wantResolved && ts <= rowMutatedAt) {
+      this.logger.debug(
+        `Skipping stale comment mark '${action}' for ${commentId} ` +
+          `(job ts ${ts} < row ${rowMutatedAt}, row resolved=${rowResolved})`,
+      );
+      return;
+    }
+
+    await this.getCollaborationGateway().handleYjsEvent(
+      'resolveCommentMark',
+      documentName,
+      { commentId, resolved: wantResolved, user },
+    );
+  }
+
   @OnWorkerEvent('active')
   onActive(job: Job) {
     this.logger.debug(`Processing ${job.name} job`);

apps/server/src/main.ts

@@ -21,10 +21,24 @@ import { recordHttpResponse } from './integrations/metrics/http-metrics.hook';
 import { startMetricsServer } from './integrations/metrics/metrics.server';
 
 async function bootstrap() {
+  // Fastify JSON body cap. Fastify defaults to 1 MiB, which a long AI-chat
+  // research turn exceeds: the client resends the FULL message history (every
+  // tool call + search result) on each turn, so a deep conversation's POST to
+  // /api/ai-chat/stream can be several MB and would otherwise be rejected with
+  // FST_ERR_CTP_BODY_TOO_LARGE (413). Raise the cap; override with
+  // HTTP_JSON_BODY_LIMIT (bytes). A missing/invalid/non-positive value keeps the
+  // 25 MiB default. Multipart uploads are unaffected (their own @fastify/multipart
+  // limits apply); this only bounds JSON/urlencoded request bodies.
+  const bodyLimitEnv = Number(process.env.HTTP_JSON_BODY_LIMIT);
+  const bodyLimit =
+    Number.isFinite(bodyLimitEnv) && bodyLimitEnv > 0
+      ? bodyLimitEnv
+      : 25 * 1024 * 1024;
   const app = await NestFactory.create<NestFastifyApplication>(
     AppModule,
     new FastifyAdapter({
       trustProxy: resolveTrustProxy(process.env.TRUST_PROXY),
+      bodyLimit,
       routerOptions: {
         maxParamLength: 1000,
         ignoreTrailingSlash: true,

docs/reading-ai-logs.md

@@ -0,0 +1,308 @@
+# Reading the AI dialog logs (how agents call tools, and where they fail)
+
+How to inspect the agent conversation history in the database — and, more
+importantly, the **one non-obvious trap that will make you report the wrong
+answer**: the persisted history *silently hides hard tool failures*. Written from
+real pain (a "which tools fail most?" analysis that confidently answered
+"patchNode: 0 errors" while the UI was visibly full of red `patchNode` failures).
+
+Read the **Gotchas** section before you trust any error count.
+
+## TL;DR
+
+- Agent chats live in Postgres, DB `docmost`, tables `ai_chat_*`.
+- Each tool invocation is stored as **two** array elements (a `tool-call` part and
+  a `tool-result` part), so naive counting double-counts.
+- **A tool that *throws* writes no result part.** Since the #407 fix its error is
+  persisted as a dedicated `{toolName, error}` element in `tool_calls` (queryable +
+  replayed to the model). **Rows written before #407 still drop it** — the error is
+  nowhere in the DB and shows only in the live UI. So `isError` / `success=false`
+  scans under-report by design, and pre-#407 thrown errors are invisible.
+- To find where agents fail: (1) soft-failure markers in `tool_calls`, (2) the new
+  `error` field for thrown errors (new rows) / the orphan-gap proxy (old rows),
+  (3) server logs / the live UI for full stack traces beyond the truncated message.
+
+## Where the data lives
+
+Host `island.lc` (`10.31.40.120`), container `gitmost-postgresql`
+(`pgvector/pgvector:pg18`), database `docmost`.
+
+```bash
+ssh island.lc
+# one-off query:
+docker exec gitmost-postgresql psql -U docmost -d docmost -P pager=off -c "SELECT ..."
+# interactive:
+docker exec -it gitmost-postgresql psql -U docmost -d docmost
+```
+
+The main app container is `gitmost` (`DATABASE_URL=postgresql://docmost:...@db:5432/docmost`).
+All workspaces (vvzvlad / wb / asakusa / …) share this **single** database — they
+are rows in `workspaces`, not separate deployments.
+
+### Relevant tables
+
+| Table | What it holds |
+| --- | --- |
+| `ai_chats` | one row per conversation (`title`, `role_id`, `page_id`, `creator_id`) |
+| `ai_chat_messages` | every message; tool calls live in `tool_calls` jsonb |
+| `ai_chat_runs` | one row per agent run (turn): `status`, `error`, `step_count` |
+| `ai_agent_roles` | agent definitions (`instructions`, `model_config`) |
+| `ai_mcp_servers` | configured MCP tool servers per workspace |
+
+`ai_chat_messages` columns that matter: `role` (`user` | `assistant` — there is **no**
+separate `tool` role), `content` (text), `tool_calls` (jsonb array), `metadata`
+(jsonb, holds run `error` + rendered `parts`), `status`, `tsv` (full-text index).
+
+## How tool calls are stored — READ THIS
+
+Tool calls are **not** one-object-per-call. Each logical invocation is split into
+two consecutive elements of the `tool_calls` array:
+
+```text
+index 0: { "toolName": "getPage",  "input":  { "pageId": "…" } }   ← tool-call   (has input, NO output)
+index 1: { "toolName": "getPage",  "output": { … } }                ← tool-result (has output, NO input)
+```
+
+The keys that appear on an element are `toolName`, `input`, `output`, and — for a
+**thrown** failure on rows written after the #407 fix — `error` (the tool's error
+message; see the "Hard failures" section below). There is no `state`, no `errorText`,
+no `type`. On pre-#407 rows a thrown failure has NO paired result element at all
+(silent orphan). Consequences:
+
+1. **Real invocation count = elements that have `output` or `error`.** Counting every
+   element double-counts (you get ~2× and a spurious "~50% of every tool has no output").
+2. **Pairing:** a call = a `tool-call` part followed by its result part. A success
+   carries `output`; a thrown failure (post-#407) carries `error` instead. Both carry
+   `toolName`, so you can group by tool on either.
+
+## The two classes of failure (and which the DB can see)
+
+### 1. Soft failures — tool RAN and returned an error-shaped result → PERSISTED ✅
+
+These are visible in the `tool-result` `output`. The marker differs per tool:
+
+| Tool(s) | Error marker in `output` |
+| --- | --- |
+| `editPageText` | `failed` is a **non-empty** array of `{find, reason}` (e.g. `text not found in the document`, `matches N times — provide a longer fragment or set replaceAll`). Also a soft `warning` when the `find` string contained markdown that only matched after stripping. |
+| `semanticSearch` | `{ "unavailable": true, "reason": "semantic search unavailable" }` (feature/infra, not the agent's fault) |
+| MCP passthrough (`Habr_*`, some `Search_*`) | `output` is an **array** (raw MCP content) whose text starts with `Error executing tool … validation error …` |
+| generic | `output.isError = true` or `output.success = false` |
+
+Note `editPageText` returns `failed: []` on success — filtering on the *presence*
+of the key gives false positives; filter on **non-empty**.
+
+### 2. Hard failures — tool THREW → NOW PERSISTED ✅ (since the #407 fix)
+
+When a tool throws (the classic one is `patchNode` / `insertNode` / `tableUpdateCell`
+→ `Failed to encode document to Yjs (fromJSON): Unknown node type: undefined`), the
+runtime still writes **no `tool-result` part** — the failure is an ai@6 `tool-error`
+content part instead. **Since the #407 fix, that error is persisted**: `serializeSteps`
+appends a dedicated element `{toolName, error: "<message>"}` right after the failed
+call, mirroring how a successful `{toolName, output}` element is appended. So a thrown
+error now leaves a queryable `error` field carrying its (truncated) reason, and the
+same real text is replayed to the model on the next turn (an `output-error` part with
+the real `errorText`, no longer the `'Tool call did not complete.'` placeholder).
+
+**Cutover caveat — old rows keep the old blind shape.** Rows written **before** this
+change have the two-part shape (`call` + `output` only) and simply **drop** thrown
+errors, leaving a silent **orphan** (a `call` with no `output` *and* no `error`). Rows
+written **after** the fix additionally carry the `error` element. So:
+
+- **New rows:** query the `error` field directly (see the hard-error query below) — no
+  orphan heuristic needed for thrown failures.
+- **Old rows (pre-#407):** the only DB-side proxy is still an **orphan**: a `tool-call`
+  part with no matching `tool-result` *and* no `error`. Orphans also appear when a run
+  is **aborted** mid-flight (server restart), so a high-volume tool (`createComment`,
+  `searchInPage`, `Search_web_search`) shows orphans from aborts, not real errors on
+  old rows. Treat the orphan gap as an *upper bound*, and cross-check the tool: a gap on
+  a structural editor (`patchNode`, `insertNode`, `updatePageJson`, `transformPage`) is
+  almost certainly a thrown Yjs-encode error; a gap on `createComment` is mostly aborts.
+
+A note on the aborted-call fallback: a call with **neither** a result **nor** a
+`tool-error` (genuinely interrupted mid-step) still replays with the
+`'Tool call did not complete.'` placeholder and persists as an orphan — that path is
+unchanged, and is distinct from a real thrown error, which now carries `error`.
+
+### 3. Run-level failures → `ai_chat_runs`
+
+`status` ∈ `succeeded | aborted | failed | running`; `error` holds the text. Seen in
+the wild: `Run interrupted by a server restart.` (aborts) and
+`Failed after N attempts. Last error: The service may be temporarily overloaded`
+(LLM provider 529). These are infra/provider, not agent tool misuse.
+
+## Ready-to-use queries
+
+Run all of these via `docker exec gitmost-postgresql psql -U docmost -d docmost -P pager=off -c "…"`.
+
+**Real invocation count per tool** (result parts only — the correct denominator):
+
+```sql
+SELECT elem->>'toolName' AS tool, count(*) AS calls
+FROM ai_chat_messages m, jsonb_array_elements(m.tool_calls) elem
+WHERE jsonb_typeof(m.tool_calls) = 'array' AND elem ? 'output'
+GROUP BY 1 ORDER BY 2 DESC;
+```
+
+**Soft errors per tool** (everything the DB can honestly see):
+
+```sql
+WITH res AS (
+  SELECT elem->>'toolName' AS tool, elem->'output' AS o
+  FROM ai_chat_messages m, jsonb_array_elements(m.tool_calls) elem
+  WHERE jsonb_typeof(m.tool_calls) = 'array' AND elem ? 'output'
+)
+SELECT tool, count(*) AS calls,
+       sum(COALESCE(
+         (o->>'isError') = 'true'
+         OR (o->>'success') = 'false'
+         OR (jsonb_typeof(o->'failed') = 'array' AND o->'failed' <> '[]'::jsonb)
+         OR (o->>'unavailable') = 'true'
+         OR o::text ~* 'error executing tool|validation error'
+       , false)::int) AS soft_errors
+FROM res GROUP BY tool HAVING sum(COALESCE(
+         (o->>'isError') = 'true' OR (o->>'success') = 'false'
+         OR (jsonb_typeof(o->'failed') = 'array' AND o->'failed' <> '[]'::jsonb)
+         OR (o->>'unavailable') = 'true' OR o::text ~* 'error executing tool|validation error'
+       , false)::int) > 0
+ORDER BY soft_errors DESC;
+```
+
+**`editPageText` failure reasons** (the most common real agent mistake — bad `find`):
+
+```sql
+WITH res AS (
+  SELECT elem->'output' AS o
+  FROM ai_chat_messages m, jsonb_array_elements(m.tool_calls) elem
+  WHERE jsonb_typeof(m.tool_calls) = 'array'
+    AND elem->>'toolName' = 'editPageText' AND elem ? 'output'
+)
+SELECT f->>'reason' AS reason, count(*)
+FROM res, jsonb_array_elements(o->'failed') f
+WHERE jsonb_typeof(o->'failed') = 'array'
+GROUP BY 1 ORDER BY 2 DESC;
+```
+
+**Hard errors — persisted `error` field per tool (NEW rows, since #407)** — thrown
+tool failures now carry their real reason, so query them directly:
+
+```sql
+SELECT elem->>'toolName' AS tool, count(*) AS thrown_errors,
+       min(elem->>'error') AS sample_error
+FROM ai_chat_messages m, jsonb_array_elements(m.tool_calls) elem
+WHERE jsonb_typeof(m.tool_calls) = 'array' AND elem ? 'error'
+GROUP BY 1 ORDER BY 2 DESC;
+```
+
+**Hard-error proxy for OLD rows (pre-#407) — orphan gap per tool, WITH a spread column**
+(call parts minus result parts, plus how many distinct chats the gap is spread across).
+This covers rows written before thrown errors were persisted; on new rows a thrown
+failure now has its own `error` element (use the query above) and an orphan means only
+a genuinely aborted mid-step call:
+
+```sql
+WITH parts AS (
+  SELECT m.chat_id, elem->>'toolName' AS tool,
+         (elem ? 'input' AND NOT (elem ? 'output')) AS is_call,
+         (elem ? 'output' OR elem ? 'error')        AS is_result
+  FROM ai_chat_messages m, jsonb_array_elements(m.tool_calls) elem
+  WHERE jsonb_typeof(m.tool_calls) = 'array' AND m.role = 'assistant'
+),
+per_chat AS (
+  SELECT tool, chat_id, sum(is_call::int) - sum(is_result::int) AS gap
+  FROM parts GROUP BY tool, chat_id
+)
+SELECT tool,
+       sum(gap) FILTER (WHERE gap > 0)   AS missing_results,
+       count(*) FILTER (WHERE gap > 0)   AS chats_spread,   -- disambiguates!
+       max(gap)                          AS worst_single_chat
+FROM per_chat GROUP BY tool
+HAVING sum(gap) FILTER (WHERE gap > 0) > 0
+ORDER BY missing_results DESC;
+```
+
+The `is_result` predicate counts an `error` element as a paired result too, so on new
+rows a persisted thrown error no longer inflates the orphan gap; a remaining gap is an
+aborted/interrupted call.
+
+**On OLD rows, `missing_results` mixes thrown errors AND aborted/interrupted runs — you
+cannot split them from `output` alone** (a positional "what follows the orphan" heuristic
+breaks on parallel tool batches, which persist as `call,call,…,result,result`). Use
+`chats_spread` to disambiguate:
+
+- **spread across many chats** (e.g. `createComment` 96 over 29 chats) → a **systemic
+  real error** (here: inline-comment anchor text not found on the page).
+- **concentrated in one chat** (e.g. `searchInPage` 55, of which 51 in a single chat)
+  → **one runaway/aborted session**, not a real per-call error — discount it.
+- a gap on a **structural editor** (`patchNode`, `insertNode`, `tableUpdateCell`,
+  `updatePageJson`, `transformPage`) is almost always a thrown Yjs-encode error.
+
+**Run-level failures:**
+
+```sql
+SELECT status, count(*), min(error) AS sample_error
+FROM ai_chat_runs GROUP BY status ORDER BY 2 DESC;
+```
+
+**Full-text search across messages.** The `tsv` GIN index is built as
+`to_tsvector('english', unaccent(content))` — so it **stems English** but **not
+Russian** (Russian lexemes are stored unstemmed, so only exact word forms match).
+Most content here is Russian, so prefer `ILIKE` for substring search:
+
+```sql
+-- Russian / substring — reliable:
+SELECT chat_id, left(content, 120)
+FROM ai_chat_messages WHERE content ILIKE '%иранск%' LIMIT 20;
+
+-- English phrase — can use the index:
+SELECT chat_id, left(content, 120)
+FROM ai_chat_messages
+WHERE tsv @@ websearch_to_tsquery('english', 'some phrase') LIMIT 20;
+```
+
+## Don't blow up your context
+
+A single `tool_calls` row can be **300–400 KB** (results embed full page content and
+search payloads). Never `SELECT tool_calls` (or `jsonb_pretty(tool_calls)`) raw.
+Always project just the keys you need and truncate:
+
+```sql
+SELECT elem->>'toolName',
+       left(regexp_replace((elem->'output')::text, '\s+', ' ', 'g'), 200)
+FROM ai_chat_messages m, jsonb_array_elements(m.tool_calls) elem
+WHERE elem ? 'output' LIMIT 5;
+```
+
+## Server logs & live UI (for the error text the DB drops)
+
+```bash
+docker logs -f --tail=100 gitmost            # main app
+docker compose -p gitmost logs -f --tail=100 # whole stack
+```
+
+Logging is `json-file`, `max-size=10m max-file=5` → ~50 MB retained, then rotated,
+and **wiped on container recreate**. Since the #407 fix, thrown-tool error text is
+**persisted in the `error` field** of `tool_calls` (see the hard-error query above), so
+you no longer depend on live logs for it. Logs/live UI remain useful for **pre-#407
+rows** (whose thrown errors were dropped) and for full stack traces beyond the
+truncated stored message. A per-tool `tool_calls_total{tool,status}` metric to
+VictoriaMetrics is still a possible future add for aggregate dashboards.
+
+## Gotchas checklist
+
+- [ ] Counting every `tool_calls` element → **overcount**. Count `output` elements; add `error` elements for thrown failures (new rows), but don't count both as invocations.
+- [ ] `isError` / `success=false` ≈ 0 does **not** mean "no errors" — thrown errors are a separate `error` element (new rows) or dropped entirely (pre-#407 rows).
+- [ ] Thrown errors persist only on rows written **after the #407 fix** — pre-#407 rows still drop them (orphan only). Mind the cutover when trending over time.
+- [ ] `editPageText.failed` is `[]` on success — test for **non-empty**, not presence.
+- [ ] Orphan gap on OLD rows mixes thrown errors **and** aborted runs — split by tool. On NEW rows a thrown error is its own `error` element, so a gap ≈ aborted call.
+- [ ] `aborted` runs = server restarts, `failed` runs = provider overload — not agent mistakes.
+- [ ] Never dump a raw `tool_calls` cell — it can be hundreds of KB.
+- [ ] Logs are ephemeral (≤50 MB, wiped on recreate) — grab hard-error text live.
+
+## Snapshot (2026-07-07, illustrative — rerun the queries for current numbers)
+
+- 226 chats, 732 messages, 46 runs; ~4 400 real tool invocations.
+- Soft errors (persisted): `editPageText` 4/79 (bad/non-unique `find`) + 9 markdown-in-`find` warnings; `semanticSearch` 3/4 (`unavailable`); `Habr_update_draft_from_docmost` 1/2 (`doc` sent as object, not string).
+- Missing-result proxy, read WITH the spread column:
+  - **Systemic (spread) → real errors:** `createComment` 96 over **29 chats** (comment anchor text not found — the biggest real error hotspot); `editPageText` 31 over 12 chats (+ the 4 soft above); structural-editor Yjs throws `insertNode` 10 / `updatePageContent` 9 / `tableUpdateCell` 6 / `patchNode` 5 / `updatePageJson` 2 / `transformPage` 2.
+  - **Concentrated → NOT real errors:** `searchInPage` 55 (51 in one chat); `Search_web_search` 15 & `Search_searxng_web_search` 6 (timeouts/aborts in long research sessions).
+- Runs: 34 succeeded, 10 aborted (server restart), 1 failed (provider overload).

package.json

@@ -97,7 +97,8 @@
     "patchedDependencies": {
       "scimmy@1.3.5": "patches/scimmy@1.3.5.patch",
       "yjs@13.6.30": "patches/yjs@13.6.30.patch",
-      "ai@6.0.134": "patches/ai@6.0.134.patch"
+      "ai@6.0.134": "patches/ai@6.0.134.patch",
+      "@hocuspocus/server@3.4.4": "patches/@hocuspocus__server@3.4.4.patch"
     },
     "overrides": {
       "prosemirror-changeset": "2.4.0",

packages/mcp/package.json

@@ -52,6 +52,7 @@
     "form-data": "^4.0.0",
     "jsdom": "^27.4.0",
     "marked": "^17.0.1",
+    "pako": "^2.0.3",
     "re2": "^1.21.0",
     "ws": "^8.19.0",
     "y-prosemirror": "1.3.7",

packages/mcp/src/client.ts

@@ -8,10 +8,6 @@ import {
   filterComment,
   filterSearchResult,
 } from "./lib/filters.js";
-import { HocuspocusProvider } from "@hocuspocus/provider";
-import { TiptapTransformer } from "@hocuspocus/transformer";
-import * as Y from "yjs";
-import WebSocket from "ws";
 import { convertProseMirrorToMarkdown } from "./lib/markdown-converter.js";
 import {
   collectInternalFileNodes,
@@ -24,11 +20,10 @@ import {
   markdownToProseMirror,
   markdownToProseMirrorCanonical,
   mutatePageContent,
-  buildCollabWsUrl,
   assertYjsEncodable,
-  applyDocToFragment,
   MutationResult,
 } from "./lib/collaboration.js";
+import { acquireCollabSession } from "./lib/collab-session.js";
 import { footnoteWarningsField } from "./lib/footnote-analyze.js";
 import { buildPageTree } from "./lib/tree.js";
 import {
@@ -40,6 +35,7 @@ import {
   deleteNodeById,
   assertUnambiguousMatch,
   insertNodeRelative,
+  blockPlainText,
   buildOutline,
   getNodeByRef,
   readTable,
@@ -49,6 +45,15 @@ import {
 } from "./lib/node-ops.js";
 import { searchInDoc, SearchOptions } from "./lib/page-search.js";
 import { withPageLock } from "./lib/page-lock.js";
+import {
+  prepareModel,
+  decodeDrawioSvg,
+  buildDrawioSvg,
+  mxHash,
+  normalizeXml,
+  countUserCells,
+} from "./lib/drawio-xml.js";
+import { renderDiagramShapes } from "./lib/drawio-preview.js";
 import {
   applyTextEdits,
   TextEdit,
@@ -59,10 +64,12 @@ import { getCollabToken, performLogin } from "./lib/auth-utils.js";
 import { diffDocs, summarizeChange } from "./lib/diff.js";
 import {
   applyAnchorInDoc,
-  canAnchorInDoc,
   countAnchorMatches,
   getAnchoredText,
+  resolveAnchorSelection,
+  normalizeForMatch,
 } from "./lib/comment-anchor.js";
+import { closestBlockHint } from "./lib/text-normalize.js";
 import {
   blockText,
   walk,
@@ -137,6 +144,15 @@ export type DocmostMcpConfig = { apiUrl: string } & (
       has?: (uri: string) => boolean;
       evict?: (uri: string) => void;
     };
+    // Dependency-neutral metrics sink. When present, the client emits generic
+    // (name, value, labels) samples; the HOST maps those names onto its own
+    // metrics registry (the package never depends on prom-client or the server).
+    // Absent in standalone/stdio mode → the client is a complete no-op here.
+    onMetric?: (
+      name: string,
+      value: number,
+      labels?: Record<string, string>,
+    ) => void;
   };
 
 // Canonical UUID shape (versions 1–8, matching the `uuid` package's `validate`
@@ -173,6 +189,11 @@ export class DocmostClient {
   // op's image blobs if the final doc put throws. Null when the sink omits them.
   private sandboxHas: ((uri: string) => boolean) | null = null;
   private sandboxEvict: ((uri: string) => void) | null = null;
+  // Optional dependency-neutral metrics sink (see DocmostMcpConfig.onMetric).
+  // Null on the legacy positional form and whenever the host omits it → no-op.
+  private onMetricFn:
+    | ((name: string, value: number, labels?: Record<string, string>) => void)
+    | null = null;
   // In-flight login dedup: when the token expires, the 401 interceptor,
   // ensureAuthenticated, getCollabTokenWithReauth and the two multipart retries
   // can all call login() at once. Memoizing a single promise collapses that
@@ -222,6 +243,8 @@ export class DocmostClient {
       this.sandboxHas = config.sandbox.has ?? null;
       this.sandboxEvict = config.sandbox.evict ?? null;
     }
+    // Legacy positional form carries no onMetric → null (complete no-op).
+    this.onMetricFn = config.onMetric ?? null;
     this.client = axios.create({
       baseURL: this.apiUrl,
       // Default request timeout so a hung connection cannot wedge a per-page
@@ -401,173 +424,32 @@ export class DocmostClient {
    * change report. The report is computed AFTER the atomic read->write and
    * never throws.
    */
-  private mutateLiveContentUnlocked(
+  private async mutateLiveContentUnlocked(
     pageId: string,
     collabToken: string,
     transform: (liveDoc: any) => any | null,
   ): Promise<MutationResult> {
-    const CONNECT_TIMEOUT_MS = 25000;
-    const PERSIST_TIMEOUT_MS = 20000;
-    const ydoc = new Y.Doc();
-    const wsUrl = buildCollabWsUrl(this.apiUrl);
-
-    return new Promise<MutationResult>((resolve, reject) => {
-      let provider: HocuspocusProvider | undefined;
-      let applied = false; // onSynced may fire again on reconnect — apply once.
-      let settled = false;
-      let connectionLost = false;
-      let connectTimer: ReturnType<typeof setTimeout> | undefined;
-      let persistTimer: ReturnType<typeof setTimeout> | undefined;
-      let unsyncedHandler: ((data: { number: number }) => void) | undefined;
-      // The verifiable result resolved on every success/abort path. Set on abort
-      // (no-op report) and after a real write (computed change report).
-      let mutationResult: MutationResult;
-
-      const cleanup = () => {
-        if (connectTimer) clearTimeout(connectTimer);
-        if (persistTimer) clearTimeout(persistTimer);
-        if (provider) {
-          if (unsyncedHandler) {
-            try {
-              provider.off("unsyncedChanges", unsyncedHandler);
-            } catch (err) {}
-          }
-          try {
-            provider.destroy();
-          } catch (err) {}
-        }
-      };
-
-      const finish = (err: Error | null, value?: MutationResult) => {
-        if (settled) return;
-        settled = true;
-        cleanup();
-        if (err) reject(err);
-        else resolve(value as MutationResult);
-      };
-
-      connectTimer = setTimeout(() => {
-        finish(new Error("Connection timeout to collaboration server"));
-      }, CONNECT_TIMEOUT_MS);
-
-      const waitForPersistence = () => {
-        if (settled) return;
-        if (!provider) {
-          finish(new Error("collab provider gone before persistence"));
-          return;
-        }
-        if (provider.unsyncedChanges === 0) {
-          finish(null, mutationResult);
-          return;
-        }
-        persistTimer = setTimeout(() => {
-          finish(
-            new Error(
-              "Timeout waiting for collaboration server to persist the update",
-            ),
-          );
-        }, PERSIST_TIMEOUT_MS);
-        unsyncedHandler = (data: { number: number }) => {
-          if (data.number === 0 && !connectionLost) {
-            finish(null, mutationResult);
-          }
-        };
-        provider.on("unsyncedChanges", unsyncedHandler);
-      };
-
-      provider = new HocuspocusProvider({
-        url: wsUrl,
-        name: `page.${pageId}`,
-        document: ydoc,
-        token: collabToken,
-        // @ts-ignore - Required for Node.js environment
-        WebSocketPolyfill: WebSocket,
-        onDisconnect: () => {
-          connectionLost = true;
-          finish(
-            new Error(
-              "Collaboration connection closed before the update was persisted/synced",
-            ),
-          );
-        },
-        onClose: () => {
-          connectionLost = true;
-          finish(
-            new Error(
-              "Collaboration connection closed before the update was persisted/synced",
-            ),
-          );
-        },
-        onSynced: () => {
-          if (applied || settled) return;
-          applied = true;
-
-          // CRITICAL: keep everything between reading and writing the live doc
-          // synchronous (no await) so no remote update can interleave.
-          let newDoc: any;
-          let beforeDoc: any;
-          try {
-            let liveDoc = TiptapTransformer.fromYdoc(ydoc, "default");
-            if (
-              !liveDoc ||
-              typeof liveDoc !== "object" ||
-              !Array.isArray(liveDoc.content)
-            ) {
-              liveDoc = { type: "doc", content: [] };
-            }
-
-            // Snapshot the before-doc for the change report (safe deep clone).
-            beforeDoc = JSON.parse(JSON.stringify(liveDoc));
-
-            newDoc = transform(liveDoc);
-
-            if (newDoc == null) {
-              // Transform aborted — write nothing, return the live doc with a
-              // no-op change report.
-              mutationResult = {
-                doc: liveDoc,
-                verify: {
-                  changed: false,
-                  textInserted: 0,
-                  textDeleted: 0,
-                  blocksChanged: 0,
-                  marks: {},
-                  summary: "no changes (transform aborted)",
-                },
-              };
-              finish(null, mutationResult);
-              return;
-            }
-
-            // Structural diff into the live fragment (issue #152), mirroring
-            // the main write path: preserves the Yjs ids of unchanged nodes so
-            // an open editor's cursor is not yanked to the end of the document.
-            // The previous destructive rewrite (delete-all + applyUpdate of a
-            // fresh Y.Doc) discarded every node id, so replaceImage — the only
-            // caller of this method — still reproduced the #152 cursor jump
-            // (#164). applyDocToFragment runs its own atomic `transact`.
-            applyDocToFragment(ydoc, newDoc);
-          } catch (e) {
-            finish(e instanceof Error ? e : new Error(String(e)));
-            return;
-          }
-
-          // Compute the verifiable change report AFTER the transact write: it
-          // only needs the JSON before/after, so it cannot affect the atomic
-          // read->write window, and summarizeChange never throws.
-          mutationResult = {
-            doc: newDoc,
-            verify: summarizeChange(beforeDoc, newDoc),
-          };
-          waitForPersistence();
-        },
-        onAuthenticationFailed: () => {
-          finish(
-            new Error("Authentication failed for collaboration connection"),
-          );
-        },
-      });
+    // Reuse a live CollabSession for the page (issue #400) instead of opening a
+    // fresh provider per op. acquireCollabSession does NOT take the per-page
+    // lock — the caller (replaceImage) already holds ONE withPageLock across its
+    // scan -> upload -> write sequence, and the mutex is not reentrant, so
+    // taking it here would deadlock. The synchronous read->write section and the
+    // unsyncedChanges/connectionLost ack logic live in CollabSession.mutate,
+    // preserved verbatim from the old inline machine (incl. the #152 structural
+    // diff that keeps a live editor's cursor anchored).
+    const session = await acquireCollabSession(pageId, collabToken, this.apiUrl, {
+      // Only the actual 25s collab connect timeout emits this — the connect-vs-
+      // unload signal; the other failure paths must NOT emit it.
+      onConnectTimeout: () =>
+        this.onMetricFn?.("collab_connect_timeouts_total", 1),
     });
+    try {
+      return await session.mutate(transform);
+    } catch (e) {
+      // Drop the session on any failure so the next call reconnects fresh.
+      session.destroy("mutate failed");
+      throw e;
+    }
   }
 
   /**
@@ -2454,6 +2336,64 @@ export class DocmostClient {
     };
   }
 
+  /** Plain text of each TOP-LEVEL block of `doc`, for anchor-failure hints. */
+  private topLevelBlockTexts(doc: any): string[] {
+    const content = doc && Array.isArray(doc.content) ? doc.content : [];
+    return content
+      .map((b: any) => blockPlainText(b))
+      .filter((t: string) => t.length > 0);
+  }
+
+  /**
+   * True when per-block anchoring failed but the (normalized) selection DOES
+   * appear in the blocks' joined plain text — i.e. it straddles a block
+   * boundary. Blocks are joined with a newline (collapsed to one space by
+   * normalizeForMatch) so a selection whose parts are separated by a paragraph
+   * break still matches. Callers only reach here after single-block anchoring
+   * (incl. the markdown-strip fallback) has already failed.
+   */
+  private selectionSpansMultipleBlocks(
+    blockTexts: string[],
+    selection: string,
+  ): boolean {
+    const normSel = normalizeForMatch(selection).norm.trim();
+    if (normSel.length === 0) return false;
+    const joined = normalizeForMatch(blockTexts.join("\n")).norm;
+    return joined.indexOf(normSel) !== -1;
+  }
+
+  /**
+   * Build the actionable error for a create_comment anchor MISS, porting
+   * edit_page_text's self-correction affordances: an explicit "spans multiple
+   * blocks" message when the selection straddles a block boundary, otherwise a
+   * "closest block text" hint quoting the block that holds the selection's
+   * longest token. `live` switches the wording between the pre-check (reading the
+   * persisted page) and the post-create live-anchor failure (which rolls back).
+   */
+  private anchorNotFoundError(
+    doc: any,
+    selection: string,
+    live: boolean,
+  ): Error {
+    const blockTexts = this.topLevelBlockTexts(doc);
+    const rolled = live ? " The comment was rolled back." : "";
+    if (this.selectionSpansMultipleBlocks(blockTexts, selection)) {
+      return new Error(
+        "create_comment: the selection spans multiple blocks; anchor on a " +
+          "contiguous fragment within a SINGLE paragraph/block (<=250 chars)." +
+          rolled,
+      );
+    }
+    const where = live ? "in the live document" : "in the page";
+    return new Error(
+      `create_comment: could not find the selection text ${where} to anchor ` +
+        "the comment. Provide the EXACT contiguous text from a single " +
+        "paragraph/block (<=250 chars)." +
+        closestBlockHint(blockTexts, selection) +
+        rolled,
+    );
+  }
+
   /**
    * Create an inline comment anchored to its `selection` text, or a reply.
    *
@@ -2515,6 +2455,10 @@ export class DocmostClient {
     // Captured in the pre-check below (which already reads the page) and used as
     // payload.selection. Ordinary comments keep sending the raw agent selection.
     let anchoredSelection: string | null = null;
+    // Set when the anchor matched only after stripping markdown from the
+    // selection (the strip fallback); surfaced as a soft warning like
+    // edit_page_text does, so a stale-markdown selection is flagged.
+    let anchorNormalized = false;
 
     // For a top-level comment, fail BEFORE creating anything when the selection
     // is not present in the persisted document — this avoids leaving an orphan
@@ -2530,10 +2474,7 @@ export class DocmostClient {
           // rejected BEFORE creating the comment.
           const matches = countAnchorMatches(page.content, selection);
           if (matches === 0) {
-            throw new Error(
-              "create_comment: could not find the selection text in the page to anchor the comment. " +
-                "Provide the EXACT contiguous text from a single paragraph/block (<=250 chars).",
-            );
+            throw this.anchorNotFoundError(page.content, selection, false);
           }
           if (matches >= 2) {
             throw new Error(
@@ -2547,18 +2488,27 @@ export class DocmostClient {
           // null despite countAnchorMatches===1 (shouldn't happen), fall back to
           // the raw agent selection below rather than crash.
           anchoredSelection = getAnchoredText(page.content, selection);
-        } else if (!canAnchorInDoc(page.content, selection)) {
-          throw new Error(
-            "create_comment: could not find the selection text in the page to anchor the comment. " +
-              "Provide the EXACT contiguous text from a single paragraph/block (<=250 chars).",
-          );
+          anchorNormalized = resolveAnchorSelection(
+            page.content,
+            selection,
+          ).normalized;
+        } else {
+          const resolved = resolveAnchorSelection(page.content, selection);
+          if (!resolved.found) {
+            throw this.anchorNotFoundError(page.content, selection, false);
+          }
+          anchorNormalized = resolved.normalized;
         }
       } catch (e) {
-        // Rethrow our own "not found"/"ambiguous" errors; swallow read/network
-        // errors so the live anchor step can still try (and enforce) anchoring.
+        // Rethrow our own "not found"/"ambiguous"/"spans multiple blocks" errors;
+        // swallow read/network errors so the live anchor step can still try (and
+        // enforce) anchoring.
         if (
           e instanceof Error &&
           (e.message.startsWith("create_comment: could not find the selection") ||
+            e.message.startsWith(
+              "create_comment: the selection spans multiple blocks",
+            ) ||
             e.message.startsWith(
               "create_comment: the suggestion's selection is ambiguous",
             ))
@@ -2630,6 +2580,10 @@ export class DocmostClient {
     // Set inside the transform when a suggestion's live anchor is ambiguous
     // (>=2 occurrences), so the rollback path can surface the right error.
     let ambiguousInLiveDoc = false;
+    // Captured inside the transform on a not-found abort, so the rollback path
+    // can surface the closest-block / spans-multiple-blocks hint built from the
+    // LIVE document (the pre-check page is not in scope there).
+    let liveNotFoundError: Error | null = null;
     try {
       const collabToken = await this.getCollabTokenWithReauth();
       // Open the collab doc by the canonical UUID, never the slugId (#260). The
@@ -2657,6 +2611,13 @@ export class DocmostClient {
             const liveCount = countAnchorMatches(doc, selection as string);
             if (liveCount !== 1) {
               ambiguousInLiveDoc = liveCount >= 2;
+              if (liveCount === 0) {
+                liveNotFoundError = this.anchorNotFoundError(
+                  doc,
+                  selection as string,
+                  true,
+                );
+              }
               return null;
             }
           }
@@ -2666,6 +2627,11 @@ export class DocmostClient {
           }
           // Selection text not found in the LIVE document: abort the write. The
           // rollback + throw below turns this into a hard error.
+          liveNotFoundError = this.anchorNotFoundError(
+            doc,
+            selection as string,
+            true,
+          );
           return null;
         },
       );
@@ -2682,13 +2648,28 @@ export class DocmostClient {
       // suggestion, was ambiguous) in the live document. Roll back the comment
       // and surface a hard error.
       await this.safeDeleteComment(newCommentId);
-      throw new Error(
-        ambiguousInLiveDoc
-          ? "create_comment: the suggestion's selection is ambiguous in the live document (multiple occurrences); the comment was rolled back. Expand the selection with surrounding context so it is unique."
-          : "create_comment: failed to anchor the comment (selection not found in the live document); the comment was rolled back",
+      if (ambiguousInLiveDoc) {
+        throw new Error(
+          "create_comment: the suggestion's selection is ambiguous in the live document (multiple occurrences); the comment was rolled back. Expand the selection with surrounding context so it is unique.",
+        );
+      }
+      throw (
+        liveNotFoundError ??
+        new Error(
+          "create_comment: failed to anchor the comment (selection not found in the live document); the comment was rolled back",
+        )
       );
     }
 
+    // Soft warning (like edit_page_text): the selection only matched after
+    // stripping markdown, so the caller likely quoted a styled fragment.
+    if (anchorNormalized) {
+      result.warning =
+        "The selection matched only after stripping markdown syntax; the comment " +
+        "was anchored on the document's plain text. Copy the selection verbatim " +
+        "from get_page / search_in_page output to avoid this.";
+    }
+
     result.anchored = true;
     return result;
   }
@@ -3412,6 +3393,453 @@ export class DocmostClient {
     });
   }
 
+  // --- draw.io diagrams (issue #423) ---
+
+  /**
+   * Upload a ready-made byte buffer as a page attachment via the same
+   * multipart /files/upload endpoint uploadImage uses. Split out as its own
+   * (overridable) seam so drawio_create/update can upload the generated
+   * `.drawio.svg` without going through the URL-fetch path, and so tests can
+   * stub the network. Mirrors uploadImage's fresh-FormData + one-shot 401/403
+   * re-auth handling (a FormData body is single-use, so it must be rebuilt per
+   * attempt).
+   */
+  protected async uploadAttachmentBuffer(
+    pageId: string,
+    buffer: Buffer,
+    fileName: string,
+    mime: string,
+  ): Promise<{ id: string; fileName: string; fileSize: number }> {
+    await this.ensureAuthenticated();
+    const buildForm = () => {
+      const form = new FormData();
+      form.append("pageId", pageId);
+      form.append("file", buffer, { filename: fileName, contentType: mime });
+      return form;
+    };
+    const uploadUrl = `${this.apiUrl}/files/upload`;
+    let response;
+    try {
+      const form = buildForm();
+      response = await axios.post(uploadUrl, form, {
+        headers: {
+          ...form.getHeaders(),
+          Authorization: this.client.defaults.headers.common["Authorization"],
+        },
+        timeout: 60000,
+      });
+    } catch (error) {
+      if (
+        axios.isAxiosError(error) &&
+        (error.response?.status === 401 || error.response?.status === 403)
+      ) {
+        await this.login();
+        const form2 = buildForm();
+        response = await axios.post(uploadUrl, form2, {
+          headers: {
+            ...form2.getHeaders(),
+            Authorization: this.client.defaults.headers.common["Authorization"],
+          },
+          timeout: 60000,
+        });
+      } else if (axios.isAxiosError(error)) {
+        if (process.env.DEBUG) {
+          console.error(
+            "Attachment upload failed; response body:",
+            JSON.stringify(error.response?.data),
+          );
+        }
+        throw new Error(
+          `Attachment upload failed: ${error.response?.status} ${error.response?.statusText}`,
+        );
+      } else {
+        throw error;
+      }
+    }
+    const att = response.data?.data ?? response.data;
+    if (!att?.id || !att?.fileName) {
+      throw new Error(
+        "Unexpected /files/upload response: " + JSON.stringify(response.data),
+      );
+    }
+    return {
+      id: att.id,
+      fileName: att.fileName,
+      fileSize: att.fileSize ?? buffer.length,
+    };
+  }
+
+  /**
+   * Fetch a stored `.drawio.svg` attachment as text. Overridable seam over
+   * fetchInternalFile (the authed loopback fetch, which also rejects any
+   * traversal/SSRF src) so drawio_get/update can read the current diagram and
+   * tests can stub the bytes.
+   */
+  protected async fetchAttachmentText(src: string): Promise<string> {
+    const { buffer } = await this.fetchInternalFile(src);
+    return buffer.toString("utf-8");
+  }
+
+  /**
+   * Resolve a drawio node on a page by `attrs.id` or `#<index>` and return the
+   * node plus its ref. Throws a clear error if the ref does not resolve to a
+   * drawio node.
+   */
+  private async resolveDrawioNode(
+    pageId: string,
+    node: string,
+  ): Promise<{ node: any; ref: string }> {
+    const data = await this.getPageRaw(pageId);
+    const hit = getNodeByRef(
+      data.content ?? { type: "doc", content: [] },
+      node,
+    );
+    if (!hit) {
+      throw new Error(
+        `drawio: no node found for "${node}" on page ${pageId} (use the drawio node's attrs.id or "#<index>" from get_outline)`,
+      );
+    }
+    if (hit.type !== "drawio") {
+      throw new Error(
+        `drawio: node "${node}" on page ${pageId} is a ${hit.type}, not a drawio diagram`,
+      );
+    }
+    return { node: hit.node, ref: node };
+  }
+
+  /**
+   * Read a drawio diagram as mxGraph XML (default) or as the raw `.drawio.svg`.
+   * Runs the decode chain (base64/entity content= → drawio file → nested XML or
+   * pako-inflated compressed <diagram>). The returned `hash` is the
+   * optimistic-lock key for drawio_update.
+   */
+  async drawioGet(
+    pageId: string,
+    node: string,
+    format: "xml" | "svg" = "xml",
+  ): Promise<{
+    pageId: string;
+    nodeId: string;
+    format: "xml" | "svg";
+    content: string;
+    meta: {
+      attachmentId: string | null;
+      title: string | null;
+      width: number | null;
+      height: number | null;
+      cellCount: number;
+      hash: string;
+    };
+  }> {
+    await this.ensureAuthenticated();
+    const { node: drawio } = await this.resolveDrawioNode(pageId, node);
+    const attrs = drawio.attrs || {};
+    const src = attrs.src;
+    if (!src) {
+      throw new Error(
+        `drawio: node "${node}" on page ${pageId} has no src to read`,
+      );
+    }
+    const svg = await this.fetchAttachmentText(src);
+    const modelXml = decodeDrawioSvg(svg);
+    const meta = {
+      attachmentId: attrs.attachmentId ?? null,
+      title: attrs.title ?? null,
+      width: attrs.width != null ? Number(attrs.width) : null,
+      height: attrs.height != null ? Number(attrs.height) : null,
+      cellCount: countUserCells(modelXml),
+      hash: mxHash(modelXml),
+    };
+    return {
+      pageId,
+      nodeId: attrs.id ?? node,
+      format,
+      content: format === "svg" ? svg : normalizeXml(modelXml),
+      meta,
+    };
+  }
+
+  /**
+   * Create a drawio diagram from mxGraph XML: lint → schematic SVG preview
+   * (pure TS) → build the `.drawio.svg` (createDrawioSvg contract) → create the
+   * attachment → insert a `drawio` node before/after an anchor or appended.
+   * `xml` is a bare `<mxGraphModel>` or a list of `<mxCell>` (the server wraps
+   * it and adds the id=0/id=1 sentinels).
+   */
+  async drawioCreate(
+    pageId: string,
+    where: {
+      position: "before" | "after" | "append";
+      anchorNodeId?: string;
+      anchorText?: string;
+    },
+    xml: string,
+    title?: string,
+  ): Promise<{
+    success: boolean;
+    nodeId: string;
+    attachmentId: string;
+    warnings: string[];
+    verify?: any;
+  }> {
+    await this.ensureAuthenticated();
+    if (
+      !where ||
+      (where.position !== "before" &&
+        where.position !== "after" &&
+        where.position !== "append")
+    ) {
+      throw new Error(
+        'drawio_create: `where.position` must be one of "before", "after", "append"',
+      );
+    }
+    if (where.position === "before" || where.position === "after") {
+      const hasId =
+        typeof where.anchorNodeId === "string" && where.anchorNodeId.length > 0;
+      const hasText =
+        typeof where.anchorText === "string" && where.anchorText.length > 0;
+      if (hasId === hasText) {
+        throw new Error(
+          `drawio_create: position "${where.position}" requires exactly one of anchorNodeId or anchorText`,
+        );
+      }
+    }
+
+    // Pre-write pipeline (throws a structured DrawioLintError on any violation).
+    const prepared = prepareModel(xml);
+    const inner = renderDiagramShapes(prepared.cells, prepared.bbox);
+    const diagramTitle = title || "Page-1";
+    const svg = buildDrawioSvg(prepared.modelXml, inner, prepared.bbox, diagramTitle);
+
+    const att = await this.uploadAttachmentBuffer(
+      pageId,
+      Buffer.from(svg, "utf-8"),
+      "diagram.drawio.svg",
+      "image/svg+xml",
+    );
+
+    // NOTE: no `id` attribute is set here. The vendored `drawio` node schema
+    // (diagramAttributes) declares no `id`, so any block id would be silently
+    // dropped by PMNode.fromJSON on save and the returned handle would fail to
+    // resolve. The addressable handle is the node's "#<index>" (like image/table
+    // nodes), computed after the insert below.
+    const drawioNode: any = {
+      type: "drawio",
+      attrs: {
+        src: `/api/files/${att.id}/${att.fileName}`,
+        attachmentId: att.id,
+        width: prepared.bbox.width,
+        height: prepared.bbox.height,
+        align: "center",
+      },
+    };
+    if (title) drawioNode.attrs.title = title;
+    // Reuse the existing URL trust boundary (rejects unsafe src schemes).
+    this.validateDocUrls(drawioNode);
+
+    const collabToken = await this.getCollabTokenWithReauth();
+    const pageUuid = await this.resolvePageId(pageId);
+
+    let inserted = false;
+    let insertedIndex = -1;
+    const mutation = await this.mutatePage(
+      pageUuid,
+      collabToken,
+      this.apiUrl,
+      (liveDoc) => {
+        inserted = false;
+        insertedIndex = -1;
+        const { doc: nd, inserted: ins } = insertNodeRelative(
+          liveDoc,
+          drawioNode,
+          where,
+        );
+        inserted = ins;
+        if (!inserted) return null; // anchor not found -> skip the write
+        // Locate the freshly-inserted node to derive its "#<index>" handle. The
+        // just-uploaded attachmentId is unique, so it identifies our node.
+        if (Array.isArray(nd.content)) {
+          insertedIndex = nd.content.findIndex(
+            (b: any) =>
+              b &&
+              b.type === "drawio" &&
+              b.attrs &&
+              b.attrs.attachmentId === att.id,
+          );
+        }
+        return nd;
+      },
+    );
+
+    if (!inserted) {
+      const anchorDesc = where.anchorNodeId
+        ? `anchorNodeId "${where.anchorNodeId}"`
+        : `anchorText "${where.anchorText}"`;
+      throw new Error(
+        `drawio_create: anchor not found (${anchorDesc}) on page ${pageId}. The diagram attachment ${att.id} is now an unreferenced orphan.`,
+      );
+    }
+
+    if (insertedIndex < 0) {
+      // The node was inserted nested (e.g. inside a callout/table cell via an
+      // anchor), where "#<index>" — which addresses only top-level blocks —
+      // cannot reference it. drawio nodes carry no persisted id, so there is no
+      // stable handle for a nested diagram.
+      throw new Error(
+        `drawio_create: the diagram was inserted on page ${pageId} but not as a ` +
+          `top-level block, so it has no addressable "#<index>" handle. Anchor ` +
+          `on a top-level block (or append) so the diagram can be re-read.`,
+      );
+    }
+
+    // The returned handle is POSITIONAL ("#<index>"): valid for the immediate
+    // create -> get/update flow, but re-resolve via get_outline if the document
+    // structure changes (blocks added/removed before it shift the index).
+    const nodeId = `#${insertedIndex}`;
+
+    return {
+      success: true,
+      nodeId,
+      attachmentId: att.id,
+      warnings: prepared.warnings,
+      verify: mutation.verify,
+    };
+  }
+
+  /**
+   * Full-replacement update of a drawio diagram. `baseHash` is MANDATORY: it is
+   * compared against the hash of the diagram's CURRENT XML (from drawio_get);
+   * any mismatch means a human or another agent edited the diagram after the
+   * read, so the write is refused with a conflict error. On success the new
+   * `.drawio.svg` is uploaded as a FRESH attachment (in-place byte overwrite is
+   * avoided — some Docmost versions corrupt an attachment on overwrite, exactly
+   * as replaceImage documents) and the node is repointed with new dimensions.
+   */
+  async drawioUpdate(
+    pageId: string,
+    node: string,
+    xml: string,
+    baseHash: string,
+  ): Promise<{
+    success: boolean;
+    nodeId: string;
+    attachmentId: string;
+    warnings: string[];
+    verify?: any;
+  }> {
+    await this.ensureAuthenticated();
+    if (typeof baseHash !== "string" || baseHash.length === 0) {
+      throw new Error(
+        "drawio_update: baseHash is mandatory — read the diagram with drawio_get first and pass back its meta.hash",
+      );
+    }
+
+    // Resolve the node and read the CURRENT diagram to enforce the optimistic
+    // lock before doing any write or upload.
+    const { node: drawio, ref } = await this.resolveDrawioNode(pageId, node);
+    const oldAttrs = drawio.attrs || {};
+    const oldSrc = oldAttrs.src;
+    // The returned handle is the caller-supplied reference. drawio nodes carry
+    // no persisted id, so `ref` (an "#<index>" or a rare legacy attrs.id) is the
+    // honest identifier to hand back.
+    const nodeId = oldAttrs.id ?? ref;
+    if (!oldSrc) {
+      throw new Error(
+        `drawio_update: node "${node}" on page ${pageId} has no src to compare against`,
+      );
+    }
+    const currentSvg = await this.fetchAttachmentText(oldSrc);
+    const currentHash = mxHash(decodeDrawioSvg(currentSvg));
+    if (currentHash !== baseHash) {
+      throw new Error(
+        `drawio_update: conflict — the diagram changed since it was read ` +
+          `(baseHash ${baseHash} != current ${currentHash}). Re-read it with drawio_get and retry.`,
+      );
+    }
+
+    // Pipeline for the new content (throws a structured DrawioLintError).
+    const prepared = prepareModel(xml);
+    const inner = renderDiagramShapes(prepared.cells, prepared.bbox);
+    const diagramTitle = oldAttrs.title || "Page-1";
+    const svg = buildDrawioSvg(prepared.modelXml, inner, prepared.bbox, diagramTitle);
+
+    const att = await this.uploadAttachmentBuffer(
+      pageId,
+      Buffer.from(svg, "utf-8"),
+      "diagram.drawio.svg",
+      "image/svg+xml",
+    );
+    const newSrc = `/api/files/${att.id}/${att.fileName}`;
+
+    const collabToken = await this.getCollabTokenWithReauth();
+    const pageUuid = await this.resolvePageId(pageId);
+
+    let repointed = 0;
+    const repoint = (n: any) => {
+      n.attrs = {
+        ...n.attrs,
+        src: newSrc,
+        attachmentId: att.id,
+        width: prepared.bbox.width,
+        height: prepared.bbox.height,
+      };
+      repointed++;
+    };
+
+    const mutation = await this.mutatePage(
+      pageUuid,
+      collabToken,
+      this.apiUrl,
+      (liveDoc) => {
+        repointed = 0;
+        const doc =
+          liveDoc && liveDoc.type === "doc"
+            ? liveDoc
+            : { type: "doc", content: [] };
+        if (!Array.isArray(doc.content)) doc.content = [];
+        // Repoint ONLY the resolved node — never every node that happens to
+        // share this attachmentId (a copied diagram is two nodes with one
+        // attachmentId; keying on it would clobber both). Re-resolve the same
+        // handle against the live doc and walk to its exact position.
+        const hit = getNodeByRef(doc, ref);
+        if (!hit || hit.type !== "drawio") return null; // vanished/changed -> skip
+        let target: any = doc;
+        for (const idx of hit.path) {
+          if (!target || !Array.isArray(target.content)) {
+            target = null;
+            break;
+          }
+          target = target.content[idx];
+        }
+        if (!target || target.type !== "drawio") return null;
+        repoint(target);
+        if (repointed === 0) return null; // node vanished concurrently -> skip
+        return doc;
+      },
+    );
+
+    if (repointed === 0) {
+      return {
+        success: true,
+        nodeId,
+        attachmentId: att.id,
+        warnings: [
+          ...prepared.warnings,
+          "target drawio node was removed concurrently; uploaded attachment is unreferenced",
+        ],
+        verify: mutation.verify,
+      };
+    }
+
+    return {
+      success: true,
+      nodeId,
+      attachmentId: att.id,
+      warnings: prepared.warnings,
+      verify: mutation.verify,
+    };
+  }
+
   // --- Page history / diff / transform ---
 
   /**

packages/mcp/src/index.ts

@@ -13,6 +13,11 @@ import { SHARED_TOOL_SPECS, SharedToolSpec } from "./tool-specs.js";
 export { DocmostClient } from "./client.js";
 export type { DocmostMcpConfig } from "./client.js";
 
+// Teardown for the live per-page CollabSession cache (issue #400). An embedding
+// HTTP host (the gitmost NestJS server) should call this from its own shutdown
+// hook so no cached collab provider outlives the process.
+export { destroyAllSessions } from "./lib/collab-session.js";
+
 // Re-export the zod-agnostic shared tool-spec registry so the in-app AI-SDK
 // service can read it off the loaded module (it cannot import the ESM package's
 // internals directly; it goes through loadDocmostMcp()).
@@ -47,7 +52,7 @@ const VERSION = packageJson.version;
 export const SERVER_INSTRUCTIONS =
   "Docmost editing guide — choose the tool by intent.\n" +
   "READ: find a page -> search (workspace-wide full-text); list -> list_pages / list_spaces. Locate blocks and their ids CHEAPLY -> get_outline (compact top-level map; start here, not get_page_json). One block's subtree -> get_node (by attrs.id, or \"#<index>\" for tables, which carry no id). Find every occurrence of a string/regex ON a page (and where each is) -> search_in_page, NOT block-by-block get_node — it returns each hit's node ref + block index + context for a targeted comment. Whole page -> get_page (Markdown, lossy; inline <span data-comment-id> tags are comment anchors — markup, not text) or get_page_json (lossless ProseMirror with block ids). Hand a huge page (with images) to an external consumer without pulling it through the model context -> stash_page (returns a short-lived anonymous URL).\n" +
-  "EDIT: fix wording/typos/numbers -> edit_page_text (find/replace inside blocks, no node id needed). Change ONE block (paragraph/heading/callout/etc.) structurally -> patch_node (by attrs.id from get_outline). Add a block -> insert_node (before/after a block by attrs.id or by anchor text, or append). Remove a block -> delete_node (by attrs.id). Tables -> table_get / table_update_cell / table_insert_row / table_delete_row (address by \"#<index>\" from get_outline; table nodes have no attrs.id). Images -> insert_image (add from a web URL) / replace_image (swap an existing image). Footnotes -> insert_footnote. Bulk/structural rewrite -> update_page_json (full ProseMirror replace; prefer the granular tools above to avoid resending the whole ~100KB+ document). Complex/scripted rewrite (multiple coordinated edits, renumbering) -> docmost_transform: write a JS `(doc, ctx) => doc` transform, preview the diff with dryRun (default), then apply with dryRun:false; ctx.helpers includes commentsToFootnotes for turning inline comments into numbered footnotes.\n" +
+  "EDIT: fix wording/typos/numbers -> edit_page_text (find/replace inside blocks, no node id needed). Change ONE block (paragraph/heading/callout/etc.) structurally -> patch_node (by attrs.id from get_outline). Add a block -> insert_node (before/after a block by attrs.id or by anchor text, or append). Remove a block -> delete_node (by attrs.id). Tables -> table_get / table_update_cell / table_insert_row / table_delete_row (address by \"#<index>\" from get_outline; table nodes have no attrs.id). Images -> insert_image (add from a web URL) / replace_image (swap an existing image). Draw.io diagrams -> drawio_create (create from mxGraph XML and insert), drawio_get (read a diagram as mxGraph XML + a hash), drawio_update (replace a diagram; pass the hash from drawio_get as baseHash for optimistic locking). Footnotes -> insert_footnote. Bulk/structural rewrite -> update_page_json (full ProseMirror replace; prefer the granular tools above to avoid resending the whole ~100KB+ document). Complex/scripted rewrite (multiple coordinated edits, renumbering) -> docmost_transform: write a JS `(doc, ctx) => doc` transform, preview the diff with dryRun (default), then apply with dryRun:false; ctx.helpers includes commentsToFootnotes for turning inline comments into numbered footnotes.\n" +
   "PAGES: new -> create_page (Markdown). Rename (title only) -> rename_page. Move -> move_page. Delete -> delete_page (SOFT delete — the page goes to trash and is restorable; nothing is permanent). Copy/replace a page's whole content from another page (server-side, no document through the model) -> copy_page_content. Sharing -> share_page / unshare_page / list_shares; share_page makes the page PUBLICLY accessible — do it only when explicitly asked.\n" +
   "COMMENTS: create_comment is always inline and requires an EXACT selection — contiguous text from a single block, <=250 chars (fails rather than leaving an unanchored comment); reply to a thread via parentCommentId. Propose a concrete text fix for one-click human approval -> create_comment with suggestedText (the exact plain-text replacement for the selection; the selection must then be UNIQUE in the page — extend it with context if needed); prefer this over editing directly when the change is subjective or needs the author's sign-off. Manage -> list_comments, update_comment, resolve_comment (resolve/reopen, reversible — prefer over delete to close), delete_comment, check_new_comments.\n" +
   "HISTORY: review what changed -> diff_page_versions (a historyId vs current, or two versions). List saved versions -> list_page_history. Undo a bad edit -> restore_page_version (writes a past version back as current; itself revertible). Lossless markdown round-trip (download, edit, re-upload, incl. comment anchors) -> export_page_markdown / import_page_markdown.";
@@ -64,6 +69,33 @@ const jsonContent = (data: any) => ({
  * REST + the collaboration WebSocket using the provided service-account
  * credentials and auto-re-authenticates.
  */
+/**
+ * Wrap a tool handler so its wall-clock duration is reported through the host's
+ * dependency-neutral sink as `mcp_tool_duration_seconds` (labelled by tool
+ * name). Pure and side-effect-free apart from the optional `onMetric` call:
+ *  - preserves the handler's exact return value (awaited);
+ *  - observes in a `finally`, so it records on BOTH success and throw, then
+ *    rethrows the original error unchanged (never swallowed);
+ *  - with no `onMetric` (standalone/stdio) it is a transparent pass-through.
+ * Exported so the timing contract can be unit-tested without a live transport.
+ */
+export function timeToolHandler(
+  name: string,
+  handler: (...args: any[]) => any,
+  onMetric?: (name: string, value: number, labels?: Record<string, string>) => void,
+): (...args: any[]) => Promise<any> {
+  return async (...handlerArgs: any[]) => {
+    const start = performance.now();
+    try {
+      return await handler(...handlerArgs);
+    } finally {
+      onMetric?.("mcp_tool_duration_seconds", (performance.now() - start) / 1000, {
+        tool: name,
+      });
+    }
+  };
+}
+
 export function createDocmostMcpServer(config: DocmostMcpConfig): McpServer {
   // Pass the whole config union through: the client branches internally on
   // credentials vs. getToken, so both the external /mcp (creds) and the
@@ -78,6 +110,26 @@ export function createDocmostMcpServer(config: DocmostMcpConfig): McpServer {
     { instructions: SERVER_INSTRUCTIONS },
   );
 
+  // Single choke point for MCP tool timing. Both `registerShared` (below) and
+  // the inline `server.registerTool(...)` calls funnel through this one method,
+  // so monkeypatching it HERE — before any tool is registered and before
+  // `registerShared` captures a reference to it — times every tool with no
+  // per-tool boilerplate. The wrapped handler records wall-clock duration and,
+  // in a `finally`, feeds the host's dependency-neutral sink
+  // `config.onMetric("mcp_tool_duration_seconds", seconds, { tool })`. The tool
+  // name is the registration name (bounded cardinality). When no onMetric is
+  // provided (standalone/stdio) the wrapper is a pure pass-through: it still
+  // returns the original result and rethrows the original error unchanged.
+  const originalRegisterTool = server.registerTool.bind(server) as (
+    ...args: any[]
+  ) => any;
+  (server as any).registerTool = (...args: any[]) => {
+    const name = args[0] as string;
+    const handler = args[args.length - 1];
+    const timedHandler = timeToolHandler(name, handler, config.onMetric);
+    return originalRegisterTool(...args.slice(0, -1), timedHandler);
+  };
+
   // Register a tool from the shared, zod-agnostic spec registry. The spec owns
   // the canonical name + model-facing description + (optional) schema builder;
   // only the execute body is supplied per call. buildShape is invoked with THIS
@@ -380,43 +432,10 @@ registerShared(SHARED_TOOL_SPECS.deleteNode, async ({ pageId, nodeId }) => {
 });
 
 // Tool: insert_image
-// MCP-only by design (NOT in the shared registry): the in-app AI-chat agent
-// exposes no image tools (insert/replace), so there is no second layer to unify
-// — a SHARED_TOOL_SPECS entry's tier/catalogLine are in-app metadata and the
-// catalog-partition test forbids a spec without a live in-app tool (#294).
-server.registerTool(
-  "insert_image",
-  {
-    description:
-      "Download an image from a web (http/https) URL and insert it into " +
-      "a page in one step. By default " +
-      "appends the image at the end of the page. With replaceText, replaces the " +
-      "first top-level block whose text contains that string (handy for " +
-      'swapping a text placeholder like "[image: foo.png]" for the real image). ' +
-      "With afterText, inserts the image right after the first block containing " +
-      "that string. Preserves all other block ids.",
-    inputSchema: {
-      pageId: z.string().min(1),
-      imageUrl: z
-        .string()
-        .min(1)
-        .describe("http(s) URL of the image to download and upload"),
-      align: z.enum(["left", "center", "right"]).optional(),
-      alt: z.string().optional(),
-      replaceText: z
-        .string()
-        .optional()
-        .describe(
-          "Replace the first top-level block whose text contains this string with the image",
-        ),
-      afterText: z
-        .string()
-        .optional()
-        .describe(
-          "Insert the image right after the first top-level block whose text contains this string",
-        ),
-    },
-  },
+// Schema + description now live in the shared registry (#410) so BOTH this MCP
+// server and the in-app AI-chat agent expose it. The execute body is unchanged.
+registerShared(
+  SHARED_TOOL_SPECS.insertImage,
   async ({ pageId, imageUrl, align, alt, replaceText, afterText }) => {
     const result = await docmostClient.insertImage(pageId, imageUrl, {
       align,
@@ -429,34 +448,9 @@ server.registerTool(
 );
 
 // Tool: replace_image
-// MCP-only by design (see insert_image): no in-app equivalent, stays inline.
-server.registerTool(
-  "replace_image",
-  {
-    description:
-      "Replace an existing image on a page with a new image fetched from a web " +
-      "(http/https) URL: uploads the new file as a NEW " +
-      "attachment (fresh clean URL that renders and busts browser caches), then " +
-      "repoints every image node referencing the old attachmentId (recursively, " +
-      "incl. callouts/tables) via the live document, preserving comments, " +
-      "alignment and alt. The old attachment is left as an unreferenced orphan " +
-      "(Docmost has no API to delete a single attachment; it is removed only when " +
-      "the page/space is deleted). In-place byte overwrite is avoided because some " +
-      "Docmost versions corrupt the attachment (HTTP 500) on overwrite.",
-    inputSchema: {
-      pageId: z.string().min(1),
-      attachmentId: z
-        .string()
-        .min(1)
-        .describe("attachmentId of the image currently in the page to replace"),
-      imageUrl: z
-        .string()
-        .min(1)
-        .describe("http(s) URL of the new image to download"),
-      align: z.enum(["left", "center", "right"]).optional(),
-      alt: z.string().optional(),
-    },
-  },
+// Schema + description now live in the shared registry (#410).
+registerShared(
+  SHARED_TOOL_SPECS.replaceImage,
   async ({ pageId, attachmentId, imageUrl, align, alt }) => {
     const result = await docmostClient.replaceImage(
       pageId,
@@ -471,6 +465,38 @@ server.registerTool(
   },
 );
 
+// Tool: drawio_get — read a draw.io diagram as mxGraph XML (or the raw SVG).
+registerShared(
+  SHARED_TOOL_SPECS.drawioGet,
+  async ({ pageId, node, format }) => {
+    const result = await docmostClient.drawioGet(pageId, node, format ?? "xml");
+    return jsonContent(result);
+  },
+);
+
+// Tool: drawio_create — lint mxGraph XML, build the .drawio.svg, insert a node.
+registerShared(
+  SHARED_TOOL_SPECS.drawioCreate,
+  async ({ pageId, xml, position, anchorNodeId, anchorText, title }) => {
+    const result = await docmostClient.drawioCreate(
+      pageId,
+      { position, anchorNodeId, anchorText },
+      xml,
+      title,
+    );
+    return jsonContent(result);
+  },
+);
+
+// Tool: drawio_update — optimistic-locked full replacement of a diagram.
+registerShared(
+  SHARED_TOOL_SPECS.drawioUpdate,
+  async ({ pageId, node, xml, baseHash }) => {
+    const result = await docmostClient.drawioUpdate(pageId, node, xml, baseHash);
+    return jsonContent(result);
+  },
+);
+
 // Tool: share_page
 // Schema + description now live in the shared registry (#294). The execute body
 // keeps this transport's own `searchIndexing ?? true` default.
@@ -779,36 +805,10 @@ server.registerTool(
 );
 
 // Tool: insert_footnote
-// MCP-only by design (see insert_image): the in-app AI-chat agent exposes no
-// footnote tool, so there is no second layer to unify — stays inline (#294).
-server.registerTool(
-  "insert_footnote",
-  {
-    description:
-      "Insert an AUTHOR-INLINE footnote: you specify only WHERE (anchorText) " +
-      "and WHAT (text). The footnote marker is placed right after anchorText in " +
-      "the body, and the bottom footnotes list + the numbering are derived " +
-      "deterministically server-side. You do NOT assign a number, and you " +
-      "never see or edit the footnotes list — so footnotes cannot end up out " +
-      "of order, orphaned, or as a raw '[^id]' block. If a footnote with the " +
-      "SAME text already exists, its number is REUSED (one definition, several " +
-      "references). The write is atomic and won't clobber concurrent edits; if " +
-      "anchorText is not found, nothing is written and an error is returned.",
-    inputSchema: {
-      pageId: z.string().min(1),
-      anchorText: z
-        .string()
-        .min(1)
-        .describe(
-          "A snippet of existing body text; the footnote marker is inserted " +
-            "immediately after its first occurrence (mark-safe).",
-        ),
-      text: z
-        .string()
-        .min(1)
-        .describe("The footnote content as markdown (becomes the definition)."),
-    },
-  },
+// Schema + description now live in the shared registry (#410) so the in-app
+// AI-chat agent exposes it too. The execute body is unchanged.
+registerShared(
+  SHARED_TOOL_SPECS.insertFootnote,
   async ({ pageId, anchorText, text }) => {
     const result = await docmostClient.insertFootnote(pageId, anchorText, text);
     return jsonContent(result);

packages/mcp/src/lib/collab-session.ts

@@ -0,0 +1,668 @@
+import { HocuspocusProvider } from "@hocuspocus/provider";
+import { TiptapTransformer } from "@hocuspocus/transformer";
+import * as Y from "yjs";
+import WebSocket from "ws";
+import {
+  buildCollabWsUrl,
+  applyDocToFragment,
+  MutationResult,
+} from "./collaboration.js";
+import { summarizeChange } from "./diff.js";
+
+/**
+ * Live per-page collaboration session cache (issue #400).
+ *
+ * The one-shot write path (collaboration.mutatePageContent /
+ * client.mutateLiveContentUnlocked) used to open a NEW HocuspocusProvider, run
+ * the full connect -> auth -> onLoadDocument -> initial-sync handshake, apply a
+ * single edit, wait for persistence, and then `provider.destroy()` — for EVERY
+ * content mutation. Disconnecting after every edit means that once the pause
+ * between calls exceeds the server's write debounce, the server does a full
+ * store -> unload -> reload per cell, causing 25s connect timeouts and
+ * event-loop lag under a burst of edits on one page.
+ *
+ * This module keeps ONE live provider + ydoc per (wsUrl, pageId, token) alive
+ * across a SERIES of edits. While the provider stays connected the server never
+ * enters store -> unload -> reload, its debounce coalesces N writes into 1-2
+ * stores, and the repeated auth/load/initial-sync disappears.
+ *
+ * The synchronous read -> transform -> write section and the per-edit
+ * persistence-ack logic are preserved VERBATIM from the one-shot machine — the
+ * only change is that they run on a persistent provider instead of a throwaway
+ * one. See CollabSession.mutate.
+ */
+
+/** Time we wait for the initial handshake/sync before giving up. */
+const CONNECT_TIMEOUT_MS = 25000;
+/** Time we wait for the server to acknowledge our write before giving up. */
+const PERSIST_TIMEOUT_MS = 20000;
+
+/**
+ * Tunables, read fresh from the environment on every acquire so tests (and a
+ * live rollback) can change them without reloading the module. Mirrors how
+ * http.ts parses MCP_SESSION_IDLE_MS.
+ *   - MCP_COLLAB_SESSION_IDLE_MS: idle TTL, reset after every op. Default 60s.
+ *     0 (or negative) DISABLES the cache — every op opens its own provider and
+ *     destroys it after the op, i.e. the exact legacy per-op-provider behavior
+ *     (the rollback path).
+ *   - MCP_COLLAB_SESSION_MAX_AGE_MS: hard lifetime checked at acquire; bounds
+ *     the permission-staleness window. Default 10 min.
+ *   - MCP_COLLAB_SESSION_MAX_ENTRIES: registry cap; the least-recently-used
+ *     session is destroy-evicted when the cap is reached. Default 32.
+ */
+interface SessionConfig {
+  idleMs: number;
+  maxAgeMs: number;
+  maxEntries: number;
+}
+
+function parseEnvInt(value: string | undefined, fallback: number): number {
+  const parsed = parseInt(value ?? "", 10);
+  return Number.isFinite(parsed) ? parsed : fallback;
+}
+
+function readConfig(): SessionConfig {
+  // idleMs: allow 0 (disable). A malformed value falls back to the default.
+  const idleRaw = parseInt(process.env.MCP_COLLAB_SESSION_IDLE_MS ?? "", 10);
+  const idleMs = Number.isFinite(idleRaw) ? Math.max(0, idleRaw) : 60 * 1000;
+  const maxAgeMs = Math.max(
+    0,
+    parseEnvInt(process.env.MCP_COLLAB_SESSION_MAX_AGE_MS, 10 * 60 * 1000),
+  );
+  const maxEntriesRaw = parseEnvInt(
+    process.env.MCP_COLLAB_SESSION_MAX_ENTRIES,
+    32,
+  );
+  const maxEntries = maxEntriesRaw > 0 ? maxEntriesRaw : 32;
+  return { idleMs, maxAgeMs, maxEntries };
+}
+
+/**
+ * The subset of HocuspocusProvider this module depends on, so the provider can
+ * be replaced with a fake in unit tests (there is no server in the test env).
+ */
+export interface CollabProviderLike {
+  synced: boolean;
+  unsyncedChanges: number;
+  destroy(): void;
+  on(event: "unsyncedChanges", handler: (data: { number: number }) => void): void;
+  off(event: "unsyncedChanges", handler: (data: { number: number }) => void): void;
+}
+
+/** The configuration object passed to the provider factory. */
+export interface CollabProviderConfig {
+  url: string;
+  name: string;
+  document: Y.Doc;
+  token: string;
+  WebSocketPolyfill: unknown;
+  onConnect: () => void;
+  onSynced: () => void;
+  onDisconnect: () => void;
+  onClose: () => void;
+  onAuthenticationFailed: () => void;
+}
+
+export type CollabProviderFactory = (
+  config: CollabProviderConfig,
+) => CollabProviderLike;
+
+const defaultProviderFactory: CollabProviderFactory = (config) =>
+  // @ts-ignore - WebSocketPolyfill is required for the Node.js environment.
+  new HocuspocusProvider(config) as unknown as CollabProviderLike;
+
+let providerFactory: CollabProviderFactory = defaultProviderFactory;
+
+/**
+ * TEST SEAM: swap the provider factory (pass null to restore the real one).
+ * Not part of the public API — used only by the unit tests, which cannot reach
+ * a real collaboration server.
+ */
+export function __setCollabProviderFactory(
+  factory: CollabProviderFactory | null,
+): void {
+  providerFactory = factory ?? defaultProviderFactory;
+}
+
+/** Optional per-acquire hooks (metrics), passed through from the call site. */
+export interface AcquireOptions {
+  /** Invoked when the initial connect handshake times out (CONNECT_TIMEOUT_MS). */
+  onConnectTimeout?: () => void;
+}
+
+type SessionState = "connecting" | "ready" | "dead";
+
+/**
+ * One live provider + ydoc for a single (wsUrl, pageId, token) triple.
+ *
+ * Lifecycle: connecting -> ready -> dead. A session becomes `dead` on the first
+ * disconnect/close/auth-failure at ANY time, on an idle/eviction/max-age
+ * teardown, or on an explicit destroy(); death is terminal and removes the
+ * session from the registry so the next acquire opens a fresh one. We never use
+ * the provider's auto-reconnect — destroying on the first disconnect closes the
+ * "reconnect drove unsyncedChanges to 0 without retransmitting our write" class
+ * of false success.
+ */
+export class CollabSession {
+  readonly key: string;
+  readonly pageId: string;
+  readonly wsUrl: string;
+  readonly token: string;
+  readonly createdAt: number;
+  state: SessionState = "connecting";
+  /**
+   * Set true on disconnect/close/auth-failure so a reconnect-driven
+   * unsyncedChanges->0 cannot be mistaken for a successful persist of our
+   * write (preserved verbatim from the one-shot machine).
+   */
+  connectionLost = false;
+
+  provider: CollabProviderLike | undefined;
+  private readonly ydoc: Y.Doc;
+  private readonly cfg: SessionConfig;
+  /**
+   * Ephemeral sessions (cache disabled, MCP_COLLAB_SESSION_IDLE_MS<=0) are never
+   * registered and self-destroy after their single op — the legacy
+   * provider-per-op behavior.
+   */
+  private readonly ephemeral: boolean;
+  private readonly opts: AcquireOptions | undefined;
+
+  private dead = false;
+  private connectTimer: ReturnType<typeof setTimeout> | undefined;
+  private idleTimer: ReturnType<typeof setTimeout> | undefined;
+  private openPromise: Promise<void> | undefined;
+  private openResolve: (() => void) | undefined;
+  private openReject: ((err: Error) => void) | undefined;
+  private openSettled = false;
+  /**
+   * The rejector of the CURRENT in-flight mutate, if any. A disconnect/close/
+   * auth-failure or timeout at ANY time rejects the in-flight op through this
+   * with the SAME error text the one-shot machine emitted.
+   */
+  private inflightReject: ((err: Error) => void) | undefined;
+
+  constructor(
+    key: string,
+    pageId: string,
+    wsUrl: string,
+    token: string,
+    cfg: SessionConfig,
+    ephemeral: boolean,
+    opts: AcquireOptions | undefined,
+  ) {
+    this.key = key;
+    this.pageId = pageId;
+    this.wsUrl = wsUrl;
+    this.token = token;
+    this.cfg = cfg;
+    this.ephemeral = ephemeral;
+    this.opts = opts;
+    this.createdAt = Date.now();
+    this.ydoc = new Y.Doc();
+  }
+
+  /**
+   * A cached session may be reused only when it is fully ready, still synced,
+   * has not lost its connection, and has not exceeded its max age (invariant 5
+   * "validate on reuse" + the max-age acquire check).
+   */
+  isReusable(): boolean {
+    return (
+      !this.dead &&
+      this.state === "ready" &&
+      !this.connectionLost &&
+      !!this.provider &&
+      this.provider.synced === true &&
+      Date.now() - this.createdAt < this.cfg.maxAgeMs
+    );
+  }
+
+  /**
+   * Connect and wait for the initial sync (onSynced) within CONNECT_TIMEOUT_MS.
+   * Idempotent: repeated calls return the same in-flight/settled promise.
+   */
+  open(): Promise<void> {
+    if (this.openPromise) return this.openPromise;
+    this.openPromise = new Promise<void>((resolve, reject) => {
+      this.openResolve = resolve;
+      this.openReject = reject;
+
+      this.connectTimer = setTimeout(() => {
+        // The 25s connect timeout: the collab connection never became ready.
+        this.opts?.onConnectTimeout?.();
+        this.teardown(
+          new Error("Connection timeout to collaboration server"),
+          false,
+        );
+      }, CONNECT_TIMEOUT_MS);
+
+      if (process.env.DEBUG)
+        console.error(`Connecting to WebSocket: ${this.wsUrl}`);
+
+      this.provider = providerFactory({
+        url: this.wsUrl,
+        name: `page.${this.pageId}`,
+        document: this.ydoc,
+        token: this.token,
+        WebSocketPolyfill: WebSocket,
+        onConnect: () => {
+          if (process.env.DEBUG) console.error("WS Connect");
+        },
+        // An unexpected disconnect/close at ANY time (during the connect-wait,
+        // between edits, or during a persistence wait) makes the session dead:
+        // surface it now instead of hanging, reject any in-flight op with the
+        // same error text as the one-shot machine, and remove ourselves from
+        // the registry so the next acquire opens fresh. `teardown` is idempotent
+        // so the onClose our own destroy() triggers is a harmless no-op.
+        onDisconnect: () => {
+          if (process.env.DEBUG) console.error("WS Disconnect");
+          this.teardown(
+            new Error(
+              "Collaboration connection closed before the update was persisted/synced",
+            ),
+            true,
+          );
+        },
+        onClose: () => {
+          if (process.env.DEBUG) console.error("WS Close");
+          this.teardown(
+            new Error(
+              "Collaboration connection closed before the update was persisted/synced",
+            ),
+            true,
+          );
+        },
+        onSynced: () => {
+          if (this.dead || this.openSettled) return;
+          if (process.env.DEBUG) console.error("Connected and synced!");
+          if (this.connectTimer) {
+            clearTimeout(this.connectTimer);
+            this.connectTimer = undefined;
+          }
+          this.state = "ready";
+          this.openSettled = true;
+          this.openResolve?.();
+        },
+        onAuthenticationFailed: () => {
+          this.teardown(
+            new Error("Authentication failed for collaboration connection"),
+            true,
+          );
+        },
+      });
+    });
+    return this.openPromise;
+  }
+
+  /**
+   * Run one atomic read -> transform -> write against the LIVE doc and wait for
+   * the server to acknowledge the write.
+   *
+   * INVARIANT 1 (read->write atomicity): between `TiptapTransformer.fromYdoc`
+   * and `applyDocToFragment` there is NO `await`. Yjs applies remote updates
+   * only when the event loop yields, so this synchronous block sees a consistent
+   * live doc and no concurrent human edit can interleave and be clobbered —
+   * exactly as in the one-shot onSynced code, just on a persistent provider.
+   *
+   * INVARIANT 2 (per-edit ack): after the write, resolve immediately if
+   * unsyncedChanges is already 0, else wait for the unsyncedChanges->0 event
+   * (PERSIST_TIMEOUT_MS), guarded by connectionLost so a reconnect handshake
+   * cannot report a false success.
+   *
+   * CONCURRENCY: not safe to invoke concurrently on ONE session — the caller
+   * MUST serialize (hold the per-page lock), mirroring acquireCollabSession.
+   * The in-flight op is tracked in a single `inflightReject` field, so an
+   * overlapping second call would clobber the first's rejector and leave it
+   * hanging on disconnect. A fail-fast guard below rejects the overlap instead.
+   * Sequential (awaited) mutates are fine: localFinish clears inflightReject
+   * before the promise settles, so the guard is clear by the time the next runs.
+   */
+  mutate(
+    transform: (liveDoc: any) => any | null,
+  ): Promise<MutationResult> {
+    // Belt-and-suspenders (acquire already validated): refuse to write on a
+    // session that is not in a live, synced, ready state.
+    if (
+      this.dead ||
+      this.state !== "ready" ||
+      this.connectionLost ||
+      !this.provider ||
+      this.provider.synced !== true
+    ) {
+      return Promise.reject(
+        new Error("Collaboration session is not in a ready state"),
+      );
+    }
+
+    // Fail-fast on concurrent use: a second overlapping mutate would overwrite
+    // the first's inflightReject, so a disconnect would only reject the second
+    // and hang the first until PERSIST_TIMEOUT_MS. Reject the overlap WITHOUT
+    // touching the in-flight op's state (no localFinish/teardown here).
+    if (this.inflightReject) {
+      return Promise.reject(
+        new Error(
+          "mutate already in-flight; caller must serialize (hold the page lock)",
+        ),
+      );
+    }
+
+    return new Promise<MutationResult>((resolve, reject) => {
+      let settled = false;
+      let persistTimer: ReturnType<typeof setTimeout> | undefined;
+      let unsyncedHandler:
+        | ((data: { number: number }) => void)
+        | undefined;
+      // The verifiable result resolved on every success/abort path. Set on
+      // abort (no-op report) and after a real write (computed change report).
+      let mutationResult: MutationResult;
+
+      const localFinish = (err: Error | null, value?: MutationResult) => {
+        if (settled) return;
+        settled = true;
+        if (persistTimer) clearTimeout(persistTimer);
+        if (unsyncedHandler && this.provider) {
+          try {
+            this.provider.off("unsyncedChanges", unsyncedHandler);
+          } catch (e) {}
+        }
+        this.inflightReject = undefined;
+        if (err) reject(err);
+        else resolve(value as MutationResult);
+        // Post-settle lifecycle: an ephemeral (cache-disabled) session dies with
+        // its single op; a cached session that is still alive re-arms its idle
+        // TTL so the clock starts from the LAST op.
+        if (this.ephemeral) {
+          this.destroy("ephemeral op complete");
+        } else if (!this.dead) {
+          this.armIdle();
+        }
+      };
+
+      // Register so a disconnect/close/auth-failure/teardown rejects THIS op
+      // with the connection-loss error text. localFinish's `settled` guard makes
+      // a racing teardown + normal resolve safe (first one wins).
+      this.inflightReject = (e: Error) => localFinish(e);
+
+      // Resolve once the server acknowledges our update: the provider increments
+      // unsyncedChanges when the local update is sent and decrements it on the
+      // server's SyncStatus(applied=true); reaching 0 means the authoritative
+      // in-memory ydoc on the server now contains our write.
+      const waitForPersistence = () => {
+        if (settled) return;
+        // A missing provider is a failure, not a success: without it the write
+        // can never have been acknowledged.
+        if (!this.provider) {
+          localFinish(new Error("collab provider gone before persistence"));
+          return;
+        }
+        if (this.provider.unsyncedChanges === 0) {
+          localFinish(null, mutationResult);
+          return;
+        }
+        persistTimer = setTimeout(() => {
+          localFinish(
+            new Error(
+              "Timeout waiting for collaboration server to persist the update",
+            ),
+          );
+        }, PERSIST_TIMEOUT_MS);
+        unsyncedHandler = (data: { number: number }) => {
+          // Only treat unsyncedChanges->0 as success when the connection is
+          // still up. A transient disconnect + reconnect handshake can drive the
+          // counter back to 0 without our write being re-transmitted; in that
+          // case let the disconnect/close error win instead.
+          if (data.number === 0 && !this.connectionLost) {
+            localFinish(null, mutationResult);
+          }
+        };
+        this.provider.on("unsyncedChanges", unsyncedHandler);
+      };
+
+      // CRITICAL: everything between reading the live doc and writing it back
+      // must stay synchronous (no await). While the JS event loop is not
+      // yielded, no incoming remote update can interleave, so any already-synced
+      // concurrent edits are preserved in liveDoc.
+      let newDoc: any;
+      let beforeDoc: any;
+      try {
+        let liveDoc = TiptapTransformer.fromYdoc(this.ydoc, "default");
+        if (
+          !liveDoc ||
+          typeof liveDoc !== "object" ||
+          !Array.isArray(liveDoc.content)
+        ) {
+          liveDoc = { type: "doc", content: [] };
+        }
+
+        // Snapshot the before-doc for the change report. Docs are
+        // JSON-serializable, so this is a safe deep clone.
+        beforeDoc = JSON.parse(JSON.stringify(liveDoc));
+
+        newDoc = transform(liveDoc);
+
+        if (newDoc == null) {
+          // Transform aborted — write nothing, return the live doc with a no-op
+          // change report.
+          mutationResult = {
+            doc: liveDoc,
+            verify: {
+              changed: false,
+              textInserted: 0,
+              textDeleted: 0,
+              blocksChanged: 0,
+              marks: {},
+              summary: "no changes (transform aborted)",
+            },
+          };
+          localFinish(null, mutationResult);
+          return;
+        }
+
+        // Structural diff into the live fragment (issue #152): preserves the Yjs
+        // ids of unchanged nodes, so an open editor's cursor is not yanked to the
+        // end of the document on every agent write.
+        applyDocToFragment(this.ydoc, newDoc);
+      } catch (e) {
+        // Includes errors thrown by transform (e.g. "afterText not found",
+        // "text not found"): propagate them verbatim to the caller.
+        localFinish(e instanceof Error ? e : new Error(String(e)));
+        return;
+      }
+
+      // Compute the verifiable change report AFTER the transact write: it only
+      // needs the JSON before/after, so it cannot affect the atomic read->write
+      // window, and summarizeChange never throws.
+      mutationResult = {
+        doc: newDoc,
+        verify: summarizeChange(beforeDoc, newDoc),
+      };
+      if (process.env.DEBUG)
+        console.error("Content written, waiting for server to persist...");
+      waitForPersistence();
+    });
+  }
+
+  /** (Re)arm the idle TTL so the clock starts from the most recent activity. */
+  armIdle(): void {
+    if (this.dead || this.ephemeral) return;
+    if (this.idleTimer) clearTimeout(this.idleTimer);
+    if (this.cfg.idleMs > 0) {
+      this.idleTimer = setTimeout(() => {
+        this.destroy("idle timeout");
+      }, this.cfg.idleMs);
+      // Never let the idle timer keep the process alive.
+      (this.idleTimer as any).unref?.();
+    }
+  }
+
+  /**
+   * Idempotent teardown: mark dead, clear timers, remove from the registry, fail
+   * any pending open/in-flight op, and destroy the provider. `inflightError` is
+   * the error a pending open or in-flight op is rejected with; `connectionLoss`
+   * marks the session as connection-lost so the ack guard cannot report a false
+   * success on a racing unsyncedChanges->0.
+   */
+  private teardown(inflightError: Error | null, connectionLoss: boolean): void {
+    if (this.dead) return;
+    this.dead = true;
+    this.state = "dead";
+    if (connectionLoss) this.connectionLost = true;
+
+    if (this.connectTimer) {
+      clearTimeout(this.connectTimer);
+      this.connectTimer = undefined;
+    }
+    if (this.idleTimer) {
+      clearTimeout(this.idleTimer);
+      this.idleTimer = undefined;
+    }
+
+    // Remove ourselves from the registry (only if we are still the live entry —
+    // a re-open under the same key must not be evicted by our teardown).
+    if (sessions.get(this.key) === this) {
+      sessions.delete(this.key);
+    }
+
+    // Fail a pending open() and any in-flight mutate with the terminal error.
+    if (!this.openSettled) {
+      this.openSettled = true;
+      this.openReject?.(
+        inflightError ?? new Error("Collaboration session destroyed"),
+      );
+    }
+    if (this.inflightReject) {
+      const rej = this.inflightReject;
+      this.inflightReject = undefined;
+      rej(inflightError ?? new Error("Collaboration session destroyed"));
+    }
+
+    if (this.provider) {
+      try {
+        this.provider.destroy();
+      } catch (e) {}
+      this.provider = undefined;
+    }
+  }
+
+  /**
+   * Public idempotent teardown used by the acquire/eviction paths and by a
+   * caller that wants the session dropped after a failed op ("next call
+   * reconnects fresh").
+   */
+  destroy(reason: string): void {
+    if (this.dead) return;
+    if (process.env.DEBUG)
+      console.error(`Destroying collab session ${this.pageId}: ${reason}`);
+    this.teardown(new Error(`Collaboration session destroyed: ${reason}`), false);
+  }
+}
+
+/** key = wsUrl + pageId + collabToken (identity isolation: invariant 4). */
+const sessions = new Map<string, CollabSession>();
+
+function sessionKey(wsUrl: string, pageId: string, token: string): string {
+  // The token is part of the key so sessions are NEVER shared between different
+  // users' MCP sessions (HTTP mode), and a token rotation makes a new entry
+  // while the old one idles out.
+  return `${wsUrl}${pageId}${token}`;
+}
+
+/**
+ * Get a live, synced CollabSession for a page, reusing a cached one when it is
+ * still valid or opening a fresh one otherwise. Does NOT take the per-page lock
+ * — the caller MUST already hold it (both call sites run inside withPageLock,
+ * which is not reentrant, so acquiring the lock here would deadlock
+ * mutateLiveContentUnlocked).
+ */
+export async function acquireCollabSession(
+  pageId: string,
+  collabToken: string,
+  baseUrl: string,
+  opts?: AcquireOptions,
+): Promise<CollabSession> {
+  const cfg = readConfig();
+  const wsUrl = buildCollabWsUrl(baseUrl);
+
+  // Cache disabled (rollback path): open an unregistered ephemeral session that
+  // self-destroys after its single op — the exact legacy per-op-provider flow.
+  if (cfg.idleMs <= 0) {
+    const session = new CollabSession(
+      sessionKey(wsUrl, pageId, collabToken),
+      pageId,
+      wsUrl,
+      collabToken,
+      cfg,
+      true,
+      opts,
+    );
+    await session.open();
+    return session;
+  }
+
+  const key = sessionKey(wsUrl, pageId, collabToken);
+  const existing = sessions.get(key);
+  if (existing) {
+    if (existing.isReusable()) {
+      // Reuse. Refresh LRU order (re-insert = most recently used) and re-arm the
+      // idle TTL so the reuse counts as activity.
+      sessions.delete(key);
+      sessions.set(key, existing);
+      existing.armIdle();
+      if (process.env.DEBUG)
+        console.error(`Reusing collab session for page ${pageId}`);
+      return existing;
+    }
+    // Stale (not synced / past max age / lost): drop it and open fresh.
+    existing.destroy("stale on reuse");
+  }
+
+  // Enforce the registry cap before inserting: destroy-evict the least recently
+  // used (the first entry in insertion order) until there is room.
+  while (sessions.size >= cfg.maxEntries) {
+    const oldestKey: string | undefined = sessions.keys().next().value;
+    if (oldestKey === undefined) break;
+    const victim = sessions.get(oldestKey);
+    if (victim) victim.destroy("evicted (LRU cap)");
+    // destroy() removes it from the map; guard against a no-op destroy.
+    if (sessions.has(oldestKey)) sessions.delete(oldestKey);
+  }
+
+  const session = new CollabSession(
+    key,
+    pageId,
+    wsUrl,
+    collabToken,
+    cfg,
+    false,
+    opts,
+  );
+  sessions.set(key, session);
+  try {
+    await session.open();
+  } catch (e) {
+    // Failed connect/sync: make sure it is not left cached.
+    session.destroy("open failed");
+    throw e;
+  }
+  session.armIdle();
+  if (process.env.DEBUG)
+    console.error(`Opened new collab session for page ${pageId}`);
+  return session;
+}
+
+/**
+ * Destroy every cached session. Wired into the process shutdown so a hanging
+ * session does not keep a doc loaded on the server past exit.
+ */
+export function destroyAllSessions(): void {
+  for (const session of [...sessions.values()]) {
+    session.destroy("process shutdown");
+  }
+  sessions.clear();
+}
+
+/** TEST-ONLY: number of currently cached sessions. */
+export function __sessionCountForTests(): number {
+  return sessions.size;
+}

packages/mcp/src/lib/collaboration.ts

@@ -1,4 +1,3 @@
-import { HocuspocusProvider } from "@hocuspocus/provider";
 import { TiptapTransformer } from "@hocuspocus/transformer";
 import * as Y from "yjs";
 import WebSocket from "ws";
@@ -16,7 +15,8 @@ import { docmostExtensions, docmostSchema } from "./docmost-schema.js";
 import { withPageLock } from "./page-lock.js";
 import { sanitizeForYjs, findUnstorableAttr } from "./node-ops.js";
 import { canonicalizeFootnotes } from "./footnote-canonicalize.js";
-import { summarizeChange, VerifyReport } from "./diff.js";
+import { VerifyReport } from "./diff.js";
+import { acquireCollabSession } from "./collab-session.js";
 
 export { markdownToProseMirror };
 
@@ -194,26 +194,27 @@ export function assertYjsEncodable(doc: any): void {
   }
 }
 
-/** Time we wait for the initial handshake/sync before giving up. */
-const CONNECT_TIMEOUT_MS = 25000;
-/** Time we wait for the server to acknowledge our write before giving up. */
-const PERSIST_TIMEOUT_MS = 20000;
-
 /**
  * Safely mutate the live content of a page over the collaboration websocket.
  *
  * This is the single safe write path for every MCP content mutation. It:
  *   1. serializes per-page writes through withPageLock (no two MCP writes on
  *      the same page overlap);
- *   2. connects to Hocuspocus and waits for the initial sync so the local ydoc
- *      mirrors the authoritative server doc — INCLUDING edits/comments/images
- *      that are not yet in the debounced REST snapshot;
- *   3. inside onSynced, SYNCHRONOUSLY reads the live doc, runs `transform`, and
- *      writes the result back — with no `await` between read and write so no
- *      remote update can interleave and clobber concurrent human edits;
+ *   2. acquires a LIVE, synced CollabSession for the page (issue #400) — a
+ *      cached provider whose local ydoc mirrors the authoritative server doc
+ *      (INCLUDING edits/comments/images not yet in the debounced REST snapshot),
+ *      reused across a series of edits instead of a fresh connect/auth/sync per
+ *      call;
+ *   3. SYNCHRONOUSLY reads the live doc, runs `transform`, and writes the result
+ *      back — with no `await` between read and write so no remote update can
+ *      interleave and clobber concurrent human edits (CollabSession.mutate);
  *   4. waits for the server to acknowledge the write (unsyncedChanges -> 0)
  *      before resolving, so the next operation observes our change.
  *
+ * On any mutate failure the session is destroyed so the next call reconnects
+ * fresh; the page lock is held for the whole acquire+mutate so the session's
+ * synchronous read->write window never overlaps another MCP write on the page.
+ *
  * `transform` receives the live ProseMirror doc and returns the NEW full
  * ProseMirror doc to write, or `null` to abort with no write (a no-op). If
  * `transform` throws, the error is propagated to the caller (not swallowed).
@@ -230,7 +231,7 @@ export async function mutatePageContent(
   baseUrl: string,
   transform: (liveDoc: any) => any | null,
 ): Promise<MutationResult> {
-  return withPageLock(pageId, () => {
+  return withPageLock(pageId, async () => {
     if (process.env.DEBUG) {
       console.error(`Starting realtime content mutate for page ${pageId}`);
       // Token prefix is sensitive; only log it under DEBUG.
@@ -239,202 +240,15 @@ export async function mutatePageContent(
       );
     }
 
-    const ydoc = new Y.Doc();
-    const wsUrl = buildCollabWsUrl(baseUrl);
-    if (process.env.DEBUG) console.error(`Connecting to WebSocket: ${wsUrl}`);
-
-    return new Promise<MutationResult>((resolve, reject) => {
-      let provider: HocuspocusProvider | undefined;
-      let applied = false; // onSynced may fire again on reconnect — apply once.
-      let settled = false;
-      // Set true on disconnect/close so a reconnect-driven unsyncedChanges->0
-      // cannot be mistaken for a successful persist of our write.
-      let connectionLost = false;
-      let connectTimer: ReturnType<typeof setTimeout> | undefined;
-      let persistTimer: ReturnType<typeof setTimeout> | undefined;
-      let unsyncedHandler: ((data: { number: number }) => void) | undefined;
-
-      const cleanup = () => {
-        if (connectTimer) clearTimeout(connectTimer);
-        if (persistTimer) clearTimeout(persistTimer);
-        if (provider) {
-          if (unsyncedHandler) {
-            try {
-              provider.off("unsyncedChanges", unsyncedHandler);
-            } catch (err) {}
-          }
-          try {
-            provider.destroy();
-          } catch (err) {}
-        }
-      };
-
-      const finish = (err: Error | null, value?: MutationResult) => {
-        if (settled) return;
-        settled = true;
-        cleanup();
-        if (err) reject(err);
-        else resolve(value as MutationResult);
-      };
-
-      connectTimer = setTimeout(() => {
-        finish(new Error("Connection timeout to collaboration server"));
-      }, CONNECT_TIMEOUT_MS);
-
-      // Resolve once the server has acknowledged our update. The provider
-      // increments unsyncedChanges when our local update is sent and
-      // decrements it when the server replies with a SyncStatus(applied=true);
-      // reaching 0 means the authoritative in-memory ydoc on the server now
-      // contains our write.
-      const waitForPersistence = () => {
-        if (settled) return;
-        // A missing provider is a failure, not a success: without it the write
-        // can never have been acknowledged. Only an actual unsyncedChanges===0
-        // on a live provider counts as persisted.
-        if (!provider) {
-          finish(new Error("collab provider gone before persistence"));
-          return;
-        }
-        if (provider.unsyncedChanges === 0) {
-          finish(null, mutationResult);
-          return;
-        }
-        persistTimer = setTimeout(() => {
-          finish(
-            new Error(
-              "Timeout waiting for collaboration server to persist the update",
-            ),
-          );
-        }, PERSIST_TIMEOUT_MS);
-        unsyncedHandler = (data: { number: number }) => {
-          // Only treat unsyncedChanges->0 as success when the connection is
-          // still up. A transient disconnect + reconnect handshake can drive
-          // the counter back to 0 without our write being re-transmitted; in
-          // that case let the disconnect/close error win instead.
-          if (data.number === 0 && !connectionLost) {
-            finish(null, mutationResult);
-          }
-        };
-        provider.on("unsyncedChanges", unsyncedHandler);
-      };
-
-      // The verifiable result resolved on every success/abort path. Set on
-      // abort (no-op report) and after a real write (computed change report).
-      let mutationResult: MutationResult;
-
-      provider = new HocuspocusProvider({
-        url: wsUrl,
-        name: `page.${pageId}`,
-        document: ydoc,
-        token: collabToken,
-        // @ts-ignore - Required for Node.js environment
-        WebSocketPolyfill: WebSocket,
-        onConnect: () => {
-          if (process.env.DEBUG) console.error("WS Connect");
-        },
-        // An unexpected disconnect/close while we are still waiting (during the
-        // connect-wait before onSynced, or during the persistence wait after the
-        // write) means the update will never be acknowledged — surface it now
-        // instead of hanging until the connect/persist timeout fires. `finish`
-        // is idempotent via the `settled` flag, so the onClose that our own
-        // cleanup()->provider.destroy() triggers (after settled=true is set) is
-        // a harmless no-op and cannot cause a double-resolve.
-        onDisconnect: () => {
-          if (process.env.DEBUG) console.error("WS Disconnect");
-          // Mark BEFORE finish so the unsyncedChanges handler (if it races)
-          // sees the connection as lost and won't report a false success.
-          connectionLost = true;
-          finish(
-            new Error(
-              "Collaboration connection closed before the update was persisted/synced",
-            ),
-          );
-        },
-        onClose: () => {
-          if (process.env.DEBUG) console.error("WS Close");
-          // Mark BEFORE finish so the unsyncedChanges handler (if it races)
-          // sees the connection as lost and won't report a false success.
-          connectionLost = true;
-          finish(
-            new Error(
-              "Collaboration connection closed before the update was persisted/synced",
-            ),
-          );
-        },
-        onSynced: () => {
-          if (applied || settled) return;
-          applied = true;
-          if (process.env.DEBUG) console.error("Connected and synced!");
-
-          // CRITICAL: everything between reading the live doc and writing it
-          // back must stay synchronous (no await). While the JS event loop is
-          // not yielded, no incoming remote update can interleave, so any
-          // already-synced concurrent edits are preserved in liveDoc.
-          let newDoc: any;
-          let beforeDoc: any;
-          try {
-            let liveDoc = TiptapTransformer.fromYdoc(ydoc, "default");
-            if (
-              !liveDoc ||
-              typeof liveDoc !== "object" ||
-              !Array.isArray(liveDoc.content)
-            ) {
-              liveDoc = { type: "doc", content: [] };
-            }
-
-            // Snapshot the before-doc for the change report. Docs are
-            // JSON-serializable, so this is a safe deep clone.
-            beforeDoc = JSON.parse(JSON.stringify(liveDoc));
-
-            newDoc = transform(liveDoc);
-
-            if (newDoc == null) {
-              // Transform aborted — write nothing, return the live doc with a
-              // no-op change report.
-              mutationResult = {
-                doc: liveDoc,
-                verify: {
-                  changed: false,
-                  textInserted: 0,
-                  textDeleted: 0,
-                  blocksChanged: 0,
-                  marks: {},
-                  summary: "no changes (transform aborted)",
-                },
-              };
-              finish(null, mutationResult);
-              return;
-            }
-
-            // Structural diff into the live fragment (issue #152): preserves
-            // the Yjs ids of unchanged nodes, so an open editor's cursor is not
-            // yanked to the end of the document on every agent write.
-            applyDocToFragment(ydoc, newDoc);
-          } catch (e) {
-            // Includes errors thrown by transform (e.g. "afterText not found",
-            // "text not found"): propagate them verbatim to the caller.
-            finish(e instanceof Error ? e : new Error(String(e)));
-            return;
-          }
-
-          // Compute the verifiable change report AFTER the transact write: it
-          // only needs the JSON before/after, so it cannot affect the atomic
-          // read->write window, and summarizeChange never throws.
-          mutationResult = {
-            doc: newDoc,
-            verify: summarizeChange(beforeDoc, newDoc),
-          };
-          if (process.env.DEBUG)
-            console.error("Content written, waiting for server to persist...");
-          waitForPersistence();
-        },
-        onAuthenticationFailed: () => {
-          finish(
-            new Error("Authentication failed for collaboration connection"),
-          );
-        },
-      });
-    });
+    const session = await acquireCollabSession(pageId, collabToken, baseUrl);
+    try {
+      return await session.mutate(transform);
+    } catch (e) {
+      // Drop the session on any failure so the next call reconnects fresh (this
+      // also closes the "reconnect drove the counter to 0" false-success class).
+      session.destroy("mutate failed");
+      throw e;
+    }
   });
 }
 

packages/mcp/src/lib/comment-anchor.ts

@@ -17,8 +17,23 @@
  * comparing and match across maximal runs of consecutive text nodes within a
  * single block, while mapping every normalized character back to its raw index
  * so the mark lands on the exact original characters.
+ *
+ * MARKDOWN-STRIP FALLBACK: when the agent copies a selection that still carries
+ * inline markdown (`**bold**`, `` `code` ``, `[t](u)`), the raw locator will not
+ * match the document's plain text. Exactly like edit_page_text's json-edit
+ * fallback, we first try the verbatim selection and, ONLY if it anchors nowhere
+ * in the whole document, retry with `stripInlineMarkdown` applied. `canAnchorInDoc`,
+ * `getAnchoredText` and `applyAnchorInDoc` share this decision via
+ * `resolveAnchorSelection`. `countAnchorMatches` keeps its OWN parallel exact-wins
+ * implementation (it needs a raw match COUNT, not a single resolved locator), kept
+ * deliberately in sync with `resolveAnchorSelection`: raw match ⇒ use raw, else fall
+ * back to the stripped count. All four therefore agree on which locator matched —
+ * the suggestion-uniqueness gate depends on count and can/get never disagreeing, so
+ * these two exact-wins implementations MUST stay in sync if either is changed.
  */
 
+import { stripInlineMarkdown } from "./text-normalize.js";
+
 /** Typographic double-quote variants mapped to ASCII `"`. */
 const DOUBLE_QUOTES = "«»„“”‟〝〞＂";
 /** Typographic single-quote/apostrophe variants mapped to ASCII `'`. */
@@ -214,15 +229,17 @@ function reconstructRawText(blockContent: any[], match: AnchorMatch): string {
  * un-appliable (spurious 409).
  */
 export function getAnchoredText(doc: any, selection: string): string | null {
+  const { selection: effective, found } = resolveAnchorSelection(doc, selection);
+  if (!found) return null;
   const visit = (node: any, depth: number): string | null => {
     if (depth > MAX_DEPTH || !node || typeof node !== "object") return null;
     if (!Array.isArray(node.content)) return null;
-    const match = findAnchorInBlock(node.content, selection);
+    const match = findAnchorInBlock(node.content, effective);
     if (match) return reconstructRawText(node.content, match);
     for (const child of node.content) {
       if (child && typeof child === "object" && Array.isArray(child.content)) {
-        const found = visit(child, depth + 1);
-        if (found !== null) return found;
+        const foundText = visit(child, depth + 1);
+        if (foundText !== null) return foundText;
       }
     }
     return null;
@@ -231,12 +248,11 @@ export function getAnchoredText(doc: any, selection: string): string | null {
 }
 
 /**
- * Depth-first, document-order check for whether `selection` can be anchored
- * anywhere in `doc`. At each node with an array `content`, first try to match
- * within that node's own content, then recurse into children that themselves
- * have a `content` array.
+ * RAW (no markdown-strip fallback) depth-first check that `selection` anchors
+ * somewhere in `doc`. This is the primitive `resolveAnchorSelection` builds on;
+ * public callers should use `canAnchorInDoc`, which adds the strip fallback.
  */
-export function canAnchorInDoc(doc: any, selection: string): boolean {
+function rawCanAnchorInDoc(doc: any, selection: string): boolean {
   const visit = (node: any, depth: number): boolean => {
     if (depth > MAX_DEPTH || !node || typeof node !== "object") return false;
     if (!Array.isArray(node.content)) return false;
@@ -251,6 +267,43 @@ export function canAnchorInDoc(doc: any, selection: string): boolean {
   return visit(doc, 0);
 }
 
+/**
+ * Decide the locator that ACTUALLY anchors `selection` in `doc`, applying the
+ * markdown-strip fallback once (so every public entry point agrees):
+ *  - EXACT WINS: if the verbatim selection anchors anywhere, use it as-is.
+ *  - FALLBACK: only if the verbatim selection anchors nowhere, and the
+ *    markdown-stripped form differs and DOES anchor, use the stripped form and
+ *    flag `normalized` so callers can surface a soft warning.
+ *  - otherwise `found` is false and `selection` is returned unchanged.
+ *
+ * The stripped form is used ONLY to LOCATE the anchor; getAnchoredText still
+ * reconstructs and stores the RAW document substring, so the strip never leaks
+ * into what gets persisted.
+ */
+export function resolveAnchorSelection(
+  doc: any,
+  selection: string,
+): { selection: string; found: boolean; normalized: boolean } {
+  if (rawCanAnchorInDoc(doc, selection)) {
+    return { selection, found: true, normalized: false };
+  }
+  const stripped = stripInlineMarkdown(selection);
+  if (stripped !== selection && rawCanAnchorInDoc(doc, stripped)) {
+    return { selection: stripped, found: true, normalized: true };
+  }
+  return { selection, found: false, normalized: false };
+}
+
+/**
+ * Depth-first, document-order check for whether `selection` can be anchored
+ * anywhere in `doc` (with the markdown-strip fallback). At each node with an
+ * array `content`, first try to match within that node's own content, then
+ * recurse into children that themselves have a `content` array.
+ */
+export function canAnchorInDoc(doc: any, selection: string): boolean {
+  return resolveAnchorSelection(doc, selection).found;
+}
+
 /**
  * Split the matched text nodes and splice the comment mark across the range.
  * `blockContent` is mutated IN PLACE. `match.startChild..endChild` are all text
@@ -315,7 +368,7 @@ function spliceCommentMark(
  * not use this. (Note: counts OCCURRENCES, not just matching blocks, so two
  * occurrences inside one block are correctly reported as 2.)
  */
-export function countAnchorMatches(doc: any, selection: string): number {
+function rawCountAnchorMatches(doc: any, selection: string): number {
   const normSel = normalizeForMatch(selection).norm.trim();
   if (normSel.length === 0) return 0;
 
@@ -369,6 +422,25 @@ export function countAnchorMatches(doc: any, selection: string): number {
   return total;
 }
 
+/**
+ * Uniqueness gate for suggestions, with the SAME markdown-strip fallback as the
+ * other entry points so count never disagrees with can/get/apply. EXACT WINS: if
+ * the verbatim selection occurs at all, return its raw occurrence count (so a
+ * selection that is unique raw stays unique — the fallback never runs and cannot
+ * introduce a spurious second match). Only when the verbatim selection is absent
+ * do we count occurrences of the markdown-stripped form.
+ */
+export function countAnchorMatches(doc: any, selection: string): number {
+  const raw = rawCountAnchorMatches(doc, selection);
+  if (raw > 0) return raw;
+  const stripped = stripInlineMarkdown(selection);
+  if (stripped !== selection) {
+    const strippedCount = rawCountAnchorMatches(doc, stripped);
+    if (strippedCount > 0) return strippedCount;
+  }
+  return 0;
+}
+
 /**
  * Depth-first (same order as canAnchorInDoc) over `doc`; on the FIRST block
  * whose content matches `selection`, splice the comment mark across the matched
@@ -380,10 +452,12 @@ export function applyAnchorInDoc(
   selection: string,
   commentId: string,
 ): boolean {
+  const { selection: effective, found } = resolveAnchorSelection(doc, selection);
+  if (!found) return false;
   const visit = (node: any, depth: number): boolean => {
     if (depth > MAX_DEPTH || !node || typeof node !== "object") return false;
     if (!Array.isArray(node.content)) return false;
-    const match = findAnchorInBlock(node.content, selection);
+    const match = findAnchorInBlock(node.content, effective);
     if (match) {
       spliceCommentMark(node.content, match, commentId);
       return true;

packages/mcp/src/lib/drawio-preview.ts

@@ -0,0 +1,193 @@
+// Pure-TS schematic SVG preview for draw.io diagrams (issue #423, stage 1).
+//
+// HARD CONSTRAINT: no backend rendering. This is a dependency-free string
+// builder — given the parsed mxGraph cells it draws a rough schematic (rects,
+// ellipses, diamonds, edges + labels) that stands in as the diagram's visible
+// image UNTIL a human first opens it in the draw.io editor and saves, at which
+// point the client replaces this with the pixel-perfect export SVG. It is
+// deliberately approximate: it exists so a freshly-agent-created diagram is not
+// an empty box in the page.
+
+import type { DrawioCell, DrawioBBox } from "./drawio-xml.js";
+import { absolutePos } from "./drawio-xml.js";
+
+function esc(s: string): string {
+  return s
+    .replace(/&/g, "&")
+    .replace(/</g, "&lt;")
+    .replace(/>/g, "&gt;")
+    .replace(/"/g, "&quot;");
+}
+
+/**
+ * Strip HTML markup from a cell value (draw.io labels are HTML when html=1),
+ * decode the handful of entities we care about, and collapse whitespace so the
+ * label fits on the schematic. `<br>` becomes a space (this is a one-line
+ * preview label, not a faithful multi-line render).
+ */
+function labelText(value: string): string {
+  return value
+    .replace(/<br\s*\/?>/gi, " ")
+    .replace(/<[^>]+>/g, "")
+    .replace(/&lt;/g, "<")
+    .replace(/&gt;/g, ">")
+    .replace(/&quot;/g, '"')
+    .replace(/&#39;|&apos;/g, "'")
+    .replace(/&#xa;|&#10;/gi, " ")
+    .replace(/&amp;/g, "&")
+    .replace(/\s+/g, " ")
+    .trim();
+}
+
+function centeredLabel(cx: number, cy: number, value: string, color = "#000000"): string {
+  const text = labelText(value);
+  if (!text) return "";
+  return (
+    `<text x="${round(cx)}" y="${round(cy)}" ` +
+    `font-family="Helvetica, Arial, sans-serif" font-size="12" ` +
+    `text-anchor="middle" dominant-baseline="middle" fill="${esc(color)}">` +
+    `${esc(text)}</text>`
+  );
+}
+
+function round(n: number): number {
+  return Math.round(n * 100) / 100;
+}
+
+interface ShapeKind {
+  kind: "ellipse" | "rhombus" | "triangle" | "rect";
+}
+
+/**
+ * Decide which schematic primitive to draw for a vertex. A shape can be named
+ * either as the style's base token (e.g. "ellipse;…") or as a key (e.g.
+ * "shape=rhombus" / "ellipse=1"), so both the base style and the map are
+ * checked.
+ */
+function shapeKind(
+  styleMap: Record<string, string>,
+  baseStyle?: string,
+): ShapeKind {
+  const shape = styleMap.shape ?? baseStyle;
+  const has = (name: string) => shape === name || styleMap[name] != null;
+  if (has("ellipse")) return { kind: "ellipse" };
+  if (has("rhombus")) return { kind: "rhombus" };
+  if (has("triangle")) return { kind: "triangle" };
+  // Everything else — including unknown stencils (shape=mxgraph.*), swimlanes,
+  // and plain boxes — is drawn as a (rounded) rectangle.
+  return { kind: "rect" };
+}
+
+function fill(styleMap: Record<string, string>): string {
+  const c = styleMap.fillColor;
+  if (!c || c.toLowerCase() === "none") return "#ffffff";
+  return c;
+}
+
+function stroke(styleMap: Record<string, string>): string {
+  const c = styleMap.strokeColor;
+  if (!c || c.toLowerCase() === "none") return "#000000";
+  return c;
+}
+
+/**
+ * Render the schematic shapes as the INNER content of the `.drawio.svg` (the
+ * outer <svg> wrapper is added by drawio-xml.buildDrawioSvg). Coordinates are
+ * absolute (container children are resolved via the parent chain).
+ */
+export function renderDiagramShapes(cells: DrawioCell[], _bbox: DrawioBBox): string {
+  const byId = new Map(cells.map((c) => [c.id, c]));
+  const parts: string[] = [];
+
+  // Edges first so vertices sit on top of their connectors.
+  for (const c of cells) {
+    if (!c.edge) continue;
+    parts.push(renderEdge(c, byId));
+  }
+
+  for (const c of cells) {
+    if (!c.vertex || !c.geometry.hasGeometry) continue;
+    const g = c.geometry;
+    if (g.width == null || g.height == null) continue;
+    const { x, y } = absolutePos(c, byId);
+    parts.push(renderVertex(c, x, y, g.width, g.height));
+  }
+
+  return `<g>${parts.filter(Boolean).join("")}</g>`;
+}
+
+function renderVertex(
+  c: DrawioCell,
+  x: number,
+  y: number,
+  w: number,
+  h: number,
+): string {
+  const f = esc(fill(c.styleMap));
+  const s = esc(stroke(c.styleMap));
+  const { kind } = shapeKind(c.styleMap, c.baseStyle);
+  const cx = x + w / 2;
+  const cy = y + h / 2;
+  let shape = "";
+  switch (kind) {
+    case "ellipse":
+      shape =
+        `<ellipse cx="${round(cx)}" cy="${round(cy)}" rx="${round(w / 2)}" ` +
+        `ry="${round(h / 2)}" fill="${f}" stroke="${s}"/>`;
+      break;
+    case "rhombus": {
+      const pts = [
+        `${round(cx)},${round(y)}`,
+        `${round(x + w)},${round(cy)}`,
+        `${round(cx)},${round(y + h)}`,
+        `${round(x)},${round(cy)}`,
+      ].join(" ");
+      shape = `<polygon points="${pts}" fill="${f}" stroke="${s}"/>`;
+      break;
+    }
+    case "triangle": {
+      const pts = [
+        `${round(x)},${round(y)}`,
+        `${round(x + w)},${round(cy)}`,
+        `${round(x)},${round(y + h)}`,
+      ].join(" ");
+      shape = `<polygon points="${pts}" fill="${f}" stroke="${s}"/>`;
+      break;
+    }
+    default: {
+      const rounded = c.styleMap.rounded === "1";
+      const rx = rounded ? Math.min(12, w / 2, h / 2) : 0;
+      shape =
+        `<rect x="${round(x)}" y="${round(y)}" width="${round(w)}" ` +
+        `height="${round(h)}" rx="${round(rx)}" ry="${round(rx)}" ` +
+        `fill="${f}" stroke="${s}"/>`;
+    }
+  }
+  return shape + centeredLabel(cx, cy, c.value, c.styleMap.fontColor || "#000000");
+}
+
+function renderEdge(c: DrawioCell, byId: Map<string, DrawioCell>): string {
+  const src = c.source != null ? byId.get(c.source) : undefined;
+  const tgt = c.target != null ? byId.get(c.target) : undefined;
+  const p1 = anchorPoint(src, byId);
+  const p2 = anchorPoint(tgt, byId);
+  if (!p1 || !p2) return ""; // a floating endpoint with no fixed point: skip
+  const line =
+    `<line x1="${round(p1.x)}" y1="${round(p1.y)}" ` +
+    `x2="${round(p2.x)}" y2="${round(p2.y)}" ` +
+    `stroke="#000000" stroke-width="1"/>`;
+  const mid = { x: (p1.x + p2.x) / 2, y: (p1.y + p2.y) / 2 };
+  return line + centeredLabel(mid.x, mid.y, c.value);
+}
+
+/** Center point of a vertex used as an edge anchor (approximate). */
+function anchorPoint(
+  cell: DrawioCell | undefined,
+  byId: Map<string, DrawioCell>,
+): { x: number; y: number } | null {
+  if (!cell || !cell.geometry.hasGeometry) return null;
+  const g = cell.geometry;
+  if (g.width == null || g.height == null) return null;
+  const { x, y } = absolutePos(cell, byId);
+  return { x: x + g.width / 2, y: y + g.height / 2 };
+}

packages/mcp/src/lib/drawio-xml.ts

@@ -0,0 +1,771 @@
+// draw.io (mxGraph) XML support for the MCP drawio tools (issue #423, stage 1).
+//
+// This module owns everything that is pure data-plumbing for draw.io diagrams:
+//   - the DECODE CHAIN that turns a stored `diagram.drawio.svg` attachment back
+//     into mxGraph XML (handles both the plain nested-XML form Docmost writes
+//     and draw.io's own COMPRESSED `<diagram>` payload — base64 + raw-deflate);
+//   - the ENCODE side that wraps mxGraph XML into the `.drawio.svg` attachment
+//     using the exact same contract as the import service's createDrawioSvg;
+//   - a deterministic LINTER that rejects the structural mistakes generators
+//     make before anything is written (each violation carries the offending
+//     cellId + position so the model can auto-retry);
+//   - a stable HASH over the normalized XML, used as the optimistic-lock key.
+//
+// HARD CONSTRAINT: no backend rendering. Nothing here shells out or renders a
+// bitmap; the only runtime dependencies are jsdom (already used across this
+// package for XML parsing) and pako (raw-inflate for the compressed format).
+
+import { createHash } from "node:crypto";
+import { JSDOM } from "jsdom";
+import pako from "pako";
+
+// --- shared XML parser -----------------------------------------------------
+
+// A single reusable JSDOM window; constructing one per parse is wasteful and
+// these tools are low-frequency. Only the DOMParser is used.
+let _window: any = null;
+function xmlWindow(): any {
+  if (!_window) _window = new JSDOM("").window;
+  return _window;
+}
+
+/** Default mxGraphModel attributes used when the server wraps a cell list. */
+const DEFAULT_MODEL_ATTRS =
+  'dx="0" dy="0" grid="1" gridSize="10" page="1" pageWidth="850" pageHeight="1100"';
+
+// --- structured lint errors ------------------------------------------------
+
+export interface DrawioLintIssue {
+  /** Machine-readable rule id, e.g. "edge-geometry". */
+  rule: string;
+  /** Human-readable explanation the model can act on. */
+  message: string;
+  /** The offending cell's id, when the rule is cell-scoped. */
+  cellId?: string;
+  /** Extra location info: cell index in <root>, or a parser line:col. */
+  position?: string;
+}
+
+/**
+ * Thrown by the linter and by decode/prepare when the input is unusable. Carries
+ * the full list of issues so the caller can surface a structured tool-error the
+ * model auto-retries against.
+ */
+export class DrawioLintError extends Error {
+  issues: DrawioLintIssue[];
+  constructor(issues: DrawioLintIssue[]) {
+    const summary = issues
+      .map((i) => {
+        const where = [
+          i.cellId != null ? `cellId=${i.cellId}` : null,
+          i.position != null ? `at ${i.position}` : null,
+        ]
+          .filter(Boolean)
+          .join(", ");
+        return `[${i.rule}] ${i.message}${where ? ` (${where})` : ""}`;
+      })
+      .join("; ");
+    super(`drawio lint failed: ${summary}`);
+    this.name = "DrawioLintError";
+    this.issues = issues;
+  }
+}
+
+// --- parsed-cell model -----------------------------------------------------
+
+export interface DrawioGeometry {
+  x?: number;
+  y?: number;
+  width?: number;
+  height?: number;
+  relative: boolean;
+  hasGeometry: boolean;
+}
+
+export interface DrawioCell {
+  id: string;
+  parent?: string;
+  source?: string;
+  target?: string;
+  vertex: boolean;
+  edge: boolean;
+  value: string;
+  style: string;
+  styleMap: Record<string, string>;
+  /** Non-key/value leading token of the style (a base stylename), if any. */
+  baseStyle?: string;
+  geometry: DrawioGeometry;
+}
+
+export interface DrawioBBox {
+  width: number;
+  height: number;
+}
+
+// --- style parsing ---------------------------------------------------------
+
+/**
+ * Parse a draw.io style string into { baseStyle, map }. Grammar:
+ *   [stylename;]key=value;key=value;...
+ * A single leading token without '=' is the base stylename (e.g. "text" or
+ * "ellipse"). Every other non-empty segment must be exactly one key=value pair.
+ * Returns `null` (the segment index) on the first malformed segment so the
+ * linter can report a precise error.
+ */
+export function parseStyle(
+  style: string,
+): { baseStyle?: string; map: Record<string, string>; badSegment?: string } {
+  const map: Record<string, string> = {};
+  let baseStyle: string | undefined;
+  const segments = style.split(";");
+  for (let i = 0; i < segments.length; i++) {
+    const seg = segments[i].trim();
+    if (seg === "") continue; // trailing/empty segments are fine
+    const eq = seg.indexOf("=");
+    if (eq === -1) {
+      // A bare token is only valid as the FIRST meaningful segment (base style).
+      if (baseStyle === undefined && Object.keys(map).length === 0) {
+        baseStyle = seg;
+        continue;
+      }
+      return { baseStyle, map, badSegment: seg };
+    }
+    // A second '=' inside the same segment is malformed.
+    if (seg.indexOf("=", eq + 1) !== -1) {
+      return { baseStyle, map, badSegment: seg };
+    }
+    const key = seg.slice(0, eq).trim();
+    const val = seg.slice(eq + 1).trim();
+    if (key === "") return { baseStyle, map, badSegment: seg };
+    map[key] = val;
+  }
+  return { baseStyle, map };
+}
+
+// --- low-level XML helpers -------------------------------------------------
+
+function parseXml(xml: string): { doc: any; error: string | null } {
+  const parser = new (xmlWindow().DOMParser)();
+  const doc = parser.parseFromString(xml, "application/xml");
+  const err = doc.getElementsByTagName("parsererror");
+  if (err.length > 0) {
+    // jsdom prefixes the message with "line:col:" — keep it as the position.
+    return { doc, error: (err[0].textContent || "malformed XML").trim() };
+  }
+  return { doc, error: null };
+}
+
+function num(v: string | null): number | undefined {
+  if (v == null || v === "") return undefined;
+  const n = Number(v);
+  return Number.isFinite(n) ? n : undefined;
+}
+
+/** Extract the raw `<mxGraphModel …>…</mxGraphModel>` substring, or null. */
+function sliceModel(xml: string): string | null {
+  const open = xml.indexOf("<mxGraphModel");
+  if (open === -1) return null;
+  const close = xml.indexOf("</mxGraphModel>", open);
+  if (close === -1) {
+    // Self-closed empty model, e.g. `<mxGraphModel .../>`.
+    const selfClose = xml.indexOf("/>", open);
+    if (selfClose !== -1) return xml.slice(open, selfClose + 2);
+    return null;
+  }
+  return xml.slice(open, close + "</mxGraphModel>".length);
+}
+
+// --- decode chain ----------------------------------------------------------
+
+/**
+ * Read the `content=` attribute out of a `.drawio.svg` string. Docmost stores a
+ * base64 payload there (createDrawioSvg); draw.io's own SVG export may store the
+ * XML entity-encoded instead. The DOM decodes entities for us, so the caller
+ * only has to distinguish "starts with '<'" (raw XML) from base64.
+ */
+export function extractContentAttr(svg: string): string {
+  const { doc, error } = parseXml(svg);
+  if (!error) {
+    const root = doc.documentElement;
+    if (root && root.hasAttribute && root.hasAttribute("content")) {
+      return root.getAttribute("content") || "";
+    }
+  }
+  // Fallback for a malformed wrapper: pull the attribute directly. The content
+  // value itself never contains a double-quote (base64 / entity-encoded XML).
+  const m = /content="([^"]*)"/.exec(svg);
+  if (m) {
+    // Decode the handful of XML entities a raw regex would leave encoded.
+    return m[1]
+      .replace(/&lt;/g, "<")
+      .replace(/&gt;/g, ">")
+      .replace(/&quot;/g, '"')
+      .replace(/&#39;/g, "'")
+      .replace(/&amp;/g, "&");
+  }
+  throw new Error("drawio: SVG has no content= attribute to decode");
+}
+
+/**
+ * Turn a decoded draw.io file (`<mxfile>` or a bare `<mxGraphModel>`, possibly
+ * with a COMPRESSED `<diagram>` payload) into the mxGraphModel XML. For the
+ * plain form the raw substring is returned verbatim so a round-trip stays
+ * byte-stable; the compressed form is inflated (base64 → raw-deflate →
+ * decodeURIComponent), which is how draw.io stores diagrams by default.
+ */
+export function decodeDrawioFileToModel(fileXml: string): string {
+  // Plain, nested XML: return the model substring untouched (byte-stable).
+  const sliced = sliceModel(fileXml);
+  if (sliced) return sliced;
+
+  // Otherwise it must be the compressed `<diagram>…</diagram>` text payload.
+  const open = fileXml.indexOf("<diagram");
+  if (open !== -1) {
+    const gt = fileXml.indexOf(">", open);
+    const close = fileXml.indexOf("</diagram>", gt);
+    if (gt !== -1 && close !== -1) {
+      const payload = fileXml.slice(gt + 1, close).trim();
+      if (payload) {
+        const inflated = inflateDiagramPayload(payload);
+        const model = sliceModel(inflated);
+        if (model) return model;
+        return inflated;
+      }
+    }
+  }
+  throw new Error(
+    "drawio: could not decode file — no <mxGraphModel> and no compressed <diagram> payload",
+  );
+}
+
+/**
+ * Upper bound on the inflated size of a compressed `<diagram>` payload
+ * (decompression-bomb guard). `fetchInternalFile` caps the DOWNLOAD at 64 MiB,
+ * but a tiny crafted compressed payload can inflate to gigabytes and OOM the
+ * process. A real diagram's mxGraphModel XML is small (KBs to low MBs even for
+ * large diagrams), so 16 MiB is far above any legitimate payload while keeping
+ * memory bounded. Chars ~= bytes for the (mostly ASCII) URI-encoded XML.
+ */
+export const MAX_INFLATED_DIAGRAM_BYTES = 16 * 1024 * 1024;
+
+/**
+ * Inflate draw.io's compressed diagram payload:
+ *   base64-decode → raw-inflate (raw deflate, windowBits -15) →
+ *   decodeURIComponent.
+ *
+ * Uses pako's streaming Inflate so we can abort as soon as the decompressed
+ * output exceeds MAX_INFLATED_DIAGRAM_BYTES — the full bomb is never
+ * materialised in memory.
+ */
+export function inflateDiagramPayload(base64: string): string {
+  const bytes = Buffer.from(base64, "base64");
+  const inflator = new pako.Inflate({ raw: true, to: "string" });
+  let total = 0;
+  const passthrough = inflator.onData.bind(inflator);
+  inflator.onData = (chunk: string | Uint8Array) => {
+    total += chunk.length;
+    if (total > MAX_INFLATED_DIAGRAM_BYTES) {
+      // Throwing here propagates out of push(), aborting inflation immediately.
+      throw new Error(
+        `drawio: refusing to decode diagram — decompressed size exceeds ` +
+          `${MAX_INFLATED_DIAGRAM_BYTES} bytes (possible decompression bomb)`,
+      );
+    }
+    passthrough(chunk);
+  };
+  inflator.push(bytes, true);
+  if (inflator.err) {
+    throw new Error(
+      `drawio: failed to inflate compressed <diagram> payload (${inflator.msg || inflator.err})`,
+    );
+  }
+  const uriEncoded = inflator.result as string;
+  return decodeURIComponent(uriEncoded);
+}
+
+/** Full decode chain: `.drawio.svg` string → mxGraphModel XML. */
+export function decodeDrawioSvg(svg: string): string {
+  const content = extractContentAttr(svg).trim();
+  const fileXml = content.startsWith("<")
+    ? content
+    : Buffer.from(content, "base64").toString("utf-8");
+  return decodeDrawioFileToModel(fileXml);
+}
+
+// --- encode side -----------------------------------------------------------
+
+/**
+ * Wrap an mxGraphModel in the plain (uncompressed) `<mxfile><diagram>` envelope.
+ * draw.io opens uncompressed XML fine, and staying uncompressed keeps the
+ * write path deterministic and the round-trip byte-stable.
+ */
+export function encodeDrawioFile(modelXml: string, title = "Page-1"): string {
+  const safeTitle = xmlEscape(title);
+  return `<mxfile host="drawio"><diagram id="page-1" name="${safeTitle}">${modelXml}</diagram></mxfile>`;
+}
+
+/**
+ * Build the `diagram.drawio.svg` attachment. Mirrors the import service's
+ * createDrawioSvg contract exactly:
+ *   <svg xmlns=… xmlns:xlink=… content="${base64(drawioFile)}">${inner}</svg>
+ * plus width/height/viewBox from the diagram bounding box and the schematic
+ * preview as the visible children (`inner`).
+ */
+export function buildDrawioSvg(
+  modelXml: string,
+  inner: string,
+  bbox: DrawioBBox,
+  title = "Page-1",
+): string {
+  const file = encodeDrawioFile(modelXml, title);
+  const base64 = Buffer.from(file, "utf-8").toString("base64");
+  const w = Math.max(1, Math.round(bbox.width));
+  const h = Math.max(1, Math.round(bbox.height));
+  return (
+    `<svg xmlns="http://www.w3.org/2000/svg" ` +
+    `xmlns:xlink="http://www.w3.org/1999/xlink" ` +
+    `width="${w}" height="${h}" viewBox="0 0 ${w} ${h}" ` +
+    `content="${base64}">${inner}</svg>`
+  );
+}
+
+function xmlEscape(s: string): string {
+  return s
+    .replace(/&/g, "&amp;")
+    .replace(/</g, "&lt;")
+    .replace(/>/g, "&gt;")
+    .replace(/"/g, "&quot;");
+}
+
+// --- normalization + hash --------------------------------------------------
+
+/**
+ * Normalize mxGraph XML for hashing / stable comparison: drop the whitespace
+ * between tags and trim. This is intentionally conservative — it never reorders
+ * attributes or cells (that would be lossy) — so two documents hash equal iff
+ * they differ only in inter-tag formatting.
+ */
+export function normalizeXml(xml: string): string {
+  return xml.replace(/>\s+</g, "><").trim();
+}
+
+/** Stable optimistic-lock hash over the normalized model XML (sha256, hex). */
+export function mxHash(modelXml: string): string {
+  return createHash("sha256").update(normalizeXml(modelXml), "utf-8").digest("hex");
+}
+
+// --- cell parsing ----------------------------------------------------------
+
+/** Parse every `<mxCell>` in a model into a structured DrawioCell list. */
+export function parseCells(modelXml: string): DrawioCell[] {
+  const { doc, error } = parseXml(modelXml);
+  if (error) {
+    throw new DrawioLintError([
+      { rule: "well-formed-xml", message: error, position: firstLineCol(error) },
+    ]);
+  }
+  const cells: DrawioCell[] = [];
+  const els = doc.getElementsByTagName("mxCell");
+  for (let i = 0; i < els.length; i++) {
+    cells.push(readCell(els[i]));
+  }
+  return cells;
+}
+
+function readCell(el: any): DrawioCell {
+  const style = el.getAttribute("style") || "";
+  const parsed = parseStyle(style);
+  const geoEl = firstChildByTag(el, "mxGeometry");
+  const geometry: DrawioGeometry = geoEl
+    ? {
+        x: num(geoEl.getAttribute("x")),
+        y: num(geoEl.getAttribute("y")),
+        width: num(geoEl.getAttribute("width")),
+        height: num(geoEl.getAttribute("height")),
+        relative: geoEl.getAttribute("relative") === "1",
+        hasGeometry: true,
+      }
+    : { relative: false, hasGeometry: false };
+  return {
+    id: el.getAttribute("id") ?? "",
+    parent: el.getAttribute("parent") ?? undefined,
+    source: el.getAttribute("source") ?? undefined,
+    target: el.getAttribute("target") ?? undefined,
+    vertex: el.getAttribute("vertex") === "1",
+    edge: el.getAttribute("edge") === "1",
+    value: el.getAttribute("value") ?? "",
+    style,
+    styleMap: parsed.map,
+    baseStyle: parsed.baseStyle,
+    geometry,
+  };
+}
+
+function firstChildByTag(el: any, tag: string): any {
+  for (let i = 0; i < el.childNodes.length; i++) {
+    const c = el.childNodes[i];
+    if (c.nodeType === 1 && c.tagName === tag) return c;
+  }
+  return null;
+}
+
+function firstLineCol(msg: string): string | undefined {
+  const m = /^(\d+:\d+)/.exec(msg);
+  return m ? m[1] : undefined;
+}
+
+// --- bounding box ----------------------------------------------------------
+
+/**
+ * Absolute bounding box of the diagram from its vertex geometries. Container
+ * children are relative, so absolute positions are resolved along the parent
+ * chain before taking the extent. Falls back to a default canvas when empty.
+ */
+export function computeBBox(cells: DrawioCell[]): DrawioBBox {
+  const byId = new Map(cells.map((c) => [c.id, c]));
+  let maxX = 0;
+  let maxY = 0;
+  let any = false;
+  for (const c of cells) {
+    if (!c.vertex || !c.geometry.hasGeometry) continue;
+    const g = c.geometry;
+    if (g.width == null || g.height == null) continue;
+    const { x, y } = absolutePos(c, byId);
+    maxX = Math.max(maxX, x + g.width);
+    maxY = Math.max(maxY, y + g.height);
+    any = true;
+  }
+  if (!any) return { width: 300, height: 200 };
+  // A small margin so borders/labels are not clipped at the edge.
+  return { width: Math.ceil(maxX) + 20, height: Math.ceil(maxY) + 20 };
+}
+
+/** Absolute (x,y) of a vertex, following its parent chain (containers). */
+export function absolutePos(
+  cell: DrawioCell,
+  byId: Map<string, DrawioCell>,
+): { x: number; y: number } {
+  let x = cell.geometry.x ?? 0;
+  let y = cell.geometry.y ?? 0;
+  const seen = new Set<string>([cell.id]);
+  let parentId = cell.parent;
+  while (parentId && !seen.has(parentId)) {
+    seen.add(parentId);
+    const p = byId.get(parentId);
+    // Sentinels (0/1) carry no geometry; stop there.
+    if (!p || !p.vertex || !p.geometry.hasGeometry) break;
+    x += p.geometry.x ?? 0;
+    y += p.geometry.y ?? 0;
+    parentId = p.parent;
+  }
+  return { x, y };
+}
+
+// --- linter ----------------------------------------------------------------
+
+/**
+ * Run every deterministic pre-write rule over a full mxGraphModel string. On any
+ * violation it throws a DrawioLintError carrying one issue per violation, each
+ * with the offending cellId + position. Returns the parsed cells on success.
+ */
+export function lintModel(modelXml: string): {
+  cells: DrawioCell[];
+  warnings: string[];
+} {
+  const issues: DrawioLintIssue[] = [];
+  const warnings: string[] = [];
+
+  // Rule: no XML comments. Checked on the raw string (a comment survives DOM
+  // parsing as a comment node, but the intent is to reject them outright — they
+  // routinely wrap "TODO" cruft that breaks downstream tooling).
+  if (modelXml.includes("<!--")) {
+    issues.push({
+      rule: "no-comments",
+      message: "XML comments (<!-- -->) are not allowed in diagram XML",
+    });
+  }
+
+  // Rule: value escaping + literal newline. Scan raw <mxCell> tags so the error
+  // can name the cell id even when the whole document is otherwise malformed.
+  scanRawValues(modelXml, issues);
+
+  // Well-formedness — everything below needs a parsed DOM.
+  const { doc, error } = parseXml(modelXml);
+  if (error) {
+    issues.push({
+      rule: "well-formed-xml",
+      message: error,
+      position: firstLineCol(error),
+    });
+    throw new DrawioLintError(issues);
+  }
+
+  const root = doc.documentElement;
+  if (!root || root.tagName !== "mxGraphModel") {
+    issues.push({
+      rule: "structure",
+      message: `root element must be <mxGraphModel>, got <${root ? root.tagName : "?"}>`,
+    });
+    throw new DrawioLintError(issues);
+  }
+  if (!firstChildByTag(root, "root")) {
+    issues.push({
+      rule: "structure",
+      message: "<mxGraphModel> must contain a <root> element",
+    });
+    throw new DrawioLintError(issues);
+  }
+
+  const cells = parseCells(modelXml);
+  const ids = new Set<string>();
+
+  // Rule: sentinel cells id="0" and id="1"(parent="0").
+  const cell0 = cells.find((c) => c.id === "0");
+  const cell1 = cells.find((c) => c.id === "1");
+  if (!cell0) {
+    issues.push({
+      rule: "sentinel-cells",
+      message: 'missing the root sentinel cell <mxCell id="0"/>',
+      cellId: "0",
+    });
+  }
+  if (!cell1) {
+    issues.push({
+      rule: "sentinel-cells",
+      message: 'missing the layer sentinel cell <mxCell id="1" parent="0"/>',
+      cellId: "1",
+    });
+  } else if (cell1.parent !== "0") {
+    issues.push({
+      rule: "sentinel-cells",
+      message: 'the layer sentinel <mxCell id="1"> must have parent="0"',
+      cellId: "1",
+    });
+  }
+
+  cells.forEach((c, index) => {
+    const pos = `cell #${index}`;
+    const isSentinel = c.id === "0" || c.id === "1";
+
+    // Rule: unique, non-empty ids; user cells must not reuse 0/1.
+    if (c.id === "") {
+      issues.push({ rule: "cell-id", message: "cell has an empty id", position: pos });
+    } else if (ids.has(c.id)) {
+      issues.push({
+        rule: "duplicate-id",
+        message: `duplicate cell id "${c.id}"`,
+        cellId: c.id,
+        position: pos,
+      });
+    }
+    ids.add(c.id);
+
+    if (isSentinel) return; // sentinels are exempt from the shape rules below
+
+    // Rule: vertex XOR edge (a cell may be neither: groups/containers).
+    if (c.vertex && c.edge) {
+      issues.push({
+        rule: "vertex-edge-exclusive",
+        message: 'a cell cannot be both vertex="1" and edge="1"',
+        cellId: c.id,
+        position: pos,
+      });
+    }
+
+    // Rule: every edge has a child <mxGeometry as="geometry"/>.
+    if (c.edge && !c.geometry.hasGeometry) {
+      issues.push({
+        rule: "edge-geometry",
+        message:
+          'edge is missing its child <mxGeometry relative="1" as="geometry"/> — it will not render',
+        cellId: c.id,
+        position: pos,
+      });
+    }
+
+    // Rule: edge endpoints resolve to existing ids.
+    if (c.edge) {
+      for (const end of ["source", "target"] as const) {
+        const ref = c[end];
+        if (ref != null && ref !== "" && !cellExists(cells, ref)) {
+          issues.push({
+            rule: "edge-endpoint",
+            message: `edge ${end} "${ref}" does not resolve to any cell`,
+            cellId: c.id,
+            position: pos,
+          });
+        }
+      }
+    }
+
+    // Rule: parent must exist.
+    if (c.parent != null && c.parent !== "" && !cellExists(cells, c.parent)) {
+      issues.push({
+        rule: "parent-exists",
+        message: `parent "${c.parent}" does not resolve to any cell`,
+        cellId: c.id,
+        position: pos,
+      });
+    }
+
+    // Rule: style parses as key=value; pairs.
+    if (c.style !== "") {
+      const parsed = parseStyle(c.style);
+      if (parsed.badSegment !== undefined) {
+        issues.push({
+          rule: "style-format",
+          message: `malformed style segment "${parsed.badSegment}" (expected key=value)`,
+          cellId: c.id,
+          position: pos,
+        });
+      }
+    }
+  });
+
+  if (issues.length > 0) throw new DrawioLintError(issues);
+  return { cells, warnings };
+}
+
+function cellExists(cells: DrawioCell[], id: string): boolean {
+  return cells.some((c) => c.id === id);
+}
+
+/**
+ * Raw-string scan of every `value="…"`/`value='…'` on an mxCell tag. Catches an
+ * unescaped `&`/`<`/`>` and a literal newline character inside a value, keyed to
+ * the cell's id. Runs before DOM parsing so a value bug is reported with its
+ * cellId even when the document is otherwise malformed.
+ */
+function scanRawValues(xml: string, issues: DrawioLintIssue[]): void {
+  const tagRe = /<mxCell\b([^>]*?)\/?>/g;
+  let m: RegExpExecArray | null;
+  while ((m = tagRe.exec(xml)) !== null) {
+    const attrs = m[1];
+    const idM = /\bid\s*=\s*"([^"]*)"/.exec(attrs);
+    const cellId = idM ? idM[1] : undefined;
+    const valM = /\bvalue\s*=\s*"([^"]*)"/.exec(attrs) || /\bvalue\s*=\s*'([^']*)'/.exec(attrs);
+    if (!valM) continue;
+    const raw = valM[1];
+    // Literal newline (0x0A / 0x0D) inside the attribute value.
+    if (/[\n\r]/.test(raw)) {
+      issues.push({
+        rule: "value-newline",
+        message:
+          "value contains a literal newline; use &#xa; (or <br> with html=1) instead",
+        cellId,
+      });
+    }
+    // Unescaped '<' or '>' inside a value.
+    if (raw.includes("<") || raw.includes(">")) {
+      issues.push({
+        rule: "value-escaping",
+        message: "value contains an unescaped '<' or '>'; use &lt; / &gt;",
+        cellId,
+      });
+    }
+    // '&' that does not begin a valid entity.
+    const badAmp = /&(?!(amp|lt|gt|quot|apos|#[0-9]+|#x[0-9a-fA-F]+);)/.test(raw);
+    if (badAmp) {
+      issues.push({
+        rule: "value-escaping",
+        message: "value contains an unescaped '&'; use &amp;",
+        cellId,
+      });
+    }
+  }
+}
+
+// --- input normalization + prepare -----------------------------------------
+
+/**
+ * Normalize an accepted tool input into a full mxGraphModel string:
+ *   - a bare `<mxGraphModel>` is used as-is;
+ *   - an `<mxfile>` is decoded to its first page's model;
+ *   - a list of `<mxCell>` is wrapped with the mxGraphModel/root envelope and
+ *     the sentinel cells (id=0, id=1 parent=0) are added when absent.
+ */
+export function normalizeInput(inputXml: string): string {
+  let xml = inputXml.trim();
+  // Strip an optional XML prolog.
+  if (xml.startsWith("<?xml")) {
+    const end = xml.indexOf("?>");
+    if (end !== -1) xml = xml.slice(end + 2).trim();
+  }
+  if (xml.startsWith("<mxfile")) {
+    return decodeDrawioFileToModel(xml);
+  }
+  if (xml.startsWith("<mxGraphModel")) {
+    return xml;
+  }
+  if (xml.includes("<mxCell")) {
+    return wrapCellFragment(xml);
+  }
+  throw new DrawioLintError([
+    {
+      rule: "unrecognized-input",
+      message:
+        "input must be a <mxGraphModel>, an <mxfile>, or a list of <mxCell> elements",
+    },
+  ]);
+}
+
+function wrapCellFragment(fragment: string): string {
+  // Validate the fragment is well-formed (wrapped so a bare list parses) and
+  // discover which sentinels are already present.
+  const { doc, error } = parseXml(`<root>${fragment}</root>`);
+  if (error) {
+    throw new DrawioLintError([
+      {
+        rule: "well-formed-xml",
+        message: error,
+        position: firstLineCol(error),
+      },
+    ]);
+  }
+  const existing = new Set<string>();
+  const els = doc.getElementsByTagName("mxCell");
+  for (let i = 0; i < els.length; i++) {
+    existing.add(els[i].getAttribute("id") ?? "");
+  }
+  let prefix = "";
+  if (!existing.has("0")) prefix += '<mxCell id="0"/>';
+  if (!existing.has("1")) prefix += '<mxCell id="1" parent="0"/>';
+  return `<mxGraphModel ${DEFAULT_MODEL_ATTRS}><root>${prefix}${fragment}</root></mxGraphModel>`;
+}
+
+export interface PreparedModel {
+  /** Canonical (normalized) mxGraphModel XML that gets written. */
+  modelXml: string;
+  cells: DrawioCell[];
+  bbox: DrawioBBox;
+  /** Number of user cells (excludes the id=0/id=1 sentinels). */
+  cellCount: number;
+  warnings: string[];
+  hash: string;
+}
+
+/**
+ * Full pre-write pipeline for create/update: normalize the input into a model,
+ * lint it (throws DrawioLintError on any violation), then compute the canonical
+ * form, bounding box, cell count and hash. Never touches the network.
+ */
+export function prepareModel(inputXml: string): PreparedModel {
+  const rawModel = normalizeInput(inputXml);
+  const { cells, warnings } = lintModel(rawModel);
+  const modelXml = normalizeXml(rawModel);
+  const bbox = computeBBox(cells);
+  const cellCount = cells.filter((c) => c.id !== "0" && c.id !== "1").length;
+  return {
+    modelXml,
+    cells,
+    bbox,
+    cellCount,
+    warnings,
+    hash: mxHash(modelXml),
+  };
+}
+
+/** Cell count of a decoded model (user cells only) — used by drawio_get meta. */
+export function countUserCells(modelXml: string): number {
+  return parseCells(modelXml).filter((c) => c.id !== "0" && c.id !== "1").length;
+}

packages/mcp/src/lib/json-edit.ts

@@ -12,7 +12,11 @@
  * re-import for small wording fixes.
  */
 
-import { stripInlineMarkdown, stripBalancedWrappers } from "./text-normalize.js";
+import {
+  stripInlineMarkdown,
+  stripBalancedWrappers,
+  closestBlockHint,
+} from "./text-normalize.js";
 
 export interface TextEdit {
   find: string;
@@ -305,6 +309,21 @@ export function applyTextEdits(
       continue;
     }
 
+    // HARD-REFUSE inline footnote tokens (#410). `^[...]` in a `replace` is
+    // markdown that only becomes a real footnote when a whole markdown body is
+    // written (create_page / update_page_content / import_page_markdown). Written
+    // through edit_page_text it stays a LITERAL string in the text — the exact
+    // failure mode #410 fixes — so refuse it here (defense-in-depth) and point the
+    // caller at insert_footnote, mirroring the formatting-marker refusal above.
+    if (/\^\[[\s\S]*?\]/.test(edit.replace)) {
+      failed.push({
+        find: edit.find,
+        reason:
+          "edit_page_text writes the replacement as LITERAL text, so a `^[...]` footnote token does not parse into a real footnote (it would appear verbatim in the page). To add a footnote to existing text, use insert_footnote (anchorText = where, text = the note).",
+      });
+      continue;
+    }
+
     // Gather every inline block in document order (recurse the whole tree so
     // nested containers — callouts, list items, table cells, blockquotes — are
     // all covered).
@@ -366,29 +385,9 @@ export function applyTextEdits(
       } else {
         // Append a bounded "closest text" hint: find the FIRST block that
         // contains the longest whitespace-delimited token (>= 3 chars) of the
-        // (stripped, then raw) locator, and quote that block's plain text.
-        reason = "text not found in the document.";
-        const tokenSource = stripped.length > 0 ? stripped : edit.find;
-        const longestToken = tokenSource
-          .split(/\s+/)
-          .filter((t) => t.length >= 3)
-          .sort((a, b) => b.length - a.length)[0];
-        if (longestToken) {
-          const hitBlock = blockPlain.find((plain) =>
-            plain.includes(longestToken),
-          );
-          if (hitBlock) {
-            // Truncate by code point (spread iterates by code point) so a
-            // surrogate pair is never split; append the ellipsis only when the
-            // text was actually longer than the limit.
-            const points = [...hitBlock];
-            const snippet =
-              points.length > 120
-                ? points.slice(0, 120).join("") + "…"
-                : hitBlock;
-            reason += ` Closest block text: "${snippet}".`;
-          }
-        }
+        // (stripped, then raw) locator, and quote that block's plain text. Shared
+        // with create_comment via closestBlockHint so both give the same hint.
+        reason = "text not found in the document." + closestBlockHint(blockPlain, edit.find);
       }
       failed.push({ find: edit.find, reason });
       continue;

packages/mcp/src/lib/pako.d.ts

@@ -0,0 +1,61 @@
+// Minimal ambient type declaration for `pako` (no @types/pako is installed and
+// pako 2.x ships no bundled .d.ts). We only use the raw-deflate codec to read
+// draw.io's compressed `<diagram>` payload, so declare just that surface.
+declare module "pako" {
+  interface RawOptions {
+    /** When "string", the result is returned as a (binary/UTF-8) string. */
+    to?: "string";
+    /** Raw-deflate window bits; draw.io uses raw deflate (no zlib header). */
+    windowBits?: number;
+    level?: number;
+  }
+
+  /** Raw-inflate (windowBits: -15). `to:"string"` yields a string. */
+  export function inflateRaw(
+    data: Uint8Array | ArrayBuffer | number[],
+    options: RawOptions & { to: "string" },
+  ): string;
+  export function inflateRaw(
+    data: Uint8Array | ArrayBuffer | number[],
+    options?: RawOptions,
+  ): Uint8Array;
+
+  /** Raw-deflate (windowBits: -15). Used only by tests to build fixtures. */
+  export function deflateRaw(
+    data: Uint8Array | string,
+    options?: RawOptions,
+  ): Uint8Array;
+
+  interface InflateStreamOptions {
+    to?: "string";
+    windowBits?: number;
+    /** Raw deflate (no zlib header) — equivalent to windowBits: -15. */
+    raw?: boolean;
+    chunkSize?: number;
+  }
+
+  /**
+   * Streaming inflate. We use it to bound the decompressed size: `onData` is
+   * invoked per output chunk, letting us abort a decompression bomb before the
+   * full output is materialised.
+   */
+  export class Inflate {
+    constructor(options?: InflateStreamOptions);
+    onData: (chunk: string | Uint8Array) => void;
+    onEnd: (status: number) => void;
+    push(
+      data: Uint8Array | ArrayBuffer | number[] | string,
+      flushMode?: boolean | number,
+    ): boolean;
+    result: string | Uint8Array;
+    err: number;
+    msg: string;
+  }
+
+  const _default: {
+    inflateRaw: typeof inflateRaw;
+    deflateRaw: typeof deflateRaw;
+    Inflate: typeof Inflate;
+  };
+  export default _default;
+}

packages/mcp/src/lib/text-normalize.ts

@@ -114,3 +114,37 @@ export function stripInlineMarkdown(s: string): string {
 
   return out;
 }
+
+/**
+ * Build a bounded "closest text" hint for an anchor/find MISS, shared by
+ * edit_page_text (json-edit) and create_comment (client) so both surface the
+ * same self-correction affordance.
+ *
+ * Take the longest whitespace-delimited token (>= 3 chars) of the locator
+ * (markdown-stripped first, so `**bold**` contributes `bold`), find the FIRST
+ * of `blockTexts` that contains it, and return ` Closest block text: "…".` with
+ * the block quoted (truncated to 120 code points + ellipsis). Returns "" when
+ * no token qualifies or no block contains it, so the caller can append it
+ * unconditionally.
+ */
+export function closestBlockHint(
+  blockTexts: string[],
+  locator: string,
+): string {
+  if (typeof locator !== "string" || locator.length === 0) return "";
+  const stripped = stripInlineMarkdown(locator);
+  const tokenSource = stripped.length > 0 ? stripped : locator;
+  const longestToken = tokenSource
+    .split(/\s+/)
+    .filter((t) => t.length >= 3)
+    .sort((a, b) => b.length - a.length)[0];
+  if (!longestToken) return "";
+  const hitBlock = blockTexts.find((plain) => plain.includes(longestToken));
+  if (!hitBlock) return "";
+  // Truncate by code point (spread iterates by code point) so a surrogate pair
+  // is never split; append the ellipsis only when the text was actually longer.
+  const points = [...hitBlock];
+  const snippet =
+    points.length > 120 ? points.slice(0, 120).join("") + "…" : hitBlock;
+  return ` Closest block text: "${snippet}".`;
+}

packages/mcp/src/stdio.ts

@@ -1,6 +1,7 @@
 #!/usr/bin/env node
 import { StdioServerTransport } from "@modelcontextprotocol/sdk/server/stdio.js";
 import { createDocmostMcpServer } from "./index.js";
+import { destroyAllSessions } from "./lib/collab-session.js";
 
 // Standalone stdio entrypoint. This restores the original behavior of the
 // package when run as a CLI (`docmost-mcp`): it reads credentials from the
@@ -33,6 +34,20 @@ async function run() {
     console.error("Uncaught exception:", error);
   });
 
+  // Teardown hook (issue #400): destroy every cached live CollabSession on exit
+  // so a hanging session does not keep a doc loaded on the server (which would
+  // also defer the server's afterUnloadDocument cleanup). `exit` runs the
+  // synchronous idempotent teardown; SIGINT/SIGTERM also run it, then exit.
+  process.on("exit", () => {
+    destroyAllSessions();
+  });
+  for (const signal of ["SIGINT", "SIGTERM"] as const) {
+    process.on(signal, () => {
+      destroyAllSessions();
+      process.exit(0);
+    });
+  }
+
   const server = createDocmostMcpServer({
     apiUrl: API_URL!,
     email: EMAIL!,

packages/mcp/src/tool-specs.ts

@@ -771,9 +771,13 @@ export const SHARED_TOOL_SPECS = {
       'The comment is anchored inline to the given exact `selection` text ' +
       '(which gets highlighted); page-level comments are NOT supported. A ' +
       'new top-level comment REQUIRES a `selection`. Replies inherit the ' +
-      "parent's anchor and take no selection. If the call fails with a " +
-      '"selection not found" error, retry with a corrected EXACT selection ' +
-      'copied verbatim from a single paragraph/block. You may also attach a ' +
+      "parent's anchor and take no selection. Always COPY the `selection` " +
+      'VERBATIM from get_page / search_in_page output — do NOT quote it from ' +
+      'memory (stale-memory quoting is the top cause of anchor misses). If the ' +
+      'call fails with a "selection not found" error, the error quotes the ' +
+      "closest block text (or says the selection spans multiple blocks); retry " +
+      "with a corrected EXACT selection copied verbatim from a single " +
+      'paragraph/block. You may also attach a ' +
       '`suggestedText` proposing a replacement for the `selection` (a human ' +
       'applies it from the UI); when set, the `selection` must occur exactly ' +
       'once in the page. Reversible via the comment UI.',
@@ -1003,4 +1007,224 @@ export const SHARED_TOOL_SPECS = {
       text: z.string().describe('The new cell text.'),
     }),
   },
+
+  // --- footnote + image write tools (promoted from inline MCP-only, #410) ---
+  //
+  // These three were previously registered inline in index.ts as MCP-only,
+  // because the in-app AI-chat agent had no equivalent. #410 promotes them so the
+  // in-app agent (esp. the Researcher role) can attach real footnotes/images
+  // instead of writing literal `^[...]` / placeholder text via editPageText. The
+  // schema + description are MOVED VERBATIM from the old inline registrations so
+  // external MCP clients see identical tool names, fields and text.
+
+  insertFootnote: {
+    mcpName: 'insert_footnote',
+    inAppKey: 'insertFootnote',
+    description:
+      'Insert an AUTHOR-INLINE footnote: you specify only WHERE (anchorText) ' +
+      'and WHAT (text). The footnote marker is placed right after anchorText in ' +
+      'the body, and the bottom footnotes list + the numbering are derived ' +
+      'deterministically server-side. You do NOT assign a number, and you ' +
+      "never see or edit the footnotes list — so footnotes cannot end up out " +
+      "of order, orphaned, or as a raw '[^id]' block. If a footnote with the " +
+      'SAME text already exists, its number is REUSED (one definition, several ' +
+      "references). The write is atomic and won't clobber concurrent edits; if " +
+      'anchorText is not found, nothing is written and an error is returned.',
+    // CORE for the in-app agent (#410): keeping it deferred would recreate the
+    // original asymmetry (footnote tool hidden while editPageText is core), which
+    // is exactly what makes the agent fall back to literal `^[...]`.
+    tier: 'core',
+    catalogLine:
+      'insertFootnote — attach a numbered footnote right after a snippet of existing body text.',
+    buildShape: (z) => ({
+      pageId: z.string().min(1),
+      anchorText: z
+        .string()
+        .min(1)
+        .describe(
+          'A snippet of existing body text; the footnote marker is inserted ' +
+            'immediately after its first occurrence (mark-safe).',
+        ),
+      text: z
+        .string()
+        .min(1)
+        .describe('The footnote content as markdown (becomes the definition).'),
+    }),
+  },
+
+  insertImage: {
+    mcpName: 'insert_image',
+    inAppKey: 'insertImage',
+    description:
+      'Download an image from a web (http/https) URL and insert it into ' +
+      'a page in one step. By default ' +
+      'appends the image at the end of the page. With replaceText, replaces the ' +
+      'first top-level block whose text contains that string (handy for ' +
+      'swapping a text placeholder like "[image: foo.png]" for the real image). ' +
+      'With afterText, inserts the image right after the first block containing ' +
+      'that string. Preserves all other block ids.',
+    tier: 'deferred',
+    catalogLine:
+      'insertImage — download a web image and insert it into a page.',
+    buildShape: (z) => ({
+      pageId: z.string().min(1),
+      imageUrl: z
+        .string()
+        .min(1)
+        .describe('http(s) URL of the image to download and upload'),
+      align: z.enum(['left', 'center', 'right']).optional(),
+      alt: z.string().optional(),
+      replaceText: z
+        .string()
+        .optional()
+        .describe(
+          'Replace the first top-level block whose text contains this string with the image',
+        ),
+      afterText: z
+        .string()
+        .optional()
+        .describe(
+          'Insert the image right after the first top-level block whose text contains this string',
+        ),
+    }),
+  },
+
+  replaceImage: {
+    mcpName: 'replace_image',
+    inAppKey: 'replaceImage',
+    description:
+      'Replace an existing image on a page with a new image fetched from a web ' +
+      '(http/https) URL: uploads the new file as a NEW ' +
+      'attachment (fresh clean URL that renders and busts browser caches), then ' +
+      'repoints every image node referencing the old attachmentId (recursively, ' +
+      'incl. callouts/tables) via the live document, preserving comments, ' +
+      'alignment and alt. The old attachment is left as an unreferenced orphan ' +
+      '(Docmost has no API to delete a single attachment; it is removed only when ' +
+      'the page/space is deleted). In-place byte overwrite is avoided because some ' +
+      'Docmost versions corrupt the attachment (HTTP 500) on overwrite.',
+    tier: 'deferred',
+    catalogLine:
+      'replaceImage — swap an existing page image for one fetched from a web URL.',
+    buildShape: (z) => ({
+      pageId: z.string().min(1),
+      attachmentId: z
+        .string()
+        .min(1)
+        .describe('attachmentId of the image currently in the page to replace'),
+      imageUrl: z
+        .string()
+        .min(1)
+        .describe('http(s) URL of the new image to download'),
+      align: z.enum(['left', 'center', 'right']).optional(),
+      alt: z.string().optional(),
+    }),
+  },
+
+  // --- draw.io diagrams (issue #423, stage 1) ---
+
+  drawioGet: {
+    mcpName: 'drawio_get',
+    inAppKey: 'drawioGet',
+    description:
+      'Read a draw.io diagram on a page as mxGraph XML (default) or as its raw ' +
+      '`.drawio.svg`. `node` is the drawio node\'s attrs.id (from get_outline / ' +
+      'get_page_json) or "#<index>" for a top-level block. Returns the decoded ' +
+      'mxGraphModel XML plus meta { attachmentId, title, width, height, ' +
+      'cellCount, hash }. `hash` is the optimistic-lock key you MUST pass back ' +
+      'as baseHash to drawio_update. Diagrams a human saved from the editor ' +
+      '(including draw.io\'s compressed format) decode losslessly.',
+    tier: 'deferred',
+    catalogLine:
+      'drawioGet — read a draw.io diagram as mxGraph XML (+ hash for updates).',
+    buildShape: (z) => ({
+      pageId: z.string().min(1),
+      node: z
+        .string()
+        .min(1)
+        .describe('The drawio node attrs.id, or "#<index>" for a top-level block.'),
+      format: z
+        .enum(['xml', 'svg'])
+        .optional()
+        .describe('"xml" (default) for mxGraph XML, or "svg" for the raw .drawio.svg.'),
+    }),
+  },
+
+  drawioCreate: {
+    mcpName: 'drawio_create',
+    inAppKey: 'drawioCreate',
+    description:
+      'Create a draw.io diagram from mxGraph XML and insert it as a diagram ' +
+      'block. `xml` is a bare `<mxGraphModel>` OR a list of `<mxCell>` elements ' +
+      '(the server wraps it and adds the id=0 / id=1 sentinel cells). The XML is ' +
+      'LINTED first (well-formedness, sentinel cells, unique ids, vertex XOR ' +
+      'edge, every edge has a child <mxGeometry as="geometry"/>, edge ' +
+      'source/target and every parent resolve, style parses, no XML comments, ' +
+      'value escaping) — a violation returns a structured error naming the rule ' +
+      'and cellId so you can fix and retry. `where` positions the block like ' +
+      'insert_node: position before/after (with exactly one of anchorNodeId or ' +
+      'anchorText) or append. Returns { nodeId, attachmentId, warnings }. The ' +
+      'returned `nodeId` is an index-based "#<index>" handle (drawio nodes carry ' +
+      'no attrs.id): it addresses the new top-level block and can be fed straight ' +
+      'back into drawio_get / drawio_update for THIS document. It is positional, ' +
+      'so if you add or remove blocks before it, re-resolve via get_outline. The ' +
+      'diagram is editable in the draw.io editor and can be re-read with ' +
+      'drawio_get.',
+    tier: 'deferred',
+    catalogLine:
+      'drawioCreate — create a draw.io diagram from mxGraph XML and insert it.',
+    buildShape: (z) => ({
+      pageId: z.string().min(1),
+      xml: z
+        .string()
+        .min(1)
+        .describe(
+          'mxGraph XML: a bare <mxGraphModel> or a list of <mxCell> elements.',
+        ),
+      position: z
+        .enum(['before', 'after', 'append'])
+        .describe('Where to insert relative to the anchor.'),
+      anchorNodeId: z
+        .string()
+        .optional()
+        .describe('Anchor block id (for before/after).'),
+      anchorText: z
+        .string()
+        .optional()
+        .describe('Anchor text fragment (for before/after).'),
+      title: z.string().optional().describe('Optional diagram title.'),
+    }),
+  },
+
+  drawioUpdate: {
+    mcpName: 'drawio_update',
+    inAppKey: 'drawioUpdate',
+    description:
+      'Replace a draw.io diagram\'s content with new mxGraph XML (same lint ' +
+      'pipeline as drawio_create). `baseHash` is MANDATORY: pass the hash from ' +
+      'the drawio_get you based the edit on. If the diagram changed since ' +
+      '(a human or another agent edited it) the hash mismatches and the update ' +
+      'is refused with a conflict error — re-read with drawio_get and retry. On ' +
+      'success it overwrites the diagram attachment and updates the node ' +
+      'width/height. `node` is the drawio node attrs.id or "#<index>".',
+    tier: 'deferred',
+    catalogLine:
+      'drawioUpdate — replace a draw.io diagram (optimistic-locked by baseHash).',
+    buildShape: (z) => ({
+      pageId: z.string().min(1),
+      node: z
+        .string()
+        .min(1)
+        .describe('The drawio node attrs.id, or "#<index>" for a top-level block.'),
+      xml: z
+        .string()
+        .min(1)
+        .describe(
+          'New mxGraph XML: a bare <mxGraphModel> or a list of <mxCell> elements.',
+        ),
+      baseHash: z
+        .string()
+        .min(1)
+        .describe('The meta.hash from the drawio_get this edit is based on.'),
+    }),
+  },
 } satisfies Record<string, SharedToolSpec>;

packages/mcp/test/mock/create-comment.test.mjs

@@ -548,3 +548,94 @@ test("suggestedText: the stored selection is the doc's RAW typographic substring
   );
   assert.equal(createPayload.suggestedText, "goodbye");
 });
+
+// -----------------------------------------------------------------------------
+// 8) #408: a not-found selection error QUOTES the closest block text so the
+//    model can self-correct instead of blind-retrying.
+// -----------------------------------------------------------------------------
+test("a not-found selection error includes a 'Closest block text' hint", async () => {
+  let createCalls = 0;
+  const { baseURL } = await spawn(async (req, res) => {
+    await readBody(req);
+    if (req.url === "/api/auth/login") {
+      sendJson(res, 200, { success: true }, {
+        "Set-Cookie": "authToken=t; Path=/; HttpOnly",
+      });
+      return;
+    }
+    if (req.url === "/api/pages/info") {
+      sendJson(res, 200, {
+        data: {
+          id: "page-1",
+          content: {
+            type: "doc",
+            content: [
+              { type: "paragraph", content: [{ type: "text", text: "The quick brown fox jumps" }] },
+            ],
+          },
+        },
+      });
+      return;
+    }
+    if (req.url === "/api/comments/create") {
+      createCalls++;
+      sendJson(res, 200, { data: { id: "should-not-happen" } });
+      return;
+    }
+    sendJson(res, 404, { message: "not found" });
+  });
+
+  const client = new DocmostClient(baseURL, "user@example.com", "pw");
+  await assert.rejects(
+    () => client.createComment("page-1", "body", "inline", "quick brown cat"),
+    /Closest block text: "The quick brown fox jumps"/,
+    "a not-found selection must quote the closest block text",
+  );
+  assert.equal(createCalls, 0, "/comments/create must NOT be called on a miss");
+});
+
+// -----------------------------------------------------------------------------
+// 9) #408: a selection that straddles two blocks gets the explicit
+//    "spans multiple blocks" message instead of a bare not-found.
+// -----------------------------------------------------------------------------
+test("a selection spanning multiple blocks gets the explicit spans-multiple-blocks message", async () => {
+  let createCalls = 0;
+  const { baseURL } = await spawn(async (req, res) => {
+    await readBody(req);
+    if (req.url === "/api/auth/login") {
+      sendJson(res, 200, { success: true }, {
+        "Set-Cookie": "authToken=t; Path=/; HttpOnly",
+      });
+      return;
+    }
+    if (req.url === "/api/pages/info") {
+      sendJson(res, 200, {
+        data: {
+          id: "page-1",
+          content: {
+            type: "doc",
+            content: [
+              { type: "paragraph", content: [{ type: "text", text: "the quick brown" }] },
+              { type: "paragraph", content: [{ type: "text", text: "fox jumps over" }] },
+            ],
+          },
+        },
+      });
+      return;
+    }
+    if (req.url === "/api/comments/create") {
+      createCalls++;
+      sendJson(res, 200, { data: { id: "should-not-happen" } });
+      return;
+    }
+    sendJson(res, 404, { message: "not found" });
+  });
+
+  const client = new DocmostClient(baseURL, "user@example.com", "pw");
+  await assert.rejects(
+    () => client.createComment("page-1", "body", "inline", "brown fox"),
+    /spans multiple blocks/,
+    "a cross-block selection must report the spans-multiple-blocks hint",
+  );
+  assert.equal(createCalls, 0, "/comments/create must NOT be called on a miss");
+});

packages/mcp/test/mock/drawio-tools.test.mjs

@@ -0,0 +1,467 @@
+// Contract tests for the drawio_get / drawio_create / drawio_update client
+// methods (issue #423). Follows the repo's seam-override pattern (see
+// full-doc-write-canonicalize.test.mjs): a DocmostClient subclass stubs the I/O
+// seams (auth, collab token, page read, attachment upload/fetch, the mutatePage
+// write) so the tool logic is exercised without a live Docmost or collab socket.
+import { test } from "node:test";
+import assert from "node:assert/strict";
+import pako from "pako";
+import { DocmostClient } from "../../build/client.js";
+import {
+  buildDrawioSvg,
+  encodeDrawioFile,
+  normalizeXml,
+  mxHash,
+  decodeDrawioSvg,
+} from "../../build/lib/drawio-xml.js";
+
+const MODEL =
+  '<mxGraphModel><root>' +
+  '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+  '<mxCell id="2" value="Hi" style="rounded=1;" vertex="1" parent="1">' +
+  '<mxGeometry x="20" y="20" width="120" height="60" as="geometry"/></mxCell>' +
+  '</root></mxGraphModel>';
+
+// Build a Docmost-style `.drawio.svg` (base64 content) for a model.
+function svgFor(model) {
+  return buildDrawioSvg(normalizeXml(model), "<g/>", { width: 200, height: 120 });
+}
+
+// Build a human/compressed-export `.drawio.svg` (base64 content wrapping a
+// compressed <diagram> payload), mimicking a diagram a person saved.
+function compressedSvgFor(model) {
+  const compressed = Buffer.from(
+    pako.deflateRaw(encodeURIComponent(normalizeXml(model))),
+  ).toString("base64");
+  const file = `<mxfile host="Electron"><diagram id="a" name="Page-1">${compressed}</diagram></mxfile>`;
+  const content = Buffer.from(file, "utf-8").toString("base64");
+  return `<svg xmlns="http://www.w3.org/2000/svg" content="${content}"><image href="x"/></svg>`;
+}
+
+// The vendored `drawio` node schema (diagramAttributes) declares ONLY these
+// attributes; PMNode.fromJSON drops anything else on save. Mirror that here so
+// the mock write path behaves like the real one — in particular, a block `id`
+// set on a drawio node does NOT survive the save, so a handle keyed on it is
+// un-resolvable. This is exactly what the production bug (issue #423 Fix 1) was.
+const DRAWIO_SCHEMA_ATTRS = new Set([
+  "src",
+  "title",
+  "alt",
+  "width",
+  "height",
+  "size",
+  "aspectRatio",
+  "align",
+  "attachmentId",
+]);
+
+function applyDrawioSchemaDrop(node) {
+  if (!node || typeof node !== "object") return;
+  if (node.type === "drawio" && node.attrs && typeof node.attrs === "object") {
+    for (const key of Object.keys(node.attrs)) {
+      if (!DRAWIO_SCHEMA_ATTRS.has(key)) delete node.attrs[key];
+    }
+  }
+  if (Array.isArray(node.content)) for (const c of node.content) applyDrawioSchemaDrop(c);
+}
+
+function makeClient({ pageDoc, attachmentSvg } = {}) {
+  const calls = { uploads: [], mutations: [] };
+  class TestClient extends DocmostClient {
+    async ensureAuthenticated() {}
+    async getCollabTokenWithReauth() {
+      return "collab-token";
+    }
+    async resolvePageId(pageId) {
+      return `uuid-${pageId}`;
+    }
+    async getPageRaw(pageId) {
+      return {
+        id: pageId,
+        slugId: "s",
+        title: "P",
+        spaceId: "sp",
+        content: pageDoc ?? { type: "doc", content: [] },
+      };
+    }
+    async uploadAttachmentBuffer(pageId, buffer, fileName, mime) {
+      const id = `att-${calls.uploads.length + 1}`;
+      calls.uploads.push({ pageId, fileName, mime, svg: buffer.toString("utf-8") });
+      return { id, fileName, fileSize: buffer.length };
+    }
+    async fetchAttachmentText(src) {
+      return attachmentSvg;
+    }
+    mutatePage(pageId, token, apiUrl, transform) {
+      // Run the transform against a clone of the source doc, capture the result.
+      const clone = structuredClone(pageDoc ?? { type: "doc", content: [] });
+      const doc = transform(clone);
+      // Mirror the real schema: unknown drawio attrs (e.g. a block `id`) are
+      // dropped on save, so callers can never rely on them to address the node.
+      if (doc) applyDrawioSchemaDrop(doc);
+      calls.mutations.push({ pageId, doc });
+      return Promise.resolve({ doc, verify: { changed: doc != null } });
+    }
+  }
+  const client = new TestClient("http://127.0.0.1:1/api", "e@x.com", "pw");
+  return { client, calls };
+}
+
+function findDrawio(node, acc = []) {
+  if (!node || typeof node !== "object") return acc;
+  if (node.type === "drawio") acc.push(node);
+  if (Array.isArray(node.content)) for (const c of node.content) findDrawio(c, acc);
+  return acc;
+}
+
+// --- drawio_create ---------------------------------------------------------
+
+test("drawio_create: lints, builds the .drawio.svg, uploads and inserts a node", async () => {
+  const pageDoc = {
+    type: "doc",
+    content: [{ type: "paragraph", attrs: { id: "p1" }, content: [] }],
+  };
+  const { client, calls } = makeClient({ pageDoc });
+  const res = await client.drawioCreate("page1", { position: "append" }, MODEL, "My diagram");
+
+  assert.equal(res.success, true);
+  // The returned handle is an index-based "#<index>" ref (drawio nodes carry no
+  // persisted attrs.id), addressing the appended top-level block (index 1, after
+  // the existing paragraph).
+  assert.equal(res.nodeId, "#1");
+  assert.equal(res.attachmentId, "att-1");
+  assert.equal(calls.uploads.length, 1);
+  assert.equal(calls.uploads[0].fileName, "diagram.drawio.svg");
+  assert.equal(calls.uploads[0].mime, "image/svg+xml");
+  // The uploaded SVG carries the model back (round-trips through the decode chain).
+  assert.equal(decodeDrawioSvg(calls.uploads[0].svg), normalizeXml(MODEL));
+
+  // A drawio node was appended with src/attachmentId/dimensions and the title.
+  const drawios = findDrawio(calls.mutations[0].doc);
+  assert.equal(drawios.length, 1);
+  const n = drawios[0];
+  // No `id` attribute is set/persisted on the node (schema has none).
+  assert.equal(n.attrs.id, undefined);
+  assert.equal(n.attrs.attachmentId, "att-1");
+  assert.match(n.attrs.src, /^\/api\/files\/att-1\//);
+  assert.ok(n.attrs.width > 0 && n.attrs.height > 0);
+  assert.equal(n.attrs.title, "My diagram");
+});
+
+test("drawio_create: a lint violation throws before any upload", async () => {
+  const { client, calls } = makeClient({ pageDoc: { type: "doc", content: [] } });
+  // Edge with no child geometry -> edge-geometry rule.
+  const bad =
+    '<mxGraphModel><root><mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '<mxCell id="3" edge="1" parent="1" source="2" target="2"/></root></mxGraphModel>';
+  await assert.rejects(
+    () => client.drawioCreate("page1", { position: "append" }, bad, undefined),
+    /edge-geometry/,
+  );
+  assert.equal(calls.uploads.length, 0, "no attachment uploaded on lint failure");
+});
+
+test("drawio_create: before/after requires exactly one anchor", async () => {
+  const { client } = makeClient({ pageDoc: { type: "doc", content: [] } });
+  await assert.rejects(
+    () => client.drawioCreate("page1", { position: "before" }, MODEL),
+    /exactly one of anchorNodeId or anchorText/,
+  );
+});
+
+// --- drawio_get ------------------------------------------------------------
+
+test("drawio_get: decodes the model and returns meta with a hash", async () => {
+  const pageDoc = {
+    type: "doc",
+    content: [
+      {
+        type: "drawio",
+        attrs: {
+          id: "d1",
+          src: "/api/files/att-1/diagram.drawio.svg",
+          attachmentId: "att-1",
+          title: "T",
+          width: 200,
+          height: 120,
+        },
+      },
+    ],
+  };
+  const { client } = makeClient({ pageDoc, attachmentSvg: svgFor(MODEL) });
+  const res = await client.drawioGet("page1", "d1", "xml");
+  assert.equal(res.content, normalizeXml(MODEL));
+  assert.equal(res.meta.attachmentId, "att-1");
+  assert.equal(res.meta.title, "T");
+  assert.equal(res.meta.cellCount, 1);
+  assert.equal(res.meta.hash, mxHash(normalizeXml(MODEL)));
+});
+
+test("drawio_get: format=svg returns the raw .drawio.svg", async () => {
+  const svg = svgFor(MODEL);
+  const pageDoc = {
+    type: "doc",
+    content: [
+      { type: "drawio", attrs: { id: "d1", src: "/api/files/att-1/x.svg", attachmentId: "att-1" } },
+    ],
+  };
+  const { client } = makeClient({ pageDoc, attachmentSvg: svg });
+  const res = await client.drawioGet("page1", "d1", "svg");
+  assert.equal(res.content, svg);
+});
+
+test("drawio_get: reads a HUMAN-saved compressed diagram losslessly (pako)", async () => {
+  const pageDoc = {
+    type: "doc",
+    content: [
+      { type: "drawio", attrs: { id: "d1", src: "/api/files/att-1/x.svg", attachmentId: "att-1" } },
+    ],
+  };
+  const { client } = makeClient({ pageDoc, attachmentSvg: compressedSvgFor(MODEL) });
+  const res = await client.drawioGet("page1", "d1", "xml");
+  assert.equal(res.content, normalizeXml(MODEL));
+});
+
+// --- drawio_update ---------------------------------------------------------
+
+const UPDATED_MODEL =
+  '<mxGraphModel><root>' +
+  '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+  '<mxCell id="2" value="Changed" style="rounded=1;" vertex="1" parent="1">' +
+  '<mxGeometry x="20" y="20" width="300" height="200" as="geometry"/></mxCell>' +
+  '</root></mxGraphModel>';
+
+function updatePageDoc() {
+  return {
+    type: "doc",
+    content: [
+      {
+        type: "drawio",
+        attrs: {
+          id: "d1",
+          src: "/api/files/att-1/diagram.drawio.svg",
+          attachmentId: "att-1",
+          width: 200,
+          height: 120,
+        },
+      },
+    ],
+  };
+}
+
+test("drawio_update: stale baseHash -> conflict, no upload", async () => {
+  const { client, calls } = makeClient({
+    pageDoc: updatePageDoc(),
+    attachmentSvg: svgFor(MODEL),
+  });
+  await assert.rejects(
+    () => client.drawioUpdate("page1", "d1", UPDATED_MODEL, "deadbeef-stale"),
+    /conflict/,
+  );
+  assert.equal(calls.uploads.length, 0, "no upload on conflict");
+});
+
+test("drawio_update: current baseHash -> uploads new attachment and repoints node dims", async () => {
+  const currentHash = mxHash(normalizeXml(MODEL));
+  const { client, calls } = makeClient({
+    pageDoc: updatePageDoc(),
+    attachmentSvg: svgFor(MODEL),
+  });
+  const res = await client.drawioUpdate("page1", "d1", UPDATED_MODEL, currentHash);
+  assert.equal(res.success, true);
+  assert.equal(res.attachmentId, "att-1"); // fresh id from the stub sequence
+  assert.equal(calls.uploads.length, 1);
+  // The uploaded SVG carries the NEW model.
+  assert.equal(decodeDrawioSvg(calls.uploads[0].svg), normalizeXml(UPDATED_MODEL));
+  // The node was repointed with the new bounding-box dimensions:
+  // vertex maxX=320,maxY=220 + the 20px preview margin -> 340 x 240.
+  const n = findDrawio(calls.mutations[0].doc)[0];
+  assert.equal(n.attrs.attachmentId, "att-1");
+  assert.equal(n.attrs.width, 340);
+  assert.equal(n.attrs.height, 240);
+  // The block `id` used as the legacy resolution handle is dropped on save
+  // (schema declares no `id`); the update still targeted the correct node.
+  assert.equal(n.attrs.id, undefined);
+});
+
+test("drawio_update: baseHash is mandatory", async () => {
+  const { client } = makeClient({ pageDoc: updatePageDoc(), attachmentSvg: svgFor(MODEL) });
+  await assert.rejects(
+    () => client.drawioUpdate("page1", "d1", UPDATED_MODEL, ""),
+    /baseHash is mandatory/,
+  );
+});
+
+// --- Fix 1: the create handle must resolve on the SAVED doc (no id) ---------
+
+test("drawio_create -> get/update: returned #<index> handle resolves on the saved doc (id dropped)", async () => {
+  // Create appends a drawio node after the existing paragraph.
+  const createDoc = {
+    type: "doc",
+    content: [{ type: "paragraph", attrs: { id: "p1" }, content: [] }],
+  };
+  const create = makeClient({ pageDoc: createDoc });
+  const res = await create.client.drawioCreate(
+    "page1",
+    { position: "append" },
+    MODEL,
+    "T",
+  );
+  // The handle is index-based, not a block id.
+  assert.equal(res.nodeId, "#1");
+
+  // Take the document EXACTLY as it was saved: the schema drop stripped the
+  // node's id, so no id-based handle could ever resolve against it.
+  const savedDoc = create.calls.mutations[0].doc;
+  assert.equal(findDrawio(savedDoc)[0].attrs.id, undefined);
+
+  // drawio_get with the returned handle resolves the just-created node.
+  const getClient = makeClient({ pageDoc: savedDoc, attachmentSvg: svgFor(MODEL) });
+  const got = await getClient.client.drawioGet("page1", res.nodeId, "xml");
+  assert.equal(got.nodeId, res.nodeId);
+  assert.equal(got.content, normalizeXml(MODEL));
+
+  // drawio_update with the same handle + the hash from get repoints that node.
+  const upClient = makeClient({ pageDoc: savedDoc, attachmentSvg: svgFor(MODEL) });
+  const upd = await upClient.client.drawioUpdate(
+    "page1",
+    res.nodeId,
+    UPDATED_MODEL,
+    got.meta.hash,
+  );
+  assert.equal(upd.success, true);
+  assert.equal(upd.nodeId, res.nodeId);
+  const updated = findDrawio(upClient.calls.mutations[0].doc)[0];
+  assert.equal(
+    decodeDrawioSvg(upClient.calls.uploads[0].svg),
+    normalizeXml(UPDATED_MODEL),
+  );
+  assert.equal(updated.attrs.width, 340);
+});
+
+// --- error paths: the LLM must get a clean error, not a crash --------------
+
+test("drawio_get: a bad node ref -> clean 'no node found' error", async () => {
+  // Page has one paragraph; the requested ref resolves to nothing.
+  const pageDoc = {
+    type: "doc",
+    content: [{ type: "paragraph", attrs: { id: "p1" }, content: [] }],
+  };
+  const { client } = makeClient({ pageDoc, attachmentSvg: svgFor(MODEL) });
+  await assert.rejects(
+    () => client.drawioGet("page1", "does-not-exist", "xml"),
+    /no node found for "does-not-exist"/,
+  );
+});
+
+test("drawio_get: a drawio node with no src -> clean 'has no src to read' error", async () => {
+  const pageDoc = {
+    type: "doc",
+    content: [
+      // A drawio node that carries no `src` (e.g. a half-written node).
+      { type: "drawio", attrs: { id: "d1", attachmentId: "att-1" } },
+    ],
+  };
+  const { client } = makeClient({ pageDoc, attachmentSvg: svgFor(MODEL) });
+  await assert.rejects(
+    () => client.drawioGet("page1", "d1", "xml"),
+    /node "d1" on page page1 has no src to read/,
+  );
+});
+
+test("drawio_update: the resolved node is NOT a drawio node -> clean error, no upload", async () => {
+  // "#0" resolves to a paragraph. The update must refuse cleanly rather than
+  // crash or repoint the wrong node.
+  const pageDoc = {
+    type: "doc",
+    content: [{ type: "paragraph", attrs: { id: "p1" }, content: [] }],
+  };
+  const { client, calls } = makeClient({ pageDoc, attachmentSvg: svgFor(MODEL) });
+  await assert.rejects(
+    () => client.drawioUpdate("page1", "#0", UPDATED_MODEL, "any-nonempty-hash"),
+    /node "#0" on page page1 is a paragraph, not a drawio diagram/,
+  );
+  assert.equal(calls.uploads.length, 0, "no upload when the node is not a diagram");
+  assert.equal(calls.mutations.length, 0, "no write when the node is not a diagram");
+});
+
+test("drawio_create: anchor not found -> clean error that reports the orphan attachment", async () => {
+  // The upload happens before the mutate transform; when the anchor cannot be
+  // found the write is skipped and the (now unreferenced) attachment is named
+  // in the error, exactly as the code documents.
+  const pageDoc = {
+    type: "doc",
+    content: [{ type: "paragraph", attrs: { id: "p1" }, content: [] }],
+  };
+  const { client, calls } = makeClient({ pageDoc });
+  await assert.rejects(
+    () =>
+      client.drawioCreate(
+        "page1",
+        { position: "after", anchorNodeId: "nope" },
+        MODEL,
+        "T",
+      ),
+    (err) =>
+      /anchor not found/.test(err.message) &&
+      /unreferenced orphan/.test(err.message) &&
+      /att-1/.test(err.message),
+  );
+  // The orphan was uploaded (and reported), but no node was written.
+  assert.equal(calls.uploads.length, 1, "attachment uploaded before the failed insert");
+  const drawios = calls.mutations.length ? findDrawio(calls.mutations[0].doc) : [];
+  assert.equal(drawios.length, 0, "no drawio node written when the anchor is missing");
+});
+
+// --- Fix 2: update targets ONLY the resolved node --------------------------
+
+test("drawio_update: repoints ONLY the addressed node, not siblings sharing an attachmentId", async () => {
+  // A copied diagram: two drawio nodes share one attachmentId. Updating via the
+  // "#0" handle must touch node #0 only, never the sibling copy.
+  const shared = {
+    type: "doc",
+    content: [
+      {
+        type: "drawio",
+        attrs: {
+          src: "/api/files/shared/x.svg",
+          attachmentId: "shared",
+          width: 200,
+          height: 120,
+        },
+      },
+      {
+        type: "drawio",
+        attrs: {
+          src: "/api/files/shared/x.svg",
+          attachmentId: "shared",
+          width: 200,
+          height: 120,
+        },
+      },
+    ],
+  };
+  const { client, calls } = makeClient({
+    pageDoc: shared,
+    attachmentSvg: svgFor(MODEL),
+  });
+  const res = await client.drawioUpdate(
+    "page1",
+    "#0",
+    UPDATED_MODEL,
+    mxHash(normalizeXml(MODEL)),
+  );
+  assert.equal(res.success, true);
+
+  const drawios = findDrawio(calls.mutations[0].doc);
+  assert.equal(drawios.length, 2);
+  // Node #0 repointed to the NEW attachment ("att-1" from the stub) and dims.
+  assert.equal(drawios[0].attrs.attachmentId, "att-1");
+  assert.equal(drawios[0].attrs.width, 340);
+  assert.match(drawios[0].attrs.src, /^\/api\/files\/att-1\//);
+  // Node #1 (the sibling copy) is untouched despite sharing the old attachmentId.
+  assert.equal(drawios[1].attrs.attachmentId, "shared");
+  assert.equal(drawios[1].attrs.width, 200);
+  assert.equal(drawios[1].attrs.src, "/api/files/shared/x.svg");
+});

packages/mcp/test/mock/resolve-page-id-collab-doc-name.test.mjs

@@ -19,6 +19,7 @@ import { WebSocketServer } from "ws";
 import { Hocuspocus } from "@hocuspocus/server";
 import { DocmostClient } from "../../build/client.js";
 import { buildYDoc } from "../../build/lib/collaboration.js";
+import { destroyAllSessions } from "../../build/lib/collab-session.js";
 // Import the SAME page-lock module instance that build/client.js imports. ESM
 // caches modules by resolved URL, so this `withPageLock` shares the very
 // per-page mutex map (`chains`) the client uses — letting the replaceImage test
@@ -188,6 +189,10 @@ async function spawnCollabStack(opts = {}) {
 
 const openStacks = [];
 after(async () => {
+  // #400: tests now leave a cached live CollabSession per page. Destroy them
+  // first (closes the client ws) so the server.close() below is not racing an
+  // open collab connection.
+  destroyAllSessions();
   await Promise.all(
     openStacks.map(
       ({ server, hocuspocus }) =>
@@ -270,17 +275,23 @@ test("a UUID input is passed through unchanged and triggers NO /pages/info fetch
   );
 });
 
-test("a repeated slugId edit resolves the UUID only once (cache)", async () => {
+test("repeated slugId edits reuse ONE live collab session and resolve the UUID only once (#400 cache)", async () => {
   const { state, baseURL } = await spawnCollabStack();
   const client = new DocmostClient(baseURL, "user@example.com", "pw");
 
-  // Each mock connection re-seeds a fresh "hello world" doc (the mock does not
-  // persist across connects), so both edits target "hello". The cache assertion
-  // only concerns the slugId->uuid resolution, not the document content.
+  // #400: a series of edits on the same page reuses ONE live CollabSession, so
+  // the connect/handshake happens once and the collab doc is OPENED a single
+  // time (not per edit). The live ydoc persists between edits (the whole point),
+  // so the second edit sees the first edit's result: after "hello" -> "hi world"
+  // it targets the still-present "world".
   await client.editPageText(SLUG, [{ find: "hello", replace: "hi" }]);
-  await client.editPageText(SLUG, [{ find: "hello", replace: "hey" }]);
+  await client.editPageText(SLUG, [{ find: "world", replace: "planet" }]);
 
-  assert.deepEqual(state.docNames, [`page.${UUID}`, `page.${UUID}`]);
+  assert.deepEqual(
+    state.docNames,
+    [`page.${UUID}`],
+    "the two edits must reuse one live collab session -> a single collab-doc open (#400)",
+  );
   assert.equal(
     state.pagesInfoCalls.length,
     1,
@@ -325,8 +336,9 @@ test("replaceImage opens by the resolved UUID AND keys its page lock by that UUI
   await uploadStarted; // deterministic: replaceImage now holds its page lock.
 
   // (a) OPEN BY UUID: the only collab doc opened so far (the scan pass) used the
-  // canonical UUID, never the slugId. (The write pass opens a second time after
-  // we release the gate; asserted at the end.)
+  // canonical UUID, never the slugId. (#400: the write pass will REUSE this same
+  // live session rather than reopen, so docNames stays a single entry — asserted
+  // at the end.)
   assert.deepEqual(
     state.docNames,
     [`page.${UUID}`],
@@ -378,8 +390,9 @@ test("replaceImage opens by the resolved UUID AND keys its page lock by that UUI
 
   assert.equal(res.success, true);
   assert.equal(res.replaced, 1, "the one seeded image must be repointed");
-  // Both opens (scan pass + write pass) used the UUID; the slugId never appears.
-  assert.deepEqual(state.docNames, [`page.${UUID}`, `page.${UUID}`]);
+  // #400: the write pass REUSES the scan pass's live session, so the collab doc
+  // is opened ONCE across both passes (never reopened, never by the slugId).
+  assert.deepEqual(state.docNames, [`page.${UUID}`]);
   assert.ok(
     !state.docNames.includes(`page.${SLUG}`),
     "replaceImage must NEVER open the collab doc by the slugId (the #260 bug)",

packages/mcp/test/mock/tool-timing-server.test.mjs

@@ -0,0 +1,87 @@
+// #402 — INTEGRATION test that locks the registerTool monkeypatch installed by
+// createDocmostMcpServer (src/index.ts). The sibling unit test
+// (test/unit/tool-timing.test.mjs) only exercises the timeToolHandler helper in
+// ISOLATION; it never constructs the server, so nothing there proves the factory
+// actually (a) wraps every registered tool through that helper and (b) labels
+// each sample with the tool's REGISTRATION name.
+//
+// Here we stand up a real McpServer via the factory, connect a real MCP Client
+// over the SDK's in-memory transport, invoke one registered tool, and assert the
+// host's onMetric sink received `("mcp_tool_duration_seconds", <number>, { tool
+// })` with tool === the exact registration name. This locks both the "monkeypatch
+// wraps tools" and "label = registration name" halves of the contract, so a
+// mutation to args.slice(0, -1) / the handler-arg detection / the capture order
+// is caught.
+import { test } from "node:test";
+import assert from "node:assert/strict";
+
+import { Client } from "@modelcontextprotocol/sdk/client/index.js";
+import { InMemoryTransport } from "@modelcontextprotocol/sdk/inMemory.js";
+
+import { createDocmostMcpServer } from "../../build/index.js";
+
+// The tool we drive. get_workspace has NO input schema, so protocol-level input
+// validation cannot short-circuit before the handler runs — the wrapped handler
+// is guaranteed to execute (and then fail on the unreachable backend, which is
+// exactly what we want: the wrapper times in a finally on throw too).
+const TOOL_NAME = "get_workspace";
+
+test("the factory's registerTool monkeypatch times a live tool call and labels it with the registration name", async () => {
+  const calls = [];
+  const onMetric = (name, value, labels) => calls.push({ name, value, labels });
+
+  // Minimal valid credentials config. apiUrl points at a port that refuses
+  // connections immediately so the tool's backend call fails FAST (ECONNREFUSED)
+  // rather than hanging — the wrapper still emits the metric from its finally.
+  const server = createDocmostMcpServer({
+    apiUrl: "http://127.0.0.1:1",
+    email: "x@example.com",
+    password: "pw",
+    onMetric,
+  });
+
+  const [clientTransport, serverTransport] =
+    InMemoryTransport.createLinkedPair();
+
+  const client = new Client(
+    { name: "test-client", version: "0.0.0" },
+    { capabilities: {} },
+  );
+
+  await Promise.all([
+    server.connect(serverTransport),
+    client.connect(clientTransport),
+  ]);
+
+  try {
+    // Invoke the tool. The backend is unreachable, so this either resolves with
+    // an error result (isError) or rejects — both are fine. What matters is that
+    // the handler ran through the timing wrapper, which fires onMetric either way.
+    try {
+      await client.callTool({ name: TOOL_NAME, arguments: {} });
+    } catch {
+      // Tolerate the expected backend failure surfacing as a thrown protocol error.
+    }
+
+    // The wrapper must have fed exactly the timing sample for THIS tool.
+    const timing = calls.filter(
+      (c) => c.name === "mcp_tool_duration_seconds",
+    );
+    assert.ok(
+      timing.length >= 1,
+      "onMetric must receive a mcp_tool_duration_seconds sample from the wrapped handler",
+    );
+
+    const sample = timing.find((c) => c.labels && c.labels.tool === TOOL_NAME);
+    assert.ok(
+      sample,
+      `a timing sample must be labelled with the registration name "${TOOL_NAME}"; ` +
+        `got labels: ${JSON.stringify(timing.map((c) => c.labels))}`,
+    );
+    assert.equal(typeof sample.value, "number");
+    assert.ok(sample.value >= 0, "duration must be non-negative seconds");
+  } finally {
+    await client.close();
+    await server.close();
+  }
+});

packages/mcp/test/unit/client-host-contract.test.mjs

@@ -28,8 +28,9 @@ import { DocmostClient } from "../../build/index.js";
 // in the server's DocmostClientLike interface (the in-app per-user tool adapter
 // only — it is a SUBSET of the DocmostClient surface — covers only what the in-app adapter
 // consumes; the standalone MCP transport (packages/mcp/src/index.ts) calls additional
-// client methods (insertImage/replaceImage/deleteComment/updateComment/insertFootnote)
-// that this guard does NOT track — the MCP transport's own typecheck covers those). Full type-derivation
+// client methods (deleteComment/updateComment) that this guard does NOT track — the
+// MCP transport's own typecheck covers those. insertImage/replaceImage/insertFootnote
+// were MCP-only but are now in-app-consumed too (#410), so they ARE tracked below. Full type-derivation
 // of DocmostClientLike from this class is deferred (see the staged plan in
 // docmost-client.loader.ts): the package emits no declarations and the real
 // (inferred, concrete) return types conflict with the host's loose
@@ -76,6 +77,14 @@ const HOST_CONTRACT_METHODS = [
   "restorePageVersion",
   "transformPage",
   "stashPage",
+  // write (image / footnote) — MCP-only until #410 promoted them to in-app tools
+  "insertImage",
+  "replaceImage",
+  "insertFootnote",
+  // draw.io diagrams (#423, stage 1) — read + create + optimistic-locked update
+  "drawioGet",
+  "drawioCreate",
+  "drawioUpdate",
   // write (comment)
   "createComment",
   "resolveComment",

packages/mcp/test/unit/collab-session.test.mjs

@@ -0,0 +1,348 @@
+import { test, beforeEach, afterEach, mock } from "node:test";
+import assert from "node:assert/strict";
+import { EventEmitter } from "node:events";
+
+import {
+  acquireCollabSession,
+  destroyAllSessions,
+  __setCollabProviderFactory,
+  __sessionCountForTests,
+} from "../../build/lib/collab-session.js";
+import { withPageLock } from "../../build/lib/page-lock.js";
+
+// A stand-in for HocuspocusProvider: it shares the ydoc (so the real yjs
+// read/transform/write in CollabSession.mutate runs unchanged), auto-completes
+// the connect+sync handshake on a microtask (unaffected by mock timers), and
+// exposes hooks to drive disconnect/close/auth-failure and the unsyncedChanges
+// ack. There is no collaboration server in the test env, so every test drives
+// the provider through this fake.
+class FakeProvider extends EventEmitter {
+  static instances = [];
+  static connectCount = 0;
+
+  static reset() {
+    FakeProvider.instances = [];
+    FakeProvider.connectCount = 0;
+  }
+
+  static last() {
+    return FakeProvider.instances[FakeProvider.instances.length - 1];
+  }
+
+  constructor(config, opts = {}) {
+    super();
+    this.config = config;
+    this.ydoc = config.document;
+    this.synced = false;
+    this.unsyncedChanges = opts.unsynced ?? 0;
+    this.destroyed = false;
+    FakeProvider.instances.push(this);
+    FakeProvider.connectCount += 1;
+    if (opts.autoSync !== false) {
+      // Real HocuspocusProvider fires onSynced asynchronously after the
+      // handshake; a microtask reproduces that without depending on timers.
+      queueMicrotask(() => {
+        if (this.destroyed) return;
+        this.config.onConnect?.();
+        this.synced = true;
+        this.config.onSynced?.();
+      });
+    }
+  }
+
+  destroy() {
+    this.destroyed = true;
+  }
+
+  // --- test drivers ---
+  _disconnect() {
+    this.config.onDisconnect?.();
+  }
+  _close() {
+    this.config.onClose?.();
+  }
+  _authFail() {
+    this.config.onAuthenticationFailed?.();
+  }
+  _ack() {
+    this.unsyncedChanges = 0;
+    this.emit("unsyncedChanges", { number: 0 });
+  }
+}
+
+/** Build a provider factory that stamps every provider with the given opts. */
+function factory(opts = {}) {
+  return (config) => new FakeProvider(config, opts);
+}
+
+/** A minimal, schema-valid ProseMirror doc for a write. */
+function docWith(text) {
+  return {
+    type: "doc",
+    content: [
+      { type: "paragraph", content: [{ type: "text", text: String(text) }] },
+    ],
+  };
+}
+
+const ENV_KEYS = [
+  "MCP_COLLAB_SESSION_IDLE_MS",
+  "MCP_COLLAB_SESSION_MAX_AGE_MS",
+  "MCP_COLLAB_SESSION_MAX_ENTRIES",
+];
+let savedEnv;
+
+beforeEach(() => {
+  savedEnv = {};
+  for (const k of ENV_KEYS) savedEnv[k] = process.env[k];
+  FakeProvider.reset();
+  __setCollabProviderFactory(factory());
+});
+
+afterEach(() => {
+  destroyAllSessions();
+  __setCollabProviderFactory(null);
+  mock.timers.reset();
+  for (const k of ENV_KEYS) {
+    if (savedEnv[k] === undefined) delete process.env[k];
+    else process.env[k] = savedEnv[k];
+  }
+});
+
+test("acquire opens one provider; reuse returns the SAME live session", async () => {
+  const a = await acquireCollabSession("page-1", "tok", "http://h/api");
+  const b = await acquireCollabSession("page-1", "tok", "http://h/api");
+  assert.equal(a, b, "same (wsUrl,page,token) must reuse the session");
+  assert.equal(FakeProvider.connectCount, 1, "exactly one connect/sync");
+  assert.equal(__sessionCountForTests(), 1);
+});
+
+test("N mutates on one page open the provider ONCE (coalesced series)", async () => {
+  const session = await acquireCollabSession("page-1", "tok", "http://h/api");
+  for (let i = 0; i < 20; i++) {
+    const r = await session.mutate(() => docWith(`edit ${i}`));
+    assert.ok(r && r.doc, "each mutate resolves a MutationResult");
+  }
+  assert.equal(
+    FakeProvider.connectCount,
+    1,
+    "20 mutates must not reconnect — one live provider for the whole series",
+  );
+});
+
+test("mutate preserves the transform-abort no-op report (null transform)", async () => {
+  const session = await acquireCollabSession("page-1", "tok", "http://h/api");
+  const r = await session.mutate(() => null);
+  assert.equal(r.verify.changed, false);
+  assert.equal(r.verify.summary, "no changes (transform aborted)");
+});
+
+test("registry key includes the token: different tokens => different sessions", async () => {
+  const a = await acquireCollabSession("page-1", "tok-A", "http://h/api");
+  const b = await acquireCollabSession("page-1", "tok-B", "http://h/api");
+  assert.notEqual(a, b, "different tokens must never share a session");
+  assert.equal(FakeProvider.connectCount, 2);
+  assert.equal(__sessionCountForTests(), 2);
+  // Same token reuses.
+  const a2 = await acquireCollabSession("page-1", "tok-A", "http://h/api");
+  assert.equal(a, a2);
+  assert.equal(FakeProvider.connectCount, 2);
+});
+
+test("disconnect at any time kills the session and removes it from the registry", async () => {
+  const a = await acquireCollabSession("page-1", "tok", "http://h/api");
+  assert.equal(__sessionCountForTests(), 1);
+  FakeProvider.last()._disconnect();
+  assert.equal(__sessionCountForTests(), 0, "dead session is deregistered");
+  // Re-acquire opens a brand new provider.
+  const b = await acquireCollabSession("page-1", "tok", "http://h/api");
+  assert.notEqual(a, b);
+  assert.equal(FakeProvider.connectCount, 2);
+});
+
+test("an in-flight mutate rejects with the connection-closed text on disconnect", async () => {
+  __setCollabProviderFactory(factory({ unsynced: 1 })); // stay pending after write
+  const session = await acquireCollabSession("page-1", "tok", "http://h/api");
+  const p = session.mutate(() => docWith("x"));
+  // The write happened synchronously; persistence is pending. Now the socket drops.
+  FakeProvider.last()._disconnect();
+  await assert.rejects(
+    p,
+    /Collaboration connection closed before the update was persisted\/synced/,
+  );
+});
+
+test("auth failure rejects the pending open with the auth error text", async () => {
+  __setCollabProviderFactory(factory({ autoSync: false }));
+  const p = acquireCollabSession("page-1", "tok", "http://h/api");
+  // Let the provider be constructed, then fail auth.
+  await Promise.resolve();
+  FakeProvider.last()._authFail();
+  await assert.rejects(
+    p,
+    /Authentication failed for collaboration connection/,
+  );
+  assert.equal(__sessionCountForTests(), 0);
+});
+
+test("mutate-error invalidates the session (caller destroys; re-acquire is fresh)", async () => {
+  const session = await acquireCollabSession("page-1", "tok", "http://h/api");
+  await assert.rejects(
+    session.mutate(() => {
+      throw new Error("afterText not found");
+    }),
+    /afterText not found/,
+  );
+  // The production caller destroys on failure; mirror that here.
+  session.destroy("mutate failed");
+  assert.equal(__sessionCountForTests(), 0);
+  const fresh = await acquireCollabSession("page-1", "tok", "http://h/api");
+  assert.notEqual(fresh, session);
+  assert.equal(FakeProvider.connectCount, 2);
+});
+
+test("a pending write resolves when the server acks (unsyncedChanges -> 0)", async () => {
+  __setCollabProviderFactory(factory({ unsynced: 1 }));
+  const session = await acquireCollabSession("page-1", "tok", "http://h/api");
+  const p = session.mutate(() => docWith("y"));
+  FakeProvider.last()._ack();
+  const r = await p;
+  assert.ok(r.doc);
+});
+
+test("concurrent mutate on one session: the second rejects, the first is unaffected", async () => {
+  __setCollabProviderFactory(factory({ unsynced: 1 })); // first stays pending after write
+  const session = await acquireCollabSession("page-1", "tok", "http://h/api");
+  // First mutate: write happens synchronously, persistence ack still pending.
+  const first = session.mutate(() => docWith("first"));
+  // Second overlapping mutate on the SAME session must fail fast.
+  await assert.rejects(
+    session.mutate(() => docWith("second")),
+    /mutate already in-flight; caller must serialize \(hold the page lock\)/,
+  );
+  // The first op is untouched: its rejector was not clobbered. Ack it now.
+  FakeProvider.last()._ack();
+  const r = await first;
+  assert.ok(r.doc, "the first in-flight mutate still resolves on its own ack");
+  assert.equal(FakeProvider.connectCount, 1, "no reconnect from the rejected overlap");
+});
+
+test("sequential mutates on one session both succeed (the guard doesn't break serialized use)", async () => {
+  const session = await acquireCollabSession("page-1", "tok", "http://h/api");
+  // Await the first fully, then run the second: inflightReject was cleared by
+  // localFinish before the first settled, so the guard is clear for the second.
+  const r1 = await session.mutate(() => docWith("one"));
+  assert.ok(r1.doc, "first sequential mutate resolves");
+  const r2 = await session.mutate(() => docWith("two"));
+  assert.ok(r2.doc, "second sequential mutate resolves — guard not tripped");
+  assert.equal(FakeProvider.connectCount, 1, "sequential mutates reuse one provider");
+});
+
+test("connect timeout rejects with the connect-timeout text and fires the metric hook", async () => {
+  mock.timers.enable({ apis: ["setTimeout"] });
+  __setCollabProviderFactory(factory({ autoSync: false }));
+  let metricFired = 0;
+  const p = acquireCollabSession("page-1", "tok", "http://h/api", {
+    onConnectTimeout: () => {
+      metricFired += 1;
+    },
+  });
+  mock.timers.tick(25000);
+  await assert.rejects(p, /Connection timeout to collaboration server/);
+  assert.equal(metricFired, 1);
+  assert.equal(__sessionCountForTests(), 0);
+});
+
+test("idle TTL destroys the session; re-acquire reconnects", async () => {
+  mock.timers.enable({ apis: ["setTimeout"] });
+  process.env.MCP_COLLAB_SESSION_IDLE_MS = "1000";
+  const a = await acquireCollabSession("page-1", "tok", "http://h/api");
+  assert.equal(__sessionCountForTests(), 1);
+  mock.timers.tick(1000); // idle fires
+  assert.equal(__sessionCountForTests(), 0, "idle timeout destroyed it");
+  const b = await acquireCollabSession("page-1", "tok", "http://h/api");
+  assert.notEqual(a, b);
+  assert.equal(FakeProvider.connectCount, 2);
+});
+
+test("max age is enforced at acquire (destroy + open fresh), idle held off", async () => {
+  mock.timers.enable({ apis: ["setTimeout", "Date"] });
+  process.env.MCP_COLLAB_SESSION_MAX_AGE_MS = "1000";
+  process.env.MCP_COLLAB_SESSION_IDLE_MS = "10000000"; // never fires in this test
+  const a = await acquireCollabSession("page-1", "tok", "http://h/api");
+  mock.timers.tick(2000); // past max age, below idle
+  const b = await acquireCollabSession("page-1", "tok", "http://h/api");
+  assert.notEqual(a, b, "a session past its max age must be replaced");
+  assert.equal(FakeProvider.connectCount, 2);
+});
+
+test("registry cap: least-recently-used session is destroy-evicted", async () => {
+  process.env.MCP_COLLAB_SESSION_MAX_ENTRIES = "2";
+  const s1 = await acquireCollabSession("page-1", "tok", "http://h/api");
+  const p1prov = FakeProvider.last();
+  const s2 = await acquireCollabSession("page-2", "tok", "http://h/api");
+  const p2prov = FakeProvider.last();
+  assert.equal(__sessionCountForTests(), 2);
+
+  // Touch page-1 so page-2 becomes the least-recently-used entry.
+  assert.equal(await acquireCollabSession("page-1", "tok", "http://h/api"), s1);
+  assert.equal(FakeProvider.connectCount, 2, "reuse must not reconnect");
+
+  // A third distinct page (cap 2) must evict the LRU (page-2), not page-1.
+  const s3 = await acquireCollabSession("page-3", "tok", "http://h/api");
+  assert.equal(__sessionCountForTests(), 2);
+  assert.equal(FakeProvider.connectCount, 3);
+  assert.equal(p2prov.destroyed, true, "the LRU provider was destroy-evicted");
+  assert.equal(p1prov.destroyed, false, "the MRU page-1 survived");
+
+  // page-1 still reused (survived), page-3 still reused.
+  assert.equal(await acquireCollabSession("page-1", "tok", "http://h/api"), s1);
+  assert.equal(await acquireCollabSession("page-3", "tok", "http://h/api"), s3);
+  assert.equal(FakeProvider.connectCount, 3, "no extra reconnects");
+});
+
+test("MCP_COLLAB_SESSION_IDLE_MS=0 disables the cache (legacy provider-per-op)", async () => {
+  process.env.MCP_COLLAB_SESSION_IDLE_MS = "0";
+  const s1 = await acquireCollabSession("page-1", "tok", "http://h/api");
+  // Never registered (ephemeral).
+  assert.equal(__sessionCountForTests(), 0);
+  const r1 = await s1.mutate(() => docWith("a"));
+  assert.ok(r1.doc);
+  // After its single op the ephemeral session self-destroyed.
+  assert.equal(FakeProvider.instances[0].destroyed, true);
+  // A second op opens a BRAND NEW provider (no reuse).
+  const s2 = await acquireCollabSession("page-1", "tok", "http://h/api");
+  assert.notEqual(s1, s2);
+  assert.equal(FakeProvider.connectCount, 2);
+});
+
+test("replaceImage-shaped flow: acquire under an EXTERNAL page lock does not deadlock and reuses one session", async () => {
+  const pageId = "page-lock";
+  // Mirror replaceImage: hold ONE withPageLock across scan (read-only) + write,
+  // each going through the non-locking acquireCollabSession.
+  const result = await withPageLock(pageId, async () => {
+    // pass 1: read-only scan (transform returns null -> no write)
+    const scan = await acquireCollabSession(pageId, "tok", "http://h/api");
+    const scanRes = await scan.mutate(() => null);
+    assert.equal(scanRes.verify.changed, false);
+    // pass 2: the actual write, same held lock
+    const write = await acquireCollabSession(pageId, "tok", "http://h/api");
+    return write.mutate(() => docWith("repointed"));
+  });
+  assert.ok(result.doc, "the locked scan+write completed without deadlock");
+  assert.equal(
+    FakeProvider.connectCount,
+    1,
+    "both passes under the held lock reuse ONE live session",
+  );
+});
+
+test("destroyAllSessions tears down every cached session", async () => {
+  await acquireCollabSession("page-1", "tok", "http://h/api");
+  await acquireCollabSession("page-2", "tok", "http://h/api");
+  assert.equal(__sessionCountForTests(), 2);
+  const provs = [...FakeProvider.instances];
+  destroyAllSessions();
+  assert.equal(__sessionCountForTests(), 0);
+  assert.ok(provs.every((p) => p.destroyed), "all providers destroyed");
+});

packages/mcp/test/unit/comment-anchor.test.mjs

@@ -8,6 +8,7 @@ import {
   applyAnchorInDoc,
   countAnchorMatches,
   getAnchoredText,
+  resolveAnchorSelection,
 } from "../../build/lib/comment-anchor.js";
 
 const COMMENT_ID = "cmt-123";
@@ -308,3 +309,70 @@ test("getAnchoredText returns null when the selection does not anchor", () => {
   const doc = paragraphDoc([{ type: "text", text: "hello world" }]);
   assert.equal(getAnchoredText(doc, "not present"), null);
 });
+
+// ---------------------------------------------------------------------------
+// #408 MARKDOWN-STRIP FALLBACK. A selection copied with inline markdown still
+// carries `**`/`` ` ``/`[t](u)` markers the plain document text lacks. When the
+// verbatim selection anchors nowhere, all four entry points retry with the
+// markdown stripped — consistently, so the suggestion-uniqueness gate stays
+// coherent — while what gets STORED remains the raw document substring.
+// ---------------------------------------------------------------------------
+test("a markdown-styled selection anchors against plain doc text via the strip fallback", () => {
+  const doc = paragraphDoc([{ type: "text", text: "a bold word here" }]);
+  // The agent quoted "**bold** word" from a styled view; the doc is plain text.
+  const sel = "**bold** word";
+  const resolved = resolveAnchorSelection(doc, sel);
+  assert.equal(resolved.found, true, "strip fallback finds the anchor");
+  assert.equal(resolved.normalized, true, "reports the soft-warning flag");
+  assert.equal(canAnchorInDoc(doc, sel), true);
+  assert.equal(countAnchorMatches(doc, sel), 1);
+
+  const ok = applyAnchorInDoc(doc, sel, COMMENT_ID);
+  assert.equal(ok, true);
+  const marked = doc.content[0].content.filter((p) => commentMark(p));
+  assert.equal(marked.map((m) => m.text).join(""), "bold word",
+    "the mark lands on the plain-text span");
+});
+
+test("getAnchoredText stores the RAW doc substring even when matched via the strip fallback", () => {
+  // Doc uses a smart apostrophe; the agent typed ASCII + markdown emphasis.
+  const doc = paragraphDoc([{ type: "text", text: "it’s bold now" }]);
+  const stored = getAnchoredText(doc, "it's **bold**");
+  assert.equal(stored, "it’s bold",
+    "stored selection is the raw document text, not the stripped/ASCII locator");
+});
+
+test("the strip fallback does not flip a raw-unique selection to ambiguous", () => {
+  // "config" appears twice, but the raw phrase "config value" appears once.
+  const doc = {
+    type: "doc",
+    content: [
+      { type: "paragraph", content: [{ type: "text", text: "the config value here" }] },
+      { type: "paragraph", content: [{ type: "text", text: "another config here" }] },
+    ],
+  };
+  // Raw phrase is unique -> exactly 1, and no strip happens (nothing to strip).
+  assert.equal(countAnchorMatches(doc, "config value"), 1);
+  assert.equal(resolveAnchorSelection(doc, "config value").normalized, false);
+});
+
+test("EXACT WINS: a raw match short-circuits the strip fallback (count reflects raw)", () => {
+  // A literal "**" run exists raw once; its stripped form would also appear.
+  const doc = paragraphDoc([{ type: "text", text: "use **stars** and stars" }]);
+  // Raw "**stars**" occurs once -> count 1 from the verbatim locator; the
+  // fallback (which would find two "stars") never runs.
+  assert.equal(countAnchorMatches(doc, "**stars**"), 1);
+  assert.equal(resolveAnchorSelection(doc, "**stars**").normalized, false);
+});
+
+test("a markdown selection whose stripped form is ambiguous is counted as ambiguous", () => {
+  const doc = {
+    type: "doc",
+    content: [
+      { type: "paragraph", content: [{ type: "text", text: "first config here" }] },
+      { type: "paragraph", content: [{ type: "text", text: "second config here" }] },
+    ],
+  };
+  // Verbatim "**config**" matches nothing; stripped "config" matches twice.
+  assert.equal(countAnchorMatches(doc, "**config**"), 2);
+});

packages/mcp/test/unit/drawio-preview.test.mjs

@@ -0,0 +1,84 @@
+// Unit tests for the pure-TS schematic SVG preview (issue #423). Asserts that
+// the preview emits well-formed SVG covering each primitive (rect/ellipse/
+// rhombus/edge), resolves container-relative coordinates to absolute, and that
+// the full `.drawio.svg` wrapper parses.
+import { test } from "node:test";
+import assert from "node:assert/strict";
+import { JSDOM } from "jsdom";
+import { renderDiagramShapes } from "../../build/lib/drawio-preview.js";
+import {
+  parseCells,
+  computeBBox,
+  buildDrawioSvg,
+  normalizeXml,
+} from "../../build/lib/drawio-xml.js";
+
+const { window } = new JSDOM("");
+function parseSvg(svg) {
+  const doc = new window.DOMParser().parseFromString(svg, "application/xml");
+  const err = doc.getElementsByTagName("parsererror");
+  assert.equal(err.length, 0, `SVG did not parse: ${err[0]?.textContent}`);
+  return doc;
+}
+
+const MODEL =
+  '<mxGraphModel><root>' +
+  '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+  '<mxCell id="2" value="Box &amp; Co" style="rounded=1;fillColor=#dae8fc;strokeColor=#6c8ebf;" vertex="1" parent="1">' +
+  '<mxGeometry x="40" y="40" width="120" height="60" as="geometry"/></mxCell>' +
+  '<mxCell id="3" value="Circle" style="ellipse;fillColor=#d5e8d4;" vertex="1" parent="1">' +
+  '<mxGeometry x="240" y="40" width="80" height="80" as="geometry"/></mxCell>' +
+  '<mxCell id="5" value="Dec" style="rhombus;" vertex="1" parent="1">' +
+  '<mxGeometry x="40" y="160" width="100" height="60" as="geometry"/></mxCell>' +
+  '<mxCell id="4" value="link" edge="1" parent="1" source="2" target="3"><mxGeometry relative="1" as="geometry"/></mxCell>' +
+  '</root></mxGraphModel>';
+
+test("renderDiagramShapes emits rect, ellipse, polygon and a line", () => {
+  const cells = parseCells(MODEL);
+  const inner = renderDiagramShapes(cells, computeBBox(cells));
+  assert.ok(inner.includes("<rect"), "has a rect");
+  assert.ok(inner.includes("<ellipse"), "has an ellipse");
+  assert.ok(inner.includes("<polygon"), "has a polygon (rhombus)");
+  assert.ok(inner.includes("<line"), "has an edge line");
+  // Labels are HTML-escaped.
+  assert.ok(inner.includes("Box &amp; Co"));
+});
+
+test("the full .drawio.svg wrapper parses as valid XML", () => {
+  const cells = parseCells(MODEL);
+  const bbox = computeBBox(cells);
+  const inner = renderDiagramShapes(cells, bbox);
+  const svg = buildDrawioSvg(normalizeXml(MODEL), inner, bbox);
+  const doc = parseSvg(svg);
+  assert.equal(doc.documentElement.tagName, "svg");
+  assert.ok(doc.documentElement.getAttribute("content"), "carries content=");
+  // The visible children exist.
+  assert.ok(doc.getElementsByTagName("rect").length >= 1);
+});
+
+test("container children resolve to absolute coordinates", () => {
+  // A group at (100,100) with a child rect at relative (10,10,20,20) -> abs 110,110.
+  const model =
+    '<mxGraphModel><root>' +
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="g" style="group;" vertex="1" parent="1"><mxGeometry x="100" y="100" width="200" height="200" as="geometry"/></mxCell>' +
+    '<mxCell id="c" value="in" vertex="1" parent="g"><mxGeometry x="10" y="10" width="20" height="20" as="geometry"/></mxCell>' +
+    '</root></mxGraphModel>';
+  const cells = parseCells(model);
+  const inner = renderDiagramShapes(cells, computeBBox(cells));
+  // The child rect must be placed at absolute x=110,y=110.
+  assert.ok(/<rect x="110" y="110"/.test(inner), `expected abs child rect, got: ${inner}`);
+});
+
+test("unknown stencil (shape=mxgraph.*) degrades to a labeled rectangle", () => {
+  const model =
+    '<mxGraphModel><root>' +
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" value="AWS" style="shape=mxgraph.aws4.lambda;" vertex="1" parent="1">' +
+    '<mxGeometry x="0" y="0" width="60" height="60" as="geometry"/></mxCell>' +
+    '</root></mxGraphModel>';
+  const cells = parseCells(model);
+  const inner = renderDiagramShapes(cells, computeBBox(cells));
+  assert.ok(inner.includes("<rect"), "unknown stencil -> rect");
+  assert.ok(inner.includes(">AWS<"), "keeps the label");
+});

packages/mcp/test/unit/drawio-xml.test.mjs

@@ -0,0 +1,360 @@
+// Unit tests for the drawio-xml module (issue #423): the linter (a positive
+// baseline + a negative case per rule, each asserting rule + cellId), the
+// decode chain (plain nested XML AND draw.io's compressed <diagram> via pako),
+// encode/round-trip byte-stability, hash stability, style parsing and the
+// bounding box.
+import { test } from "node:test";
+import assert from "node:assert/strict";
+import pako from "pako";
+import {
+  parseStyle,
+  lintModel,
+  prepareModel,
+  normalizeInput,
+  normalizeXml,
+  mxHash,
+  computeBBox,
+  parseCells,
+  decodeDrawioSvg,
+  decodeDrawioFileToModel,
+  buildDrawioSvg,
+  encodeDrawioFile,
+  countUserCells,
+  DrawioLintError,
+  inflateDiagramPayload,
+  MAX_INFLATED_DIAGRAM_BYTES,
+} from "../../build/lib/drawio-xml.js";
+
+// A well-formed model with one vertex and a valid edge to it.
+const VALID_MODEL =
+  '<mxGraphModel><root>' +
+  '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+  '<mxCell id="2" value="Hello" style="rounded=1;whiteSpace=wrap;html=1;" vertex="1" parent="1">' +
+  '<mxGeometry x="100" y="100" width="120" height="60" as="geometry"/></mxCell>' +
+  '<mxCell id="3" value="Two" style="ellipse;" vertex="1" parent="1">' +
+  '<mxGeometry x="300" y="100" width="80" height="80" as="geometry"/></mxCell>' +
+  '<mxCell id="4" edge="1" parent="1" source="2" target="3">' +
+  '<mxGeometry relative="1" as="geometry"/></mxCell>' +
+  '</root></mxGraphModel>';
+
+function issuesOf(fn) {
+  try {
+    fn();
+    return null;
+  } catch (e) {
+    assert.ok(e instanceof DrawioLintError, `expected DrawioLintError, got ${e}`);
+    return e.issues;
+  }
+}
+const hasRule = (issues, rule, cellId) =>
+  issues.some(
+    (i) => i.rule === rule && (cellId === undefined || i.cellId === cellId),
+  );
+
+// --- style parsing ---------------------------------------------------------
+
+test("parseStyle: base stylename + key=value pairs", () => {
+  const r = parseStyle("ellipse;fillColor=#ff0000;whiteSpace=wrap;");
+  assert.equal(r.baseStyle, "ellipse");
+  assert.equal(r.map.fillColor, "#ff0000");
+  assert.equal(r.map.whiteSpace, "wrap");
+  assert.equal(r.badSegment, undefined);
+});
+
+test("parseStyle: flags a segment with two '='", () => {
+  const r = parseStyle("a=b=c;");
+  assert.equal(r.badSegment, "a=b=c");
+});
+
+test("parseStyle: a second bare token is malformed", () => {
+  const r = parseStyle("rounded=1;bareword");
+  assert.equal(r.badSegment, "bareword");
+});
+
+// --- linter: positive baseline ---------------------------------------------
+
+test("lintModel: the canonical valid model passes", () => {
+  const { cells } = lintModel(VALID_MODEL);
+  assert.equal(cells.length, 5);
+});
+
+// --- linter: one negative case per rule ------------------------------------
+
+test("rule well-formed-xml: malformed XML", () => {
+  const issues = issuesOf(() => lintModel("<mxGraphModel><root><mxCell id=\"0\"></root>"));
+  assert.ok(hasRule(issues, "well-formed-xml"));
+  assert.ok(issues[0].position, "carries a line:col position");
+});
+
+test("rule structure: root is not mxGraphModel", () => {
+  const issues = issuesOf(() => lintModel("<foo><root/></foo>"));
+  assert.ok(hasRule(issues, "structure"));
+});
+
+test("rule sentinel-cells: missing id=0 / id=1", () => {
+  const m =
+    '<mxGraphModel><root>' +
+    '<mxCell id="2" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '</root></mxGraphModel>';
+  const issues = issuesOf(() => lintModel(m));
+  assert.ok(hasRule(issues, "sentinel-cells", "0"));
+  assert.ok(hasRule(issues, "sentinel-cells", "1"));
+});
+
+test("rule duplicate-id: two cells share an id", () => {
+  const m =
+    '<mxGraphModel><root>' +
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '<mxCell id="2" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '</root></mxGraphModel>';
+  const issues = issuesOf(() => lintModel(m));
+  assert.ok(hasRule(issues, "duplicate-id", "2"));
+});
+
+test("rule vertex-edge-exclusive: cell is both vertex and edge", () => {
+  const m =
+    '<mxGraphModel><root>' +
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" vertex="1" edge="1" parent="1"><mxGeometry as="geometry"/></mxCell>' +
+    '</root></mxGraphModel>';
+  const issues = issuesOf(() => lintModel(m));
+  assert.ok(hasRule(issues, "vertex-edge-exclusive", "2"));
+});
+
+test("rule edge-geometry: self-closed edge without child mxGeometry", () => {
+  const m =
+    '<mxGraphModel><root>' +
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '<mxCell id="3" vertex="1" parent="1"><mxGeometry x="30" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '<mxCell id="4" edge="1" parent="1" source="2" target="3"/>' +
+    '</root></mxGraphModel>';
+  const issues = issuesOf(() => lintModel(m));
+  assert.ok(hasRule(issues, "edge-geometry", "4"));
+});
+
+test("rule edge-endpoint: source/target does not resolve", () => {
+  const m =
+    '<mxGraphModel><root>' +
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '<mxCell id="4" edge="1" parent="1" source="2" target="99"><mxGeometry relative="1" as="geometry"/></mxCell>' +
+    '</root></mxGraphModel>';
+  const issues = issuesOf(() => lintModel(m));
+  assert.ok(hasRule(issues, "edge-endpoint", "4"));
+});
+
+test("rule parent-exists: parent points at a missing id", () => {
+  const m =
+    '<mxGraphModel><root>' +
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" vertex="1" parent="42"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '</root></mxGraphModel>';
+  const issues = issuesOf(() => lintModel(m));
+  assert.ok(hasRule(issues, "parent-exists", "2"));
+});
+
+test("rule no-comments: XML comment present", () => {
+  const m =
+    '<mxGraphModel><root>' +
+    '<!-- a comment --><mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '</root></mxGraphModel>';
+  const issues = issuesOf(() => lintModel(m));
+  assert.ok(hasRule(issues, "no-comments"));
+});
+
+test("rule style-format: malformed style segment (cellId reported)", () => {
+  const m =
+    '<mxGraphModel><root>' +
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" style="rounded=1;a=b=c;" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '</root></mxGraphModel>';
+  const issues = issuesOf(() => lintModel(m));
+  assert.ok(hasRule(issues, "style-format", "2"));
+});
+
+test("rule value-newline: literal newline in a value (cellId reported)", () => {
+  const m =
+    '<mxGraphModel><root>' +
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" value="line1\nline2" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '</root></mxGraphModel>';
+  const issues = issuesOf(() => lintModel(m));
+  assert.ok(hasRule(issues, "value-newline", "2"));
+});
+
+test("rule value-escaping: unescaped ampersand in a value (cellId reported)", () => {
+  const m =
+    '<mxGraphModel><root>' +
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" value="A & B" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '</root></mxGraphModel>';
+  const issues = issuesOf(() => lintModel(m));
+  assert.ok(hasRule(issues, "value-escaping", "2"));
+});
+
+test("rule reserved id: escaped entity value passes (no false positive)", () => {
+  const m =
+    '<mxGraphModel><root>' +
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" value="A &amp; B &lt;ok&gt;" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>' +
+    '</root></mxGraphModel>';
+  assert.doesNotThrow(() => lintModel(m));
+});
+
+// --- input normalization ---------------------------------------------------
+
+test("normalizeInput: a list of <mxCell> is wrapped and sentinels added", () => {
+  const frag =
+    '<mxCell id="2" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>';
+  const model = normalizeInput(frag);
+  assert.ok(model.startsWith("<mxGraphModel"));
+  assert.ok(model.includes('<mxCell id="0"/>'));
+  assert.ok(model.includes('<mxCell id="1" parent="0"/>'));
+  // And it lints clean.
+  assert.doesNotThrow(() => lintModel(model));
+});
+
+test("normalizeInput: an existing sentinel is not duplicated", () => {
+  const frag =
+    '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+    '<mxCell id="2" vertex="1" parent="1"><mxGeometry x="0" y="0" width="10" height="10" as="geometry"/></mxCell>';
+  const model = normalizeInput(frag);
+  const count0 = (model.match(/id="0"/g) || []).length;
+  assert.equal(count0, 1);
+});
+
+test("prepareModel: returns bbox, cellCount, hash and lints", () => {
+  const p = prepareModel(VALID_MODEL);
+  assert.equal(p.cellCount, 3); // 2, 3, 4 (sentinels excluded)
+  assert.ok(p.bbox.width > 0 && p.bbox.height > 0);
+  assert.equal(p.hash, mxHash(normalizeXml(VALID_MODEL)));
+});
+
+// --- decode chain: plain -----------------------------------------------------
+
+test("decode chain (plain): buildDrawioSvg -> decodeDrawioSvg round-trips byte-stable", () => {
+  const model = normalizeXml(VALID_MODEL);
+  const svg = buildDrawioSvg(model, "<g/>", { width: 400, height: 200 });
+  const decoded = decodeDrawioSvg(svg);
+  assert.equal(decoded, model);
+});
+
+test("decode chain: entity-encoded content= (draw.io export style) is read directly", () => {
+  const model = normalizeXml(VALID_MODEL);
+  const file = encodeDrawioFile(model, "Page-1");
+  const escaped = file
+    .replace(/&/g, "&amp;")
+    .replace(/</g, "&lt;")
+    .replace(/>/g, "&gt;")
+    .replace(/"/g, "&quot;");
+  const svg = `<svg xmlns="http://www.w3.org/2000/svg" content="${escaped}"></svg>`;
+  const decoded = decodeDrawioSvg(svg);
+  assert.equal(decoded, model);
+});
+
+// --- decode chain: compressed (pako) ---------------------------------------
+
+test("decode chain (compressed pako): human-saved <diagram> payload decodes losslessly", () => {
+  const model = normalizeXml(VALID_MODEL);
+  // Reproduce draw.io's compression: encodeURIComponent -> raw deflate -> base64.
+  const compressed = Buffer.from(
+    pako.deflateRaw(encodeURIComponent(model)),
+  ).toString("base64");
+  const file = `<mxfile host="Electron"><diagram id="abc" name="Page-1">${compressed}</diagram></mxfile>`;
+  // Docmost stores the file base64 in content=.
+  const contentB64 = Buffer.from(file, "utf-8").toString("base64");
+  const svg = `<svg xmlns="http://www.w3.org/2000/svg" content="${contentB64}"><image href="x"/></svg>`;
+  const decoded = decodeDrawioSvg(svg);
+  assert.equal(decoded, model);
+});
+
+test("decodeDrawioFileToModel: bare mxGraphModel file returns the model substring", () => {
+  const model = normalizeXml(VALID_MODEL);
+  assert.equal(decodeDrawioFileToModel(model), model);
+});
+
+// --- hash stability --------------------------------------------------------
+
+test("mxHash: stable across inter-tag whitespace, sensitive to content", () => {
+  const a = VALID_MODEL;
+  const b = VALID_MODEL.replace(/></g, ">\n  <"); // reformat only
+  assert.equal(mxHash(a), mxHash(b));
+  const c = VALID_MODEL.replace('value="Hello"', 'value="Changed"');
+  assert.notEqual(mxHash(a), mxHash(c));
+});
+
+// --- bounding box + cell count ---------------------------------------------
+
+test("computeBBox + countUserCells", () => {
+  const cells = parseCells(VALID_MODEL);
+  const bbox = computeBBox(cells);
+  // Vertex 3 spans to x=380,y=180; plus the 20px margin.
+  assert.equal(bbox.width, 400);
+  assert.equal(bbox.height, 200);
+  assert.equal(countUserCells(VALID_MODEL), 3);
+});
+
+// --- decompression-bomb guard (Fix 3) --------------------------------------
+
+test("inflateDiagramPayload: a small legitimate payload inflates fine", () => {
+  const xml = normalizeXml(VALID_MODEL);
+  const base64 = Buffer.from(
+    pako.deflateRaw(encodeURIComponent(xml)),
+  ).toString("base64");
+  assert.equal(inflateDiagramPayload(base64), xml);
+});
+
+test("inflateDiagramPayload: rejects an over-cap decompression bomb", () => {
+  // A tiny compressed payload that inflates to just over the cap. Highly
+  // compressible (all one byte) -> the base64 is small, but the inflated output
+  // exceeds MAX_INFLATED_DIAGRAM_BYTES and must be refused before it is fully
+  // materialised.
+  const bombSize = MAX_INFLATED_DIAGRAM_BYTES + 1024;
+  const base64 = Buffer.from(
+    pako.deflateRaw(Buffer.alloc(bombSize, 0x41 /* 'A' */)),
+  ).toString("base64");
+  assert.ok(
+    base64.length < 1024 * 1024,
+    "the compressed bomb is tiny relative to its inflated size",
+  );
+  assert.throws(
+    () => inflateDiagramPayload(base64),
+    /decompression bomb/,
+  );
+});
+
+test("encode/build: a title with < > \" & round-trips without corrupting the SVG", async () => {
+  // A user-supplied title full of XML metacharacters must be escaped so the
+  // inner <mxfile> stays well-formed and the outer content="..." attribute is
+  // never broken out of. Prove it survives the encode -> build -> decode chain.
+  const title = 'A < B > C " D & E';
+  const model = normalizeXml(VALID_MODEL);
+  const svg = buildDrawioSvg(model, "<g/>", { width: 200, height: 120 }, title);
+
+  // The outer content="..." attribute must not be broken by the title: the raw
+  // title metacharacters never appear literally in the SVG markup (they are
+  // base64-encoded inside content=, and escaped inside the file XML).
+  const contentMatch = /content="([^"]*)"/.exec(svg);
+  assert.ok(contentMatch, "SVG has a single well-formed content= attribute");
+
+  // The diagram model still decodes losslessly despite the exotic title.
+  assert.equal(decodeDrawioSvg(svg), model);
+
+  // The file XML is well-formed: the title lives in name="..." as escaped
+  // entities, so unescaping recovers the original title byte-for-byte.
+  const fileXml = Buffer.from(contentMatch[1], "base64").toString("utf-8");
+  const nameMatch = /<diagram id="[^"]*" name="([^"]*)">/.exec(fileXml);
+  assert.ok(nameMatch, "the diagram name attribute is intact and quote-safe");
+  const decodedTitle = nameMatch[1]
+    .replace(/&lt;/g, "<")
+    .replace(/&gt;/g, ">")
+    .replace(/&quot;/g, '"')
+    .replace(/&amp;/g, "&");
+  assert.equal(decodedTitle, title);
+
+  // encodeDrawioFile alone produces the same escaped, well-formed envelope.
+  const file = encodeDrawioFile(model, title);
+  assert.match(file, /name="A &lt; B &gt; C &quot; D &amp; E">/);
+});

packages/mcp/test/unit/json-edit-refuse.test.mjs

@@ -140,6 +140,36 @@ test("typo fix wrapped in markdown still applies (not refused)", () => {
   assert.deepEqual(node.marks, [{ type: "bold" }]);
 });
 
+// ---------------------------------------------------------------------------
+// (iv) #410 footnote token: a `replace` containing `^[...]` is refused into
+// failed[] (it would be written as a LITERAL string, never a real footnote).
+// Nothing is applied; the reason points at insert_footnote.
+// ---------------------------------------------------------------------------
+test("replace containing a `^[...]` footnote token is refused, not applied", () => {
+  const input = doc(paragraph(textNode("The claim stands.")));
+  const snapshot = JSON.parse(JSON.stringify(input));
+
+  const { doc: out, results, failed } = applyTextEdits(input, [
+    { find: "The claim stands.", replace: "The claim stands.^[See source, p.42]" },
+  ]);
+
+  assert.equal(results.length, 0, "nothing applied");
+  assert.equal(failed.length, 1, "one refused edit");
+  assert.equal(failed[0].find, "The claim stands.");
+  assert.match(failed[0].reason, /insert_footnote/);
+  // The document is byte-for-byte untouched — no literal `^[` was written.
+  assert.deepEqual(out, snapshot);
+});
+
+test("a plain replace with no footnote token still applies (no false positive)", () => {
+  const input = doc(paragraph(textNode("a caret ^ and a bracket ] apart")));
+  const { results, failed } = applyTextEdits(input, [
+    { find: "apart", replace: "separate" },
+  ]);
+  assert.equal(failed.length, 0, "not refused");
+  assert.equal(results.length, 1, "applied");
+});
+
 // ---------------------------------------------------------------------------
 // A plain text fix is unaffected by the refuse logic.
 // ---------------------------------------------------------------------------

packages/mcp/test/unit/tool-timing.test.mjs

@@ -0,0 +1,67 @@
+import { test } from "node:test";
+import assert from "node:assert/strict";
+
+import { timeToolHandler } from "../../build/index.js";
+
+// #402 — the registerTool wrapper times every tool through a single choke point
+// and feeds the host's dependency-neutral onMetric sink. These assert the
+// timing contract without a live transport (the factory monkeypatches
+// server.registerTool with exactly this helper).
+
+test("times a tool and preserves the handler's return value", async () => {
+  const calls = [];
+  const onMetric = (name, value, labels) => calls.push({ name, value, labels });
+
+  const handler = async (arg) => ({ ok: true, echo: arg });
+  const wrapped = timeToolHandler("get_page", handler, onMetric);
+
+  const result = await wrapped("hello");
+  // Return value passes through untouched.
+  assert.deepEqual(result, { ok: true, echo: "hello" });
+
+  // Exactly one sample, correct name/labels, numeric non-negative duration.
+  assert.equal(calls.length, 1);
+  assert.equal(calls[0].name, "mcp_tool_duration_seconds");
+  assert.deepEqual(calls[0].labels, { tool: "get_page" });
+  assert.equal(typeof calls[0].value, "number");
+  assert.ok(calls[0].value >= 0, "duration must be non-negative seconds");
+});
+
+test("standalone (no onMetric) is a transparent pass-through", async () => {
+  const handler = async (a, b) => a + b;
+  const wrapped = timeToolHandler("noop_tool", handler, undefined);
+
+  // No throw, result unchanged, and nothing to observe.
+  const result = await wrapped(2, 3);
+  assert.equal(result, 5);
+});
+
+test("still observes on throw, then rethrows the original error", async () => {
+  const calls = [];
+  const onMetric = (name, value, labels) => calls.push({ name, value, labels });
+
+  const boom = new Error("handler failed");
+  const handler = async () => {
+    throw boom;
+  };
+  const wrapped = timeToolHandler("boom_tool", handler, onMetric);
+
+  await assert.rejects(() => wrapped(), (err) => err === boom);
+
+  // Observed exactly once despite the throw.
+  assert.equal(calls.length, 1);
+  assert.equal(calls[0].name, "mcp_tool_duration_seconds");
+  assert.deepEqual(calls[0].labels, { tool: "boom_tool" });
+});
+
+test("standalone still rethrows the original error (no swallow, no observe)", async () => {
+  const boom = new Error("standalone failure");
+  const wrapped = timeToolHandler(
+    "boom_standalone",
+    async () => {
+      throw boom;
+    },
+    undefined,
+  );
+  await assert.rejects(() => wrapped(), (err) => err === boom);
+});

patches/@hocuspocus__server@3.4.4.patch

@@ -0,0 +1,62 @@
+diff --git a/dist/hocuspocus-server.cjs b/dist/hocuspocus-server.cjs
+index b24ff6d091c32f733089eeaa47b03f7b37cf5964..f003af304fc751b7edc1aee17f3651282d70666a 100644
+--- a/dist/hocuspocus-server.cjs
++++ b/dist/hocuspocus-server.cjs
+@@ -2426,6 +2426,26 @@ class Hocuspocus {
+      * Create a new document by the given request
+      */
+     async createDocument(documentName, request, socketId, connection, context) {
++        // PATCH(gitmost #401): close the connect-vs-unload race. When the last
++        // client disconnects, storeDocumentHooks' finally schedules an unload;
++        // unloadDocument runs its beforeUnloadDocument hooks asynchronously and
++        // records an in-flight promise in `unloadingDocuments`. A NEW connection
++        // arriving in that window would otherwise fall straight through to the
++        // `documents`/`loadingDocuments` checks and could either reuse a doc that
++        // is about to be destroyed, or start loading a fresh doc concurrently
++        // with the destroy. Awaiting the in-flight unload first makes the decision
++        // deterministic: once it settles, either the doc was fully unloaded
++        // (removed from `documents`, so we do a clean fresh load below) or the
++        // unload aborted because work/connections reappeared (the healthy doc is
++        // still in `documents`, so we reuse it). Either way the new connection can
++        // never hand-shake onto an orphaned, about-to-be-destroyed Document.
++        const existingUnloadingDoc = this.unloadingDocuments.get(documentName);
++        if (existingUnloadingDoc) {
++            // Wait for the in-flight unload to settle so we never hand-shake onto a dying
++            // Document. Swallow a rejected unload — fall through to a fresh load, matching
++            // pre-patch behavior (the doc is already removed from `documents` by then).
++            try { await existingUnloadingDoc; } catch { /* unload rejected — fresh load */ }
++        }
+         const existingLoadingDoc = this.loadingDocuments.get(documentName);
+         if (existingLoadingDoc) {
+             return existingLoadingDoc;
+diff --git a/dist/hocuspocus-server.esm.js b/dist/hocuspocus-server.esm.js
+index 1f4dd80244e899128e2c4e5dad8eab7cfc1cbad6..8c2411747bba27fb9486e1df81678a14e41e884e 100644
+--- a/dist/hocuspocus-server.esm.js
++++ b/dist/hocuspocus-server.esm.js
+@@ -2406,6 +2406,26 @@ class Hocuspocus {
+      * Create a new document by the given request
+      */
+     async createDocument(documentName, request, socketId, connection, context) {
++        // PATCH(gitmost #401): close the connect-vs-unload race. When the last
++        // client disconnects, storeDocumentHooks' finally schedules an unload;
++        // unloadDocument runs its beforeUnloadDocument hooks asynchronously and
++        // records an in-flight promise in `unloadingDocuments`. A NEW connection
++        // arriving in that window would otherwise fall straight through to the
++        // `documents`/`loadingDocuments` checks and could either reuse a doc that
++        // is about to be destroyed, or start loading a fresh doc concurrently
++        // with the destroy. Awaiting the in-flight unload first makes the decision
++        // deterministic: once it settles, either the doc was fully unloaded
++        // (removed from `documents`, so we do a clean fresh load below) or the
++        // unload aborted because work/connections reappeared (the healthy doc is
++        // still in `documents`, so we reuse it). Either way the new connection can
++        // never hand-shake onto an orphaned, about-to-be-destroyed Document.
++        const existingUnloadingDoc = this.unloadingDocuments.get(documentName);
++        if (existingUnloadingDoc) {
++            // Wait for the in-flight unload to settle so we never hand-shake onto a dying
++            // Document. Swallow a rejected unload — fall through to a fresh load, matching
++            // pre-patch behavior (the doc is already removed from `documents` by then).
++            try { await existingUnloadingDoc; } catch { /* unload rejected — fresh load */ }
++        }
+         const existingLoadingDoc = this.loadingDocuments.get(documentName);
+         if (existingLoadingDoc) {
+             return existingLoadingDoc;

pnpm-lock.yaml

@@ -44,6 +44,9 @@ overrides:
   ip-address: 10.1.1
 
 patchedDependencies:
+  '@hocuspocus/server@3.4.4':
+    hash: d8dc66e5ec3b9d23a876b979f493b6aa901fd2d965be54729495da5136296a42
+    path: patches/@hocuspocus__server@3.4.4.patch
   ai@6.0.134:
     hash: f60bfc3357e01e1f3978c6c40fdd65aeb33fefaad7179cde8676465b6c5ff4d9
     path: patches/ai@6.0.134.patch
@@ -75,7 +78,7 @@ importers:
         version: 3.4.4(y-protocols@1.0.6(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810)))(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810))
       '@hocuspocus/server':
         specifier: 3.4.4
-        version: 3.4.4(y-protocols@1.0.6(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810)))(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810))
+        version: 3.4.4(patch_hash=d8dc66e5ec3b9d23a876b979f493b6aa901fd2d965be54729495da5136296a42)(y-protocols@1.0.6(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810)))(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810))
       '@hocuspocus/transformer':
         specifier: 3.4.4
         version: 3.4.4(@tiptap/core@3.20.4(@tiptap/pm@3.20.4))(@tiptap/pm@3.20.4)(y-prosemirror@1.3.7(prosemirror-model@1.25.1)(prosemirror-state@1.4.3)(prosemirror-view@1.40.0)(y-protocols@1.0.6(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810)))(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810)))(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810))
@@ -1041,6 +1044,9 @@ importers:
       marked:
         specifier: ^17.0.1
         version: 17.0.5
+      pako:
+        specifier: ^2.0.3
+        version: 2.0.3
       re2:
         specifier: ^1.21.0
         version: 1.25.0
@@ -13055,7 +13061,7 @@ snapshots:
       - bufferutil
       - utf-8-validate
 
-  '@hocuspocus/server@3.4.4(y-protocols@1.0.6(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810)))(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810))':
+  '@hocuspocus/server@3.4.4(patch_hash=d8dc66e5ec3b9d23a876b979f493b6aa901fd2d965be54729495da5136296a42)(y-protocols@1.0.6(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810)))(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810))':
     dependencies:
       '@hocuspocus/common': 3.4.4
       async-lock: 1.4.1