fix(ai-chat): ревью-раунд #500 — красный серверный сьют + регрессия Redis-health

B1: переименование строки ошибки (#394) не обновило 4 предсуществующих
share-ассерта → полный серверный сьют был красный. Обновлены ассерты в
public-share-chat.spec.ts и public-share-chat-tools.service.spec.ts под
новую классифицированную строку.

B2: /health первая проба после старта врала DOWN при живом Redis
(lazyConnect + enableOfflineQueue:false + maxRetriesPerRequest:1 → первый
ping до открытия сокета). Добавлен ensureConnected() с bounded-таймаутом
перед первым ping; покрывает и путь пересоздания после onModuleDestroy.
Тест UP-с-первой-пробы против реального ioredis (mutation-verified).

Устранён open-handle leak в redis.health.spec (drain ioredis
force-destroy-таймера в teardown; без forceExit) и окно ложного DOWN при
конкурентных пробах (мемоизированный connectingPromise).

B3: комментарий про orphan-чат при провале beginRun (insert до begin).
B4: описание listPages упоминает поле truncated в tree-режиме.

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

.env.example

@@ -124,6 +124,40 @@ MCP_DOCMOST_PASSWORD=
 # MCP_TOKEN=
 # MCP_SESSION_IDLE_MS=1800000
 #
+# --- MCP collaboration write path: concurrency + rights-staleness (#449) ------
+# MCP content writes (update_page, insert/replace nodes, comments-in-body, etc.)
+# go over the collaboration websocket and are serialized PER PAGE by an
+# in-process mutex (a module-level Map, one promise-chain per page UUID). This
+# guarantees no two MCP writes on the SAME page overlap and clobber each other.
+#
+# DEPLOY REQUIREMENT — SINGLE INSTANCE or STICKY SESSIONS. The mutex is
+# process-local. Behind a multi-replica load balancer WITHOUT sticky sessions,
+# two replicas can each "hold" the lock for the same page at the same time and
+# serialization is silently lost (concurrent full-document writes race on the
+# live Yjs fragment). Run the MCP/app as a SINGLE instance, OR pin a page's
+# traffic to one replica (sticky sessions / consistent hashing on page id). The
+# same constraint applies to the RAM-only stash_page blob store above. There is
+# deliberately no cross-process (e.g. Postgres advisory) lock yet — this is a
+# CONSCIOUS documented constraint, not an oversight (#449).
+#
+# To reduce connect-storms the write path caches ONE live collab session per
+# (wsUrl, page, token). Tunables (all optional; defaults are safe):
+# MCP_COLLAB_SESSION_IDLE_MS=60000     # idle TTL, reset per op; 0 disables cache
+# MCP_COLLAB_SESSION_MAX_ENTRIES=32    # LRU cap on cached sessions
+# MCP_COLLAB_TOKEN_TTL_MS=300000       # per-client collab-token cache (5 min)
+#
+# RIGHTS-STALENESS TRADE-OFF. A cached collab session writes under the token
+# captured at CONNECT time, and the collab-token cache reuses a token for its TTL.
+# So if a user's access to a page is REVOKED, MCP writes on an already-open
+# session may keep succeeding until the session ages out. MCP_COLLAB_SESSION_MAX_AGE_MS
+# is the HARD lifetime (checked at each acquire) that BOUNDS this window: after it,
+# the session is torn down and the next write re-auths with a fresh token, picking
+# up the revocation. Default 10 min. LOWER it to shorten the revocation lag at the
+# cost of more reconnects; RAISE it to reduce reconnects at the cost of a longer
+# stale-rights window. There is intentionally no push-based cache invalidation on
+# a rights change — this bounded window is the accepted trade-off (#449).
+# MCP_COLLAB_SESSION_MAX_AGE_MS=600000
+#
 # BLOB SANDBOX (stash_page). An in-RAM, process-local store that hands large page
 # content + images to an external consumer WITHOUT bloating the model context or
 # requiring Docmost auth. The stash_page tool serializes a page, mirrors its
@@ -301,6 +335,20 @@ MCP_DOCMOST_PASSWORD=
 #    VictoriaMetrics/Prometheus reaching it as <host>:<port>/metrics.
 # METRICS_PORT=9464
 #
+#    METRICS_BIND — interface the /metrics listener binds to. DEFAULT 127.0.0.1
+#    (loopback only), so the unauthenticated endpoint is NOT exposed on all
+#    interfaces. If the scraper runs in a SEPARATE container and reaches this as
+#    docmost:9464, set METRICS_BIND=0.0.0.0 — but then also set METRICS_TOKEN
+#    and/or keep the port on a private network, since /metrics is otherwise open.
+# METRICS_BIND=127.0.0.1
+#
+#    METRICS_TOKEN — optional Bearer token guarding /metrics. When set, every
+#    scrape MUST send `Authorization: Bearer <token>` (others get 401). Configure
+#    the scraper with the same bearer token (e.g. VictoriaMetrics/vmagent
+#    `bearer_token`, Prometheus `authorization.credentials`). Leave unset only
+#    when the endpoint is bound to loopback or an otherwise-trusted network.
+# METRICS_TOKEN=
+#
 # 2) CLIENT_TELEMETRY_ENABLED — the public client perf-telemetry sink.
 #    OFF by default. When true, the unauthenticated POST /api/telemetry/vitals
 #    endpoint is registered and browsers collect + send web-vitals / editor

.github/workflows/develop.yml

@@ -157,6 +157,12 @@ jobs:
       - name: Build prosemirror-markdown
         run: pnpm --filter @docmost/prosemirror-markdown build
 
+      # docmost-client.loader.ts type-imports from @docmost/mcp (issue #446); its
+      # build/ is gitignored and `test:e2e` type-checks, so build it here or tsc
+      # fails with TS2307 (mirrors the e2e-mcp / mcp-server-parity jobs).
+      - name: Build mcp
+        run: pnpm --filter @docmost/mcp build
+
       - name: Run migrations
         run: pnpm --filter ./apps/server migration:latest
 

.github/workflows/test.yml

@@ -1,5 +1,13 @@
 name: Test
 
+# NO `paths:` filter on purpose (issue #447). The tool-spec REGISTRY is split
+# across two packages that MUST stay in sync: the specs live in `packages/mcp`
+# but the parity/tier guard tests that read them live in the `apps/server` jest
+# suite. A PR touching only `packages/mcp/**` must therefore still run the SERVER
+# suite (and vice-versa), or an in-app wiring break slips through green and only
+# surfaces on develop after merge. The `test` job below runs BOTH suites via
+# `pnpm -r test` on every PR; the dedicated `mcp-server-parity` job makes that
+# cross-package gate explicit and fast. Do not add a `paths:` filter here.
 on:
   pull_request:
   workflow_call:
@@ -132,3 +140,53 @@ jobs:
       # isolated `docmost_test` DB and migrates it to latest.
       - name: Run server integration tests
         run: pnpm --filter server test:int
+
+  # Cross-package tool-spec parity gate (issue #447). The tool-spec registry lives
+  # in `packages/mcp` but its parity/tier guard tests live in the `apps/server`
+  # jest suite, so a PR touching ONLY one of the two packages must still run BOTH
+  # sides — otherwise an in-app wiring break (e.g. PR #434 drawio) passes the mcp
+  # suite green and only surfaces on develop after merge. The `test` job already
+  # runs everything via `pnpm -r test`; this job is a fast, explicitly-named guard
+  # that runs the mcp `node --test` suite AND the server tool-guard jest specs
+  # together, so the coupling is visible and can never be accidentally split by a
+  # path filter. No Postgres/Redis needed: these specs mock the DB/loader.
+  mcp-server-parity:
+    runs-on: ubuntu-latest
+    timeout-minutes: 15
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v4
+
+      - name: Set up pnpm
+        uses: pnpm/action-setup@v4
+
+      - name: Set up Node
+        uses: actions/setup-node@v4
+        with:
+          node-version: 22
+          cache: pnpm
+
+      - name: Install dependencies
+        run: pnpm install --frozen-lockfile
+
+      # Shared deps first (build/ dirs are gitignored; see test.yml build order).
+      - name: Build editor-ext
+        run: pnpm --filter @docmost/editor-ext build
+
+      - name: Build prosemirror-markdown
+        run: pnpm --filter @docmost/prosemirror-markdown build
+
+      # Build the mcp package so build/ carries a FRESH REGISTRY_STAMP (#447): the
+      # build runs gen-registry-stamp.mjs before tsc, so a build/ vs src/ skew
+      # cannot slip into the tests that exercise the loader's stale-check.
+      - name: Build mcp (regenerates REGISTRY_STAMP)
+        run: pnpm --filter @docmost/mcp build
+
+      # mcp side: the standalone MCP server's own tool-spec / instructions guards.
+      - name: Run mcp tool-spec suite
+        run: pnpm --filter @docmost/mcp test
+
+      # server side: the parity + tier guards that read packages/mcp/src/tool-specs
+      # and assert the in-app AI-chat wiring matches it.
+      - name: Run server tool-spec guard specs
+        run: pnpm --filter server exec jest shared-tool-specs.contract tool-tiers ai-chat-tools.service --runInBand

.gitignore

@@ -2,6 +2,11 @@
 .env.dev
 .env.prod
 data
+# Exception: the committed draw.io shape catalog (issue #424) lives in a `data/`
+# dir, but the bare `data` ignore above is meant for runtime state, not this
+# bundled build asset. Re-include the directory and its contents.
+!packages/mcp/data/
+!packages/mcp/data/**
 # compiled output
 /dist
 node_modules
@@ -19,6 +24,11 @@ packages/prosemirror-markdown/build/
 # markdown convention; the package is private and rebuilt at deploy.
 packages/mcp/build/
 
+# mcp REGISTRY_STAMP codegen output (issue #447). Regenerated into src/ by
+# scripts/gen-registry-stamp.mjs on every `build`/`pretest` (before tsc), so it
+# is a build artifact like build/ — never committed, always fresh.
+packages/mcp/src/registry-stamp.generated.ts
+
 # Logs
 logs
 *.log

AGENTS.md

@@ -5,6 +5,139 @@ repository. It has two layers: **how to run a task end-to-end** (the
 sections below), and **how the codebase is built** (the technical sections
 further down, formerly in `CLAUDE.md`).
 
+## ARCHITECTURAL INVARIANTS — NON-NEGOTIABLE
+
+THE TEN RULES BELOW ARE HARD CONSTRAINTS. Each one was paid for with a real
+production incident or a multi-PR bug chain in THIS repository (cited inline).
+They override convenience, deadlines and "it's just a small feature". A PR that
+violates any of them MUST be rejected in review regardless of how good the rest
+of it is. If a task genuinely seems to require breaking one — STOP and raise it
+with the owner; do not code around it.
+
+### 1. EVERY BUFFER, CACHE, HISTORY AND PAYLOAD HAS AN EXPLICIT SIZE BUDGET
+
+Nothing accumulates unboundedly. A row/item cap is NOT a byte cap. Anything
+replayed to a model, buffered in memory, persisted per step, or refetched by a
+poll must state its budget in bytes/tokens and enforce it. Rewriting a growing
+structure in full on every increment is FORBIDDEN — append or diff instead;
+O(n²) write/serialize patterns do not pass review.
+(Paid for by: full-row rewrite on every agent step — hundreds of MB of Postgres
+writes per 50-step run, with every tool output serialized twice; unbounded
+history replay killing long chats on the provider context window; 32 MB replay
+buffers per active run.)
+
+### 2. EVERYTHING LONG-RUNNING TERMINATES BY CONSTRUCTION
+
+Every run / row / session / lease / subscriber / queue entry must define AT
+DESIGN TIME: its owner; every terminal state; who writes the terminal state on
+EVERY path (success, error, abort, disconnect in each phase, process restart);
+retries for the terminal write; and a periodic sweeper that does not depend on
+a reboot. A best-effort terminal write with no retry and no sweep is FORBIDDEN.
+(Paid for by: assistant rows stuck 'streaming' forever; runs stuck 'running'
+409-locking their chat until a restart — the #183/#184 follow-up chain.)
+
+### 3. EVERY AWAIT IS CANCELLABLE AND DEADLINED; NEVER BLOCK THE EVENT LOOP
+
+Every async step inside a request or agent turn honors the turn's AbortSignal
+AND a wall-clock deadline — including in-app tools, lock queues and pagination
+loops, not just external calls. Synchronous CPU work beyond ~50 ms goes to a
+worker_thread. Promise.race DOES NOT cancel synchronous work — using it as a
+"timeout" for sync computation is forbidden (the timer only fires after the
+event loop is free again, i.e. after the damage is done).
+(Paid for by: in-app tools ignoring abortSignal and writing pages AFTER Stop;
+the synchronous ELK layout freezing every SSE stream in the process; the
+step-0 MCP handshake hang — #397.)
+
+### 4. ONE SOURCE OF TRUTH; EVERYTHING ELSE IS A REBUILDABLE CACHE
+
+Postgres is the authoritative state. Every in-memory structure (registries,
+caches, client stores) must be reconstructible from the DB and treated as
+lossy. The client renders SERVER-DECLARED state — "a run is active" is a server
+fact delivered as data, never inferred from side signals (204 vs 2xx, the
+flavor of a disconnect). A new feature must name the owner of each piece of
+state before implementation starts.
+(Paid for by: the strip/restore resume machinery, silently frozen UIs and
+ghost sends after unmount — the #381→#432→#456 chain.)
+
+### 5. STATE MACHINES ARE EXPLICIT — ONE-SHOT FLAGS ARE FORBIDDEN
+
+A complex lifecycle (chat thread, resume/reconnect, run) lives in a named-state
+automaton (reducer / enum) where every state has an owner and a rendered
+representation — including the failure states. Adding a boolean ref that one
+callback arms and another reads-and-clears is FORBIDDEN in the AI-chat client.
+New behavior = a new named state + explicit transitions, and the interruption
+matrix (disconnect in each phase × restart × stop × supersede) is enumerated at
+design time, not discovered one incident at a time.
+(Paid for by: 26 one-shot useRef flags in chat-thread.tsx and the drip of
+"one more missing transition" across #381→#386/#389→#432→#456.)
+
+### 6. NO NEW MODE FORKS; A FLAG IS FOR ROLLOUT, THEN IT DIES
+
+A behavior flag that forks a code path must ship with a written sunset
+condition; stacking a new flag onto the existing matrix without deleting or
+scheduling an old one is forbidden. While a temporary fork exists, BOTH sides
+must share identical lifecycle handling (abort semantics, error listeners,
+concurrency gates) — asymmetric forks are outlawed.
+(Paid for by: legacy vs autonomous divergence — the one-active-run gate and
+the socket 'error' listener each existing on only ONE side; 2^4 flag
+combinations each with different abort semantics.)
+
+### 7. NO HAND-SYNCED MIRRORS — CODEGEN OR A CI PARITY TEST, NOTHING LESS
+
+Two copies of the same knowledge (schema, tool registry, glyph map, probe
+body, hash/normalize algorithm, label list) require either generation from a
+single source or a CI test that FAILS on drift. A "mirror this change over
+there" comment is NOT a guard and does not pass review.
+(Paid for by: #293 — three drifting converter copies losing data; #447 —
+REGISTRY_STAMP covering only one of the mirrored files; ~10 still-unguarded
+mirrors across the MCP layer.)
+
+### 8. CACHES, HEADERS, BUFFERS AND FSM TRANSITIONS GET AN INTEGRATION TEST OF THE OBSERVABLE PROPERTY
+
+A unit test of a pure helper DOES NOT COUNT for these. Test the real header on
+the real HTTP response, the real cache hit under real token sources, the real
+transition under a really-killed socket. If the observable property cannot be
+tested, the design is wrong — fix the design, not the test.
+(Paid for by: #431→#439 — a cache keyed on a fresh-per-call JWT, so it NEVER
+hit and became prod incident #435 while its unit tests stayed green; and by
+the #352→#455 immutable-cache header silently overwritten by a framework
+default AFTER the unit-tested code ran.)
+
+### 9. CLIENT INPUT IS HOSTILE UNTIL VALIDATED — ALSO BEFORE PERSISTENCE
+
+Anything from the browser (message parts, ids, titles, selections, flags) is
+validated/sanitized BEFORE it is persisted into a row that will later be
+replayed into a prompt, a converter or another subsystem. A poisoned row must
+never be able to permanently brick a chat or a page on every subsequent read.
+(Paid for by: unvalidated UIMessage parts persisted verbatim — one bad row
+500s the chat on every later turn; #159 client-spoofed page titles; #388
+selection re-sanitized server-side for the same reason.)
+
+### 10. FAILURES ARE LOUD AND SPECIFIC; SILENT DEGRADATION IS FORBIDDEN
+
+Extends the error convention below: a fire-and-forget write is allowed ONLY
+with a metric or a greppable ERROR log; a degraded mode (dead cached MCP
+client, stopped poll, exhausted retries, evicted buffer) must be VISIBLE to
+the user or the operator. A feature that can quietly stop working — a frozen
+"streaming…" UI, a poll that silently gives up, a cache serving corpses — does
+not pass review.
+(Paid for by: the degraded poll's silent 10-minute death leaving a forever-
+"streaming" answer; dead MCP clients served from cache while every external
+tool call failed; #435 being caught in minutes ONLY because metrics — #403 —
+existed.)
+
+## Default skill for feature design
+
+For any feature-design request — the user hands over a raw feature idea, asks
+to design or think through a feature, or to draft an issue («спроектируй»,
+«продумай фичу», «составь ишью», "design X", "write an issue for X") — invoke
+the `orchestrator-feature-designer` skill (Skill tool) BEFORE any other work.
+It is the default operating mode for design work in this repository: research
+→ design checklist (R1–R10) → forks resolved with the human → adversarial
+self-attack → filed PR-sized issues. Do not design features or write issues
+ad-hoc while this skill is available. This does not apply to non-design work
+(bug fixes, reviews, retrospectives, refactors already specified by an issue).
+
 ## Task lifecycle
 
 ### 1. Start: sync with develop
@@ -201,7 +334,7 @@ pnpm workspace (`pnpm@10.4.0`) orchestrated by **Nx**. Four workspace packages:
 | `apps/client` | `client` | React 18 + Vite + Mantine 8 + TanStack Query + Jotai | SPA frontend |
 | `packages/editor-ext` | `@docmost/editor-ext` | Tiptap/ProseMirror | Shared Tiptap node/mark extensions, imported by both the client and the server |
 | `packages/mcp` | `@docmost/mcp` | MCP SDK, Tiptap, Yjs | Standalone MCP server, also bundled into the server at `/mcp`. Consumes the shared converter/schema from `@docmost/prosemirror-markdown` (#293) — it no longer carries its own vendored converter/schema copy |
-| `packages/prosemirror-markdown` | `@docmost/prosemirror-markdown` | Tiptap, marked, jsdom | The single, canonical ProseMirror↔Markdown converter + Docmost schema mirror (#293). Consumed by `mcp`, `git-sync`, AND `apps/server` (server-side markdown import/export, #345); there is exactly ONE copy of the converter now |
+| `packages/prosemirror-markdown` | `@docmost/prosemirror-markdown` | Tiptap, marked; jsdom (Node only) | The single, canonical ProseMirror↔Markdown converter + Docmost schema mirror (#293). Consumed by `mcp`, `git-sync`, `apps/server` (server-side markdown import/export, #345), AND `apps/client` (markdown paste/copy + AI-chat render, via the `browser` entry — native `DOMParser`, no jsdom in the client bundle, #347); there is exactly ONE copy of the converter now |
 
 `build` targets are Nx-cached and dependency-ordered (`dependsOn: ["^build"]`), so `editor-ext` builds before the apps. `nx.json` sets `affected.defaultBase: main`.
 
@@ -248,6 +381,22 @@ pnpm collab:dev              # run the collaboration server process standalone (
 > that order). Reach for it whenever you run a consumer package's checks on their
 > own rather than through the full `pnpm build`.
 
+> **Editing an MCP tool spec requires a rebuild (issue #447).** The running
+> server loads the **compiled** `packages/mcp/build/` of `@docmost/mcp` (via the
+> runtime loader in `apps/server/src/core/ai-chat/tools/docmost-client.loader.ts`),
+> but the parity/tier guard tests read `packages/mcp/src/tool-specs.ts`. So if you
+> edit `tool-specs.ts` (any tool name, description, tier, catalog line, or input
+> schema) **without rebuilding**, `build/` and `src/` silently diverge — the tests
+> stay green while the server serves the OLD tools. To close that gap, the build
+> emits a `REGISTRY_STAMP` (a deterministic hash of the tool-specs content, via
+> `scripts/gen-registry-stamp.mjs` before `tsc`); on dev/test startup the loader
+> recomputes it from `src/` and **refuses to start with a "@docmost/mcp build is
+> stale …" error** on a mismatch (a pure no-op in prod, where only `build/` ships).
+> After editing tool specs, rebuild:
+> ```bash
+> pnpm --filter @docmost/mcp build     # or: pnpm --filter @docmost/mcp watch
+> ```
+
 **Lint** (per package — there is no root lint script):
 ```bash
 pnpm --filter server lint    # eslint --fix on server .ts
@@ -311,7 +460,7 @@ The API server is a Fastify app with a global `/api` prefix (`main.ts` excludes
 ### Client structure
 Vite SPA. Code is organized by feature under `apps/client/src/features/*` (mirrors the server domains: `page`, `space`, `comment`, `ai-chat`, `editor`, …). Conventions:
 - **TanStack Query** for server state (one `queries/` file per feature), **Jotai** atoms for local/shared UI state, **Mantine 8** + CSS modules (`*.module.css`) + `postcss-preset-mantine` for UI.
-- The editor is Tiptap; shared node/mark extensions live in `packages/editor-ext` and are imported by **both the client and the server** (collaboration, schema, `canonicalizeFootnotes`) — editor schema changes often need to be made in `editor-ext`, not just the client. Server-side markdown import/export no longer lives in `editor-ext`: it goes through the canonical converter (#345, see below). The ProseMirror↔Markdown converter and its Docmost schema mirror now live in a SINGLE package, `@docmost/prosemirror-markdown` (#293), consumed by `mcp`, `git-sync`, and `apps/server` (#345) — do NOT reintroduce a per-package copy. `editor-ext` is the upstream source of the Tiptap schema; the package's `docmost-schema.ts` mirrors it and a serializer-contract test (`packages/prosemirror-markdown/test/serializer-contract.test.ts`) guards the boundary (every schema node must have a converter case), so a drift surfaces as a failing test rather than silent divergence. For the converter's property-testing and counterexample→fixture process (P1–P4 invariants, the `PROPERTY_SEED`/`PROPERTY_NUM_RUNS` knobs, and the nightly fuzz workflow), see `packages/prosemirror-markdown/README.md`.
+- The editor is Tiptap; shared node/mark extensions live in `packages/editor-ext` and are imported by **both the client and the server** (collaboration, schema, `canonicalizeFootnotes`) — editor schema changes often need to be made in `editor-ext`, not just the client. Server-side markdown import/export no longer lives in `editor-ext`: it goes through the canonical converter (#345, see below). The ProseMirror↔Markdown converter and its Docmost schema mirror now live in a SINGLE package, `@docmost/prosemirror-markdown` (#293), consumed by `mcp`, `git-sync`, `apps/server` (#345), and `apps/client` (#347) — do NOT reintroduce a per-package copy. The client uses the package's `browser` entry (`@docmost/prosemirror-markdown/browser`): markdown paste (`markdown-clipboard.ts`), copy-as-markdown, and AI-chat rendering now all go through the canonical converter, so the hand-written `marked`/`turndown` markdown layer that used to live in `editor-ext` was deleted (#347). The browser entry runs the HTML→DOM stage on the native `DOMParser`, so jsdom stays out of the client bundle. `editor-ext` is the upstream source of the Tiptap schema; the package's `docmost-schema.ts` mirrors it and a serializer-contract test (`packages/prosemirror-markdown/test/serializer-contract.test.ts`) guards the boundary (every schema node must have a converter case), so a drift surfaces as a failing test rather than silent divergence. For the converter's property-testing and counterexample→fixture process (P1–P4 invariants, the `PROPERTY_SEED`/`PROPERTY_NUM_RUNS` knobs, and the nightly fuzz workflow), see `packages/prosemirror-markdown/README.md`.
 - API access goes through `apps/client/src/lib/api-client.ts` (axios). The `@` alias maps to `apps/client/src`.
 - Runtime config is injected at build time by `vite.config.ts` via `define` (`APP_URL`, `COLLAB_URL`, `APP_VERSION`, …) — these come from the root `.env`, not from `import.meta.env`.
 
@@ -321,8 +470,8 @@ Vite SPA. Code is organized by feature under `apps/client/src/features/*` (mirro
 - **Errors must never be swallowed or shown as generic messages.** Every caught error MUST (1) be logged in full to the console/logger — error name, message, stack, `cause`, and (for HTTP/provider failures) the status code and response body — and (2) be surfaced to the user with a *specific, human-readable explanation of what actually went wrong*, never a bare generic string like "Something went wrong" / "Could not start recording" / "Transcription failed". Include the real reason (the underlying error/provider message) in the user-facing text. On the server, wrap third-party/provider failures with `describeProviderError` (or equivalent) and rethrow as a meaningful HTTP status + message — never let them collapse into an opaque 500. On the client, `console.error(<context>, err)` the raw error AND show the extracted reason (e.g. `err.response?.data?.message`, or the error `name: message`) in the notification.
 - The version string shown in the UI comes from `APP_VERSION` (CI/Docker) or `git describe --tags --always` (local), resolved in `vite.config.ts` — not from `package.json`.
 - Server TS config is permissive (`noImplicitAny: false`, `strictNullChecks: false`, `no-explicit-any` lint disabled). Follow the existing relaxed style rather than tightening types broadly.
-- Dependency versions are heavily pinned via `pnpm.overrides` and `pnpm.patchedDependencies` (`scimmy`, `yjs`, `ai`) in the root `package.json`. Don't bump pinned/patched deps casually; the patches and overrides exist for compatibility/security reasons. The `ai@6.0.134` patch disables the SDK's O(n²) cumulative `partialOutput` accumulation when no output strategy is requested (server heap OOM on long agent runs, #184; tripwire test: `apps/server/src/integrations/ai/ai-sdk-partial-output.patch.spec.ts`) — it MUST be re-created via `pnpm patch` when bumping `ai`.
-- **Adding/renaming/removing an MCP tool requires updating `SERVER_INSTRUCTIONS`** in `packages/mcp/src/index.ts` — the intent-routing guide MCP clients receive on initialize. This applies both to inline `server.registerTool(...)` calls in `index.ts` and to specs in `packages/mcp/src/tool-specs.ts`. Enforced by `packages/mcp/test/unit/server-instructions.test.mjs`, which fails when a registered tool is not mentioned in the guide (deliberate opt-outs go into its `EXCEPTIONS` list). `packages/mcp/build/` is gitignored and rebuilt in CI/Docker via `pnpm build` (same convention as `git-sync`/`prosemirror-markdown`) — never commit it; rebuild locally after editing to run the tests.
+- Dependency versions are heavily pinned via `pnpm.overrides` and `pnpm.patchedDependencies` (`scimmy`, `yjs`, `ai`) in the root `package.json`. Don't bump pinned/patched deps casually; the patches and overrides exist for compatibility/security reasons. The `ai@6.0.134` patch carries TWO independent server fixes, each with its own tripwire test: (1) it disables the SDK's O(n²) cumulative `partialOutput` accumulation when no output strategy is requested (server heap OOM on long agent runs, #184; tripwire: `apps/server/src/integrations/ai/ai-sdk-partial-output.patch.spec.ts`); (2) it fixes `writeToServerResponse`'s drain-hang — the loop awaited only `"drain"` under backpressure, so a mid-write client disconnect parked the pipe forever and leaked the reader/buffers until restart; it now races `"drain"` against `"close"`/`"error"`, cancels the reader on disconnect, and swallows the fire-and-forget read rejection (#486; tripwire: `apps/server/src/integrations/ai/ai-sdk-drain-hang.patch.spec.ts`). Both tripwires assert BOTH installed dist builds carry their patch marker. The patch MUST be re-created via `pnpm patch` when bumping `ai`.
+- **The MCP tool inventory in `SERVER_INSTRUCTIONS` is GENERATED from the registry** (`packages/mcp/src/server-instructions.ts`: `buildToolInventory()` over `SHARED_TOOL_SPECS`) and spliced into the hand-written routing prose (`ROUTING_PROSE`). So adding/renaming/removing a **shared** spec in `packages/mcp/src/tool-specs.ts` auto-updates the `<tool_inventory>` — no manual `SERVER_INSTRUCTIONS` edit needed. Only an **inline** MCP-only tool (those registered via `server.registerTool(...)` in `index.ts`, not through the registry) needs a one-line entry in `INLINE_MCP_INVENTORY`. Enforced by `packages/mcp/test/unit/tool-inventory.test.mjs`, which fails when a registered tool is missing from the generated inventory (there is no `EXCEPTIONS` opt-out anymore — every tool must appear). Update `ROUTING_PROSE` when a tool's *intent guidance* (when-to-use) changes. `packages/mcp/build/` is gitignored and rebuilt in CI/Docker via `pnpm build` (same convention as `git-sync`/`prosemirror-markdown`) — never commit it; rebuild locally after editing to run the tests.
 
 ## CI / release
 

CHANGELOG.md

@@ -10,6 +10,123 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
+### Breaking Changes
+
+- **External MCP tool names are now camelCase (all renamed).** Every tool on the
+  external `/mcp` surface was renamed from `snake_case` to `camelCase`, so the
+  external MCP name now matches the in-app tool name exactly (one logical tool,
+  one name everywhere). For example `get_node` → `getNode`, `edit_page_text` →
+  `editPageText`, `patch_node` → `patchNode`. The tools' behaviour, inputs and
+  outputs are unchanged — only the names change. The single-word `search`
+  keeps its name.
+
+  *Migration (external MCP clients only — the in-app AI agent already used these
+  names and is unaffected):* update anything that refers to a tool by its
+  string name — permission allowlists (`mcp__gitmost-*__get_node` →
+  `mcp__gitmost-*__getNode`), saved prompts/skills, `.mcp.json` tool filters,
+  and metrics dashboards that group by the `tool` label — and roll it out in
+  lockstep with this deploy, because the old snake_case names stop resolving.
+  Released together with the `import_page_markdown`/`update_page_markdown`
+  change below so external configs break exactly once.
+
+  Full mapping (old → new):
+
+  | Old (snake_case) | New (camelCase) |
+  | --- | --- |
+  | `check_new_comments` | `checkNewComments` |
+  | `copy_page_content` | `copyPageContent` |
+  | `create_comment` | `createComment` |
+  | `create_page` | `createPage` |
+  | `delete_comment` | `deleteComment` |
+  | `delete_node` | `deleteNode` |
+  | `delete_page` | `deletePage` |
+  | `diff_page_versions` | `diffPageVersions` |
+  | `docmost_transform` | `docmostTransform` |
+  | `drawio_create` | `drawioCreate` |
+  | `drawio_get` | `drawioGet` |
+  | `drawio_guide` | `drawioGuide` |
+  | `drawio_shapes` | `drawioShapes` |
+  | `drawio_update` | `drawioUpdate` |
+  | `edit_page_text` | `editPageText` |
+  | `export_page_markdown` | `exportPageMarkdown` |
+  | `get_node` | `getNode` |
+  | `get_outline` | `getOutline` |
+  | `get_page` | `getPage` |
+  | `get_page_json` | `getPageJson` |
+  | `get_workspace` | `getWorkspace` |
+  | `insert_footnote` | `insertFootnote` |
+  | `insert_image` | `insertImage` |
+  | `insert_node` | `insertNode` |
+  | `list_comments` | `listComments` |
+  | `list_page_history` | `listPageHistory` |
+  | `list_pages` | `listPages` |
+  | `list_shares` | `listShares` |
+  | `list_spaces` | `listSpaces` |
+  | `move_page` | `movePage` |
+  | `patch_node` | `patchNode` |
+  | `rename_page` | `renamePage` |
+  | `replace_image` | `replaceImage` |
+  | `resolve_comment` | `resolveComment` |
+  | `restore_page_version` | `restorePageVersion` |
+  | `search` | `search` (unchanged) |
+  | `search_in_page` | `searchInPage` |
+  | `share_page` | `sharePage` |
+  | `stash_page` | `stashPage` |
+  | `table_delete_row` | `tableDeleteRow` |
+  | `table_get` | `tableGet` |
+  | `table_insert_row` | `tableInsertRow` |
+  | `table_update_cell` | `tableUpdateCell` |
+  | `unshare_page` | `unsharePage` |
+  | `update_comment` | `updateComment` |
+  | `update_page_json` | `updatePageJson` |
+  | `update_page_markdown` | `updatePageMarkdown` |
+
+  (#412)
+
+- **External MCP: `import_page_markdown` removed, `update_page_markdown` added.**
+  The external `/mcp` surface no longer exposes `importPageMarkdown` (the
+  round-trip parser for a self-contained *exported* Docmost-Markdown file). In
+  its place it now exposes **`updatePageMarkdown`** — a plain-Markdown
+  full-body replace (`{pageId, content, title?}`) that pairs with
+  `updatePageJson`, re-imports the whole body (block ids regenerate) and
+  parses Docmost-flavoured markdown including `^[...]` inline footnotes.
+  *Migration:* MCP clients that called `importPageMarkdown` to overwrite a
+  page's body from Markdown should call `updatePageMarkdown` instead (pass the
+  markdown as `content`). Round-tripping an exported Docmost-Markdown file with
+  comment anchors/diagrams is no longer available on the external MCP surface;
+  export remains via `exportPageMarkdown`. The in-app AI agent is unaffected —
+  it keeps both `importPageMarkdown` and the renamed `updatePageMarkdown` (was
+  `updatePageContent`). The total MCP tool count is unchanged (−1 / +1). The
+  external names shown here are the post-#412 camelCase names. (#411)
+
+- **`getNode` now returns Markdown by default (was ProseMirror JSON).** The
+  block-level read/write tools default to Markdown so a block round trip is
+  `getNode` (markdown) → edit → `patchNode` (markdown). `getNode` now returns
+  `{ …, format: "markdown", markdown }` unless you pass `format: "json"` (which
+  restores the previous `{ …, node }` ProseMirror subtree); comment anchors —
+  including resolved ones — are preserved in the markdown so a write-back never
+  orphans a thread, and a node that cannot be a document top-level block
+  (`tableRow`/`tableCell`/`tableHeader` addressed via `#<index>`) auto-falls back
+  to JSON with `format: "json"` in the response. `patchNode`/`insertNode` gain a
+  `markdown` input alongside `node` (provide exactly one): the markdown fragment
+  may rewrite/insert several blocks at once and supports `^[...]` footnotes.
+  *Migration (external MCP clients only):* a client that consumed `getNode`'s
+  `node` field must now either read `markdown`, or pass `format: "json"` to keep
+  the old ProseMirror-JSON output. Released together with the `#411`/`#412`
+  breaking window so external configs break exactly once. (#413)
+
+- **The Prometheus `/metrics` listener now binds to `127.0.0.1` (loopback) by
+  default instead of `0.0.0.0` (all interfaces).** This closes an unauthenticated
+  endpoint that was previously reachable on every interface. **DEPLOY MIGRATION —
+  cross-container scraping breaks silently otherwise:** if your scraper runs in a
+  SEPARATE container and reaches the app as `docmost:9464` (the exact topology the
+  old `0.0.0.0` hardcode served), you MUST now set `METRICS_BIND=0.0.0.0` — and,
+  because that re-exposes the endpoint, also set `METRICS_TOKEN=<secret>` and
+  configure the scraper with a matching Bearer token. Without `METRICS_BIND`, the
+  scraper can no longer connect and metrics go dark with no error. See the
+  `METRICS_BIND` / `METRICS_TOKEN` block in `.env.example` for the migration.
+  Same-host (loopback) scrapers need no change. (#486)
+
 ### Added
 
 - **Place several images side by side in a row.** A new "Inline (side by
@@ -146,9 +263,37 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   by physical key position and matched against the commands; genuine Cyrillic
   search terms keep priority over remapped candidates, and short wrong-layout
   prefixes match by command title. (#283, #285, #287)
+- **Opt-in substring "lookup" search mode for agents.** `/api/search` gains an
+  additive, opt-in mode (guarded by a new `substring` flag) that matches literal
+  substrings of page titles and body text — so technical tokens the full-text
+  tokenizer mangles (`backup-srv.local`, `10.0.12.5`, `WB-MGE-30D86B`) are found
+  even when the FTS query is empty. It returns a location `path`, a windowed
+  `snippet` and a per-response relevance `score`, supports `titleOnly` and a
+  `parentPageId` subtree scope, and applies the page-level permission filter
+  before the limit. The web UI never sets `substring`, so its full-text search
+  behaviour is byte-for-byte unchanged. The leading-wildcard `LIKE` predicates
+  are backed by GIN trigram indexes on `LOWER(f_unaccent(title))` and
+  `LOWER(f_unaccent(text_content))` so lookups use a bitmap index scan instead of
+  a sequential scan. (#443)
+- **MCP `search` tool returns richer, agent-oriented results.** The external MCP
+  `search` response shape changes for the agent surface: each hit now carries
+  `pageId` (renamed from `id`), plus `path`, `snippet` and `score`; the
+  UI-oriented `spaceId`, `rank` and `highlight` fields are dropped. (#443)
 
 ### Changed
 
+- **Client markdown paste/copy and AI-chat rendering now go through the canonical
+  converter.** Pasting markdown into the editor, "Copy as markdown", the AI title
+  generator, and the AI-chat markdown renderer all now use
+  `@docmost/prosemirror-markdown` (via its new `browser` entry — native
+  `DOMParser`, no jsdom in the client bundle) instead of the hand-written
+  `marked`/`turndown` markdown layer in `editor-ext`, which was **deleted**. As a
+  result, pasting canonical markdown (`^[…]` footnotes, `<!--img …-->`,
+  `> [!type]` callouts, `$…$` math, `==…==` highlight, standalone `<!--subpages-->`
+  comments) now produces the SAME nodes the server import produces for the same
+  text. Chat/reasoning markdown now renders through the editor schema (list items
+  are wrapped in `<p>`; CSS keeps them tight). (#347)
+
 - **Enabling a public share no longer auto-shares the whole sub-tree.** Turning
   a page "Shared to web" now defaults to the page alone; descendant pages become
   public only when you explicitly turn on the dedicated "Include sub-pages"
@@ -177,6 +322,39 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   `tee()` branch of the stream result — a ~20-step, ~28k-chunk agent run
   retained ~1.7 GB and OOM'd the 2 GB JS heap. Streaming granularity is
   unchanged; the patch must be re-created if `ai` is ever bumped. (#184)
+
+- **The server no longer leaks a hung stream pipe on every mid-run client
+  disconnect.** The same `ai@6.0.134` pnpm patch now also fixes the SDK's
+  `writeToServerResponse`, which awaited only a `"drain"` event under
+  backpressure: when a client disconnected mid-write the socket never drained, so
+  the write loop parked forever, `response.end()` was unreachable, and the stream
+  reader plus buffered chunks were pinned until process restart (every mid-run
+  disconnect in autonomous mode leaked one). The patch races `"drain"` against
+  `"close"`/`"error"`, cancels the reader and ends the response on disconnect, and
+  swallows the fire-and-forget read rejection instead of crashing on an
+  unhandledRejection. (#486)
+
+- **A failed autonomous agent-run start no longer becomes an unstoppable ghost
+  run.** When `beginRun` failed for a transient reason (e.g. a DB-pool blip),
+  the turn previously continued with NO run row — invisible to `/stop`, not
+  aborted on disconnect, and able to slip a second run past the one-run-per-chat
+  gate, leaving an unstoppable run until restart. The turn now fails fast with an
+  honest `503 A_RUN_BEGIN_FAILED` before the first byte (no orphan state), and the
+  client shows a "temporary — please try again" message instead of a misleading
+  "provider not configured". (#486)
+
+- **A pathological draw.io graph can no longer wedge the whole server.** The ELK
+  auto-layout (`layout:"elk"`) ran elkjs synchronously on the main event loop, so
+  a graph at the node/edge cap blocked ALL HTTP/SSE/loopback traffic while it
+  churned — and the old `setTimeout` "timeout" could never fire because the same
+  thread was blocked. Layout now runs in a worker thread with the timeout enforced
+  by `worker.terminate()`; the main loop stays responsive. (#486)
+
+- **The `/health` Redis probe no longer leaks a client on every tick while Redis
+  is down.** It built a new `ioredis` client per probe and disconnected it only on
+  success, so during an outage each health tick added another forever-reconnecting
+  client (an unbounded handle leak). A single long-lived probe client is now
+  reused and closed on shutdown. (#486)
 - **Internal links in exported Markdown no longer lose their visible text.** A
   link whose target page name had no file extension (e.g. a bare title) was
   collapsed to empty text during export, producing an unclickable, label-less
@@ -253,6 +431,24 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   share); any other value now returns the generic "not found" instead of
   serving the page. (#218)
 
+- **Tool and provider error text no longer leaks to anonymous readers in the
+  public-share AI chat.** A failing tool's raw error (which could carry an
+  internal page title or a stack fragment) and a provider error (which bundles the
+  provider `statusCode` and response body — potentially the internal baseUrl or
+  model name) were streamed verbatim to the anonymous reader over SSE. Errors are
+  now sanitized at the source: the share toolset collapses any unclassified tool
+  error to a safe generic string (safe, classified tool messages still pass
+  through for the model's self-correction), and the anonymous stream `onError`
+  maps provider failures to a fixed set of neutral strings — the full detail goes
+  only to the server log. A UI render gate is layered on top. (closes #394)
+
+- **The Prometheus `/metrics` endpoint can now require Bearer authentication and
+  is loopback-bound by default.** Previously it listened on all interfaces with no
+  auth. Setting `METRICS_TOKEN` requires every scrape to present
+  `Authorization: Bearer <token>` (compared in constant time), and the listener
+  defaults to `127.0.0.1` (see the Breaking Changes entry for the cross-container
+  migration). (#486)
+
 ## [0.94.0] - 2026-06-26
 
 This release makes AI chat durable and fast: assistant turns are persisted to

Dockerfile

@@ -45,6 +45,11 @@ COPY --from=builder /app/packages/editor-ext/dist /app/packages/editor-ext/dist
 COPY --from=builder /app/packages/editor-ext/package.json /app/packages/editor-ext/package.json
 COPY --from=builder /app/packages/mcp/build /app/packages/mcp/build
 COPY --from=builder /app/packages/mcp/package.json /app/packages/mcp/package.json
+# The mcp package reads its data files (drawio-presets.json, drawio-shape-index.json.gz)
+# at runtime via `new URL("../../data/…", import.meta.url)` relative to build/lib/*.js,
+# i.e. from packages/mcp/data/. tsc emits only build/, so ship data/ explicitly or
+# drawioFromGraph and the shape catalog die with ENOENT on packages/mcp/data/*.
+COPY --from=builder /app/packages/mcp/data /app/packages/mcp/data
 # mcp now depends on @docmost/prosemirror-markdown (workspace:*) and eager-imports
 # it at runtime (the in-app ai-chat DocmostClient loads build/index.js -> lib/
 # markdown-converter.js). Ship the built package + its manifest, or the prod
@@ -81,4 +86,14 @@ VOLUME ["/app/data/storage"]
 
 EXPOSE 3000
 
+# DEPLOY REQUIREMENT — SINGLE INSTANCE or STICKY SESSIONS (#449).
+# MCP content writes are serialized per page by an IN-PROCESS mutex, and the
+# stash_page blob store + cached collab sessions are RAM-only and process-local.
+# Running MULTIPLE replicas of this image behind a load balancer WITHOUT sticky
+# sessions silently breaks per-page write serialization (two replicas can lock
+# the same page at once) and makes stash_page blobs unreachable across replicas.
+# Run a SINGLE instance, or pin each page's traffic to one replica (sticky
+# sessions / consistent hashing on page id). There is deliberately no
+# cross-process lock yet — a conscious constraint. See .env.example (the "MCP
+# collaboration write path" block) and packages/mcp/README.md for details.
 CMD ["pnpm", "start"]

apps/client/package.json

@@ -21,6 +21,7 @@
     "@atlaskit/pragmatic-drag-and-drop-live-region": "1.3.4",
     "@casl/react": "5.0.1",
     "@docmost/editor-ext": "workspace:*",
+    "@docmost/prosemirror-markdown": "workspace:*",
     "@excalidraw/excalidraw": "0.18.0-3a5ef40",
     "@mantine/core": "8.3.18",
     "@mantine/dates": "8.3.18",

apps/client/src/features/ai-chat/components/ai-chat.module.css

@@ -55,6 +55,15 @@
     padding-inline-start: 1.4em;
 }
 
+/* The canonical converter renders list items through the editor schema, which
+   wraps each item's content in a <p> (listItem content is `paragraph+`). Drop
+   that paragraph's block margin so list items render TIGHT (no extra vertical
+   gap), matching the previous marked output — same rule already applied to
+   table cells above (issue #347). */
+.markdown li p {
+    margin: 0;
+}
+
 /* GFM tables in assistant markdown. The chat lives in a NARROW side panel, so a
    wide LLM table must scroll horizontally instead of collapsing its columns:
    `.markdown` sets `word-break: break-word`, which (with the default table
@@ -172,6 +181,14 @@
     margin: 0 0 4px;
 }
 
+/* Same as `.markdown li p` above: the canonical converter wraps every list
+   item's content in a <p>, so without this each reasoning-panel list item would
+   pick up `.reasoningText p`'s 4px bottom margin and render too loose. Drop it
+   so Reasoning-panel lists stay tight, mirroring the pre-#347 marked output. */
+.reasoningText li p {
+    margin: 0;
+}
+
 .inputWrapper {
     flex: 0 0 auto;
     padding-top: var(--mantine-spacing-xs);

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

@@ -28,7 +28,10 @@ const h = vi.hoisted(() => ({
         body: Record<string, unknown>;
       }) => { body: Record<string, unknown> };
       prepareReconnectToStreamRequest?: () => { api?: string };
-      fetch?: (input: unknown, init?: { method?: string }) => Promise<unknown>;
+      fetch?: (
+        input: unknown,
+        init?: { method?: string; body?: unknown },
+      ) => Promise<unknown>;
     },
   },
 }));
@@ -200,6 +203,290 @@ describe("ChatThread — send now (#198)", () => {
   });
 });
 
+// #486: the final onFinish -> flushNext() must be gated on the live-mount flag.
+// A clean onFinish can land AFTER the thread unmounts (New-chat / chat-switch
+// mid-stream — the async attach/resume settles late); flushing then dequeues and
+// re-POSTs a queued message from an abandoned thread (a "ghost" send).
+describe("ChatThread — onFinish flush gated on mount (#486)", () => {
+  beforeEach(resetState);
+  afterEach(cleanup);
+
+  it("a clean onFinish WHILE MOUNTED flushes the queued message (control)", () => {
+    renderThread();
+    fireEvent.click(screen.getByTestId("queue-btn")); // enqueue "queued text"
+    expect(h.state.sendMessage).not.toHaveBeenCalled();
+
+    act(() => {
+      h.state.onFinish?.({
+        message: { id: "a", role: "assistant", parts: [] },
+        isAbort: false,
+        isDisconnect: false,
+        isError: false,
+      });
+    });
+    // Mounted: the queue flushes normally.
+    expect(h.state.sendMessage).toHaveBeenCalledWith({ text: "queued text" });
+  });
+
+  it("a clean onFinish AFTER unmount does NOT flush (no ghost send)", () => {
+    const { unmount } = renderThread();
+    fireEvent.click(screen.getByTestId("queue-btn")); // enqueue "queued text"
+    h.state.sendMessage.mockClear();
+
+    // Chat switched away mid-stream: the streamer unmounts...
+    unmount();
+    // ...and a late, clean onFinish lands on the abandoned thread.
+    act(() => {
+      h.state.onFinish?.({
+        message: { id: "a", role: "assistant", parts: [] },
+        isAbort: false,
+        isDisconnect: false,
+        isError: false,
+      });
+    });
+    // Gated on mountedRef: NOTHING is sent from the dead thread.
+    expect(h.state.sendMessage).not.toHaveBeenCalled();
+  });
+});
+
+// #396: in autonomous mode a live sendNow must additionally request the
+// AUTHORITATIVE server stop of the detached run (a local abort is only a client
+// disconnect the server ignores) and arm a bounded 409 retry so the re-POST
+// converges once the one-active-run slot frees. Legacy mode is unchanged.
+describe("ChatThread — send now server-stop + supersede retry (#396)", () => {
+  beforeEach(resetState);
+  afterEach(cleanup);
+
+  // A settled assistant tail => no mount resume (attemptResumeRef false), so the
+  // "Send now" button is visible for the NEW local streaming turn while
+  // autonomous runs are enabled.
+  const settledTail = () => [
+    row("u1", "user", undefined, "hi"),
+    row("a1", "assistant", "succeeded", "done"),
+  ];
+
+  it("autonomous: sendNow during a live stream calls onServerStop with the chat id", () => {
+    const { onServerStop } = renderThread({
+      autonomousRunsEnabled: true,
+      initialRows: settledTail(),
+    });
+    fireEvent.click(screen.getByTestId("queue-btn"));
+    fireEvent.click(screen.getByLabelText("Send now"));
+
+    expect(h.state.stop).toHaveBeenCalledTimes(1);
+    expect(onServerStop).toHaveBeenCalledWith("c1");
+  });
+
+  it("legacy (autonomous off): sendNow does NOT call onServerStop and does NOT retry the send", async () => {
+    const { onServerStop } = renderThread({
+      autonomousRunsEnabled: false,
+      initialRows: settledTail(),
+    });
+    fireEvent.click(screen.getByTestId("queue-btn"));
+    fireEvent.click(screen.getByLabelText("Send now"));
+    expect(onServerStop).not.toHaveBeenCalled();
+
+    // The supersede retry must NOT be armed: a POST that 409s is returned as-is
+    // (single fetch, no retry).
+    const fetchMock = vi
+      .fn()
+      .mockResolvedValue(
+        new Response(JSON.stringify({ code: "A_RUN_ALREADY_ACTIVE" }), {
+          status: 409,
+        }),
+      );
+    vi.stubGlobal("fetch", fetchMock);
+    let res!: Response;
+    await act(async () => {
+      res = (await h.state.transport!.fetch!("http://x", {
+        method: "POST",
+        body: "{}",
+      })) as Response;
+    });
+    expect(fetchMock).toHaveBeenCalledTimes(1);
+    expect(res.status).toBe(409);
+  });
+
+  it("armed supersede send retries 409 A_RUN_ALREADY_ACTIVE and succeeds once the slot frees", async () => {
+    renderThread({ autonomousRunsEnabled: true, initialRows: settledTail() });
+    // Arm the retry by performing a live sendNow (autonomous branch sets the ref).
+    fireEvent.click(screen.getByTestId("queue-btn"));
+    fireEvent.click(screen.getByLabelText("Send now"));
+
+    const fetchMock = vi
+      .fn()
+      // First POST: the old detached run still holds the slot -> 409.
+      .mockResolvedValueOnce(
+        new Response(JSON.stringify({ code: "A_RUN_ALREADY_ACTIVE" }), {
+          status: 409,
+        }),
+      )
+      // Retry: the server stop settled the old run -> 200.
+      .mockResolvedValueOnce(new Response("ok", { status: 200 }));
+    vi.stubGlobal("fetch", fetchMock);
+
+    let res!: Response;
+    await act(async () => {
+      res = (await h.state.transport!.fetch!("http://x", {
+        method: "POST",
+        body: "{}",
+      })) as Response;
+    });
+    expect(fetchMock).toHaveBeenCalledTimes(2);
+    expect(res.status).toBe(200);
+  });
+
+  it("supersede retry is one-shot: a later send (ref cleared) does NOT retry a 409", async () => {
+    renderThread({ autonomousRunsEnabled: true, initialRows: settledTail() });
+    fireEvent.click(screen.getByTestId("queue-btn"));
+    fireEvent.click(screen.getByLabelText("Send now")); // arms the one-shot
+
+    // First armed send: immediately succeeds, consuming the arm.
+    let fetchMock = vi
+      .fn()
+      .mockResolvedValue(new Response("ok", { status: 200 }));
+    vi.stubGlobal("fetch", fetchMock);
+    await act(async () => {
+      await h.state.transport!.fetch!("http://x", {
+        method: "POST",
+        body: "{}",
+      });
+    });
+    expect(fetchMock).toHaveBeenCalledTimes(1);
+
+    // A subsequent send is NOT armed -> a 409 is returned as-is (no retry).
+    fetchMock = vi.fn().mockResolvedValue(
+      new Response(JSON.stringify({ code: "A_RUN_ALREADY_ACTIVE" }), {
+        status: 409,
+      }),
+    );
+    vi.stubGlobal("fetch", fetchMock);
+    let res!: Response;
+    await act(async () => {
+      res = (await h.state.transport!.fetch!("http://x", {
+        method: "POST",
+        body: "{}",
+      })) as Response;
+    });
+    expect(fetchMock).toHaveBeenCalledTimes(1);
+    expect(res.status).toBe(409);
+  });
+
+  it("supersede retry is bounded: exhaustion surfaces the 409 error", async () => {
+    renderThread({ autonomousRunsEnabled: true, initialRows: settledTail() });
+    fireEvent.click(screen.getByTestId("queue-btn"));
+    fireEvent.click(screen.getByLabelText("Send now"));
+
+    // Every attempt 409s -> after 4 attempts the last 409 surfaces.
+    const fetchMock = vi.fn().mockResolvedValue(
+      new Response(JSON.stringify({ code: "A_RUN_ALREADY_ACTIVE" }), {
+        status: 409,
+      }),
+    );
+    vi.stubGlobal("fetch", fetchMock);
+    let res!: Response;
+    await act(async () => {
+      res = (await h.state.transport!.fetch!("http://x", {
+        method: "POST",
+        body: "{}",
+      })) as Response;
+    });
+    // 4 attempts total (1 immediate + 3 backoff retries), then give up.
+    expect(fetchMock).toHaveBeenCalledTimes(4);
+    expect(res.status).toBe(409);
+  });
+
+  it("armed supersede send does NOT retry a non-409 status", async () => {
+    renderThread({ autonomousRunsEnabled: true, initialRows: settledTail() });
+    fireEvent.click(screen.getByTestId("queue-btn"));
+    fireEvent.click(screen.getByLabelText("Send now"));
+    const fetchMock = vi
+      .fn()
+      .mockResolvedValue(new Response("boom", { status: 500 }));
+    vi.stubGlobal("fetch", fetchMock);
+    let res!: Response;
+    await act(async () => {
+      res = (await h.state.transport!.fetch!("http://x", {
+        method: "POST",
+        body: "{}",
+      })) as Response;
+    });
+    expect(fetchMock).toHaveBeenCalledTimes(1);
+    expect(res.status).toBe(500);
+  });
+
+  // Strand-path regression: sendNow arms the supersede retry, but if the promoted
+  // head is removed before the abort's onFinish lands, flushNext() sends nothing
+  // (returns false) and NO re-POST consumes the arm. The arm must be disarmed on
+  // that no-send branch so the NEXT unrelated NORMAL send does not inherit it and
+  // silently retry a genuine 409 (e.g. a legitimate two-tab conflict) 4x instead
+  // of surfacing it immediately.
+  it("strand-path: a stranded supersede arm (flushNext no-send) does NOT retry a later normal 409", async () => {
+    renderThread({ autonomousRunsEnabled: true, initialRows: settledTail() });
+    // Arm the retry via a live autonomous sendNow (promotes the head + arms).
+    fireEvent.click(screen.getByTestId("queue-btn"));
+    fireEvent.click(screen.getByLabelText("Send now"));
+
+    // Remove the promoted head BEFORE the abort lands, so flushNext() returns
+    // false (no POST) and the arm would strand without the disarm fix.
+    fireEvent.click(screen.getByLabelText("Remove queued message"));
+
+    // The abort's onFinish now takes the flushOnAbortRef branch, calls flushNext()
+    // which finds an empty queue and returns false -> the no-send disarm must run.
+    act(() => {
+      h.state.onFinish?.({
+        message: { id: "a1", role: "assistant", parts: [] },
+        isAbort: true,
+        isDisconnect: false,
+        isError: false,
+      });
+    });
+    // No re-POST was sent (nothing to flush).
+    expect(h.state.sendMessage).not.toHaveBeenCalled();
+
+    // A subsequent NORMAL send that 409s must be returned as-is (exactly 1 fetch):
+    // the stranded arm must NOT cause the genuine 409 to be retried.
+    const fetchMock = vi
+      .fn()
+      .mockResolvedValue(
+        new Response(JSON.stringify({ code: "A_RUN_ALREADY_ACTIVE" }), {
+          status: 409,
+        }),
+      );
+    vi.stubGlobal("fetch", fetchMock);
+    let res!: Response;
+    await act(async () => {
+      res = (await h.state.transport!.fetch!("http://x", {
+        method: "POST",
+        body: "{}",
+      })) as Response;
+    });
+    expect(fetchMock).toHaveBeenCalledTimes(1);
+    expect(res.status).toBe(409);
+  });
+
+  it("armed supersede send does NOT retry a 409 with a different (non-A_RUN_ALREADY_ACTIVE) body", async () => {
+    renderThread({ autonomousRunsEnabled: true, initialRows: settledTail() });
+    fireEvent.click(screen.getByTestId("queue-btn"));
+    fireEvent.click(screen.getByLabelText("Send now"));
+    const fetchMock = vi.fn().mockResolvedValue(
+      new Response(JSON.stringify({ code: "SOMETHING_ELSE" }), {
+        status: 409,
+      }),
+    );
+    vi.stubGlobal("fetch", fetchMock);
+    let res!: Response;
+    await act(async () => {
+      res = (await h.state.transport!.fetch!("http://x", {
+        method: "POST",
+        body: "{}",
+      })) as Response;
+    });
+    expect(fetchMock).toHaveBeenCalledTimes(1);
+    expect(res.status).toBe(409);
+  });
+});
+
 // #388: the editor selection is snapshotted at send time and nested inside
 // openPage on the wire. The getter is read live from a ref, so each send ships a
 // fresh snapshot.

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

@@ -70,6 +70,36 @@ const RECONNECT_MAX_ATTEMPTS = 5;
 // Backoff before attempt N (1-based): 1s, 2s, 4s, 8s, 16s.
 const RECONNECT_BASE_DELAY_MS = 1000;
 
+// #396: bounded retry for the "Interrupt and send now" re-send when it races the
+// authoritative server stop of the just-superseded detached run. The re-POST can
+// arrive before the old run has released the one-active-run slot, so the server
+// returns 409 A_RUN_ALREADY_ACTIVE. The server stop guarantees the slot frees, so
+// a few short backoffs converge. 4 total attempts: attempt 1 fires immediately,
+// then these are the waits BEFORE attempts 2, 3 and 4 (150ms, 300ms, 600ms). If
+// all 4 attempts 409, the last 409 surfaces (the banner) — acceptable per #396.
+const SUPERSEDE_RETRY_DELAYS_MS = [150, 300, 600];
+// The server error code that means "another run is already active for this chat".
+const A_RUN_ALREADY_ACTIVE = "A_RUN_ALREADY_ACTIVE";
+
+/**
+ * #396: defensively decide whether a 409 response is the one-active-run gate
+ * rejection (code A_RUN_ALREADY_ACTIVE) vs. some other 409. Reads a CLONE so the
+ * original response body stays intact for the caller when it is returned as-is.
+ * Any parse failure or unexpected shape => false (do NOT retry).
+ */
+async function isRunAlreadyActive(response: Response): Promise<boolean> {
+  try {
+    const body = (await response.clone().json()) as unknown;
+    return (
+      typeof body === "object" &&
+      body !== null &&
+      (body as { code?: unknown }).code === A_RUN_ALREADY_ACTIVE
+    );
+  } catch {
+    return false;
+  }
+}
+
 /** The page the user is currently viewing, sent as chat context. */
 export interface OpenPageContext {
   id: string;
@@ -326,6 +356,26 @@ export default function ChatThread({
   const flushOnAbortRef = useRef(false);
   const interruptNextSendRef = useRef(false);
 
+  // #396: one-shot arm for the bounded 409 A_RUN_ALREADY_ACTIVE retry on the
+  // "Interrupt and send now" re-send in autonomous mode. sendNow triggers the
+  // authoritative server stop of the detached run, but that stop and the
+  // onFinish->flushNext re-POST race: the new POST can hit the one-active-run
+  // gate before the old detached run has settled, yielding a spurious 409. When
+  // this ref is armed, the transport's send path retries that 409 with a short
+  // bounded backoff (the server stop guarantees convergence). A normal send (ref
+  // not armed) must STILL fail a 409 instantly (e.g. a genuine two-tab conflict).
+  //
+  // INVARIANT: sendNow arms this only to be consumed by the ONE re-POST that
+  // flushNext fires from onFinish. But that re-POST does not always happen (the
+  // promoted head may be gone, the finish may be a resumed turn, or the arm may
+  // race a stale finish). To keep the arm strictly one-shot it is disarmed on
+  // EVERY path where the paired interrupt one-shots (flushOnAbortRef /
+  // interruptNextSendRef) are cleared without a POST: the transport POST branch
+  // consumes it (read-and-clear), the onFinish `!flushNext()` no-send branch
+  // clears it, and the isStreaming-defuse effect clears it symmetrically. So it
+  // can never leak into a later, unrelated send and retry that send's genuine 409.
+  const supersedeRetryRef = useRef(false);
+
   // #234 F5: the user pressed Stop while streaming a BRAND-NEW chat whose server
   // chat id has not been adopted yet (the `start` chunk carrying it hadn't landed
   // when Stop was pressed). A local SSE abort alone does NOT stop the DETACHED
@@ -382,7 +432,43 @@ export default function ChatThread({
           }`,
         }),
         fetch: async (input: RequestInfo | URL, init: RequestInit = {}) => {
-          if ((init.method ?? "GET") !== "GET") return fetch(input, init); // send path untouched
+          if ((init.method ?? "GET") !== "GET") {
+            // Send path (POST). #396: read-and-clear the one-shot supersede arm
+            // here so it is strictly scoped to THIS send. When unarmed, behave
+            // exactly as before — a single fetch, a 409 surfaces instantly (a
+            // genuine two-tab conflict must NOT be retried).
+            const supersede = supersedeRetryRef.current;
+            supersedeRetryRef.current = false;
+            if (!supersede) return fetch(input, init);
+            // Buffer a ReadableStream body once so each retry can replay it.
+            // DefaultChatTransport sends the body as a JSON STRING (replayable as
+            // is), but guard defensively in case a future SDK streams it.
+            let sendInit = init;
+            if (init.body instanceof ReadableStream) {
+              const buffered = await new Response(init.body).arrayBuffer();
+              sendInit = { ...init, body: buffered };
+            }
+            // Bounded retry: attempt 1 fires immediately, then wait between
+            // attempts per SUPERSEDE_RETRY_DELAYS_MS. Retry ONLY on a real
+            // 409 A_RUN_ALREADY_ACTIVE; any other status/body is returned as-is.
+            for (let attempt = 0; ; attempt++) {
+              const response = await fetch(input, sendInit);
+              if (
+                response.status !== 409 ||
+                attempt >= SUPERSEDE_RETRY_DELAYS_MS.length ||
+                !(await isRunAlreadyActive(response))
+              ) {
+                return response;
+              }
+              // The old detached run has not released the one-active-run slot
+              // yet; the server stop we requested guarantees it will, so back off
+              // and re-POST (the 409 fired before the user message was persisted,
+              // so re-POSTing is safe — no duplicate rows).
+              await new Promise((r) =>
+                setTimeout(r, SUPERSEDE_RETRY_DELAYS_MS[attempt]),
+              );
+            }
+          }
           // Reconnect GET: the SDK passes no AbortSignal, so wire our own controller
           // for observer Stop / unmount abort.
           const controller = new AbortController();
@@ -562,13 +648,24 @@ export default function ChatThread({
         setStopNotice(null);
         // If the promoted head vanished (e.g. the user removed it before the
         // abort landed) flushNext sends nothing — clear the one-shot interrupt
-        // tag so it can't leak onto the next unrelated send. On a real send the
-        // tag is consumed by prepareSendMessagesRequest and stays untouched.
-        if (!flushNext()) interruptNextSendRef.current = false;
+        // tag AND the #396 supersede arm so neither can leak onto the next
+        // unrelated send (no re-POST will consume the arm here). On a real send
+        // the tag is consumed by prepareSendMessagesRequest and the arm by the
+        // transport POST branch, so both stay untouched then.
+        if (!flushNext()) {
+          interruptNextSendRef.current = false;
+          supersedeRetryRef.current = false;
+        }
         return;
       }
       if (isAbort || isDisconnect || isError) return;
-      flushNext();
+      // Gate the final flush on the live-mount flag (#486): a clean onFinish can
+      // land AFTER this thread unmounted (a New-chat / chat-switch mid-stream —
+      // the async attach/resume settles late). Flushing then dequeues and POSTs a
+      // queued message from an abandoned thread — a "ghost" send / ghost chat.
+      // Every other queue side effect already guards on mountedRef; this last one
+      // was the gap.
+      if (mountedRef.current) flushNext();
     },
     // `onError` runs in addition to `onFinish` (which ai@6 also calls on error).
     // Log the raw failure here for devtools; the UI shows a friendly classified
@@ -873,6 +970,30 @@ export default function ChatThread({
         setQueue(promoteToHead(queuedRef.current, id));
         flushOnAbortRef.current = true;
         interruptNextSendRef.current = true;
+        // #396: in autonomous mode the turn is a DETACHED run — a local stop()
+        // is only a client disconnect the server ignores, so the run keeps going.
+        // The onFinish->flushNext re-POST would then hit the one-active-run gate
+        // and get a spurious 409 A_RUN_ALREADY_ACTIVE. Mirror handleStop: request
+        // the AUTHORITATIVE server stop so the detached run settles, and arm the
+        // one-shot bounded 409 retry BEFORE stop() so the re-send converges once
+        // the slot frees. Read chatId live from chatIdRef (adopted at the `start`
+        // chunk). If it is not known yet (brand-new chat, first moment of its
+        // first turn), defer the server stop via stopPendingRef exactly as
+        // handleStop does — the onServerChatId adoption effect fires it once the
+        // id lands; the retry stays armed so the re-send still converges then.
+        if (autonomousRunsEnabled) {
+          supersedeRetryRef.current = true; // arm the bounded 409 retry
+          if (chatIdRef.current) {
+            onServerStop?.(chatIdRef.current);
+          } else {
+            // Same #234-F5 sub-window limitation documented in handleStop: if the
+            // local abort below cancels the reader before the `start` chunk lands,
+            // the adoption effect never runs and the deferred stop never fires. Not
+            // a regression; at minimum we don't strand refs (the isStreaming effect
+            // defuses stopPendingRef on the next turn start).
+            stopPendingRef.current = true;
+          }
+        }
         stop(); // -> onFinish({ isAbort: true }) flushes the promoted head
       } else {
         // Nothing to interrupt: just send it now (no interrupt note).
@@ -884,7 +1005,7 @@ export default function ChatThread({
         sendMessageRef.current?.({ text: msg.text });
       }
     },
-    [setQueue, stop, setResumedTurnPair],
+    [setQueue, stop, setResumedTurnPair, autonomousRunsEnabled, onServerStop],
   );
 
   // Stop the current turn. ALWAYS abort the local SSE (`stop()`) so the composer
@@ -944,6 +1065,13 @@ export default function ChatThread({
       setStopNotice(null);
       flushOnAbortRef.current = false;
       interruptNextSendRef.current = false;
+      // #396: symmetric with the other one-shot interrupt flags — defuse a stale
+      // supersede arm that was set but whose expected re-POST never fired (the
+      // turn finished in the same tick as the click, or the promoted head was
+      // gone), so it can never leak into this (or a later) turn's send and retry
+      // that send's genuine 409. A legit arm is consumed by the transport POST
+      // branch before this new turn streams, so this does not clobber it.
+      supersedeRetryRef.current = false;
       // #234 F5: a new turn is starting — drop any pending deferred-stop from a
       // previous turn that never adopted an id, so it can never fire against this
       // (or a later) unrelated turn's run. A deferred stop for the CURRENT turn is

apps/client/src/features/ai-chat/components/message-item.tsx

@@ -47,6 +47,13 @@ interface MessageItemProps {
    * agent's raw query/argument text.
    */
   showInput?: boolean;
+  /**
+   * Forwarded to ToolCallCard: whether a failed tool card renders its raw
+   * errorText. Defaults to true (internal chat). The public share passes false so
+   * internal detail in a tool error is never painted (belt to the server-side
+   * byte sanitization).
+   */
+  showErrors?: boolean;
   /**
    * Neutralize internal/relative markdown links in the rendered answer (drop
    * their href so they become inert text). Defaults to false (internal chat,
@@ -125,6 +132,7 @@ function MessageItem({
   message,
   showCitations = true,
   showInput = true,
+  showErrors = true,
   neutralizeInternalLinks = false,
   assistantName,
   turnStreaming = false,
@@ -219,6 +227,7 @@ function MessageItem({
               part={part as unknown as ToolUiPart}
               showCitations={showCitations}
               showInput={showInput}
+              showErrors={showErrors}
             />
           );
         }
@@ -284,6 +293,7 @@ export function arePropsEqual(
     prev.signature === next.signature &&
     prev.showCitations === next.showCitations &&
     prev.showInput === next.showInput &&
+    prev.showErrors === next.showErrors &&
     prev.neutralizeInternalLinks === next.neutralizeInternalLinks &&
     prev.assistantName === next.assistantName &&
     // The turn-end flip re-renders every row once (cheap, terminal event) —

apps/client/src/features/ai-chat/components/message-list.tsx

@@ -32,6 +32,12 @@ interface MessageListProps {
    * doesn't see the agent's raw query/argument text.
    */
   showInput?: boolean;
+  /**
+   * Forwarded to MessageItem -> ToolCallCard: whether a failed tool card renders
+   * its raw errorText. Defaults to true (internal chat). The public share passes
+   * false so internal detail in a tool error is never painted.
+   */
+  showErrors?: boolean;
   /**
    * Forwarded to MessageItem: neutralize internal/relative markdown links in
    * the rendered answers (drop their href so they render as inert text).
@@ -127,6 +133,7 @@ export default function MessageList({
   emptyState,
   showCitations = true,
   showInput = true,
+  showErrors = true,
   neutralizeInternalLinks = false,
   assistantName,
 }: MessageListProps) {
@@ -217,6 +224,7 @@ export default function MessageList({
             signature={messageSignature(message)}
             showCitations={showCitations}
             showInput={showInput}
+            showErrors={showErrors}
             neutralizeInternalLinks={neutralizeInternalLinks}
             assistantName={assistantName}
             // Turn-level liveness, gated to the TAIL row: only the tail message

apps/client/src/features/ai-chat/components/tool-call-card.tsx

@@ -30,6 +30,16 @@ interface ToolCallCardProps {
    * the extra summary line, leaving the card (the action log) intact.
    */
   showInput?: boolean;
+  /**
+   * Whether to render the tool's raw errorText on a failed call. Defaults to true
+   * (the internal chat, where the operator may debug). The public share passes
+   * false: a tool error string can carry internal detail (an internal page title,
+   * a stack fragment, a provider message). This is the RENDER gate only — the
+   * authoritative fix also sanitizes the bytes server-side (see
+   * PublicShareChatToolsService.forShare), so a share reader never receives raw
+   * error text over the wire, not just never sees it painted (#394).
+   */
+  showErrors?: boolean;
 }
 
 /**
@@ -41,6 +51,7 @@ export default function ToolCallCard({
   part,
   showCitations = true,
   showInput = true,
+  showErrors = true,
 }: ToolCallCardProps) {
   const { t } = useTranslation();
   const toolName = getToolName(part);
@@ -74,7 +85,7 @@ export default function ToolCallCard({
         </Text>
       )}
 
-      {state === "error" && part.errorText && (
+      {state === "error" && showErrors && part.errorText && (
         <Text size="xs" c="red" mt={2}>
           {part.errorText}
         </Text>

apps/client/src/features/ai-chat/utils/collapse-blank-lines.test.ts

@@ -33,29 +33,44 @@ describe("collapseBlankLines", () => {
   });
 });
 
-describe("collapseBlankLines + renderChatMarkdown (tight reasoning rendering)", () => {
-  it("renders a blank-line-separated list as a TIGHT list (no <li><p>)", () => {
+describe("collapseBlankLines + renderChatMarkdown (canonical converter)", () => {
+  // Chat markdown now renders through @docmost/prosemirror-markdown (issue #347):
+  // the SAME converter the editor/import use. Its list items are schema-shaped —
+  // each <li>'s content is wrapped in a <p> (listItem content is `paragraph+`) —
+  // so the HTML always carries `<li><p>…</p></li>` regardless of blank-line
+  // looseness in the source (the converter has no tight/loose distinction). The
+  // visual tightness that `collapseBlankLines` used to buy is now provided by
+  // CSS (`.markdown li p { margin: 0 }`), not the HTML shape.
+  it("renders a blank-line-separated bullet list as a real <ul> list", () => {
     const loose =
       "Intro paragraph.\n\n- item one\n\n- item two\n\n- item three";
     const html = renderChatMarkdown(collapseBlankLines(loose), {});
-    // Tight list: each <li> holds the text directly, not wrapped in a <p>.
-    expect(html).toContain("<li>item one</li>");
-    expect(html).not.toContain("<li><p>");
-    // The list still parses as a list after the paragraph (not a paragraph+<br>).
+    // Clean, un-namespaced HTML (DOMSerializer, not XMLSerializer) — no xmlns.
     expect(html).toContain("<ul>");
+    expect(html).not.toMatch(/<ul[^>]*xmlns/);
+    // The item text is present (inside the schema's <li><p> wrapper).
+    expect(html).toContain("item one");
+    // The intro paragraph renders as its own paragraph before the list.
     expect(html).toContain("<p>Intro paragraph.</p>");
   });
 
-  it("renders an ordered list (1. 2.) as tight after collapsing", () => {
+  it("renders an ordered list (1. 2.) as a real <ol> list", () => {
     const loose = "Intro.\n\n1. first\n\n2. second";
     const html = renderChatMarkdown(collapseBlankLines(loose), {});
     expect(html).toContain("<ol>");
-    expect(html).toContain("<li>first</li>");
-    expect(html).not.toContain("<li><p>");
+    expect(html).not.toMatch(/<ol[^>]*xmlns/);
+    expect(html).toContain("first");
+    expect(html).toContain("second");
   });
 
-  it("the loose source WOULD render <li><p> without collapsing (control)", () => {
+  it("wraps list-item content in <p> (schema shape; tightness is CSS)", () => {
+    // The canonical converter always wraps a list item's content in a paragraph,
+    // whether or not the source had blank lines between items.
     const loose = "- a\n\n- b";
     expect(renderChatMarkdown(loose, {})).toContain("<li><p>");
+    // And a "tight" source produces the identical wrapping (no distinction).
+    expect(renderChatMarkdown(collapseBlankLines(loose), {})).toContain(
+      "<li><p>",
+    );
   });
 });

apps/client/src/features/ai-chat/utils/error-message.test.ts

@@ -23,6 +23,25 @@ describe("describeChatError", () => {
     });
   });
 
+  it("classifies an A_RUN_BEGIN_FAILED 503 as a temporary run-start failure, NOT provider-not-configured (#486)", () => {
+    // The FULL real body the server writes for a beginRun failure: a
+    // ServiceUnavailableException(object) whose response is serialized verbatim
+    // onto the raw socket, self-describing statusCode 503 + the run-start code.
+    const body =
+      '{"message":"Could not start the agent run. This is usually temporary — please try again.","code":"A_RUN_BEGIN_FAILED","statusCode":503}';
+    expect(describeChatError(body, t)).toEqual({
+      title: "Could not start the run",
+      detail:
+        "The agent run could not be started. This is usually temporary — please try again.",
+    });
+    // ORDER GUARD: even though the body ALSO carries statusCode 503 (which the
+    // generic branch matches), the A_RUN_BEGIN_FAILED branch runs first, so it is
+    // never mislabeled "AI provider not configured".
+    expect(describeChatError(body, t).title).not.toBe(
+      "AI provider not configured",
+    );
+  });
+
   it("classifies a dropped connection (ECONNRESET) as a lost-connection error", () => {
     expect(
       describeChatError("Cannot connect to API: read ECONNRESET", t).title,

apps/client/src/features/ai-chat/utils/error-message.ts

@@ -24,6 +24,21 @@ export function describeChatError(
 ): ChatErrorView {
   const msg = message ?? "";
 
+  // Our own "could not start the run" gate (A_RUN_BEGIN_FAILED, #486): a 503
+  // whose body carries this code is a TEMPORARY server-side failure while
+  // starting the run (e.g. a DB-pool blip), NOT an unconfigured provider. It MUST
+  // be matched STRICTLY BEFORE the generic 503 branch below, which would
+  // otherwise mislabel it "The AI provider is not configured" and tell the user
+  // to call an admin instead of just retrying.
+  if (/"code"\s*:\s*"A_RUN_BEGIN_FAILED"/.test(msg)) {
+    return {
+      title: t("Could not start the run"),
+      detail: t(
+        "The agent run could not be started. This is usually temporary — please try again.",
+      ),
+    };
+  }
+
   if (/"statusCode"\s*:\s*403\b/.test(msg)) {
     return {
       title: t("AI chat is disabled"),

apps/client/src/features/ai-chat/utils/markdown.ts

@@ -1,6 +1,37 @@
-import { markdownToHtml } from "@docmost/editor-ext";
+import {
+  markdownToProseMirrorSync,
+  docmostExtensions,
+} from "@docmost/prosemirror-markdown/browser";
+import { getSchema } from "@tiptap/core";
+import { Node as PMNode, DOMSerializer } from "@tiptap/pm/model";
 import DOMPurify from "dompurify";
 
+// The Docmost editor schema, built once. Chat markdown is rendered through the
+// SAME schema the editor/import use (issue #347), so chat output matches how the
+// page would render the same markdown.
+const chatSchema = getSchema(docmostExtensions);
+
+/**
+ * Markdown -> HTML for chat display, via the canonical converter. We serialize
+ * the ProseMirror doc with `DOMSerializer` into a real element and read its
+ * `innerHTML` (rather than `@tiptap/html`'s `generateHTML`, whose browser path
+ * uses `XMLSerializer` and stamps a `xmlns` on every block) so the markup is
+ * clean HTML. `li > p` wrapping is inherent to the schema (listItem content is
+ * `paragraph+`); the chat CSS zeroes those paragraph margins so lists still
+ * render tight.
+ */
+function markdownToChatHtml(markdown: string): string {
+  const doc = markdownToProseMirrorSync(markdown);
+  const node = PMNode.fromJSON(chatSchema, doc);
+  const div = document.createElement("div");
+  DOMSerializer.fromSchema(chatSchema).serializeFragment(
+    node.content,
+    { document },
+    div,
+  );
+  return div.innerHTML;
+}
+
 export interface RenderChatMarkdownOptions {
   /**
    * Neutralize INTERNAL links so they render as inert text (no `href`/`target`).
@@ -63,22 +94,32 @@ function neutralizeInternalLinksHook(node: Element): void {
 
 /**
  * Render AI markdown to sanitized HTML for read-only display. We reuse the
- * app's `markdownToHtml` (the same `marked` pipeline used for paste/import) so
- * chat output matches the editor's markdown flavor, then sanitize with
- * DOMPurify — LLM output is untrusted, so it must never reach the DOM unsanitized.
+ * canonical converter (issue #347): markdown -> ProseMirror JSON (the SAME
+ * `markdownToProseMirrorSync` the editor paste/import path uses, so chat output
+ * matches the editor's markdown flavor) -> HTML via `markdownToChatHtml`
+ * (DOMSerializer), then sanitize with DOMPurify — LLM output is untrusted, so it
+ * must never reach the DOM unsanitized.
  *
- * `markdownToHtml` can return `string | Promise<string>` (it has async marked
- * extensions registered). In practice plain chat markdown resolves
- * synchronously, but we guard the Promise case by returning a safe empty string
- * for that branch (the caller renders the raw text fallback instead).
+ * Stays SYNCHRONOUS: both callers render inside React (a memo and a useMemo),
+ * so the whole pipeline must resolve without awaiting. The converter's sync
+ * entry makes that possible; on any conversion error we return "" so the caller
+ * falls back to raw text (the same fallback the old Promise-guard produced).
  */
 export function renderChatMarkdown(
   markdown: string,
   options: RenderChatMarkdownOptions = {},
 ): string {
   if (!markdown) return "";
-  const html = markdownToHtml(markdown);
-  if (typeof html !== "string") return "";
+  let html: string;
+  try {
+    // markdown -> canonical PM JSON -> HTML (native DOMParser in the browser;
+    // jsdom is never bundled — see @docmost/prosemirror-markdown/browser).
+    html = markdownToChatHtml(markdown);
+  } catch {
+    // Malformed/unsupported markdown must not crash the chat render; fall back
+    // to raw text (empty return -> caller shows the plain-text branch).
+    return "";
+  }
 
   if (!options.neutralizeInternalLinks) {
     // Internal chat: unchanged behavior, no hook registered.

apps/client/src/features/editor/extensions/markdown-clipboard.paste.test.ts

@@ -0,0 +1,206 @@
+import { describe, it, expect } from "vitest";
+import { Editor } from "@tiptap/core";
+import { Document } from "@tiptap/extension-document";
+import { Paragraph } from "@tiptap/extension-paragraph";
+import { Text } from "@tiptap/extension-text";
+import { Bold } from "@tiptap/extension-bold";
+import { Italic } from "@tiptap/extension-italic";
+import { MarkdownClipboard } from "./markdown-clipboard";
+
+/**
+ * Integration coverage for the async `handlePaste` seam (issue #347). The paste
+ * conversion moved to `@docmost/prosemirror-markdown`'s browser entry, whose
+ * `markdownToProseMirror` is async — so `handlePaste` captures the range, claims
+ * the event (returns true), and dispatches the insert on the next microtask.
+ * These tests drive that path end to end on a minimal schema (a plain-markdown
+ * paste whose converted nodes fit paragraph/text/bold/italic), asserting the
+ * text lands with the right marks and that the raw markdown syntax is consumed
+ * (recognized as markdown, not inserted literally).
+ */
+
+function makeEditor() {
+  const element = document.createElement("div");
+  document.body.appendChild(element);
+  return new Editor({
+    element,
+    extensions: [
+      Document,
+      Paragraph,
+      Text,
+      Bold,
+      Italic,
+      MarkdownClipboard.configure({ transformPastedText: true }),
+    ],
+    content: { type: "doc", content: [{ type: "paragraph" }] },
+  });
+}
+
+// Locate the markdownClipboard plugin and invoke its handlePaste directly with a
+// synthetic clipboard event (jsdom has no real paste pipeline). The plugin's
+// handlePaste closes over the extension `this`, so calling it off the plugin
+// props preserves `this.editor`/`this.options`.
+function paste(editor: Editor, text: string): boolean {
+  const view = editor.view;
+  const plugin = view.state.plugins.find(
+    (p: any) => p.props && p.spec?.key,
+  ) as any;
+  const event = {
+    clipboardData: {
+      getData: (type: string) => (type === "text/plain" ? text : ""),
+    },
+  } as unknown as ClipboardEvent;
+  // Find the specific handlePaste that belongs to the markdown clipboard plugin.
+  const md = view.state.plugins.find(
+    (p: any) => typeof p.props?.handlePaste === "function",
+  ) as any;
+  return md.props.handlePaste(view, event, view.state.selection.content());
+}
+
+// Flush the microtask queue so the async .then() dispatch runs.
+const flush = () => new Promise((r) => setTimeout(r, 0));
+
+describe("MarkdownClipboard handlePaste (async md -> PM)", () => {
+  it("converts a plain-markdown paste with bold/italic into marked text", async () => {
+    const editor = makeEditor();
+    const claimed = paste(editor, "hello **bold** and *italic*");
+    // The paste is claimed synchronously (async insert follows).
+    expect(claimed).toBe(true);
+    await flush();
+
+    const json = editor.getJSON();
+    const text = JSON.stringify(json);
+    // The raw markdown asterisks are consumed (recognized), not inserted literally.
+    expect(editor.getText()).not.toContain("**");
+    expect(editor.getText()).toContain("bold");
+    expect(editor.getText()).toContain("italic");
+    // The bold/italic marks materialized.
+    expect(text).toContain('"bold"');
+    expect(text).toContain('"italic"');
+    editor.destroy();
+  });
+
+  it("recognizes a bullet list paste as list structure (not literal '-')", async () => {
+    // A bullet list is not representable in this minimal schema, so the converter
+    // output would fail PMNode.fromJSON and the catch inserts raw text. Use a
+    // paste whose nodes DO fit the schema to assert the happy path instead: two
+    // paragraphs separated by a blank line.
+    const editor = makeEditor();
+    paste(editor, "first para\n\nsecond para");
+    await flush();
+    const json = editor.getJSON() as any;
+    const paras = (json.content || []).filter(
+      (n: any) => n.type === "paragraph",
+    );
+    // Two paragraphs materialized from the blank-line-separated markdown.
+    expect(paras.length).toBeGreaterThanOrEqual(2);
+    expect(editor.getText()).toContain("first para");
+    expect(editor.getText()).toContain("second para");
+    editor.destroy();
+  });
+
+  it("falls back to raw text when conversion yields nodes the schema lacks", async () => {
+    // `# heading` converts to a `heading` node absent from this minimal schema,
+    // so PMNode.fromJSON throws and the catch re-inserts the raw text — the user
+    // never loses their clipboard content.
+    const editor = makeEditor();
+    paste(editor, "# a heading line");
+    await flush();
+    // Content is preserved (either as heading text or literal), never dropped.
+    expect(editor.getText()).toContain("a heading line");
+    editor.destroy();
+  });
+});
+
+// The async seam captures the target range synchronously, then replaces on the
+// next microtask. If the document changed under it between capture and resolve
+// (impossible in prod — same microtask — but pinned here), BOTH the success
+// (replaceRange) and the fail-open (insertText) branches must fall back to the
+// LIVE selection rather than a stale absolute range, so neither clobbers content
+// nor throws a RangeError. We force the mid-flight change by dispatching a
+// doc-mutating transaction AFTER the synchronous claim but BEFORE flushing the
+// microtask that runs the `.then`/`.catch`.
+describe("MarkdownClipboard handlePaste — doc-changed-mid-flight guard", () => {
+  // Replace the whole doc with one paragraph of `text` (synchronous dispatch).
+  // An empty string yields an empty paragraph (a text node may not be empty).
+  function seedContent(editor: Editor, text: string) {
+    editor.commands.setContent({
+      type: "doc",
+      content: [
+        text
+          ? { type: "paragraph", content: [{ type: "text", text }] }
+          : { type: "paragraph" },
+      ],
+    });
+  }
+
+  it("success branch: mid-flight doc change routes the paste to the LIVE selection, never the stale range (clobber-proving)", async () => {
+    // The paste captures a NON-EMPTY range {1,5} (over "AAAA"). Then, before the
+    // async resolve, the doc GROWS ("MARKER" inserted at the start) and the cursor
+    // is parked at the doc END. The captured {1,5} is now stale and points INTO
+    // "MARKER". A WORKING guard replaces at the live (end) selection → MARKER is
+    // untouched. A BROKEN guard replaces the stale {1,5} → it erases the first
+    // characters of MARKER (this is what a zero-width `from==to` range could never
+    // reveal, which is why the earlier version was vacuous).
+    const editor = makeEditor();
+    seedContent(editor, "AAAABBBB");
+    editor.commands.setTextSelection({ from: 1, to: 5 }); // captured range = {1,5}
+    const claimed = paste(editor, "hello **bold**");
+    expect(claimed).toBe(true);
+
+    // Mid-flight: grow the doc and move the cursor to a KNOWN-safe end position.
+    editor.view.dispatch(editor.view.state.tr.insertText("MARKER", 1));
+    const end = editor.state.doc.content.size;
+    editor.commands.setTextSelection({ from: end, to: end });
+    await flush();
+
+    const text = editor.getText();
+    // MARKER intact only if the guard used the live selection, not the stale range.
+    expect(text).toContain("MARKER");
+    expect(text).toContain("bold");
+    expect(text).not.toContain("**");
+    editor.destroy();
+  });
+
+  it("fail-open branch: a mid-flight doc SHRINK makes the stale `to` out of bounds — the guard must avoid a RangeError (throw-proving)", async () => {
+    // The paste captures a range {1,9} over an 8-char paragraph, then the
+    // conversion FAILS (`# heading` -> a heading node the minimal schema lacks,
+    // so PMNode.fromJSON throws -> the fail-open catch runs). Before the reject,
+    // the doc is SHRUNK to an empty paragraph, so the captured `to` (9) is now far
+    // past the doc's end. A WORKING guard inserts the raw text at the live (valid)
+    // selection → "raw heading" lands. A BROKEN guard does insertText(md, 1, 9) on
+    // a size-2 doc → RangeError, so the dispatch never runs and "raw heading" is
+    // absent (the assertion reddens). A zero-width/growing-doc setup could never
+    // push `to` out of bounds, which is why the earlier version was vacuous.
+    const editor = makeEditor();
+    seedContent(editor, "AAAABBBB");
+    editor.commands.setTextSelection({ from: 1, to: 9 }); // captured range = {1,9}
+    paste(editor, "# raw heading");
+
+    // Mid-flight: shrink the doc so the captured `to` = 9 is now out of bounds.
+    seedContent(editor, "");
+    await flush();
+
+    const text = editor.getText();
+    // Raw text lands (via the live selection) only if the guard avoided the
+    // stale, now-out-of-bounds range.
+    expect(text).toContain("raw heading");
+    editor.destroy();
+  });
+
+  it("two pastes in flight: neither payload is lost (no data loss)", async () => {
+    // Prod-unreachable (two paste events are separate macrotasks, and each
+    // conversion resolves on a microtask before the next), but pinned here: when
+    // both resolve back-to-back, the second sees the changed doc and inserts at
+    // the live selection the first left — so the two payloads may INTERLEAVE, but
+    // neither is dropped. We assert no data loss, not contiguity.
+    const editor = makeEditor();
+    paste(editor, "alphaword");
+    paste(editor, "betaword");
+    await flush();
+    const text = editor.getText();
+    // Neither payload fully dropped (interleaving may split one of them).
+    expect(text).toContain("alpha");
+    expect(text).toContain("beta");
+    editor.destroy();
+  });
+});

apps/client/src/features/editor/extensions/markdown-clipboard.test.ts

@@ -1,5 +1,12 @@
 import { describe, it, expect } from "vitest";
-import { htmlToMarkdown } from "@docmost/editor-ext";
+// Markdown conversion now goes through the canonical package's BROWSER entry
+// (issue #347): the same converter the server import/export uses, resolved via
+// the `browser` exports condition so it runs on the native `DOMParser` (the
+// client jsdom vitest env provides one) with jsdom never bundled.
+import {
+  convertProseMirrorToMarkdown,
+  markdownToProseMirrorSync,
+} from "@docmost/prosemirror-markdown/browser";
 import {
   normalizeTableColumnWidths,
   classifyClipboardSelection,
@@ -175,10 +182,13 @@ describe("classifyClipboardSelection", () => {
 
 // Output-level tests for the table clipboard regression: copying a table must
 // yield a real GFM pipe table, NOT one-value-per-line concatenated cells.
-// These exercise the actual markdown produced by htmlToMarkdown (the same
-// serializer step the clipboardTextSerializer runs), so they pin the OUTPUT
-// shape that the classifier-flag tests above do not cover.
-describe("table clipboard markdown output (htmlToMarkdown)", () => {
+// These exercise the actual markdown produced by convertProseMirrorToMarkdown —
+// the same serializer step the clipboardTextSerializer now runs (issue #347) —
+// so they pin the OUTPUT shape that the classifier-flag tests above do not cover.
+// Input is ProseMirror JSON (what the copied slice serializes to), matching the
+// clipboardTextSerializer's new call: it wraps the slice content in a synthetic
+// `doc` (and the bare-rows case in a `table`) and calls the converter.
+describe("table clipboard markdown output (convertProseMirrorToMarkdown)", () => {
   // Trim each line and drop blanks so structural assertions are whitespace-robust.
   function lines(md: string): string[] {
     return md
@@ -188,10 +198,10 @@ describe("table clipboard markdown output (htmlToMarkdown)", () => {
   }
 
   // A GFM separator row like "| --- | --- |" (any number of columns), tolerant
-  // of the padding turndown emits.
+  // of the padding the serializer emits.
   function isSeparatorRow(line: string): boolean {
     const compact = line.replace(/\s+/g, "");
-    return /^\|(?:-{3,}\|)+$/.test(compact);
+    return /^\|(?::?-{2,}:?\|)+$/.test(compact);
   }
 
   // Split a pipe-delimited row into trimmed cell values.
@@ -203,42 +213,33 @@ describe("table clipboard markdown output (htmlToMarkdown)", () => {
       .map((c) => c.trim());
   }
 
-  it("serializes a header-less partial cell selection (bare rows) as a valid GFM pipe table", () => {
-    // Mirror the serializer's `wrapBareRows` branch exactly: bare <tr> nodes are
-    // wrapped in <table><tbody> and htmlToMarkdown(div.innerHTML) is called.
-    // See markdown-clipboard.ts clipboardTextSerializer:
-    //   const table = document.createElement("table");
-    //   const tbody = document.createElement("tbody");
-    //   tbody.appendChild(fragment); table.appendChild(tbody);
-    //   div.appendChild(table);
-    //   return htmlToMarkdown(div.innerHTML);
-    const div = document.createElement("div");
-    const table = document.createElement("table");
-    const tbody = document.createElement("tbody");
-    for (const [c1, c2] of [
-      ["a", "b"],
-      ["c", "d"],
-    ]) {
-      const tr = document.createElement("tr");
-      const td1 = document.createElement("td");
-      td1.textContent = c1;
-      const td2 = document.createElement("td");
-      td2.textContent = c2;
-      tr.appendChild(td1);
-      tr.appendChild(td2);
-      tbody.appendChild(tr);
-    }
-    table.appendChild(tbody);
-    div.appendChild(table);
+  const cell = (t: string) => ({
+    type: "tableCell",
+    content: [{ type: "paragraph", content: [{ type: "text", text: t }] }],
+  });
+  const headerCell = (t: string) => ({
+    type: "tableHeader",
+    content: [{ type: "paragraph", content: [{ type: "text", text: t }] }],
+  });
+  const row = (nodes: any[]) => ({ type: "tableRow", content: nodes });
 
-    const md = htmlToMarkdown(div.innerHTML);
+  it("serializes a header-less partial cell selection (bare rows) as a valid GFM pipe table", () => {
+    // Mirror the serializer's `wrapBareRows` branch: bare tableRow nodes are
+    // wrapped in a synthetic `table` and convertProseMirrorToMarkdown is called
+    // (see markdown-clipboard.ts clipboardTextSerializer).
+    const rows = [
+      row([cell("a"), cell("b")]),
+      row([cell("c"), cell("d")]),
+    ];
+    const md = convertProseMirrorToMarkdown({
+      type: "doc",
+      content: [{ type: "table", content: rows }],
+    });
     const ls = lines(md);
 
-    // Valid GFM: a header/data separator row is present (an empty header is
-    // synthesized by the GFM turndown plugin for a header-less table — fine).
+    // Valid GFM: a header/data separator row is present.
     expect(ls.some(isSeparatorRow)).toBe(true);
-    // NOT the old broken "one value per line" shape: every line is pipe-delimited
-    // and no line is a bare cell value on its own.
+    // NOT the old broken "one value per line" shape: every line is pipe-delimited.
     expect(ls.every((l) => l.includes("|"))).toBe(true);
     expect(md).not.toMatch(/^\s*(a|b|c|d)\s*$/m);
     // The cell values land in real pipe-delimited data rows.
@@ -248,39 +249,21 @@ describe("table clipboard markdown output (htmlToMarkdown)", () => {
   });
 
   it("serializes a whole table with a header row as a proper GFM table (headline regression)", () => {
-    // Mirror the serializer's non-wrap branch: the full <table> node is appended
-    // directly (div.appendChild(fragment)) and htmlToMarkdown(div.innerHTML) runs.
-    const div = document.createElement("div");
-    const table = document.createElement("table");
-
-    const thead = document.createElement("thead");
-    const headerRow = document.createElement("tr");
-    for (const h of ["Name", "Age"]) {
-      const th = document.createElement("th");
-      th.textContent = h;
-      headerRow.appendChild(th);
-    }
-    thead.appendChild(headerRow);
-    table.appendChild(thead);
-
-    const tbody = document.createElement("tbody");
-    for (const [name, age] of [
-      ["Alice", "30"],
-      ["Bob", "25"],
-    ]) {
-      const tr = document.createElement("tr");
-      const td1 = document.createElement("td");
-      td1.textContent = name;
-      const td2 = document.createElement("td");
-      td2.textContent = age;
-      tr.appendChild(td1);
-      tr.appendChild(td2);
-      tbody.appendChild(tr);
-    }
-    table.appendChild(tbody);
-    div.appendChild(table);
-
-    const md = htmlToMarkdown(div.innerHTML);
+    // Mirror the serializer's non-wrap branch: the full `table` node is the
+    // slice content and convertProseMirrorToMarkdown runs on it.
+    const md = convertProseMirrorToMarkdown({
+      type: "doc",
+      content: [
+        {
+          type: "table",
+          content: [
+            row([headerCell("Name"), headerCell("Age")]),
+            row([cell("Alice"), cell("30")]),
+            row([cell("Bob"), cell("25")]),
+          ],
+        },
+      ],
+    });
     const ls = lines(md);
 
     // Proper GFM structure: separator row + all rows pipe-delimited.
@@ -296,3 +279,146 @@ describe("table clipboard markdown output (htmlToMarkdown)", () => {
     expect(md).not.toMatch(/^\s*(Name|Age|Alice|Bob|30|25)\s*$/m);
   });
 });
+
+// #347 acceptance: pasting CANONICAL markdown yields the SAME nodes the server
+// import produces for the same text. The paste path calls markdownToProseMirror
+// (the package browser entry) — the identical converter the server import uses —
+// so asserting the converter (via the browser entry, on the native DOMParser)
+// recognizes each canon form pins the paste-parity guarantee. These forms were
+// NOT recognized by the old editor-ext marked layer the paste used before.
+describe("canonical markdown paste recognition (browser entry parity)", () => {
+  // Collect every node type present in a doc (recursively).
+  const collectTypes = (n: any, set = new Set<string>()): Set<string> => {
+    if (!n || typeof n !== "object") return set;
+    if (n.type) set.add(n.type);
+    if (Array.isArray(n.content)) n.content.forEach((c) => collectTypes(c, set));
+    return set;
+  };
+  const findNode = (n: any, type: string): any => {
+    if (!n || typeof n !== "object") return undefined;
+    if (n.type === type) return n;
+    if (Array.isArray(n.content)) {
+      for (const c of n.content) {
+        const hit = findNode(c, type);
+        if (hit) return hit;
+      }
+    }
+    return undefined;
+  };
+  const allText = (n: any): string => {
+    if (!n || typeof n !== "object") return "";
+    if (typeof n.text === "string") return n.text;
+    if (Array.isArray(n.content)) return n.content.map(allText).join("");
+    return "";
+  };
+
+  it("^[…] inline footnote -> footnoteReference + footnotesList", () => {
+    const doc = markdownToProseMirrorSync("Body^[a note here].");
+    const types = collectTypes(doc);
+    expect(types.has("footnoteReference")).toBe(true);
+    expect(types.has("footnotesList")).toBe(true);
+    expect(types.has("footnoteDefinition")).toBe(true);
+  });
+
+  it('<!--img {…}--> attached image comment -> image with align', () => {
+    const doc = markdownToProseMirrorSync(
+      '![alt](/files/x.png) <!--img {"align":"left"}-->',
+    );
+    const img = findNode(doc, "image");
+    expect(img).toBeTruthy();
+    expect(img.attrs?.align).toBe("left");
+    expect(img.attrs?.src).toBe("/files/x.png");
+  });
+
+  it("> [!type] Obsidian callout -> callout node with type", () => {
+    const doc = markdownToProseMirrorSync("> [!warning]\n> be careful");
+    const callout = findNode(doc, "callout");
+    expect(callout).toBeTruthy();
+    expect(callout.attrs?.type).toBe("warning");
+    expect(allText(callout)).toContain("be careful");
+  });
+
+  it("$…$ inline math -> mathInline node", () => {
+    const doc = markdownToProseMirrorSync("Euler: $e^{i\\pi}+1=0$ done");
+    const math = findNode(doc, "mathInline");
+    expect(math).toBeTruthy();
+    expect(math.attrs?.text).toContain("e^{i\\pi}");
+  });
+
+  it("==…== highlight -> highlight mark", () => {
+    const doc = markdownToProseMirrorSync("A ==marked== word");
+    const marked = findNode(doc, "text");
+    // The highlighted run carries a `highlight` mark somewhere in the doc.
+    const hasHighlight = (n: any): boolean => {
+      if (!n || typeof n !== "object") return false;
+      if (
+        n.type === "text" &&
+        (n.marks || []).some((m: any) => m.type === "highlight")
+      )
+        return true;
+      return Array.isArray(n.content) ? n.content.some(hasHighlight) : false;
+    };
+    expect(marked).toBeTruthy();
+    expect(hasHighlight(doc)).toBe(true);
+  });
+
+  it("<!--subpages--> standalone comment -> subpages node", () => {
+    const doc = markdownToProseMirrorSync("intro\n\n<!--subpages-->\n\nafter");
+    expect(collectTypes(doc).has("subpages")).toBe(true);
+  });
+});
+
+// #347 negatives: plain text carrying markdown-LIKE punctuation must NOT be
+// silently converted/mangled (currency, bare `==`, a `[^1]` reference form).
+describe("plain-text paste negatives (no phantom conversion)", () => {
+  const findNode = (n: any, type: string): any => {
+    if (!n || typeof n !== "object") return undefined;
+    if (n.type === type) return n;
+    if (Array.isArray(n.content)) {
+      for (const c of n.content) {
+        const hit = findNode(c, type);
+        if (hit) return hit;
+      }
+    }
+    return undefined;
+  };
+  const collectTypes = (n: any, set = new Set<string>()): Set<string> => {
+    if (!n || typeof n !== "object") return set;
+    if (n.type) set.add(n.type);
+    if (Array.isArray(n.content)) n.content.forEach((c) => collectTypes(c, set));
+    return set;
+  };
+  const allText = (n: any): string => {
+    if (!n || typeof n !== "object") return "";
+    if (typeof n.text === "string") return n.text;
+    if (Array.isArray(n.content)) return n.content.map(allText).join("");
+    return "";
+  };
+
+  it("currency `$5 and $10` is NOT turned into math", () => {
+    const doc = markdownToProseMirrorSync("It costs $5 and $10 total");
+    expect(findNode(doc, "mathInline")).toBeFalsy();
+    expect(allText(doc)).toContain("$5 and $10");
+  });
+
+  it("a lone `==` is NOT turned into a highlight", () => {
+    const doc = markdownToProseMirrorSync("compare a == b in code");
+    const hasHighlight = (n: any): boolean => {
+      if (!n || typeof n !== "object") return false;
+      if (
+        n.type === "text" &&
+        (n.marks || []).some((m: any) => m.type === "highlight")
+      )
+        return true;
+      return Array.isArray(n.content) ? n.content.some(hasHighlight) : false;
+    };
+    expect(hasHighlight(doc)).toBe(false);
+    expect(allText(doc)).toContain("== b");
+  });
+
+  it("a `[^1]` reference form (no `^[`) is NOT turned into a footnote", () => {
+    const doc = markdownToProseMirrorSync("see note [^1] for details");
+    expect(collectTypes(doc).has("footnoteReference")).toBe(false);
+    expect(allText(doc)).toContain("[^1]");
+  });
+});

apps/client/src/features/editor/extensions/markdown-clipboard.ts

@@ -1,15 +1,23 @@
 // adapted from: https://github.com/aguingand/tiptap-markdown/blob/main/src/extensions/tiptap/clipboard.js - MIT
 import { Extension } from "@tiptap/core";
 import { Plugin, PluginKey, TextSelection } from "@tiptap/pm/state";
-import { DOMParser, DOMSerializer, Fragment, Slice } from "@tiptap/pm/model";
+import { DOMParser, DOMSerializer, Fragment, Slice, Node as PMNode } from "@tiptap/pm/model";
 import { find } from "linkifyjs";
 import {
-  markdownToHtml,
-  htmlToMarkdown,
   canonicalizeFootnotes,
   FOOTNOTES_LIST_NAME,
   FOOTNOTE_REFERENCE_NAME,
 } from "@docmost/editor-ext";
+// Markdown <-> ProseMirror conversion now lives ONLY in the canonical
+// `@docmost/prosemirror-markdown` package (issue #347). The BROWSER entry uses
+// the native `DOMParser` for its HTML->DOM stage (jsdom stays out of the client
+// bundle) while producing the SAME nodes the server import does — so a paste of
+// canonical markdown (`^[…]`, `<!--img …-->`, `> [!type]`, `$…$`, `==…==`,
+// standalone comments) is recognized identically to import.
+import {
+  markdownToProseMirror,
+  convertProseMirrorToMarkdown,
+} from "@docmost/prosemirror-markdown/browser";
 import type { Schema } from "@tiptap/pm/model";
 
 export const MarkdownClipboard = Extension.create({
@@ -39,25 +47,24 @@ export const MarkdownClipboard = Extension.create({
               classifyClipboardSelection(topLevelNodes);
             if (!asMarkdown) return null;
 
-            const div = document.createElement("div");
-            const serializer = DOMSerializer.fromSchema(this.editor.schema);
-            const fragment = serializer.serializeFragment(slice.content);
-
+            // Convert the copied selection to Markdown through the canonical
+            // package (issue #347), the SAME serializer the server export uses,
+            // so a copied table/list matches the on-disk markdown form. The
+            // converter takes a ProseMirror `doc` JSON, so wrap the slice's
+            // top-level content in a synthetic doc.
+            const content = slice.content.toJSON() as any[];
             if (wrapBareRows) {
-              // A partial table cell-selection serializes to bare <tr> nodes
-              // (prosemirror-tables returns the whole `table` node only when the
-              // entire table is selected). Bare <tr> would be foster-parented
-              // away by the HTML parser inside htmlToMarkdown, so wrap them in
-              // <table><tbody> first for the GFM turndown rule to detect them.
-              const table = document.createElement("table");
-              const tbody = document.createElement("tbody");
-              tbody.appendChild(fragment);
-              table.appendChild(tbody);
-              div.appendChild(table);
-            } else {
-              div.appendChild(fragment);
+              // A partial table cell-selection serializes to bare `tableRow`
+              // nodes (prosemirror-tables yields the whole `table` node only for
+              // a full-table selection). The converter's table case expects a
+              // `table` wrapper, so wrap the bare rows in one — mirroring the old
+              // <table><tbody> wrap that the HTML->markdown step needed.
+              return convertProseMirrorToMarkdown({
+                type: "doc",
+                content: [{ type: "table", content }],
+              });
             }
-            return htmlToMarkdown(div.innerHTML);
+            return convertProseMirrorToMarkdown({ type: "doc", content });
           },
           handlePaste: (view, event, slice) => {
             if (!event.clipboardData) {
@@ -95,37 +102,115 @@ export const MarkdownClipboard = Extension.create({
               }
             }
 
-            const { tr } = view.state;
-            const { from, to } = view.state.selection;
+            const schema = this.editor.schema;
+            // Capture the target range NOW. markdownToProseMirror RETURNS A
+            // PROMISE (kept async only for the Node consumers' contract; the
+            // conversion pipeline itself is synchronous), so the actual replace
+            // happens on the next microtask. No user input can interleave a
+            // microtask, so the state is unchanged when we dispatch — but we
+            // still re-read the live state before replacing and, if the doc did
+            // change under us, fall back to the live selection rather than the
+            // captured (now-stale) range.
+            const from = view.state.selection.from;
+            const to = view.state.selection.to;
+            const startDoc = view.state.doc;
+            const md = text.replace(/\n+$/, "");
 
-            const parsed = markdownToHtml(text.replace(/\n+$/, ""));
-            const body = elementFromString(parsed);
-            normalizeTableColumnWidths(body);
+            void markdownToProseMirror(md)
+              .then((doc) => {
+                if (view.isDestroyed) return;
+                // Canonical PM-JSON -> HTML via the LIVE editor schema, then
+                // reuse the UNCHANGED downstream seam (normalizeTableColumnWidths
+                // + parseSlice + canonicalizePastedFootnotes). The JSON->HTML->
+                // JSON hop is lossless (same schema both directions); it lets the
+                // existing paste-insertion logic stay byte-identical — only the
+                // SOURCE of the markdown conversion changed (issue #347 guardrail:
+                // no converter logic in the client, only a call into the package).
+                const node = PMNode.fromJSON(schema, doc);
+                const div = document.createElement("div");
+                DOMSerializer.fromSchema(schema).serializeFragment(
+                  node.content,
+                  { document },
+                  div,
+                );
 
-            const parsedSlice = DOMParser.fromSchema(
-              this.editor.schema,
-            ).parseSlice(body, {
-              preserveWhitespace: true,
-            });
+                const body = elementFromString(div.innerHTML);
+                normalizeTableColumnWidths(body);
 
-            // A markdown paste builds its ProseMirror fragment directly (DOM ->
-            // parseSlice), bypassing the editor's footnoteSyncPlugin, which never
-            // reorders an existing list. So a pasted markdown block whose footnote
-            // definitions are out of order (or contains orphan defs) would be
-            // stored out of order. Canonicalize the self-contained pasted block so
-            // its footnotes come out reference-ordered, deduped and orphan-free
-            // (issue #228). See canonicalizePastedFootnotes for why this is scoped
-            // to whole-block pastes that carry their own footnotesList.
-            const contentNodes = canonicalizePastedFootnotes(
-              parsedSlice,
-              this.editor.schema,
-            );
+                const parsedSlice = DOMParser.fromSchema(schema).parseSlice(
+                  body,
+                  { preserveWhitespace: true },
+                );
 
-            tr.replaceRange(from, to, contentNodes);
-            const insertEnd = tr.mapping.map(from, 1);
-            tr.setSelection(TextSelection.near(tr.doc.resolve(Math.max(from, insertEnd - 2)), -1));
-            tr.setMeta('paste', true)
-            view.dispatch(tr);
+                // A markdown paste builds its ProseMirror fragment directly (DOM
+                // -> parseSlice), bypassing the editor's footnoteSyncPlugin, which
+                // never reorders an existing list. So a pasted markdown block whose
+                // footnote definitions are out of order (or contains orphan defs)
+                // would be stored out of order. Canonicalize the self-contained
+                // pasted block so its footnotes come out reference-ordered, deduped
+                // and orphan-free (issue #228). See canonicalizePastedFootnotes for
+                // why this is scoped to whole-block pastes that carry their own
+                // footnotesList.
+                const contentNodes = canonicalizePastedFootnotes(
+                  parsedSlice,
+                  schema,
+                );
+
+                // Target the captured range (normally still valid — same
+                // microtask). If the doc changed under us since capture, the
+                // captured absolute from/to are stale, so fall back to the live
+                // selection rather than StepMap-mapping the old range.
+                const tr = view.state.tr;
+                let mappedFrom = from;
+                let mappedTo = to;
+                if (view.state.doc !== startDoc) {
+                  // Defensive: if the doc changed under us, fall back to the
+                  // current selection rather than a stale absolute range.
+                  mappedFrom = view.state.selection.from;
+                  mappedTo = view.state.selection.to;
+                }
+                tr.replaceRange(mappedFrom, mappedTo, contentNodes);
+                const insertEnd = tr.mapping.map(mappedFrom, 1);
+                tr.setSelection(
+                  TextSelection.near(
+                    tr.doc.resolve(Math.max(mappedFrom, insertEnd - 2)),
+                    -1,
+                  ),
+                );
+                tr.setMeta("paste", true);
+                view.dispatch(tr);
+              })
+              .catch((err) => {
+                // Fail-open: a conversion error must not swallow the paste
+                // silently in a way that loses the text. We already claimed the
+                // event (returned true), so re-insert the raw text as a plain
+                // paragraph so the user never loses their clipboard content.
+                // Log it: this catch covers BOTH the converter and the success
+                // `.then` body (e.g. PMNode.fromJSON throwing on a schema drift
+                // between the canonical package and the live editor schema), so a
+                // silent degrade to raw text would otherwise be an invisible,
+                // non-reproducible regression ("my table pasted as text").
+                console.error(
+                  "markdown paste conversion failed, inserting raw text",
+                  err,
+                );
+                if (view.isDestroyed) return;
+                const tr = view.state.tr;
+                // Same guard the success path uses: if the doc changed under us
+                // since the range was captured (normally never — same microtask),
+                // the captured absolute from/to are stale and would throw a
+                // RangeError here (an unhandled rejection on a hot paste path).
+                // Fall back to the live selection instead of a stale range.
+                if (view.state.doc !== startDoc) {
+                  const sel = view.state.selection;
+                  tr.insertText(md, sel.from, sel.to);
+                } else {
+                  tr.insertText(md, from, to);
+                }
+                tr.setMeta("paste", true);
+                view.dispatch(tr);
+              });
+            // Claim the paste: we insert asynchronously above.
             return true;
           },
           // Strip trailing whitespace-only paragraphs from pasted content.

apps/client/src/features/editor/hooks/use-generate-page-title.test.tsx

@@ -33,10 +33,11 @@ vi.mock("@/lib/local-emitter.ts", () => ({
   default: { emit: (...args: unknown[]) => localEmitMock(...args) },
 }));
 
-// htmlToMarkdown just echoes the editor HTML so each test controls the markdown
-// purely via the fake page editor's getHTML().
-vi.mock("@docmost/editor-ext", () => ({
-  htmlToMarkdown: (html: string) => html,
+// convertProseMirrorToMarkdown echoes a marker carried on the fake editor's
+// getJSON() doc, so each test controls the markdown purely via the fake page
+// editor (issue #347: the hook now serializes editor JSON through the package).
+vi.mock("@docmost/prosemirror-markdown/browser", () => ({
+  convertProseMirrorToMarkdown: (doc: { __md?: string }) => doc?.__md ?? "",
 }));
 
 const notificationsShowMock = vi.fn();
@@ -53,10 +54,12 @@ import { useGeneratePageTitle } from "./use-generate-page-title.ts";
 
 // --- Test helpers -------------------------------------------------------------
 
-function makePageEditor(pageId: string, html = "<p>content</p>"): Editor {
+function makePageEditor(pageId: string, md = "content"): Editor {
   return {
     isDestroyed: false,
-    getHTML: () => html,
+    // The mocked convertProseMirrorToMarkdown reads `__md` back off this doc,
+    // so `md` is exactly the markdown the hook will send to the title service.
+    getJSON: () => ({ type: "doc", __md: md }),
     storage: { pageId },
   } as unknown as Editor;
 }

apps/client/src/features/editor/hooks/use-generate-page-title.ts

@@ -3,7 +3,7 @@ import { useMutation } from "@tanstack/react-query";
 import { useAtomValue } from "jotai";
 import { notifications } from "@mantine/notifications";
 import { useTranslation } from "react-i18next";
-import { htmlToMarkdown } from "@docmost/editor-ext";
+import { convertProseMirrorToMarkdown } from "@docmost/prosemirror-markdown/browser";
 import {
   pageEditorAtom,
   titleEditorAtom,
@@ -49,7 +49,9 @@ export function useGeneratePageTitle(pageId: string) {
     mutationFn: async () => {
       if (!pageEditor || pageEditor.isDestroyed) return;
 
-      const markdown = htmlToMarkdown(pageEditor.getHTML()).trim();
+      // Serialize the live editor content to markdown through the canonical
+      // converter (issue #347), matching the on-disk/export markdown form.
+      const markdown = convertProseMirrorToMarkdown(pageEditor.getJSON()).trim();
       if (!markdown) {
         notifications.show({ message: t("The note is empty"), color: "yellow" });
         return;

apps/client/src/features/page/components/header/page-header-menu.tsx

@@ -37,7 +37,7 @@ import { useTreeMutation } from "@/features/page/tree/hooks/use-tree-mutation.ts
 import { PageWidthToggle } from "@/features/user/components/page-width-pref.tsx";
 import { Trans, useTranslation } from "react-i18next";
 import ExportModal from "@/components/common/export-modal";
-import { htmlToMarkdown } from "@docmost/editor-ext";
+import { convertProseMirrorToMarkdown } from "@docmost/prosemirror-markdown/browser";
 import {
   pageEditorAtom,
   yjsConnectionStatusAtom,
@@ -199,8 +199,9 @@ function PageActionMenu({ readOnly }: PageActionMenuProps) {
 
   const handleCopyAsMarkdown = () => {
     if (!pageEditor) return;
-    const html = pageEditor.getHTML();
-    const markdown = htmlToMarkdown(html);
+    // Copy the page as canonical markdown through the shared converter (issue
+    // #347), so "Copy as markdown" matches the server export byte-for-byte.
+    const markdown = convertProseMirrorToMarkdown(pageEditor.getJSON());
     const title = page?.title ? `# ${page.title}\n\n` : "";
     clipboard.copy(`${title}${markdown}`);
     notifications.show({ message: t("Copied") });

apps/client/src/features/share/components/share-ai-widget.tsx

@@ -168,6 +168,10 @@ export default function ShareAiWidget({
             // Anonymous reader: suppress the tool-argument summary line so the
             // agent's raw query/argument text isn't shown on the public share.
             showInput={false}
+            // Anonymous reader: never paint a tool's raw errorText (it can carry
+            // internal detail). This is the render gate; the bytes are also
+            // sanitized server-side in PublicShareChatToolsService.forShare (#394).
+            showErrors={false}
             // Anonymous reader: neutralize internal/relative links in the
             // assistant's markdown so internal UUIDs/auth-gated routes don't
             // leak as clickable links (external http(s) links are kept).

apps/server/src/common/helpers/prosemirror/html-embed-import-detect.spec.ts

@@ -1,4 +1,5 @@
-import { markdownToHtml, encodeHtmlEmbedSource } from '@docmost/editor-ext';
+import { markdownToProseMirror } from '@docmost/prosemirror-markdown';
+import { encodeHtmlEmbedSource } from '@docmost/editor-ext';
 import { htmlToJson } from '../../../collaboration/collaboration.util';
 import { hasHtmlEmbedNode, stripHtmlEmbedNodes } from './html-embed.util';
 
@@ -10,13 +11,12 @@ import { hasHtmlEmbedNode, stripHtmlEmbedNodes } from './html-embed.util';
  *
  * The block renders inside a sandboxed iframe, so this is not an XSS surface;
  * this exercises the REAL server import conversion path that ImportService uses
- * (`markdownToHtml` then `htmlToJson`; `processHTML` adds only a cheerio
- * link/iframe normalize pass which does not touch htmlEmbed divs) and asserts
- * that such a node is DETECTED and STRIPPABLE — so the share read path's
+ * (`markdownToProseMirror`, the canonical converter — issue #345/#347) and
+ * asserts that such a node is DETECTED and STRIPPABLE — so the share read path's
  * master-toggle strip can remove it when the workspace toggle is OFF.
  */
 describe('htmlEmbed smuggled via the raw serialized div in imported markdown/HTML', () => {
-  it('round-trips through markdownToHtml -> htmlToJson and is DETECTED (base64 data-source)', async () => {
+  it('round-trips through markdownToProseMirror and is DETECTED (base64 data-source)', async () => {
     const source = '<script>steal()</script>';
     const encoded = encodeHtmlEmbedSource(source);
     const md = [
@@ -27,12 +27,9 @@ describe('htmlEmbed smuggled via the raw serialized div in imported markdown/HTM
       'World',
     ].join('\n');
 
-    const html = await markdownToHtml(md);
-    // marked preserves the raw block-level div verbatim.
-    expect(html).toContain('data-type="htmlEmbed"');
-
-    const json = htmlToJson(html);
-    // The div parses into a real htmlEmbed node carrying the decoded source.
+    // The canonical importer parses the raw block-level div into a real
+    // htmlEmbed node carrying the decoded source.
+    const json = await markdownToProseMirror(md);
     expect(hasHtmlEmbedNode(json)).toBe(true);
 
     // Because it is detected, the share master-toggle strip can remove it.
@@ -59,8 +56,7 @@ describe('htmlEmbed smuggled via the raw serialized div in imported markdown/HTM
     // therefore stripping) does not depend on the source being well-formed, so
     // the bypass cannot be hidden by sending a malformed data-source.
     const md = `<div data-type="htmlEmbed" data-source="&lt;script&gt;x&lt;/script&gt;"></div>`;
-    const html = await markdownToHtml(md);
-    const json = htmlToJson(html);
+    const json = await markdownToProseMirror(md);
     expect(hasHtmlEmbedNode(json)).toBe(true);
     expect(hasHtmlEmbedNode(stripHtmlEmbedNodes(json))).toBe(false);
   });

apps/server/src/core/ai-chat/ai-chat.begin-run-failure.spec.ts

@@ -0,0 +1,109 @@
+import {
+  ConflictException,
+  Logger,
+  ServiceUnavailableException,
+} from '@nestjs/common';
+import { AiChatService } from './ai-chat.service';
+import { RunAlreadyActiveError } from './ai-chat-run.service';
+
+/**
+ * Fail-fast guard for beginRun failures (#486, commit 4).
+ *
+ * When runHooks.begin() rejects for a reason OTHER than RunAlreadyActiveError
+ * (e.g. a DB-pool blip), the turn must NOT continue untracked. The old code
+ * logged and streamed anyway, leaving a run with NO run-row: in autonomous mode
+ * nobody could abort it (/stop can't see it, disconnect doesn't abort it, and the
+ * one-run gate would admit a SECOND run) — an unstoppable invisible run until
+ * restart. The fix throws A_RUN_BEGIN_FAILED (503) BEFORE the first byte and
+ * before the user row is persisted.
+ *
+ * We drive `stream()` directly on a prototype instance wired with only the
+ * collaborators it touches before the throw, so the assertion is on the REAL
+ * control flow, not a mock of it.
+ */
+describe('AiChatService beginRun failure (#486)', () => {
+  function makeService(insertSpy: jest.Mock): AiChatService {
+    // Bypass the (heavy) DI constructor: exercise the real stream() method on a
+    // bare prototype instance with just the fields reached before the throw.
+    // `any` because the private `logger` field makes a typed intersection collapse.
+    const svc = Object.create(AiChatService.prototype);
+    svc.aiChatRepo = {
+      // Existing chat -> no insert path; chatId is kept as-is.
+      findById: jest.fn().mockResolvedValue({ id: 'chat1' }),
+    };
+    svc.aiChatMessageRepo = { insert: insertSpy };
+    svc.logger = new Logger('test');
+    return svc as AiChatService;
+  }
+
+  const baseArgs = () => {
+    const write = jest.fn();
+    const res = {
+      raw: { write, writableEnded: false, headersSent: false },
+    };
+    return {
+      user: { id: 'u1' } as never,
+      workspace: { id: 'w1' } as never,
+      sessionId: 's1',
+      // openPage undefined -> resolveOpenPageContext returns null without any DB
+      // call; chatId present -> the existing-chat path.
+      body: { chatId: 'chat1', messages: [] } as never,
+      res: res as never,
+      signal: new AbortController().signal,
+      model: {} as never,
+      role: null,
+      write,
+    };
+  };
+
+  it('throws A_RUN_BEGIN_FAILED (503) before the first byte and before persisting the user turn', async () => {
+    const insertSpy = jest.fn();
+    const svc = makeService(insertSpy);
+    const { write, ...args } = baseArgs();
+
+    const runHooks = {
+      begin: jest.fn().mockRejectedValue(new Error('DB pool exhausted')),
+    } as never;
+
+    let caught: unknown;
+    try {
+      await svc.stream({ ...args, runHooks });
+    } catch (e) {
+      caught = e;
+    }
+
+    expect(caught).toBeInstanceOf(ServiceUnavailableException);
+    const http = caught as ServiceUnavailableException;
+    expect(http.getStatus()).toBe(503);
+    expect(http.getResponse()).toMatchObject({ code: 'A_RUN_BEGIN_FAILED' });
+
+    // Fail-fast: nothing was written to the socket and NO user message row was
+    // persisted, so the turn left no orphan state to clean up.
+    expect(write).not.toHaveBeenCalled();
+    expect(insertSpy).not.toHaveBeenCalled();
+  });
+
+  it('still maps a lost-the-race RunAlreadyActiveError to a 409, not A_RUN_BEGIN_FAILED', async () => {
+    const insertSpy = jest.fn();
+    const svc = makeService(insertSpy);
+    const { write, ...args } = baseArgs();
+
+    const runHooks = {
+      begin: jest.fn().mockRejectedValue(new RunAlreadyActiveError('chat1')),
+    } as never;
+
+    let caught: unknown;
+    try {
+      await svc.stream({ ...args, runHooks });
+    } catch (e) {
+      caught = e;
+    }
+
+    expect(caught).toBeInstanceOf(ConflictException);
+    expect((caught as ConflictException).getResponse()).toMatchObject({
+      code: 'A_RUN_ALREADY_ACTIVE',
+    });
+    expect(write).not.toHaveBeenCalled();
+    expect(insertSpy).not.toHaveBeenCalled();
+  });
+});

apps/server/src/core/ai-chat/ai-chat.prompt.tool-names.spec.ts

@@ -0,0 +1,125 @@
+import { readFileSync } from 'node:fs';
+import { join } from 'node:path';
+import { PROMPT_TOOL_NAMES } from './ai-chat.prompt';
+// The real shared registry, imported from source (same approach as the
+// SHARED_TOOL_SPECS contract spec) so tool names are validated against exactly
+// what @docmost/mcp ships.
+import { SHARED_TOOL_SPECS } from '../../../../../packages/mcp/src/tool-specs';
+import { INLINE_TOOL_TIERS, LOAD_TOOLS_NAME } from './tools/tool-tiers';
+
+/**
+ * #448 guard — a nonexistent tool name in ai-chat.prompt.ts must fail a test.
+ *
+ * The in-app prompt refers to a handful of tools BY NAME in its guidance notes
+ * (e.g. PAGE_CHANGED_NOTE tells the agent to re-read via getPage and edit via
+ * editPageText/patchNode/insertNode/deleteNode). Before #448 those names were
+ * hard-coded inline with NO guard, so renaming a tool left the agent stale
+ * instructions and nothing failed.
+ *
+ * APPROACH — substitution + a precise source scan:
+ *  1. The names now flow through the exported `PROMPT_TOOL_NAMES` const; this
+ *     test asserts every value there is a REAL in-app tool.
+ *  2. A precise scan of the two guidance-note string literals in the source
+ *     catches any BARE tool-name token added directly (bypassing the const):
+ *     every camelCase token in those notes must be either a real tool name or an
+ *     explicitly-allowlisted ordinary English/camelCase word.
+ *
+ * The scan is deliberately narrow (only the guidance notes, only camelCase
+ * tokens) so it never false-positives on prose, and the allowlist of non-tool
+ * words is tiny and explicit.
+ */
+
+// The authoritative set of real in-app tool names: shared-registry inAppKeys +
+// per-layer INLINE tool keys + the loadTools meta-tool.
+const VALID_TOOL_NAMES = new Set<string>([
+  ...Object.values(SHARED_TOOL_SPECS).map((s) => s.inAppKey),
+  ...Object.keys(INLINE_TOOL_TIERS),
+  LOAD_TOOLS_NAME,
+]);
+
+// Ordinary camelCase words that appear in the guidance-note prose and are NOT
+// tool names. Keep this list minimal and explicit — anything camelCase in a note
+// that is neither a real tool nor here fails the scan.
+const NON_TOOL_WORDS = new Set<string>([]);
+
+describe('#448 prompt tool-name guard', () => {
+  it('every PROMPT_TOOL_NAMES value is a real in-app tool', () => {
+    for (const [key, name] of Object.entries(PROMPT_TOOL_NAMES)) {
+      expect(typeof name).toBe('string');
+      expect(VALID_TOOL_NAMES.has(name)).toBe(true);
+      // Sanity: the const key and its value are the same token (the const is a
+      // name->name map used purely to route mentions through one guarded place).
+      expect(key).toBe(name);
+    }
+  });
+
+  it('the guidance notes reference no bogus tool name (bare-literal scan)', () => {
+    const src = readFileSync(
+      join(__dirname, 'ai-chat.prompt.ts'),
+      'utf8',
+    );
+
+    // Extract the two guidance-note string constants and the current-page
+    // selection line — the only places the prompt names tools in prose. Each is
+    // a `const NAME =` ... `;` block; we scan their raw text for camelCase
+    // tokens. (Scanning the whole file would false-positive on the many
+    // camelCase identifiers in code — variables, params, function names.)
+    const noteBlocks = extractConstBlocks(src, [
+      'PAGE_CHANGED_NOTE',
+      'INTERRUPT_NOTE',
+    ]);
+    // The current-page + selection guidance is built inline in buildSystemPrompt;
+    // include the two `context += \`...\`` template lines that mention tools.
+    const contextLines = src
+      .split('\n')
+      .filter((l) => l.includes('context +=') && l.includes('getCurrentPage'))
+      .join('\n');
+
+    // Neutralize string-literal escape sequences (\n, \t, ...) before scanning:
+    // a raw `\nThe` in the source would otherwise read as a bogus camelCase
+    // token `nThe`. Replace any backslash-escape with a space.
+    const scanText = (noteBlocks + '\n' + contextLines).replace(/\\./g, ' ');
+    expect(scanText.length).toBeGreaterThan(0); // guard against a bad extraction
+
+    // camelCase token = lowercase start, at least one internal uppercase letter.
+    const tokens = new Set(scanText.match(/\b[a-z][a-zA-Z0-9]*[A-Z][a-zA-Z0-9]*\b/g) ?? []);
+    const offenders = [...tokens].filter(
+      (t) => !VALID_TOOL_NAMES.has(t) && !NON_TOOL_WORDS.has(t),
+    );
+    expect(offenders).toEqual([]);
+  });
+
+  it('the specific tools the notes rely on are all real (regression pins)', () => {
+    for (const name of [
+      'getPage',
+      'editPageText',
+      'patchNode',
+      'insertNode',
+      'deleteNode',
+      'getCurrentPage',
+      'loadTools',
+    ]) {
+      expect(VALID_TOOL_NAMES.has(name)).toBe(true);
+    }
+  });
+});
+
+/**
+ * Extract the raw text of one or more top-level `const NAME = ... ;` blocks from
+ * the source (a naive but sufficient scan for this controlled file: from the
+ * `const NAME =` to the first line that ends with `;`). Returns the blocks
+ * concatenated.
+ */
+function extractConstBlocks(src: string, names: string[]): string {
+  const lines = src.split('\n');
+  const out: string[] = [];
+  for (const name of names) {
+    const start = lines.findIndex((l) => l.trimStart().startsWith(`const ${name} =`));
+    if (start < 0) continue;
+    for (let i = start; i < lines.length; i++) {
+      out.push(lines[i]);
+      if (lines[i].trimEnd().endsWith(';')) break;
+    }
+  }
+  return out.join('\n');
+}

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

@@ -2,6 +2,30 @@ import { Workspace } from '@docmost/db/types/entity.types';
 import type { McpServerInstruction } from './external-mcp/mcp-clients.service';
 import { CORE_TOOL_KEYS, type ToolCatalogEntry } from './tools/tool-tiers';
 
+/**
+ * The in-app tool names this prompt refers to BY NAME in its guidance notes
+ * (issue #448). Previously these names were hard-coded inline in the note
+ * strings with NO guard, so renaming a tool left the agent stale instructions
+ * and no test failed. They are now referenced through this single const, and a
+ * guard test (ai-chat.prompt.tool-names.spec.ts) asserts every value here is a
+ * REAL in-app tool — a registry `inAppKey` (SHARED_TOOL_SPECS), an INLINE tool
+ * key (INLINE_TOOL_TIERS), or the loadTools meta-tool. Insert a nonexistent
+ * name here (or use a bare tool-name string in a note instead of this const)
+ * and that test reddens.
+ *
+ * `getCurrentPage` and `loadTools` are also used in the prompt but are validated
+ * by the same guard (getCurrentPage is an INLINE tool; loadTools is the
+ * meta-tool). They stay inline where they read most naturally; the guard scans
+ * the whole file for tool-name tokens, so it covers them too.
+ */
+export const PROMPT_TOOL_NAMES = {
+  getPage: 'getPage',
+  editPageText: 'editPageText',
+  patchNode: 'patchNode',
+  insertNode: 'insertNode',
+  deleteNode: 'deleteNode',
+} as const;
+
 /**
  * Default agent persona used when the admin has not configured a custom system
  * prompt (`settings.ai.provider.systemPrompt`).
@@ -91,15 +115,15 @@ const PAGE_CHANGED_NOTE =
   'NOTE: The user edited the open page AFTER your last response in this ' +
   'conversation, so any copy of that page you produced or remember from earlier ' +
   'is now STALE and must not be reused. Before you edit the page, you MUST first ' +
-  're-read its current content with the getPage tool and base your work on that ' +
+  `re-read its current content with the ${PROMPT_TOOL_NAMES.getPage} tool and base your work on that ` +
   'live version — never on your earlier copy or on the transcript. The unified ' +
   'diff below shows exactly what the user changed since you last spoke (lines ' +
   'starting with "-" were removed, "+" were added) and is the source of truth. ' +
   'Preserve every one of the user\'s edits: make the smallest change that ' +
-  'satisfies the request using the targeted edit tools (editPageText, patchNode, ' +
-  'insertNode, deleteNode) rather than replacing the whole page, and do not ' +
-  'revert, drop, or overwrite anything the user changed. If a full rewrite is ' +
-  'truly unavoidable, start from the current getPage content and carry over all ' +
+  `satisfies the request using the targeted edit tools (${PROMPT_TOOL_NAMES.editPageText}, ${PROMPT_TOOL_NAMES.patchNode}, ` +
+  `${PROMPT_TOOL_NAMES.insertNode}, ${PROMPT_TOOL_NAMES.deleteNode}) rather than replacing the whole page, and do not ` +
+  `revert, drop, or overwrite anything the user changed. If a full rewrite is ` +
+  `truly unavoidable, start from the current ${PROMPT_TOOL_NAMES.getPage} content and carry over all ` +
   'of the user\'s edits.';
 
 /**

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

@@ -1,4 +1,8 @@
-import { ConflictException, Logger } from '@nestjs/common';
+import {
+  ConflictException,
+  Logger,
+  ServiceUnavailableException,
+} from '@nestjs/common';
 
 // Mock the AI SDK so we can PROVE no provider call is made for the turn we are
 // about to reject. The race rejection happens at runHooks.begin(), long before
@@ -360,22 +364,22 @@ describe('AiChatService.stream — abortSignal wiring (#184 F3)', () => {
 });
 
 /**
- * F14 — the begin-failure RESILIENCE branch (the `else` of the run-race guard).
+ * F14 — the begin-failure branch (the `else` of the run-race guard).
  *
  * stream() wraps runHooks.begin in try/catch with TWO branches:
  *   - RunAlreadyActiveError  -> 409 ConflictException (pinned above).
- *   - ANY OTHER begin failure -> SWALLOW + continue UNTRACKED on the socket signal
- *     (legacy fallback): it logs "...streaming without run tracking", leaves
- *     `effectiveSignal = signal` (runId undefined) and serves the turn anyway.
+ *   - ANY OTHER begin failure -> throw ServiceUnavailableException(A_RUN_BEGIN_FAILED)
+ *     BEFORE the first byte (#486, commit 4).
  *
- * The contract: a transient beginRun failure (e.g. a non-unique DB error inserting
- * the run row) must STILL serve the user's turn — it must NOT re-throw and must NOT
- * be misclassified as a 409. A regression that re-threw here would break EVERY turn
- * on a begin failure with nothing to catch it. This branch is otherwise undriven by
- * any spec, so it is pinned here SEPARATELY from the 409 path: a plain begin error
- * proceeds to streamText with the SOCKET signal and still persists the user turn.
+ * POLICY CHANGE (#486): the OLD contract here was "SWALLOW + stream the turn
+ * UNTRACKED on the socket signal". That was reversed: an untracked run is
+ * invisible to /stop, is not aborted on disconnect, and slips past the one-run
+ * gate — an unstoppable ghost run in autonomous mode. Now a plain begin failure
+ * FAILS the turn fast with a 503 A_RUN_BEGIN_FAILED, before any user row is
+ * persisted and before streamText runs. This case is INVERTED (not deleted) so
+ * the "plain begin failure" path stays explicitly pinned under the new policy.
  */
-describe('AiChatService.stream — begin-failure resilience / legacy fallback (#184 F14)', () => {
+describe('AiChatService.stream — begin-failure fails the turn (#184 F14 / #486)', () => {
   const streamTextMock = streamText as unknown as jest.Mock;
 
   function makeStreamResult() {
@@ -455,7 +459,7 @@ describe('AiChatService.stream — begin-failure resilience / legacy fallback (#
 
   afterEach(() => jest.restoreAllMocks());
 
-  it('a PLAIN begin() failure (NOT RunAlreadyActiveError) does NOT 409 — it swallows, logs, and streams the turn UNTRACKED on the socket signal', async () => {
+  it('a PLAIN begin() failure (NOT RunAlreadyActiveError) FAILS the turn with a 503 A_RUN_BEGIN_FAILED before the first byte — NO untracked stream (#486)', async () => {
     const errorSpy = jest
       .spyOn(Logger.prototype, 'error')
       .mockImplementation(() => undefined as never);
@@ -487,28 +491,26 @@ describe('AiChatService.stream — begin-failure resilience / legacy fallback (#
       } as never,
     });
 
-    // The turn proceeds: NO throw at all (in particular NOT a 409).
-    await expect(promise).resolves.toBeUndefined();
+    // NEW POLICY: the turn is REJECTED with a 503 A_RUN_BEGIN_FAILED (not a 409,
+    // and NOT swallowed into an untracked stream).
+    await expect(promise).rejects.toBeInstanceOf(ServiceUnavailableException);
+    const err = (await promise.catch(
+      (e) => e,
+    )) as ServiceUnavailableException;
+    expect(err.getStatus()).toBe(503);
+    expect(err.getResponse()).toMatchObject({ code: 'A_RUN_BEGIN_FAILED' });
 
     expect(begin).toHaveBeenCalledTimes(1);
 
-    // The resilience branch logged the legacy-fallback warning.
+    // It logged the fail-the-turn line.
     expect(errorSpy).toHaveBeenCalledWith(
-      expect.stringContaining('streaming without run tracking'),
+      expect.stringContaining('failing the turn'),
       expect.anything(),
     );
 
-    // The turn really streamed: the user message was persisted and streamText ran.
-    expect(aiChatMessageRepo.insert).toHaveBeenCalled();
-    expect(streamTextMock).toHaveBeenCalledTimes(1);
-
-    // The decisive wiring: with no run handle, the fallback uses the SOCKET signal
-    // (effectiveSignal = signal, runId undefined) — not a run-bound signal. #444:
-    // the signal is unioned with the degeneration controller via AbortSignal.any,
-    // so assert the socket abort still reaches the turn rather than identity.
-    const passed = streamTextMock.mock.calls[0][0].abortSignal as AbortSignal;
-    expect(passed.aborted).toBe(false);
-    socketController.abort();
-    expect(passed.aborted).toBe(true);
+    // Fail-fast: the turn NEVER streamed — no user row persisted, no streamText
+    // call, so no orphan/untracked run was left behind.
+    expect(aiChatMessageRepo.insert).not.toHaveBeenCalled();
+    expect(streamTextMock).not.toHaveBeenCalled();
   });
 });

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

@@ -4,6 +4,7 @@ import {
   Injectable,
   Logger,
   OnModuleInit,
+  ServiceUnavailableException,
 } from '@nestjs/common';
 import { FastifyReply } from 'fastify';
 import {
@@ -55,6 +56,7 @@ import {
 import {
   isDegenerateOutput,
   truncateDegeneratedTail,
+  shouldCheckDegeneration,
 } from './output-degeneration';
 
 // Max agent steps per turn. One step = one model generation; a step that calls
@@ -756,6 +758,13 @@ export class AiChatService implements OnModuleInit {
       // or violate the page_id FK on insert (this runs after res.hijack(), so a
       // DB error would break the stream).
       const originPageId: string | null = openPageContext?.id ?? null;
+      // ORPHAN-ON-BEGIN-FAILURE tradeoff (#486, B3): the chat row is inserted
+      // HERE, before runHooks.begin below. If begin fails (e.g. a 503 / run-slot
+      // rejection) the turn aborts before the client is told this new chatId, so
+      // an empty chat is left behind and a retry mints ANOTHER one. We accept this
+      // over reordering: begin needs a chatId to bind the run to, and inserting
+      // the chat first keeps the id stable + the FK/history-join invariants above
+      // intact. Orphan empty chats are cheap and swept by normal chat cleanup.
       const chat = await this.aiChatRepo.insert({
         creatorId: user.id,
         workspaceId: workspace.id,
@@ -797,12 +806,32 @@ export class AiChatService implements OnModuleInit {
             code: 'A_RUN_ALREADY_ACTIVE',
           });
         }
-        // Any OTHER run-start failure must not break the turn — fall back to the
-        // socket signal (legacy behavior) and stream anyway.
+        // Any OTHER run-start failure (e.g. a DB-pool blip) must FAIL THE TURN,
+        // not silently stream without a run-row. The old fallback let the turn
+        // continue untracked: in autonomous mode nobody could then abort it —
+        // /stop can't see a run that doesn't exist, a client disconnect doesn't
+        // abort it, and the one-run-per-chat gate would let a SECOND run in. That
+        // is an unstoppable, invisible run until process restart. Reject NOW,
+        // BEFORE the first byte (nothing is written yet, no user row inserted, no
+        // MCP lease taken), so the controller's post-hijack catch turns this
+        // HttpException into an honest 503 on the raw socket. Same policy for BOTH
+        // modes — #487 inherits it (no mode-branching here).
         this.logger.error(
-          `Failed to begin agent run (chat ${chatId}); streaming without run tracking`,
+          `Failed to begin agent run (chat ${chatId}); failing the turn`,
           err as Error,
         );
+        throw new ServiceUnavailableException({
+          message:
+            'Could not start the agent run. This is usually temporary — please try again.',
+          code: 'A_RUN_BEGIN_FAILED',
+          // Self-describe the status in the body: the controller's post-hijack
+          // catch writes getResponse() verbatim onto the raw socket, and an
+          // object-arg HttpException does NOT inject statusCode. Without it the
+          // client's 503 classifier (which reads the body JSON) could not see the
+          // status. With it present, the client's A_RUN_BEGIN_FAILED branch (which
+          // runs strictly before the generic-503 branch) shows "temporary, retry".
+          statusCode: 503,
+        });
       }
     }
 
@@ -1080,7 +1109,6 @@ export class AiChatService implements OnModuleInit {
       const degenerationController = new AbortController();
       let degenerationDetected = false;
       let lastDegenerationCheckLen = 0;
-      const DEGENERATION_CHECK_STEP = 2000;
 
       // Step-granular durability (#183): create the assistant row UPFRONT in the
       // 'streaming' state (before any token), then UPDATE it as each step finishes
@@ -1254,8 +1282,10 @@ export class AiChatService implements OnModuleInit {
               // trigger, abort the run ONCE with a distinguishable reason.
               if (
                 !degenerationDetected &&
-                inProgressText.length - lastDegenerationCheckLen >=
-                  DEGENERATION_CHECK_STEP
+                shouldCheckDegeneration(
+                  inProgressText.length,
+                  lastDegenerationCheckLen,
+                )
               ) {
                 lastDegenerationCheckLen = inProgressText.length;
                 if (isDegenerateOutput(inProgressText)) {
@@ -1275,6 +1305,13 @@ export class AiChatService implements OnModuleInit {
             // the in-progress accumulator for the next step.
             capturedSteps.push(step as StepLike);
             inProgressText = '';
+            // Reset the degeneration-check watermark too (#486): it tracks a byte
+            // offset INTO inProgressText, so once that resets to '' a stale (large)
+            // mark makes `inProgressText.length - lastDegenerationCheckLen` go
+            // negative and the throttled detector stays silent until a later step's
+            // text re-grows past the old offset — a whole degenerate step could slip
+            // through undetected. Zeroing it re-arms the check from the next byte.
+            lastDegenerationCheckLen = 0;
             // Step-granular durability (#183): persist this finished step (its text +
             // tool calls + tool RESULTS) the moment it ends, so a process death after
             // this point still recovers the step. Not awaited here (never block the

apps/server/src/core/ai-chat/chat-markdown.util.ts

@@ -75,7 +75,7 @@ const LABELS: Record<
       searchPages: 'Searched pages',
       getPage: 'Read page',
       createPage: 'Created page',
-      updatePageContent: 'Updated page',
+      updatePageMarkdown: 'Updated page',
       renamePage: 'Renamed page',
       movePage: 'Moved page',
       deletePage: 'Deleted page (to trash)',
@@ -96,7 +96,7 @@ const LABELS: Record<
       searchPages: 'Искал по страницам',
       getPage: 'Прочитал страницу',
       createPage: 'Создал страницу',
-      updatePageContent: 'Обновил страницу',
+      updatePageMarkdown: 'Обновил страницу',
       renamePage: 'Переименовал страницу',
       movePage: 'Переместил страницу',
       deletePage: 'Удалил страницу (в корзину)',

apps/server/src/core/ai-chat/output-degeneration.spec.ts

@@ -1,11 +1,24 @@
+import { Logger } from '@nestjs/common';
+import { streamText } from 'ai';
 import {
   hasRepeatedLineRun,
   hasPeriodicTail,
   isDegenerateOutput,
   truncateDegeneratedTail,
+  shouldCheckDegeneration,
+  DEGENERATION_CHECK_STEP,
   REPEATED_LINES_THRESHOLD,
   MIN_PERIOD_REPEATS,
 } from './output-degeneration';
+import { AiChatService } from './ai-chat.service';
+
+// Mock ONLY streamText so we can capture the onChunk/onStepFinish callbacks the
+// service registers and drive them by hand; every other `ai` export the service
+// uses (convertToModelMessages, stepCountIs, …) stays real.
+jest.mock('ai', () => {
+  const actual = jest.requireActual('ai');
+  return { ...actual, streamText: jest.fn() };
+});
 
 /**
  * Unit tests for the token-degeneration detector (#444) — the sole anti-babble
@@ -180,3 +193,188 @@ describe('truncateDegeneratedTail', () => {
     expect(truncateDegeneratedTail(text)).toBe(text);
   });
 });
+
+/**
+ * Throttle + step-boundary reset (#486). The stream keeps a watermark
+ * (`lastDegenerationCheckLen`) that is an OFFSET into the accumulated step text.
+ * On a step boundary the accumulator resets to '', so the watermark MUST reset to
+ * 0 too — otherwise the throttle goes silent for the whole next step. These tests
+ * pin the pure decision AND the reset property that ai-chat.service.onStepFinish
+ * now enforces.
+ */
+describe('shouldCheckDegeneration (throttle) + step-boundary reset (#486)', () => {
+  it('fires once the text grows a full DEGENERATION_CHECK_STEP past the mark', () => {
+    expect(shouldCheckDegeneration(DEGENERATION_CHECK_STEP, 0)).toBe(true);
+    expect(shouldCheckDegeneration(DEGENERATION_CHECK_STEP - 1, 0)).toBe(false);
+    expect(shouldCheckDegeneration(5000, 3000)).toBe(true); // grew 2000 since mark
+    expect(shouldCheckDegeneration(4000, 3000)).toBe(false); // grew only 1000
+  });
+
+  it('BUG (no reset): a stale large watermark silences the next step', () => {
+    // End of a long step: the watermark sits at 5000. The step ends and the
+    // accumulator resets to '' — but if the watermark is NOT reset, a fresh short
+    // degenerate burst (length 2000) never triggers a check: 2000 - 5000 < STEP.
+    const staleWatermark = 5000;
+    const nextStepLen = DEGENERATION_CHECK_STEP; // a fresh 2KB burst
+    expect(shouldCheckDegeneration(nextStepLen, staleWatermark)).toBe(false);
+  });
+
+  it('FIX (reset to 0): the same short degenerate burst IS checked and detected', () => {
+    // onStepFinish now zeroes the watermark, so the fresh burst re-arms the check.
+    const resetWatermark = 0;
+    const degenerateBurst = 'loadTools.\n'.repeat(300); // real degeneration
+    expect(degenerateBurst.length).toBeGreaterThanOrEqual(DEGENERATION_CHECK_STEP);
+    // The throttle now fires...
+    expect(
+      shouldCheckDegeneration(degenerateBurst.length, resetWatermark),
+    ).toBe(true);
+    // ...and the detector catches the loop that would otherwise stream unchecked.
+    expect(isDegenerateOutput(degenerateBurst)).toBe(true);
+  });
+});
+
+/**
+ * BEHAVIOR guard for the ACTUAL fix (#486, ai-chat.service.onStepFinish resets
+ * lastDegenerationCheckLen to 0). The pure tests above use a hard-coded
+ * resetWatermark, so a REVERT of the real `lastDegenerationCheckLen = 0` line
+ * would not redden any of them. This drives the REAL onChunk/onStepFinish
+ * closures from stream() end to end and asserts the run is aborted when a fresh
+ * degenerate burst arrives in the step AFTER a long clean step — which only
+ * happens if the watermark was actually zeroed on the step boundary.
+ */
+describe('AiChatService: onStepFinish re-arms the degeneration watermark (#486)', () => {
+  const streamTextMock = streamText as unknown as jest.Mock;
+
+  function makeRes() {
+    return {
+      raw: {
+        writeHead: jest.fn(),
+        write: jest.fn(),
+        once: jest.fn(),
+        on: jest.fn(),
+        flushHeaders: jest.fn(),
+        writableEnded: false,
+        destroyed: false,
+      },
+    };
+  }
+
+  function makeService() {
+    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 mcpClients = {
+      toolsFor: jest.fn(async () => ({
+        tools: {},
+        clients: [],
+        outcomes: [],
+        instructions: [],
+      })),
+    };
+    return 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
+      {} as never, // pageAccess
+      {
+        isAiChatDeferredToolsEnabled: () => false,
+        // Lockdown OFF -> the degeneration guard is the active anti-babble path.
+        isAiChatFinalStepLockdownEnabled: () => false,
+      } as never, // environment
+    );
+  }
+
+  beforeEach(() => {
+    streamTextMock.mockReset();
+    jest.spyOn(Logger.prototype, 'log').mockImplementation(() => undefined as never);
+    jest.spyOn(Logger.prototype, 'warn').mockImplementation(() => undefined as never);
+  });
+
+  afterEach(() => jest.restoreAllMocks());
+
+  it('aborts on a fresh degenerate burst in the NEXT step (reverting the reset line reddens this)', async () => {
+    let captured:
+      | {
+          onChunk?: (e: { chunk: { type: string; text: string } }) => void;
+          onStepFinish?: (step: unknown) => void;
+          abortSignal?: AbortSignal;
+        }
+      | undefined;
+    streamTextMock.mockImplementation((opts: never) => {
+      captured = opts;
+      return {
+        consumeStream: jest.fn(),
+        pipeUIMessageStreamToResponse: jest.fn(),
+      };
+    });
+
+    const svc = makeService();
+    await svc.stream({
+      user: { id: 'user-1' } as never,
+      workspace: { id: 'ws-1' } as never,
+      sessionId: 'sess-1',
+      body: {
+        chatId: 'chat-1',
+        messages: [
+          { id: 'm1', role: 'user', parts: [{ type: 'text', text: 'hi' }] },
+        ],
+      } as never,
+      res: makeRes() as never,
+      signal: new AbortController().signal,
+      model: {} as never,
+      role: null,
+      // No runHooks -> legacy path (socket signal), degeneration guard active.
+    });
+
+    expect(streamTextMock).toHaveBeenCalledTimes(1);
+    const onChunk = captured!.onChunk!;
+    const onStepFinish = captured!.onStepFinish!;
+    const abortSignal = captured!.abortSignal!;
+    expect(abortSignal.aborted).toBe(false);
+
+    // STEP 1: a LONG, non-degenerate first step. Distinct lines never trip the
+    // detector, but they advance the throttle watermark far past the burst size
+    // that follows (to ~5x the step). This is the stale watermark that, WITHOUT
+    // the reset, would silence step 2.
+    let counter = 0;
+    let accumulated = 0;
+    while (accumulated < DEGENERATION_CHECK_STEP * 5) {
+      const line = `unique clean line number ${counter++} with distinct words\n`;
+      accumulated += line.length;
+      onChunk({ chunk: { type: 'text-delta', text: line } });
+    }
+    expect(abortSignal.aborted).toBe(false); // clean step must not abort
+
+    // STEP BOUNDARY: the real onStepFinish resets inProgressText AND (the fix)
+    // zeroes lastDegenerationCheckLen.
+    onStepFinish({ text: 'a clean first step', toolCalls: [], toolResults: [] });
+
+    // STEP 2: a FRESH, short degenerate burst (~3.3KB). Its length is far below
+    // the step-1 stale watermark (~10KB), so WITHOUT the reset the throttle stays
+    // silent and this streams unchecked. WITH the reset (watermark 0) it re-arms,
+    // the detector fires, and the run aborts.
+    const burst = 'loadTools.\n'.repeat(300);
+    expect(burst.length).toBeGreaterThanOrEqual(DEGENERATION_CHECK_STEP);
+    expect(burst.length).toBeLessThan(DEGENERATION_CHECK_STEP * 5);
+    onChunk({ chunk: { type: 'text-delta', text: burst } });
+
+    // The decisive assertion: the composed abortSignal (unioned with the
+    // degeneration controller) is now aborted. Reverting `lastDegenerationCheckLen
+    // = 0` in onStepFinish makes this stay false.
+    expect(abortSignal.aborted).toBe(true);
+  });
+});

apps/server/src/core/ai-chat/output-degeneration.ts

@@ -131,6 +131,32 @@ export function isDegenerateOutput(text: string): boolean {
   return hasRepeatedLineRun(text) || hasPeriodicTail(text);
 }
 
+/**
+ * How many bytes the in-progress text must grow before the (amortized) tail
+ * heuristics are re-run. Shared with ai-chat.service so the throttle the stream
+ * applies is the SAME one the unit test drives.
+ */
+export const DEGENERATION_CHECK_STEP = 2000;
+
+/**
+ * Throttle decision for the degeneration guard (#444/#486). Returns true when
+ * the accumulated text has grown at least DEGENERATION_CHECK_STEP bytes past the
+ * last-checked offset, so the pure rules only fire every ~2KB. Pure; the caller
+ * updates its watermark to `textLen` when this returns true.
+ *
+ * The watermark is an offset INTO the accumulator, so when the accumulator is
+ * reset to '' on a step boundary the caller MUST reset the watermark to 0 too
+ * (#486). Otherwise `textLen - lastCheckLen` goes negative after the reset and
+ * this returns false until a later step re-grows past the stale offset — a whole
+ * degenerate step could stream unchecked.
+ */
+export function shouldCheckDegeneration(
+  textLen: number,
+  lastCheckLen: number,
+): boolean {
+  return textLen - lastCheckLen >= DEGENERATION_CHECK_STEP;
+}
+
 /**
  * Truncate a degenerated tail before persist so hundreds of KB of garbage never
  * reach the DB / replay (#444). Keeps everything up to and including the FIRST

apps/server/src/core/ai-chat/public-share-chat.error-leak.spec.ts

@@ -0,0 +1,241 @@
+// Break the editor-ext import chain (share.service -> collaboration.util ->
+// @docmost/editor-ext -> @tiptap/core) that is unresolvable in this jest env and
+// pre-existingly breaks these specs. jsonToMarkdown is never reached in these
+// tests (the tools fail before rendering markdown).
+jest.mock('../../collaboration/collaboration.util', () => ({
+  jsonToMarkdown: () => '',
+}));
+
+import { Logger } from '@nestjs/common';
+import { MockLanguageModelV3, simulateReadableStream } from 'ai/test';
+import { PublicShareChatService } from './public-share-chat.service';
+import { PublicShareChatToolsService } from './tools/public-share-chat-tools.service';
+
+/**
+ * SECURITY integration guard for #394 (commit 5): a tool's or the provider's raw
+ * error text must NOT leak to an anonymous public-share reader.
+ *
+ * The render gate (ToolCallCard showErrors=false) hides the text in the DOM but
+ * NOT on the wire, so this test asserts on the RAW SSE BYTES the server writes —
+ * exactly the channel the render gate masks. We drive the real
+ * PublicShareChatService.stream() with a real share toolset (its underlying
+ * services mocked to fail) and a mock model, then inspect every byte piped to the
+ * fake socket.
+ */
+
+// A minimal ServerResponse stand-in that records every written chunk.
+class FakeSocket {
+  chunks: string[] = [];
+  statusCode = 200;
+  writableEnded = false;
+  destroyed = false;
+  headersSent = false;
+  writeHead(): this {
+    this.headersSent = true;
+    return this;
+  }
+  setHeader(): void {}
+  removeHeader(): void {}
+  getHeader(): undefined {
+    return undefined;
+  }
+  flushHeaders(): void {}
+  write(chunk: unknown): boolean {
+    this.chunks.push(
+      typeof chunk === 'string' ? chunk : Buffer.from(chunk as never).toString('utf8'),
+    );
+    return true;
+  }
+  end(chunk?: unknown): void {
+    if (chunk) this.write(chunk);
+    this.writableEnded = true;
+  }
+  on(): this {
+    return this;
+  }
+  once(): this {
+    return this;
+  }
+  get body(): string {
+    return this.chunks.join('');
+  }
+}
+
+/** Mock model that issues one getSharePage tool call, then finishes with text. */
+function toolCallingModel(): MockLanguageModelV3 {
+  let call = 0;
+  return new MockLanguageModelV3({
+    doStream: async () => {
+      call++;
+      if (call === 1) {
+        return {
+          stream: simulateReadableStream({
+            chunks: [
+              { type: 'stream-start' as const, warnings: [] },
+              { type: 'tool-input-start' as const, id: 't1', toolName: 'getSharePage' },
+              { type: 'tool-input-end' as const, id: 't1' },
+              {
+                type: 'tool-call' as const,
+                toolCallId: 't1',
+                toolName: 'getSharePage',
+                input: '{"pageId":"secret-page"}',
+              },
+              {
+                type: 'finish' as const,
+                finishReason: { unified: 'tool-calls' as const, raw: 'tool_calls' },
+                usage: {
+                  inputTokens: { total: 1, noCache: undefined, cacheRead: undefined, cacheWrite: undefined },
+                  outputTokens: { total: 1, text: 1, reasoning: undefined },
+                },
+              },
+            ],
+          }),
+        };
+      }
+      return {
+        stream: simulateReadableStream({
+          chunks: [
+            { type: 'stream-start' as const, warnings: [] },
+            { type: 'text-start' as const, id: '1' },
+            { type: 'text-delta' as const, id: '1', delta: 'Sorry.' },
+            { type: 'text-end' as const, id: '1' },
+            {
+              type: 'finish' as const,
+              finishReason: { unified: 'stop' as const, raw: 'stop' },
+              usage: {
+                inputTokens: { total: 1, noCache: undefined, cacheRead: undefined, cacheWrite: undefined },
+                outputTokens: { total: 1, text: 1, reasoning: undefined },
+              },
+            },
+          ],
+        }),
+      };
+    },
+  });
+}
+
+/** Mock model whose stream emits a provider error carrying an internal secret. */
+function providerErrorModel(secret: string): MockLanguageModelV3 {
+  return new MockLanguageModelV3({
+    doStream: async () => ({
+      stream: simulateReadableStream({
+        chunks: [
+          { type: 'stream-start' as const, warnings: [] },
+          {
+            type: 'error' as const,
+            error: {
+              statusCode: 503,
+              message: 'Service Unavailable',
+              responseBody: `upstream ${secret} model=internal-gpt`,
+            },
+          },
+        ],
+      }),
+    }),
+  });
+}
+
+function makeService(toolsService: PublicShareChatToolsService): {
+  svc: PublicShareChatService;
+  logSpy: jest.SpyInstance;
+} {
+  const svc = Object.create(PublicShareChatService.prototype);
+  const logger = new Logger('test');
+  const logSpy = jest.spyOn(logger, 'error').mockImplementation(() => undefined);
+  jest.spyOn(logger, 'warn').mockImplementation(() => undefined);
+  svc.tools = toolsService;
+  svc.logger = logger;
+  svc.tokenBudget = { record: jest.fn().mockResolvedValue(undefined) };
+  return { svc, logSpy };
+}
+
+async function runStream(
+  svc: PublicShareChatService,
+  model: MockLanguageModelV3,
+): Promise<FakeSocket> {
+  const socket = new FakeSocket();
+  await svc.stream({
+    workspaceId: 'ws1',
+    shareId: 'share1',
+    share: { id: 'share1', pageId: 'p1', sharedPage: { id: 'p1', title: 'Docs' } },
+    openedPage: null,
+    messages: [
+      { id: 'm1', role: 'user', parts: [{ type: 'text', text: 'read the page' }] } as never,
+    ],
+    res: { raw: socket } as never,
+    signal: new AbortController().signal,
+    model: model as never,
+    role: null,
+  });
+  // Let the piped stream drain fully.
+  await new Promise((r) => setTimeout(r, 300));
+  return socket;
+}
+
+describe('public share chat error leak (#394)', () => {
+  afterEach(() => jest.restoreAllMocks());
+
+  it('does NOT leak a tool\'s raw internal error to the SSE bytes (generic classified string instead)', async () => {
+    const SECRET = 'INTERNAL_baseUrl_http://provider.internal:8080/v1';
+    const shareService = {
+      // The canonical boundary throws a RAW internal error (with a secret).
+      resolveReadableSharePage: jest
+        .fn()
+        .mockRejectedValue(new Error(`db failed at ${SECRET} stack@line42`)),
+    };
+    const tools = new PublicShareChatToolsService(
+      shareService as never,
+      {} as never,
+      {} as never,
+    );
+    const { svc } = makeService(tools);
+
+    const socket = await runStream(svc, toolCallingModel());
+
+    // The tool-output-error frame is present on the wire...
+    expect(socket.body).toContain('tool-output-error');
+    // ...but it carries ONLY the generic classified string — never the secret,
+    // the raw driver message, or a stack fragment.
+    expect(socket.body).toContain('The tool could not complete the request.');
+    expect(socket.body).not.toContain(SECRET);
+    expect(socket.body).not.toContain('stack@line42');
+    expect(socket.body).not.toContain('db failed');
+  });
+
+  it('passes a SAFE ShareToolError message (page not available) through to the bytes', async () => {
+    const shareService = {
+      // Not found in this share -> the tool throws the classified SAFE message.
+      resolveReadableSharePage: jest.fn().mockResolvedValue(null),
+    };
+    const tools = new PublicShareChatToolsService(
+      shareService as never,
+      {} as never,
+      {} as never,
+    );
+    const { svc } = makeService(tools);
+
+    const socket = await runStream(svc, toolCallingModel());
+    expect(socket.body).toContain('tool-output-error');
+    expect(socket.body).toContain('not available in this share');
+  });
+
+  it('does NOT leak a provider error (statusCode + response body) to the SSE bytes', async () => {
+    const SECRET = 'http://provider.internal:8080';
+    const tools = new PublicShareChatToolsService(
+      {} as never,
+      {} as never,
+      {} as never,
+    );
+    const { svc, logSpy } = makeService(tools);
+
+    const socket = await runStream(svc, providerErrorModel(SECRET));
+
+    // The anon sees a fixed classified string, not the provider body/baseUrl/model.
+    expect(socket.body).toContain('temporarily unavailable');
+    expect(socket.body).not.toContain(SECRET);
+    expect(socket.body).not.toContain('internal-gpt');
+    // The FULL provider detail is logged server-side only.
+    const logged = logSpy.mock.calls.map((c) => String(c[0])).join('\n');
+    expect(logged).toContain(SECRET);
+  });
+});

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

@@ -12,7 +12,10 @@ import { AiAgentRoleRepo } from '@docmost/db/repos/ai-agent-roles/ai-agent-roles
 import { AiAgentRole } from '@docmost/db/types/entity.types';
 import { AiService } from '../../integrations/ai/ai.service';
 import { AiSettingsService } from '../../integrations/ai/ai-settings.service';
-import { PublicShareChatToolsService } from './tools/public-share-chat-tools.service';
+import {
+  PublicShareChatToolsService,
+  ShareToolError,
+} from './tools/public-share-chat-tools.service';
 import { buildShareSystemPrompt } from './public-share-chat.prompt';
 import { roleModelOverride } from './roles/role-model-config';
 import {
@@ -102,6 +105,30 @@ export function filterShareTranscript(messages: UIMessage[]): UIMessage[] {
   );
 }
 
+/**
+ * Fixed, classified strings an ANONYMOUS share reader may see when the assistant
+ * stream fails (#394). These reveal NOTHING about the internal provider, its
+ * baseUrl, the model name, or the raw response body — unlike describeProviderError
+ * (which is for the server log / the authenticated operator only). We classify by
+ * HTTP status where available so the reader still gets a useful hint (retry vs.
+ * give up) without any internal detail.
+ */
+export function classifyAnonStreamError(error: unknown): string {
+  const status =
+    typeof error === 'object' && error !== null
+      ? (error as { statusCode?: number }).statusCode
+      : undefined;
+  if (status === 429) {
+    return 'The assistant is receiving too many requests right now. Please try again shortly.';
+  }
+  if (typeof status === 'number' && status >= 500) {
+    return 'The assistant is temporarily unavailable. Please try again.';
+  }
+  // Any other failure (including a bare connection error with no status): a
+  // single neutral line. No provider identity, no config, no response body.
+  return 'The assistant could not complete your request. Please try again.';
+}
+
 /**
  * Anonymous, read-only AI assistant for a single PUBLIC share tree.
  *
@@ -318,11 +345,28 @@ export class PublicShareChatService {
       result.pipeUIMessageStreamToResponse(res.raw, {
         headers: { 'X-Accel-Buffering': 'no' },
         onError: (error: unknown) => {
-          // Reuse the shared formatter so provider error formatting stays
-          // unified between the log line and the streamed error message — a
-          // share reader sees 402/429/503 causes consistently with the
-          // authenticated path.
-          return describeProviderError(error, 'AI stream error');
+          // SECURITY (#394): the string this returns is written verbatim into the
+          // SSE error frame delivered to an ANONYMOUS reader (for a tool failure
+          // it becomes the atomic `tool-output-error` frame's errorText; for a
+          // stream/provider failure, the terminal error frame).
+          //
+          // A ShareToolError is already a classified, safe tool message (see
+          // PublicShareChatToolsService.wrapToolErrors) — pass it through so the
+          // reader still gets the useful "page not available in this share" hint.
+          if (error instanceof ShareToolError) {
+            return error.message;
+          }
+          // Anything else is a provider/stream error. describeProviderError
+          // bundles the provider statusCode AND response body, which can carry the
+          // internal baseUrl or model name — NEVER expose that to the public. Log
+          // the full detail server-side only and return a fixed classified string.
+          this.logger.error(
+            `Public share chat pipe error: ${describeProviderError(
+              error,
+              'AI stream error',
+            )}`,
+          );
+          return classifyAnonStreamError(error);
         },
       });
 

apps/server/src/core/ai-chat/public-share-chat.spec.ts

@@ -808,7 +808,7 @@ describe('PublicShareChatToolsService share scoping', () => {
     };
 
     await expect(getSharePage.execute({ pageId: 'p-outside' })).rejects.toThrow(
-      /not part of this published share/i,
+      /not available in this share/i,
     );
     // The tool delegated the resolve to the canonical boundary with the
     // forShare-scoped shareId, and returned NO content for a non-resolving page.
@@ -841,7 +841,7 @@ describe('PublicShareChatToolsService share scoping', () => {
 
     await expect(
       getSharePage.execute({ pageId: 'p-restricted' }),
-    ).rejects.toThrow(/not part of this published share/i);
+    ).rejects.toThrow(/not available in this share/i);
     // No content was ever sanitized/returned for the blocked page.
     expect(shareService.updatePublicAttachments).not.toHaveBeenCalled();
   });
@@ -1003,7 +1003,7 @@ describe('public-share assistant boundary locks (red-team regression guards)', (
     };
     await expect(
       getSharePage.execute({ pageId: 'p-elsewhere' }),
-    ).rejects.toThrow(/not part of this published share/i);
+    ).rejects.toThrow(/not available in this share/i);
     // The forged share id is the scope the boundary re-derivation rejects against.
     expect(shareService.resolveReadableSharePage).toHaveBeenCalledWith(
       'FORGED-SHARE',

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

@@ -1,6 +1,17 @@
 import { AiChatToolsService } from './ai-chat-tools.service';
 import * as loader from './docmost-client.loader';
 import type { DocmostClientLike } from './docmost-client.loader';
+
+// Test-double type for the loopback client. `DocmostClientLike` is now DERIVED
+// from the real `DocmostClient` (issue #446), so its method RETURN types are the
+// concrete client shapes. These stubs deliberately return minimal recording
+// shapes (e.g. `{ ok: true }`), which no longer satisfy those concrete returns —
+// so the doubles are typed with the same method NAMES but loose async returns.
+// Each is still cast to `DocmostClientLike` at the (return-erased) mock site, so
+// the positional-call type-safety on the PRODUCTION client is unaffected.
+type FakeDocmostClient = Partial<
+  Record<keyof DocmostClientLike, (...args: any[]) => Promise<any>>
+>;
 // The real zod-agnostic shared tool-spec registry. It has no runtime deps, so
 // importing the TS source directly keeps these mocks honest: the service builds
 // the shared tools from exactly the specs the package ships, not a hand-stub.
@@ -12,7 +23,15 @@ import { SHARED_TOOL_SPECS } from '../../../../../../packages/mcp/src/tool-specs
 // sync.
 const mockLoaded = (DocmostClient: loader.DocmostClientCtor) => ({
   DocmostClient,
-  sharedToolSpecs: SHARED_TOOL_SPECS as Record<string, loader.SharedToolSpec>,
+  sharedToolSpecs: SHARED_TOOL_SPECS as unknown as Record<string, loader.SharedToolSpec>,
+  // Pure no-network draw.io helpers (#424). Type-correct stubs: these tests
+  // never execute the drawioShapes / drawioGuide tool bodies.
+  searchShapes: (() => []) as unknown as loader.SearchShapesFn,
+  getGuideSection: (() => ({
+    section: 'index',
+    content: '',
+    sections: [],
+  })) as unknown as loader.GetGuideSectionFn,
 });
 
 /**
@@ -31,7 +50,7 @@ describe('AiChatToolsService deletePage guardrail (H4)', () => {
 
   // Minimal fake DocmostClient: only the write methods the tools touch need to
   // exist; deletePage records its args. No network, no ESM import.
-  const fakeClient: Partial<DocmostClientLike> = {
+  const fakeClient: FakeDocmostClient = {
     deletePage: (...args: unknown[]) => {
       deletePageCalls.push(args);
       return Promise.resolve({ success: true });
@@ -160,7 +179,7 @@ describe('AiChatToolsService deletePage guardrail (H4)', () => {
 describe('AiChatToolsService expanded toolset guardrails', () => {
   // No client method is invoked here — every assertion is on tool presence /
   // input schema — so an empty fake client is sufficient.
-  const fakeClient: Partial<DocmostClientLike> = {};
+  const fakeClient: FakeDocmostClient = {};
 
   const tokenServiceStub = {
     generateAccessToken: jest.fn().mockResolvedValue('access-token'),
@@ -264,8 +283,9 @@ describe('AiChatToolsService node-arg JSON-string coercion', () => {
   const patchNodeCalls: unknown[][] = [];
   const insertNodeCalls: unknown[][] = [];
   const updatePageJsonCalls: unknown[][] = [];
+  const updatePageCalls: unknown[][] = [];
 
-  const fakeClient: Partial<DocmostClientLike> = {
+  const fakeClient: FakeDocmostClient = {
     patchNode: (...args: unknown[]) => {
       patchNodeCalls.push(args);
       return Promise.resolve({ ok: true });
@@ -278,6 +298,11 @@ describe('AiChatToolsService node-arg JSON-string coercion', () => {
       updatePageJsonCalls.push(args);
       return Promise.resolve({ ok: true });
     },
+    // Backs the plain-Markdown full-body-replace tool updatePageMarkdown (#411).
+    updatePage: (...args: unknown[]) => {
+      updatePageCalls.push(args);
+      return Promise.resolve({ success: true });
+    },
   };
 
   const tokenServiceStub = {
@@ -291,6 +316,7 @@ describe('AiChatToolsService node-arg JSON-string coercion', () => {
     patchNodeCalls.length = 0;
     insertNodeCalls.length = 0;
     updatePageJsonCalls.length = 0;
+    updatePageCalls.length = 0;
     jest.spyOn(loader, 'loadDocmostMcp').mockResolvedValue(
       mockLoaded(function () {
         return fakeClient as DocmostClientLike;
@@ -329,23 +355,32 @@ describe('AiChatToolsService node-arg JSON-string coercion', () => {
     content: [{ type: 'text', text: 'Hello' }],
   };
 
-  it('patchNode parses a JSON-string node and forwards it as an object', async () => {
+  it('patchNode parses a JSON-string node and forwards it as { node } (object)', async () => {
     const tools = await buildTools();
     await tools.patchNode.execute(
       { pageId: 'p1', nodeId: 'n1', node: JSON.stringify(NODE_OBJ) } as never,
       {} as never,
     );
     expect(patchNodeCalls).toHaveLength(1);
-    expect(patchNodeCalls[0]).toEqual(['p1', 'n1', NODE_OBJ]);
+    // #413: the 3rd arg is now the XOR input { markdown?, node? }.
+    expect(patchNodeCalls[0]).toEqual([
+      'p1',
+      'n1',
+      { markdown: undefined, node: NODE_OBJ },
+    ]);
   });
 
-  it('patchNode passes an object node through unchanged', async () => {
+  it('patchNode passes an object node through unchanged inside { node }', async () => {
     const tools = await buildTools();
     await tools.patchNode.execute(
       { pageId: 'p1', nodeId: 'n1', node: NODE_OBJ } as never,
       {} as never,
     );
-    expect(patchNodeCalls[0]).toEqual(['p1', 'n1', NODE_OBJ]);
+    expect(patchNodeCalls[0]).toEqual([
+      'p1',
+      'n1',
+      { markdown: undefined, node: NODE_OBJ },
+    ]);
   });
 
   it('patchNode throws the documented message on invalid JSON string', async () => {
@@ -359,7 +394,7 @@ describe('AiChatToolsService node-arg JSON-string coercion', () => {
     expect(patchNodeCalls).toHaveLength(0);
   });
 
-  it('insertNode parses a JSON-string node and forwards it as an object', async () => {
+  it('insertNode parses a JSON-string node and forwards it inside { node }', async () => {
     const tools = await buildTools();
     await tools.insertNode.execute(
       {
@@ -370,9 +405,15 @@ describe('AiChatToolsService node-arg JSON-string coercion', () => {
       {} as never,
     );
     expect(insertNodeCalls).toHaveLength(1);
-    const [pageId, node] = insertNodeCalls[0];
+    // #413: the 2nd arg is the XOR input { markdown?, node? }, the 3rd is opts.
+    const [pageId, input, opts] = insertNodeCalls[0] as [
+      string,
+      { markdown?: unknown; node?: unknown },
+      { position?: string },
+    ];
     expect(pageId).toBe('p1');
-    expect(node).toEqual(NODE_OBJ);
+    expect(input).toEqual({ markdown: undefined, node: NODE_OBJ });
+    expect(opts.position).toBe('append');
   });
 
   it('insertNode throws the documented message on invalid JSON string', async () => {
@@ -426,6 +467,54 @@ describe('AiChatToolsService node-arg JSON-string coercion', () => {
     ).rejects.toThrow('content was a string but not valid JSON');
     expect(updatePageJsonCalls).toHaveLength(0);
   });
+
+  // #411: the plain-Markdown full-body-replace tool is now the shared
+  // `updatePageMarkdown` (was inline `updatePageContent`). It forwards to
+  // client.updatePage(pageId, content, title) -> updatePageContentRealtime ->
+  // markdownToProseMirrorCanonical, so `^[...]` footnotes materialize.
+  it('updatePageMarkdown forwards { pageId, content, title } to client.updatePage', async () => {
+    const tools = await buildTools();
+    await tools.updatePageMarkdown.execute(
+      { pageId: 'p1', content: 'Body^[a note]', title: 'New title' } as never,
+      {} as never,
+    );
+    expect(updatePageCalls).toHaveLength(1);
+    expect(updatePageCalls[0]).toEqual(['p1', 'Body^[a note]', 'New title']);
+  });
+
+  it('updatePageMarkdown returns the RAW client result in-app (deliberate #411 shape change, documented on the spec)', async () => {
+    const tools = await buildTools();
+    // Registry canonical execute returns client.updatePage's result verbatim.
+    // The old inline tool projected to { pageId, updated }; the rename now
+    // surfaces the raw result (nothing reads the removed `.updated`; the raw
+    // shape carries footnote/verify warnings and matches the on-both-hosts
+    // registry convention). fakeClient.updatePage resolves { success: true }.
+    const result = await tools.updatePageMarkdown.execute(
+      { pageId: 'p1', content: '# Hi' } as never,
+      {} as never,
+    );
+    expect(result).toEqual({ success: true });
+  });
+
+  it('updatePageMarkdown forwards title=undefined when omitted', async () => {
+    const tools = await buildTools();
+    await tools.updatePageMarkdown.execute(
+      { pageId: 'p1', content: '# Hi' } as never,
+      {} as never,
+    );
+    expect(updatePageCalls[0]).toEqual(['p1', '# Hi', undefined]);
+  });
+
+  // #411 surface split: the plain-Markdown replace tool exists in-app under the
+  // new key; the OLD inline updatePageContent key is gone; importPageMarkdown is
+  // still present IN-APP (only the external MCP surface drops it — asserted in
+  // packages/mcp/test/unit/tool-inventory.test.mjs).
+  it('exposes updatePageMarkdown in-app, no legacy updatePageContent, keeps importPageMarkdown', async () => {
+    const tools = await buildTools();
+    expect(tools.updatePageMarkdown).toBeDefined();
+    expect((tools as Record<string, unknown>).updatePageContent).toBeUndefined();
+    expect(tools.importPageMarkdown).toBeDefined();
+  });
 });
 
 /**
@@ -439,7 +528,7 @@ describe('AiChatToolsService node-arg JSON-string coercion', () => {
  * getOutline) are exercised here end-to-end through forUser().
  */
 describe('AiChatToolsService model-friendly input validation (#190)', () => {
-  const fakeClient: Partial<DocmostClientLike> = {};
+  const fakeClient: FakeDocmostClient = {};
   const tokenServiceStub = {
     generateAccessToken: jest.fn().mockResolvedValue('access-token'),
     generateCollabToken: jest.fn().mockResolvedValue('collab-token'),
@@ -557,7 +646,7 @@ describe('AiChatToolsService #294 changed execute wirings', () => {
     tableDeleteRow: [],
     tableUpdateCell: [],
   };
-  const fakeClient: Partial<DocmostClientLike> = {
+  const fakeClient: FakeDocmostClient = {
     movePage: (...args: unknown[]) => {
       calls.movePage.push(args);
       return Promise.resolve({ success: true });
@@ -666,7 +755,7 @@ describe('AiChatToolsService #410 footnote + image tools', () => {
     insertImage: [],
     replaceImage: [],
   };
-  const fakeClient: Partial<DocmostClientLike> = {
+  const fakeClient: FakeDocmostClient = {
     insertFootnote: (...args: unknown[]) => {
       calls.insertFootnote.push(args);
       return Promise.resolve({ success: true, footnoteId: 'fn1', reused: false });
@@ -836,3 +925,109 @@ describe('AiChatToolsService getCurrentPage selection (#388)', () => {
     );
   });
 });
+
+/**
+ * #440 review: the in-app drawioCreate / drawioUpdate handlers must forward
+ * the optional `layout:"elk"` param to the client (5th positional arg), exactly
+ * like the MCP host. It was silently dropped, so ELK auto-layout worked only via
+ * the standalone MCP server, not in-app. These tests pin per-host parity.
+ */
+describe('AiChatToolsService drawio layout passthrough (#440)', () => {
+  const createCalls: unknown[][] = [];
+  const updateCalls: unknown[][] = [];
+
+  // FakeDocmostClient (not Partial<DocmostClientLike>): since #446 derived
+  // DocmostClientLike from the real client, its drawioCreate/drawioUpdate return
+  // the concrete result shape, so a minimal stub object would not be assignable.
+  // FakeDocmostClient types every method as (...args) => Promise<any>, which is
+  // exactly what these arg-capturing doubles need.
+  const fakeClient: FakeDocmostClient = {
+    drawioCreate: (...args: unknown[]) => {
+      createCalls.push(args);
+      return Promise.resolve({ success: true, nodeId: '#0' });
+    },
+    drawioUpdate: (...args: unknown[]) => {
+      updateCalls.push(args);
+      return Promise.resolve({ success: true, nodeId: '#0' });
+    },
+  };
+
+  const tokenServiceStub = {
+    generateAccessToken: jest.fn().mockResolvedValue('access-token'),
+    generateCollabToken: jest.fn().mockResolvedValue('collab-token'),
+  };
+
+  let service: AiChatToolsService;
+
+  beforeEach(() => {
+    createCalls.length = 0;
+    updateCalls.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('forwards layout:"elk" to client.drawioCreate as the 5th positional arg', async () => {
+    const tools = await buildTools();
+    await tools.drawioCreate.execute(
+      {
+        pageId: 'p-1',
+        xml: '<mxGraphModel/>',
+        position: 'append',
+        layout: 'elk',
+      } as never,
+      {} as never,
+    );
+    expect(createCalls).toHaveLength(1);
+    // drawioCreate(pageId, where, xml, title, layout) — layout is args[4].
+    expect(createCalls[0][4]).toBe('elk');
+  });
+
+  it('forwards layout:"elk" to client.drawioUpdate as the 5th positional arg', async () => {
+    const tools = await buildTools();
+    await tools.drawioUpdate.execute(
+      {
+        pageId: 'p-1',
+        node: '#0',
+        xml: '<mxGraphModel/>',
+        baseHash: 'h',
+        layout: 'elk',
+      } as never,
+      {} as never,
+    );
+    expect(updateCalls).toHaveLength(1);
+    // drawioUpdate(pageId, node, xml, baseHash, layout) — layout is args[4].
+    expect(updateCalls[0][4]).toBe('elk');
+  });
+
+  it('omits layout (undefined 5th arg) when not requested', async () => {
+    const tools = await buildTools();
+    await tools.drawioCreate.execute(
+      { pageId: 'p-1', xml: '<mxGraphModel/>', position: 'append' } as never,
+      {} as never,
+    );
+    expect(createCalls[0][4]).toBeUndefined();
+  });
+});

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

@@ -26,6 +26,125 @@ import {
   type ToolCatalogEntry,
 } from './tool-tiers';
 
+/**
+ * Compile-time contract (issue #446): the in-app tool `execute` closures below
+ * call the loopback `DocmostClient` POSITIONALLY (e.g.
+ * `client.drawioGet(pageId, node, format ?? 'xml')`). Those closures receive an
+ * AI-SDK-erased (`any`) input, so a positional call inside them is NOT checked
+ * against the real signature — a parameter reorder/type-change in
+ * `packages/mcp/src/client.ts` would otherwise reach production as a runtime
+ * "wrong argument" tool failure with zero compile signal (the restored #294
+ * debt). This never-called function reproduces every positional call with
+ * correctly-typed placeholder arguments against the DERIVED `DocmostClientLike`
+ * (a `Pick` of the real `DocmostClient`), so any such reorder/rename becomes a
+ * SERVER COMPILE ERROR here. It emits nothing (types only) and is never invoked;
+ * keep each call in lockstep with the matching `execute` body below.
+ */
+// eslint-disable-next-line @typescript-eslint/no-unused-vars
+function __assertClientCallContract(client: DocmostClientLike): void {
+  // Placeholders standing in for the AI-SDK-erased execute inputs. Their types
+  // are deliberately concrete so the positional calls are checked end-to-end.
+  const s = '' as string;
+  const n = 0 as number;
+  const node: unknown = null;
+  const edits: Array<{ find: string; replace: string; replaceAll?: boolean }> =
+    [];
+  const cells: string[] = [];
+  const align = undefined as 'left' | 'center' | 'right' | undefined;
+
+  // --- read ---
+  void client.search(s, undefined, n);
+  void client.getPage(s);
+  void client.getPageRaw(s);
+  void client.getWorkspace();
+  void client.getSpaces();
+  void client.listPages(s, n, true);
+  void client.getTree(s, s, n);
+  void client.getPageContext(s);
+  void client.listSidebarPages(s, s);
+  void client.getOutline(s);
+  void client.getPageJson(s);
+  void client.getNode(s, s, 'markdown');
+  void client.searchInPage(s, s, {
+    regex: true,
+    caseSensitive: true,
+    limit: n,
+  });
+  void client.getTable(s, s);
+  void client.listComments(s, true);
+  void client.getComment(s);
+  void client.checkNewComments(s, s, s);
+  void client.listShares();
+  void client.listPageHistory(s, s);
+  void client.getPageHistory(s);
+  void client.diffPageVersions(s, s, s);
+  void client.exportPageMarkdown(s);
+  // --- write (page) ---
+  void client.createPage(s, s, s, s);
+  void client.updatePage(s, s, s);
+  void client.renamePage(s, s);
+  void client.movePage(s, s, s);
+  void client.deletePage(s);
+  void client.editPageText(s, edits);
+  void client.patchNode(s, s, { markdown: s, node });
+  void client.insertNode(
+    s,
+    { markdown: s, node },
+    {
+      position: 'append',
+      anchorNodeId: s,
+      anchorText: s,
+    },
+  );
+  void client.deleteNode(s, s);
+  void client.updatePageJson(s, node, s);
+  void client.tableInsertRow(s, s, cells, n);
+  void client.tableDeleteRow(s, s, n);
+  void client.tableUpdateCell(s, s, n, n, s);
+  void client.copyPageContent(s, s);
+  void client.importPageMarkdown(s, s);
+  void client.sharePage(s, true);
+  void client.unsharePage(s);
+  void client.restorePageVersion(s);
+  void client.transformPage(s, s, { dryRun: true });
+  void client.stashPage(s);
+  // --- write (image / footnote), in-app since #410 ---
+  void client.insertFootnote(s, s, s);
+  void client.insertImage(s, s, {
+    align,
+    alt: s,
+    replaceText: s,
+    afterText: s,
+  });
+  void client.replaceImage(s, s, s, { align, alt: s });
+  // --- draw.io diagrams (#423 stage 1, #424 stage 2) ---
+  // The 5th `layout` arg (#424) is exercised so this parity assertion fails if the
+  // client signature drops it — it must reach the client from the shared execute.
+  void client.drawioGet(s, s, 'xml');
+  void client.drawioCreate(s, { position: 'append', anchorNodeId: s }, s, s, 'elk');
+  void client.drawioUpdate(s, s, s, s, 'elk');
+  // --- draw.io high-level semantic tools (#425 stage 3) ---
+  void client.drawioEditCells(s, s, [{ op: 'delete', cellId: s }], s);
+  void client.drawioFromGraph(
+    s,
+    { position: 'append', anchorNodeId: s },
+    { nodes: [{ id: s, label: s }] },
+    'LR',
+    s,
+    'full',
+    s,
+  );
+  void client.drawioFromMermaid(
+    s,
+    { position: 'append', anchorNodeId: s },
+    s,
+    s,
+  );
+  // --- write (comment) ---
+  void client.createComment(s, s, 'inline', s, s, s);
+  void client.resolveComment(s, true);
+}
+
 /**
  * Per-user, per-request adapter that exposes Docmost READ operations to the
  * agent as AI SDK tools (STAGE A = read only).
@@ -169,8 +288,19 @@ export class AiChatToolsService {
     // provenance tokens) and load the shared tool-spec registry. Client
     // construction is shared with the page-change detection path (#274) via
     // buildDocmostClient so both go over the exact same authenticated route.
-    const { sharedToolSpecs, createCommentSignalTracker } =
-      await loadDocmostMcp();
+    // searchShapes / getGuideSection (#424) are the PURE, no-network helpers
+    // backing drawioShapes / drawioGuide. They are `inlineBothHosts` specs (no
+    // canonical execute — their catalog loader uses import.meta and can't be
+    // value-imported into the zod-agnostic tool-specs.ts under the server's
+    // commonjs type-check), so the shared registry loop below SKIPS them and this
+    // service wires them inline (see drawioShapes/drawioGuide entries), mirroring
+    // how index.ts registers them on the standalone MCP host.
+    const {
+      sharedToolSpecs,
+      createCommentSignalTracker,
+      searchShapes,
+      getGuideSection,
+    } = await loadDocmostMcp();
     const client = await this.buildDocmostClient(
       user,
       sessionId,
@@ -198,6 +328,18 @@ export class AiChatToolsService {
         execute,
       });
 
+    // The in-app toolset. It starts with the tools kept INLINE here for a
+    // documented per-layer reason: an intentional behaviour/schema divergence from
+    // the standalone MCP surface (searchPages' hybrid RRF,
+    // transformPage's guardrailed shorter schema), a name clash the shared
+    // registry forbids (in-app `getTable` verb-first vs the MCP noun-first
+    // `tableGet` — the registry requires mcpName === inAppKey), per-request
+    // state the registry loop cannot provide
+    // (getCurrentPage reads the resolved openedPage; searchPages closes over the
+    // per-request user/embedding deps), or a tool with no MCP twin
+    // (listSidebarPages/getComment/getPageHistory). Every SHARED tool is then added
+    // by the registry loop below (see it), so there is exactly one arg-mapping per
+    // shared tool and it can never drift from the MCP host again (#445).
     const tools: Record<string, Tool> = {
       // INTENTIONAL per-transport divergence (not in the shared registry): this
       // in-app search runs a semantic + keyword hybrid (RRF) with in-process
@@ -332,180 +474,14 @@ export class AiChatToolsService {
         execute: async () => resolveCurrentPageResult(openedPage),
       }),
 
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      // The execute body keeps this layer's { title, markdown } projection.
-      getPage: sharedTool(sharedToolSpecs.getPage, async ({ pageId }) => {
-        // getPage(pageId) -> { data: filterPage(page, markdown), success }.
-        const result = await client.getPage(pageId);
-        const data = (result?.data ?? {}) as {
-          title?: string;
-          content?: string;
-        };
-        return {
-          title: data.title ?? '',
-          markdown: typeof data.content === 'string' ? data.content : '',
-        };
-      }),
-
       // --- WRITE tools (all reversible — history/trash; §6.5 / D3) ---
-
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      createPage: sharedTool(
-        sharedToolSpecs.createPage,
-        async ({ title, content, spaceId, parentPageId }) => {
-          // createPage(title, content, spaceId, parentPageId?) ->
-          // { data: filterPage(page, markdown), success }.
-          const result = await client.createPage(
-            title,
-            content ?? '',
-            spaceId,
-            parentPageId,
-          );
-          const data = (result?.data ?? {}) as {
-            id?: string;
-            slugId?: string;
-            title?: string;
-          };
-          return { id: data.id ?? data.slugId, title: data.title ?? title };
-        },
-      ),
-
-      updatePageContent: tool({
-        description:
-          "Replace a page's body with new Markdown content (and optionally its " +
-          'title). Reversible: the previous version is kept in page history.',
-        inputSchema: modelFriendlyInput({
-          pageId: z.string().describe('The id of the page to update.'),
-          content: z.string().describe('The new page body as Markdown.'),
-          title: z
-            .string()
-            .optional()
-            .describe('Optional new title for the page.'),
-        }),
-        execute: async ({ pageId, content, title }) => {
-          // updatePage mutates the live collab doc -> provenance flows from the
-          // collab-token provider. Returns { success, modified, message, pageId }.
-          const result = (await client.updatePage(pageId, content, title)) as {
-            success?: boolean;
-          };
-          return { pageId, updated: result?.success ?? true };
-        },
-      }),
-
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      renamePage: sharedTool(
-        sharedToolSpecs.renamePage,
-        async ({ pageId, title }) => {
-          // renamePage(pageId, title) -> { success, pageId, title }.
-          await client.renamePage(pageId, title);
-          return { pageId, title };
-        },
-      ),
-
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      // The shared schema adds the optional `position` field this layer lacked
-      // before; the execute now forwards it (the client already accepted it).
-      movePage: sharedTool(
-        sharedToolSpecs.movePage,
-        async ({ pageId, parentPageId, position }) => {
-          // movePage(pageId, parentPageId, position?) -> raw move response.
-          await client.movePage(pageId, parentPageId ?? null, position);
-          return { pageId, parentPageId: parentPageId ?? null, moved: true };
-        },
-      ),
-
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      // GUARDRAIL (§14 H4) preserved: the shared schema exposes ONLY pageId, so
-      // permanentlyDelete/forceDelete are never part of the input and can never
-      // be forwarded — the agent physically cannot permanently delete a page.
-      deletePage: sharedTool(sharedToolSpecs.deletePage, async ({ pageId }) => {
-        // deletePage(pageId) hits POST /pages/delete with { pageId } only,
-        // which is the soft-delete (trash) path on the server.
-        await client.deletePage(pageId);
-        return { pageId, trashed: true };
-      }),
-
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      // This layer keeps only its own execute-side guards (require a selection
-      // for a top-level comment; reject suggestedText on a reply / without a
-      // selection) — the schema+description are shared.
-      createComment: sharedTool(
-        sharedToolSpecs.createComment,
-        async ({
-          pageId,
-          content,
-          selection,
-          parentCommentId,
-          suggestedText,
-        }) => {
-          // createComment(pageId, content, type, selection?, parentCommentId?,
-          // suggestedText?). Top-level comments are inline and must carry a
-          // selection to anchor on; replies inherit the parent's anchor (no
-          // selection). Throwing here surfaces a tool error to the model (Vercel
-          // `ai` SDK) so the agent retries with a better selection — do not
-          // catch/suppress it.
-          if (!parentCommentId && (!selection || !selection.trim())) {
-            throw new Error(
-              "createComment requires a 'selection' (exact text to anchor on) for a new top-level comment.",
-            );
-          }
-          if (suggestedText !== undefined) {
-            if (parentCommentId) {
-              throw new Error(
-                "createComment: 'suggestedText' cannot be attached to a reply; it applies only to a top-level inline comment.",
-              );
-            }
-            if (!selection || !selection.trim()) {
-              throw new Error(
-                "createComment: 'suggestedText' requires a 'selection' to anchor and rewrite.",
-              );
-            }
-          }
-          const result = await client.createComment(
-            pageId,
-            content,
-            'inline',
-            selection,
-            parentCommentId,
-            suggestedText,
-          );
-          const data = (result?.data ?? {}) as { id?: string };
-          return { commentId: data.id, pageId };
-        },
-      ),
-
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      resolveComment: sharedTool(
-        sharedToolSpecs.resolveComment,
-        async ({ commentId, resolved }) => {
-          // resolveComment(commentId, resolved) -> { success, commentId, resolved }.
-          await client.resolveComment(commentId, resolved);
-          return { commentId, resolved };
-        },
-      ),
-
-      // --- READ tools (added) ---
-
-      getWorkspace: sharedTool(
-        sharedToolSpecs.getWorkspace,
-        async () => await client.getWorkspace(),
-      ),
-
-      listSpaces: sharedTool(
-        sharedToolSpecs.listSpaces,
-        async () => await client.getSpaces(),
-      ),
-
-      // INTENTIONAL per-transport divergence (not shared): keeps the `tree:true`
-      // hierarchy mode but is worded for the in-app agent; the standalone MCP
-      // `list_pages` carries its own wording. Kept per-layer so each side tunes
-      // its own guidance.
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      listPages: sharedTool(
-        sharedToolSpecs.listPages,
-        async ({ spaceId, limit, tree }) =>
-          await client.listPages(spaceId, limit, tree),
-      ),
+      //
+      // NOTE (issue #411): the plain-Markdown full-body-replace tool is no longer
+      // inline here — it moved to @docmost/mcp's SHARED_TOOL_SPECS as
+      // `updatePageMarkdown` (was inline `updatePageContent`) so it registers on
+      // BOTH the external MCP and the in-app agent. The registry loop below adds
+      // it under its inAppKey. importPageMarkdown stays a shared spec too (now
+      // inAppOnly — dropped from the external MCP surface, kept in-app).
 
       listSidebarPages: tool({
         description:
@@ -525,34 +501,9 @@ export class AiChatToolsService {
           await client.listSidebarPages(spaceId, pageId),
       }),
 
-      getOutline: sharedTool(
-        sharedToolSpecs.getOutline,
-        async ({ pageId }) => await client.getOutline(pageId),
-      ),
-
-      getPageJson: sharedTool(
-        sharedToolSpecs.getPageJson,
-        async ({ pageId }) => await client.getPageJson(pageId),
-      ),
-
-      getNode: sharedTool(
-        sharedToolSpecs.getNode,
-        async ({ pageId, nodeId }) => await client.getNode(pageId, nodeId),
-      ),
-
-      searchInPage: sharedTool(
-        sharedToolSpecs.searchInPage,
-        async ({ pageId, query, regex, caseSensitive, limit }) =>
-          await client.searchInPage(pageId, query, {
-            regex,
-            caseSensitive,
-            limit,
-          }),
-      ),
-
-      // NOT shared (kept inline): the MCP tool name `table_get` is noun-first
-      // while this key is `getTable` (verb-first), breaking the
-      // snake_case(inAppKey) convention the shared registry enforces. Its
+      // NOT shared (kept inline): the MCP tool name `tableGet` is noun-first
+      // while this key is `getTable` (verb-first), so it cannot satisfy the
+      // shared registry's `mcpName === inAppKey` convention (#412). Its
       // reference parameter is still named `table` (was `tableRef`) so it matches
       // the migrated table row/cell tools below.
       getTable: tool({
@@ -572,13 +523,6 @@ export class AiChatToolsService {
           await client.getTable(pageId, table),
       }),
 
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      listComments: sharedTool(
-        sharedToolSpecs.listComments,
-        async ({ pageId, includeResolved }) =>
-          await client.listComments(pageId, includeResolved),
-      ),
-
       getComment: tool({
         description: 'Fetch a single comment by id (content as Markdown).',
         inputSchema: modelFriendlyInput({
@@ -587,24 +531,6 @@ export class AiChatToolsService {
         execute: async ({ commentId }) => await client.getComment(commentId),
       }),
 
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      checkNewComments: sharedTool(
-        sharedToolSpecs.checkNewComments,
-        async ({ spaceId, since, parentPageId }) =>
-          await client.checkNewComments(spaceId, since, parentPageId),
-      ),
-
-      listShares: sharedTool(
-        sharedToolSpecs.listShares,
-        async () => await client.listShares(),
-      ),
-
-      listPageHistory: sharedTool(
-        sharedToolSpecs.listPageHistory,
-        async ({ pageId, cursor }) =>
-          await client.listPageHistory(pageId, cursor),
-      ),
-
       getPageHistory: tool({
         description:
           'Fetch a single page-history version including its lossless ' +
@@ -616,206 +542,11 @@ export class AiChatToolsService {
           await client.getPageHistory(historyId),
       }),
 
-      diffPageVersions: sharedTool(
-        sharedToolSpecs.diffPageVersions,
-        async ({ pageId, from, to }) =>
-          await client.diffPageVersions(pageId, from, to),
-      ),
-
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      exportPageMarkdown: sharedTool(
-        sharedToolSpecs.exportPageMarkdown,
-        async ({ pageId }) => {
-          const markdown = await client.exportPageMarkdown(pageId);
-          return { markdown };
-        },
-      ),
-
       // --- WRITE tools (added; reversible via page history/trash) ---
 
-      editPageText: sharedTool(
-        sharedToolSpecs.editPageText,
-        async ({ pageId, edits }) => await client.editPageText(pageId, edits),
-      ),
-
-      // Returns ONLY the short link object — never the document body — so a
-      // large page can be handed to an external consumer without bloating
-      // context.
-      stashPage: sharedTool(
-        sharedToolSpecs.stashPage,
-        async ({ pageId }) => await client.stashPage(pageId),
-      ),
-
-      // Schema + description from the shared registry (identical across both
-      // transports). The execute body keeps its OWN parseNodeArg normalization:
-      // the model sometimes serializes the node as a JSON string, and we parse it
-      // before the client's typeof-object guard rejects it (parity with the
-      // standalone MCP server, index.ts patch_node).
-      patchNode: sharedTool(
-        sharedToolSpecs.patchNode,
-        async ({ pageId, nodeId, node }) => {
-          const parsedNode = parseNodeArg(node);
-          return await client.patchNode(pageId, nodeId, parsedNode);
-        },
-      ),
-
-      // Shared registry schema + description; execute retains parseNodeArg on the
-      // incoming node (parity with the standalone MCP server, index.ts
-      // insert_node).
-      insertNode: sharedTool(
-        sharedToolSpecs.insertNode,
-        async ({ pageId, node, position, anchorNodeId, anchorText }) => {
-          const parsedNode = parseNodeArg(node);
-          return await client.insertNode(pageId, parsedNode, {
-            position,
-            anchorNodeId,
-            anchorText,
-          });
-        },
-      ),
-
-      deleteNode: sharedTool(
-        sharedToolSpecs.deleteNode,
-        async ({ pageId, nodeId }) => await client.deleteNode(pageId, nodeId),
-      ),
-
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      // The execute body keeps this layer's content normalization (parity with
-      // the standalone MCP server, index.ts update_page_json).
-      updatePageJson: sharedTool(
-        sharedToolSpecs.updatePageJson,
-        async ({ pageId, content, title }) => {
-          // undefined/null pass through as undefined (title-only / no-op); any
-          // string is JSON.parsed (so an empty string "" throws, matching the
-          // MCP server); an object is passed through unchanged.
-          let doc;
-          if (content === undefined || content === null) {
-            doc = undefined;
-          } else {
-            // String -> JSON.parse (throwing on invalid); object passes through.
-            doc = parseNodeArg(content, 'content was a string but not valid JSON');
-          }
-          return await client.updatePageJson(pageId, doc, title);
-        },
-      ),
-
-      // 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(
-        sharedToolSpecs.tableInsertRow,
-        async ({ pageId, table, cells, index }) =>
-          await client.tableInsertRow(pageId, table, cells, index),
-      ),
-
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      tableDeleteRow: sharedTool(
-        sharedToolSpecs.tableDeleteRow,
-        async ({ pageId, table, index }) =>
-          await client.tableDeleteRow(pageId, table, index),
-      ),
-
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      tableUpdateCell: sharedTool(
-        sharedToolSpecs.tableUpdateCell,
-        async ({ pageId, table, row, col, text }) =>
-          await client.tableUpdateCell(pageId, table, row, col, text),
-      ),
-
-      copyPageContent: sharedTool(
-        sharedToolSpecs.copyPageContent,
-        async ({ sourcePageId, targetPageId }) =>
-          await client.copyPageContent(sourcePageId, targetPageId),
-      ),
-
-      importPageMarkdown: sharedTool(
-        sharedToolSpecs.importPageMarkdown,
-        async ({ pageId, markdown }) =>
-          await client.importPageMarkdown(pageId, markdown),
-      ),
-
-      // Schema + description now live in @docmost/mcp's SHARED_TOOL_SPECS (#294).
-      // Both layers already carried the security-confirmation framing, so there
-      // was no real divergence to preserve — only wording drift.
-      sharePage: sharedTool(
-        sharedToolSpecs.sharePage,
-        async ({ pageId, searchIndexing }) =>
-          await client.sharePage(pageId, searchIndexing),
-      ),
-
-      unsharePage: sharedTool(
-        sharedToolSpecs.unsharePage,
-        async ({ pageId }) => await client.unsharePage(pageId),
-      ),
-
-      restorePageVersion: sharedTool(
-        sharedToolSpecs.restorePageVersion,
-        async ({ historyId }) => await client.restorePageVersion(historyId),
-      ),
-
       // INTENTIONAL per-transport divergence (not shared): deliberately omits the
       // `deleteComments` schema field (comment-deletion guardrail) and carries a
-      // much shorter description; the standalone MCP `docmost_transform` exposes
+      // much shorter description; the standalone MCP `docmostTransform` exposes
       // the full helper catalogue. Different schema, so kept per-layer.
       transformPage: tool({
         description:
@@ -841,6 +572,51 @@ export class AiChatToolsService {
       }),
     };
 
+    // Add EVERY shared tool from the zod-agnostic registry in one loop (#445).
+    // The spec owns the canonical arg->client mapping; this host only decides
+    // WHICH mapping to run and returns its value directly (no envelope). For each
+    // spec:
+    //   - skip `mcpOnly` specs (they belong to the standalone MCP host only);
+    //   - skip `inlineBothHosts` specs (drawioShapes / drawioGuide): they carry
+    //     no execute and are wired INLINE just below, calling the pure helpers;
+    //   - use `inAppExecute` when the spec declares a DELIBERATE per-layer
+    //     difference (a projected result shape, a different guardrail message);
+    //   - otherwise use the canonical `execute` (raw client result, identical to
+    //     the MCP host's before it wraps it as JSON).
+    // The execute receives the AI-SDK-validated, type-erased input; the spec reads
+    // the same fields its buildShape declares. This is the SINGLE place the in-app
+    // arg mapping lives — it can no longer silently drift from the MCP host.
+    for (const spec of Object.values(sharedToolSpecs)) {
+      if (spec.mcpOnly) continue;
+      if (spec.inlineBothHosts) continue;
+      const run = spec.inAppExecute ?? spec.execute;
+      if (!run) continue; // defensive: a shared spec always carries one of them.
+      tools[spec.inAppKey] = sharedTool(
+        spec,
+        (async (args) =>
+          run(client, args as Record<string, unknown>)) as Tool['execute'],
+      );
+    }
+
+    // drawioShapes / drawioGuide (#424): `inlineBothHosts` registry specs wired
+    // here with the SAME schema+description the shared spec pins, but calling the
+    // pure searchShapes / getGuideSection helpers off the loaded @docmost/mcp
+    // module — they are not client methods and their catalog loader uses
+    // import.meta, so they cannot live in the zod-agnostic shared execute. The raw
+    // result is identical to the MCP host's (which wraps it as JSON text); here
+    // the in-app host returns it plain, exactly like every other shared tool.
+    tools[sharedToolSpecs.drawioShapes.inAppKey] = sharedTool(
+      sharedToolSpecs.drawioShapes,
+      async ({ query, category, limit }) => {
+        const results = searchShapes(query, { category, limit });
+        return { query, count: results.length, results };
+      },
+    );
+    tools[sharedToolSpecs.drawioGuide.inAppKey] = sharedTool(
+      sharedToolSpecs.drawioGuide,
+      async ({ section }) => getGuideSection(section),
+    );
+
     // Passive "new comments: N" signal (#417). PER-TURN state (forUser runs once
     // per turn), so the watermark starts now and only comments a human leaves
     // WHILE this turn runs are signalled — exactly the mid-turn loop; between-turn

apps/server/src/core/ai-chat/tools/comment-signal-inapp.spec.ts

@@ -7,6 +7,16 @@ import type {
   DocmostClientLike,
   CommentSignalTrackerLike,
 } from './docmost-client.loader';
+
+// Test-double type for the loopback client. `DocmostClientLike` is now DERIVED
+// from the real `DocmostClient` (issue #446), so its method RETURN types are the
+// concrete client shapes. These probe stubs deliberately return minimal shapes
+// (e.g. `getPageRaw` yielding only `{ title }`), so the doubles use the same
+// method NAMES but loose async returns; each is cast to `DocmostClientLike` at
+// the (return-erased) mock site, leaving production positional-call safety intact.
+type FakeDocmostClient = Partial<
+  Record<keyof DocmostClientLike, (...args: any[]) => Promise<any>>
+>;
 import { SHARED_TOOL_SPECS } from '../../../../../../packages/mcp/src/tool-specs';
 // The REAL shared tracker factory, imported from source (same cross-boundary
 // approach the tool-specs spec uses) so the in-app wiring is exercised against
@@ -268,15 +278,23 @@ describe('AiChatToolsService forUser + comment signal (real tracker)', () => {
   // seeded at forUser time).
   const future = new Date(Date.now() + 3_600_000).toISOString();
 
-  function buildService(fakeClient: Partial<DocmostClientLike>) {
+  function buildService(fakeClient: FakeDocmostClient) {
     jest.spyOn(loader, 'loadDocmostMcp').mockResolvedValue({
       DocmostClient: function () {
         return fakeClient as DocmostClientLike;
       } as unknown as loader.DocmostClientCtor,
-      sharedToolSpecs: SHARED_TOOL_SPECS as Record<string, loader.SharedToolSpec>,
+      sharedToolSpecs: SHARED_TOOL_SPECS as unknown as Record<string, loader.SharedToolSpec>,
       // Wire the REAL factory so the in-app path is exercised end to end.
       createCommentSignalTracker:
         createCommentSignalTracker as unknown as loader.CommentSignalTrackerFactory,
+      // Pure no-network draw.io helpers (#424) — required on the loader return;
+      // this comment-signal test doesn't exercise them, so no-op stubs suffice.
+      searchShapes: (() => []) as unknown as loader.SearchShapesFn,
+      getGuideSection: (() => ({
+        section: '',
+        content: '',
+        sections: [],
+      })) as unknown as loader.GetGuideSectionFn,
     });
     return new AiChatToolsService(
       tokenServiceStub as never,
@@ -317,7 +335,7 @@ describe('AiChatToolsService forUser + comment signal (real tracker)', () => {
   afterEach(() => jest.restoreAllMocks());
 
   it('emits the signal (model-only) on a non-comment tool when a new comment exists', async () => {
-    const fakeClient: Partial<DocmostClientLike> = {
+    const fakeClient: FakeDocmostClient = {
       getPage: async () => ({
         data: { title: 'Иранские языки', content: 'body' },
         success: true,
@@ -342,7 +360,7 @@ describe('AiChatToolsService forUser + comment signal (real tracker)', () => {
   });
 
   it('does NOT add the signal to the listComments tool itself (tautological)', async () => {
-    const fakeClient: Partial<DocmostClientLike> = {
+    const fakeClient: FakeDocmostClient = {
       listComments: async () => ({
         items: [{ createdAt: future }],
         resolvedThreadsHidden: 0,
@@ -356,7 +374,7 @@ describe('AiChatToolsService forUser + comment signal (real tracker)', () => {
   });
 
   it('no new comments => tool output is byte-identical AND the model sees no signal', async () => {
-    const fakeClient: Partial<DocmostClientLike> = {
+    const fakeClient: FakeDocmostClient = {
       getPage: async () => ({
         data: { title: 'T', content: 'body' },
         success: true,
@@ -372,7 +390,7 @@ describe('AiChatToolsService forUser + comment signal (real tracker)', () => {
   });
 
   it('injection-safety: a malicious page title cannot forge a second signal', async () => {
-    const fakeClient: Partial<DocmostClientLike> = {
+    const fakeClient: FakeDocmostClient = {
       getPage: async () => ({
         data: { title: 'body-title', content: 'body' },
         success: true,

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

@@ -0,0 +1,265 @@
+import { createHash } from 'node:crypto';
+import {
+  mkdtempSync,
+  mkdirSync,
+  writeFileSync,
+  rmSync,
+  readdirSync,
+  statSync,
+  readFileSync,
+} from 'node:fs';
+import { tmpdir } from 'node:os';
+import { dirname, join, relative, sep } from 'node:path';
+
+import { computeSrcRegistryStamp } from './docmost-client.loader';
+
+// The exact message the loader throws on a build/src skew (issue #447). Kept as a
+// literal here so a reworded prod message reddens this test (the message is a
+// developer-facing contract: it tells them how to fix it).
+const STALE_BUILD_MESSAGE =
+  '@docmost/mcp build is stale (tool-specs changed since last build) — run: pnpm --filter @docmost/mcp build';
+
+// Replica of the loader's inline stale-check predicate + throw from
+// `loadDocmostMcp`. That guard is not independently exported (it lives inside the
+// dynamic-import IIFE, wired to a fixed `require.resolve('@docmost/mcp')`), so we
+// exercise the exact same three-condition logic against a stamp produced by the
+// REAL `computeSrcRegistryStamp`. This documents and locks the throw/no-throw
+// behaviour; if the prod predicate changes, this replica must change with it.
+function assertStaleGuard(
+  srcStamp: string | null,
+  registryStamp: string | undefined,
+): void {
+  if (
+    srcStamp !== null &&
+    typeof registryStamp === 'string' &&
+    srcStamp !== registryStamp
+  ) {
+    throw new Error(STALE_BUILD_MESSAGE);
+  }
+}
+
+// Build a throwaway `<pkg>/build/index.js` + optional `<pkg>/src/` tree so
+// `computeSrcRegistryStamp(<pkg>/build/index.js)` resolves src the same way the
+// loader does (dirname(dirname(entry))/src). Since #486 the stamp hashes the WHOLE
+// src tree, so a fixture is a { relPath: content } map. A bare string is sugar for
+// a single `tool-specs.ts`; `null` means "no src tree" (the prod no-op path).
+function makeFakePackage(
+  src: string | Record<string, string> | null,
+): {
+  entry: string;
+  cleanup: () => void;
+} {
+  const root = mkdtempSync(join(tmpdir(), 'mcp-stamp-'));
+  const buildDir = join(root, 'build');
+  mkdirSync(buildDir, { recursive: true });
+  const entry = join(buildDir, 'index.js');
+  writeFileSync(entry, '// fake @docmost/mcp build entry\n', 'utf8');
+  if (src !== null) {
+    const files =
+      typeof src === 'string' ? { 'tool-specs.ts': src } : src;
+    const srcDir = join(root, 'src');
+    for (const [rel, content] of Object.entries(files)) {
+      const full = join(srcDir, rel);
+      mkdirSync(dirname(full), { recursive: true });
+      writeFileSync(full, content, 'utf8');
+    }
+  }
+  return { entry, cleanup: () => rmSync(root, { recursive: true, force: true }) };
+}
+
+describe('computeSrcRegistryStamp (#447 stale-build guard)', () => {
+  it('returns null when src/tool-specs.ts is absent (prod no-op path)', () => {
+    // A prod image ships only build/, no src/ — the guard must be a silent no-op.
+    const { entry, cleanup } = makeFakePackage(null);
+    try {
+      expect(computeSrcRegistryStamp(entry)).toBeNull();
+    } finally {
+      cleanup();
+    }
+  });
+
+  it('returns null for a bogus package entry (swallowed error path)', () => {
+    // A resolution/read hiccup must NEVER break startup — it resolves to null.
+    expect(
+      computeSrcRegistryStamp('/no/such/pkg/build/index.js'),
+    ).toBeNull();
+  });
+
+  it('computes a 64-char sha256 hex when src/tool-specs.ts exists', () => {
+    const { entry, cleanup } = makeFakePackage('export const specs = 1;\n');
+    try {
+      const stamp = computeSrcRegistryStamp(entry);
+      expect(stamp).toMatch(/^[0-9a-f]{64}$/);
+    } finally {
+      cleanup();
+    }
+  });
+
+  it('normalizes CRLF->LF and strips a single trailing newline', () => {
+    // A CRLF+trailing-newline variant of the same content hashes identically to
+    // the bare-LF form — the guard must not fire on a checkout-style difference.
+    const bare = makeFakePackage('alpha\nbeta');
+    const crlfTrailing = makeFakePackage('alpha\r\nbeta\r\n');
+    try {
+      expect(computeSrcRegistryStamp(crlfTrailing.entry)).toBe(
+        computeSrcRegistryStamp(bare.entry),
+      );
+    } finally {
+      bare.cleanup();
+      crlfTrailing.cleanup();
+    }
+  });
+
+  // #486 CORE (negative): an edit to a NON-tool-specs src file (client.ts) with a
+  // rebuild NOT run must move the src stamp away from the built REGISTRY_STAMP, so
+  // the loader's stale-check refuses. Under the old tool-specs.ts-only hash this
+  // edit was invisible and a stale build/ served the old client.ts silently.
+  it('a client.ts edit (no rebuild) moves the src stamp -> loader refuses (#486)', () => {
+    // "Built" state: the package as it was compiled.
+    const built = makeFakePackage({
+      'tool-specs.ts': 'export const SPECS = 1;\n',
+      'client.ts': "export const impl = 'v1';\n",
+    });
+    // "Dev edited src, forgot to rebuild": client.ts changed, tool-specs.ts not.
+    const edited = makeFakePackage({
+      'tool-specs.ts': 'export const SPECS = 1;\n',
+      'client.ts': "export const impl = 'v2';\n",
+    });
+    try {
+      const builtStamp = computeSrcRegistryStamp(built.entry);
+      const editedStamp = computeSrcRegistryStamp(edited.entry);
+      expect(builtStamp).not.toBeNull();
+      expect(editedStamp).not.toBe(builtStamp);
+      // build/ still carries builtStamp; src now hashes to editedStamp -> refuse.
+      expect(() => assertStaleGuard(editedStamp, builtStamp as string)).toThrow(
+        STALE_BUILD_MESSAGE,
+      );
+    } finally {
+      built.cleanup();
+      edited.cleanup();
+    }
+  });
+
+  // *.generated.ts is excluded (the codegen's own output — a fixed-point cycle
+  // otherwise): its presence/content must not move the stamp.
+  it('excludes *.generated.ts from the stamp', () => {
+    const without = makeFakePackage({ 'tool-specs.ts': 'x\n' });
+    const withGen = makeFakePackage({
+      'tool-specs.ts': 'x\n',
+      'registry-stamp.generated.ts': 'export const REGISTRY_STAMP = "abc";\n',
+    });
+    try {
+      expect(computeSrcRegistryStamp(withGen.entry)).toBe(
+        computeSrcRegistryStamp(without.entry),
+      );
+    } finally {
+      without.cleanup();
+      withGen.cleanup();
+    }
+  });
+
+  // CROSS-IMPL EQUALITY (covers reviewer suggestion 2). The SAME fixed tree and
+  // EXPECTED hash are asserted in the mcp-side node test
+  // (packages/mcp/test/unit/registry-stamp.test.mjs) against the codegen's
+  // `computeRegistryStamp`. Asserting the SAME pair here against the loader's
+  // `computeSrcRegistryStamp` proves both implementations enumerate+normalize+hash
+  // identically; a divergence in EITHER side reddens one of the two tests.
+  const CROSS_IMPL_TREE = {
+    'tool-specs.ts': 'line1\r\nline2\n',
+    'client/read.ts': 'export const R = 1;\n',
+    'registry-stamp.generated.ts': 'export const REGISTRY_STAMP="ignored";\n',
+  };
+  const CROSS_IMPL_EXPECTED =
+    '131c1b9e4e2f5a7d6cef91ca8df619822b442f52bc45ebd09474a4c1d6728616';
+
+  it('matches the documented cross-impl hash for a fixed tree', () => {
+    const { entry, cleanup } = makeFakePackage(CROSS_IMPL_TREE);
+    try {
+      expect(computeSrcRegistryStamp(entry)).toBe(CROSS_IMPL_EXPECTED);
+    } finally {
+      cleanup();
+    }
+  });
+
+  it('the documented EXPECTED is the enumerate+normalize+sha256 of the tree', () => {
+    // Proves EXPECTED is not a magic constant but the documented computation — a
+    // local re-implementation of the loader's tree walk.
+    const { entry, cleanup } = makeFakePackage(CROSS_IMPL_TREE);
+    try {
+      const srcDir = join(dirname(dirname(entry)), 'src');
+      const collect = (dir: string): string[] => {
+        const out: string[] = [];
+        for (const e of readdirSync(dir)) {
+          const f = join(dir, e);
+          if (statSync(f).isDirectory()) out.push(...collect(f));
+          else if (e.endsWith('.ts') && !e.endsWith('.generated.ts'))
+            out.push(f);
+        }
+        return out;
+      };
+      const files = collect(srcDir)
+        .map((abs) => ({ rel: relative(srcDir, abs).split(sep).join('/'), abs }))
+        .sort((a, b) => (a.rel < b.rel ? -1 : a.rel > b.rel ? 1 : 0));
+      const h = createHash('sha256');
+      for (const { rel, abs } of files) {
+        const n = readFileSync(abs, 'utf8')
+          .replace(/\r\n/g, '\n')
+          .replace(/\n$/, '');
+        h.update(rel, 'utf8');
+        h.update('\0', 'utf8');
+        h.update(n, 'utf8');
+        h.update('\0', 'utf8');
+      }
+      const localHash = h.digest('hex');
+      expect(computeSrcRegistryStamp(entry)).toBe(localHash);
+      expect(localHash).toBe(CROSS_IMPL_EXPECTED);
+    } finally {
+      cleanup();
+    }
+  });
+});
+
+describe('loadDocmostMcp stale-check predicate (#447)', () => {
+  it('THROWS the exact stale message when src stamp != built REGISTRY_STAMP', () => {
+    const { entry, cleanup } = makeFakePackage('export const specs = 1;\n');
+    try {
+      const srcStamp = computeSrcRegistryStamp(entry);
+      expect(srcStamp).not.toBeNull();
+      // Simulate a stale build: build/ carries a DIFFERENT stamp than src.
+      expect(() => assertStaleGuard(srcStamp, 'a'.repeat(64))).toThrow(
+        STALE_BUILD_MESSAGE,
+      );
+    } finally {
+      cleanup();
+    }
+  });
+
+  it('does NOT throw when src stamp equals the built REGISTRY_STAMP', () => {
+    const { entry, cleanup } = makeFakePackage('export const specs = 1;\n');
+    try {
+      const srcStamp = computeSrcRegistryStamp(entry);
+      // Fresh build: build/ stamp == src stamp -> guard is a no-op.
+      expect(() => assertStaleGuard(srcStamp, srcStamp as string)).not.toThrow();
+    } finally {
+      cleanup();
+    }
+  });
+
+  it('does NOT throw when src is absent (prod: srcStamp === null)', () => {
+    // Even against a present-but-mismatched REGISTRY_STAMP, a null src stamp
+    // (prod image with build/ only) must skip the check entirely.
+    expect(() => assertStaleGuard(null, 'a'.repeat(64))).not.toThrow();
+  });
+
+  it('does NOT throw when REGISTRY_STAMP is absent (pre-#447 build)', () => {
+    // An older @docmost/mcp build has no REGISTRY_STAMP export; the guard must be
+    // a no-op so an out-of-date build never wrongly blocks startup.
+    const { entry, cleanup } = makeFakePackage('export const specs = 1;\n');
+    try {
+      const srcStamp = computeSrcRegistryStamp(entry);
+      expect(() => assertStaleGuard(srcStamp, undefined)).not.toThrow();
+    } finally {
+      cleanup();
+    }
+  });
+});

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

@@ -1,264 +1,102 @@
+import { createHash } from 'node:crypto';
+import { existsSync, readdirSync, readFileSync, statSync } from 'node:fs';
+import { dirname, join, relative, sep } from 'node:path';
 import { pathToFileURL } from 'node:url';
+import type { DocmostClient, SharedToolSpec } from '@docmost/mcp';
+
+// Re-export SharedToolSpec so downstream server modules keep a single import
+// path (they import it from this loader). The shape is DERIVED from the package
+// entry, not re-declared here — see the import above (issue #446).
+export type { SharedToolSpec } from '@docmost/mcp';
 
 /**
- * Minimal structural type for the `DocmostClient` class we consume from the
- * ESM-only `@docmost/mcp` package. We only need the constructor + the read/write
- * methods used by the per-user tool adapter; the full client surface lives in
- * `packages/mcp/src/client.ts`. Signatures here mirror that file exactly.
- *
- * DRIFT GUARD: the method NAMES below are runtime-checked against the real
- * `DocmostClient` by `packages/mcp/test/unit/client-host-contract.test.mjs`
- * (which can import the ESM class directly). If you rename/remove a method here
- * or in client.ts, that test fails — so a stale mirror cannot silently ship a
- * runtime "x is not a function" into an agent tool call. Keep the two in sync.
- *
- * STAGED PLAN — full derivation `DocmostClientLike = <real DocmostClient type>`
- * (issue #193, layer 3) is intentionally NOT done; it stays a hand-mirror for
- * now because of two verified blockers across the ESM(mcp)/CJS(server) boundary:
- *   1. `@docmost/mcp` emits NO declaration files (its tsconfig has no
- *      `declaration`, package.json has no `types`/types-export) and the server
- *      tsconfig has no path mapping for it — the server only loads it via the
- *      runtime `import()` trick below, so there is no type to import today.
- *   2. The real client methods have inferred, CONCRETE return types; the in-app
- *      tool adapter reads results through loose `Record<string,unknown>` returns
- *      + `as` casts (e.g. `(result?.data ?? {}) as { title?: string }`).
- *      Deriving the exact type would make those casts non-overlapping ("may be a
- *      mistake") and break the build, and `Partial<DocmostClientLike>` test stubs
- *      would have to satisfy the full concrete surface.
- * To do it safely later (incrementally): (a) turn on `declaration: true` in
- * packages/mcp/tsconfig.json + add a `types` export condition and commit the
- * emitted `.d.ts`; (b) `import type { DocmostClient } from '@docmost/mcp'` here
- * and replace this interface with a `Pick<DocmostClient, ...>` of the consumed
- * methods; (c) audit every `as` cast in ai-chat-tools.service.ts against the now
- * concrete return types (double-cast through `unknown` only where genuinely
- * needed); (d) keep the runtime guard test as a belt-and-braces check. Until
- * then the guard test above is the cheap, behaviour-neutral protection.
+ * The exact set of `DocmostClient` methods the per-user in-app tool adapter
+ * consumes. This is the AUTHORITATIVE list of the client surface the server
+ * depends on; the adapter calls these methods POSITIONALLY, so this set is what
+ * the derived type below type-checks against the real class (issue #446).
  */
-export interface DocmostClientLike {
+type DocmostClientMethod =
   // --- read ---
-  search(
-    query: string,
-    spaceId?: string,
-    limit?: number,
-  ): Promise<{ items: unknown[]; success: boolean }>;
-  getPage(
-    pageId: string,
-  ): Promise<{ data: Record<string, unknown>; success: boolean }>;
-  // Light raw page info (`/pages/info`): title + slugId + ProseMirror content,
-  // WITHOUT the Markdown render / subpage expansion getPage does. Used by the
-  // comment-signal probe to read just the page title on a hit.
-  getPageRaw(pageId: string): Promise<Record<string, unknown> | null>;
-  getWorkspace(): Promise<{ data: Record<string, unknown>; success: boolean }>;
-  getSpaces(): Promise<unknown[]>;
-  listPages(
-    spaceId?: string,
-    limit?: number,
-    tree?: boolean,
-  ): Promise<unknown[]>;
-  listSidebarPages(spaceId: string, pageId?: string): Promise<unknown[]>;
-  getOutline(pageId: string): Promise<Record<string, unknown>>;
-  getPageJson(pageId: string): Promise<Record<string, unknown>>;
-  getNode(pageId: string, nodeId: string): Promise<Record<string, unknown>>;
-  searchInPage(
-    pageId: string,
-    query: string,
-    opts?: { regex?: boolean; caseSensitive?: boolean; limit?: number },
-  ): Promise<Record<string, unknown>>;
-  getTable(pageId: string, tableRef: string): Promise<Record<string, unknown>>;
-  // Returns `{ items, resolvedThreadsHidden }`. DEFAULT (includeResolved unset/
-  // false) hides resolved threads wholesale; pass true for the full feed.
-  listComments(
-    pageId: string,
-    includeResolved?: boolean,
-  ): Promise<{ items: unknown[]; resolvedThreadsHidden: number }>;
-  getComment(
-    commentId: string,
-  ): Promise<{ data: Record<string, unknown>; success: boolean }>;
-  checkNewComments(
-    spaceId: string,
-    since: string,
-    parentPageId?: string,
-  ): Promise<unknown>;
-  listShares(): Promise<unknown[]>;
-  listPageHistory(
-    pageId: string,
-    cursor?: string,
-  ): Promise<{ items: unknown[]; nextCursor: string | null }>;
-  getPageHistory(historyId: string): Promise<Record<string, unknown>>;
-  diffPageVersions(
-    pageId: string,
-    from?: string,
-    to?: string,
-  ): Promise<Record<string, unknown>>;
-  exportPageMarkdown(pageId: string): Promise<string>;
+  | 'search'
+  | 'getPage'
+  | 'getPageRaw'
+  | 'getWorkspace'
+  | 'getSpaces'
+  | 'listPages'
+  | 'getTree'
+  | 'getPageContext'
+  | 'listSidebarPages'
+  | 'getOutline'
+  | 'getPageJson'
+  | 'getNode'
+  | 'searchInPage'
+  | 'getTable'
+  | 'listComments'
+  | 'getComment'
+  | 'checkNewComments'
+  | 'listShares'
+  | 'listPageHistory'
+  | 'getPageHistory'
+  | 'diffPageVersions'
+  | 'exportPageMarkdown'
   // --- write (page) ---
-  createPage(
-    title: string,
-    content: string,
-    spaceId: string,
-    parentPageId?: string,
-  ): Promise<{ data: Record<string, unknown>; success: boolean }>;
-  // Markdown content update via the collab path (carries provenance via the
-  // collab-token provider). Optionally also updates the title.
-  updatePage(
-    pageId: string,
-    content: string,
-    title?: string,
-  ): Promise<Record<string, unknown>>;
-  // Title-only rename via REST.
-  renamePage(
-    pageId: string,
-    title: string,
-  ): Promise<Record<string, unknown>>;
-  // Move via REST. parentPageId null => move to space root.
-  movePage(
-    pageId: string,
-    parentPageId: string | null,
-    position?: string,
-  ): Promise<unknown>;
-  // SOFT delete only (POST /pages/delete with { pageId }). NEVER permanent.
-  deletePage(pageId: string): Promise<unknown>;
-  editPageText(
-    pageId: string,
-    edits: Array<{ find: string; replace: string; replaceAll?: boolean }>,
-  ): Promise<Record<string, unknown>>;
-  patchNode(
-    pageId: string,
-    nodeId: string,
-    node: unknown,
-  ): Promise<Record<string, unknown>>;
-  insertNode(
-    pageId: string,
-    node: unknown,
-    opts: {
-      position: 'before' | 'after' | 'append';
-      anchorNodeId?: string;
-      anchorText?: string;
-    },
-  ): Promise<Record<string, unknown>>;
-  deleteNode(
-    pageId: string,
-    nodeId: string,
-  ): Promise<Record<string, unknown>>;
-  updatePageJson(
-    pageId: string,
-    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,
-    cells: string[],
-    index?: number,
-  ): Promise<Record<string, unknown>>;
-  tableDeleteRow(
-    pageId: string,
-    tableRef: string,
-    index: number,
-  ): Promise<Record<string, unknown>>;
-  tableUpdateCell(
-    pageId: string,
-    tableRef: string,
-    row: number,
-    col: number,
-    text: string,
-  ): Promise<Record<string, unknown>>;
-  copyPageContent(
-    sourcePageId: string,
-    targetPageId: string,
-  ): Promise<Record<string, unknown>>;
-  importPageMarkdown(
-    pageId: string,
-    fullMarkdown: string,
-  ): Promise<Record<string, unknown>>;
-  sharePage(
-    pageId: string,
-    searchIndexing?: boolean,
-  ): Promise<Record<string, unknown>>;
-  unsharePage(pageId: string): Promise<Record<string, unknown>>;
-  restorePageVersion(historyId: string): Promise<Record<string, unknown>>;
-  // The opts type declares deleteComments? to match the real client signature,
-  // but the agent tool NEVER sets it (comment deletion stays unreachable).
-  transformPage(
-    pageId: string,
-    transformJs: string,
-    opts?: { dryRun?: boolean; deleteComments?: boolean },
-  ): Promise<Record<string, unknown>>;
+  | 'createPage'
+  | 'updatePage'
+  | 'renamePage'
+  | 'movePage'
+  | 'deletePage'
+  | 'editPageText'
+  | 'patchNode'
+  | 'insertNode'
+  | 'deleteNode'
+  | 'updatePageJson'
+  | 'tableInsertRow'
+  | 'tableDeleteRow'
+  | 'tableUpdateCell'
+  | 'copyPageContent'
+  | 'importPageMarkdown'
+  | 'sharePage'
+  | 'unsharePage'
+  | 'restorePageVersion'
+  | 'transformPage'
+  | 'stashPage'
+  // --- write (image / footnote), in-app since #410 ---
+  | 'insertImage'
+  | 'replaceImage'
+  | 'insertFootnote'
+  // --- draw.io diagrams (#423 stage 1, #424 stage 2) ---
+  // DERIVED from the real DocmostClient (#446): drawioCreate/drawioUpdate carry
+  // the optional layout:"elk" 5th arg in the real signature, so the layout parity
+  // (#440) is inherited automatically — no hand-written mirror to keep in sync.
+  | 'drawioGet'
+  | 'drawioCreate'
+  | 'drawioUpdate'
+  // --- draw.io high-level semantic tools (#425 stage 3) ---
+  | 'drawioEditCells'
+  | 'drawioFromGraph'
+  | 'drawioFromMermaid'
   // --- write (comment) ---
-  createComment(
-    pageId: string,
-    content: string,
-    type?: 'page' | 'inline',
-    selection?: string,
-    parentCommentId?: string,
-    suggestedText?: string,
-  ): Promise<{ data: Record<string, unknown>; success: boolean }>;
-  resolveComment(
-    commentId: string,
-    resolved: boolean,
-  ): Promise<Record<string, unknown>>;
-  // Serialize a page + mirror its internal images into the blob sandbox; returns
-  // ONLY a short anonymous URL (the body never enters the model context).
-  stashPage(pageId: string): Promise<{
-    uri: string;
-    sha256: string;
-    size: number;
-    images: { mirrored: number; failed: number };
-  }>;
-}
+  | 'createComment'
+  | 'resolveComment';
+
+/**
+ * The client surface the per-user tool adapter consumes, DERIVED from the real
+ * `DocmostClient` type in `@docmost/mcp` (issue #446, restored #294 debt). This
+ * replaces the former hand-mirror of ~45 method signatures.
+ *
+ * `import type` (above) is fully ERASED at compile time, so nothing is actually
+ * imported from the ESM-only package at runtime — the server still loads the
+ * class through the dynamic `import()` trick in `loadDocmostMcp` below; this is
+ * purely a compile-time type. Deriving via `Pick` means a parameter reorder or a
+ * type change to any of these methods in `client.ts` now becomes a SERVER
+ * COMPILE ERROR at the positional call sites in ai-chat-tools.service.ts,
+ * instead of a silent runtime "wrong argument" failure inside an agent tool.
+ *
+ * This made the old name-only drift-guard test
+ * (packages/mcp/test/unit/client-host-contract.test.mjs) redundant — tsc now
+ * enforces both names AND signatures — so that test was removed.
+ */
+export type DocmostClientLike = Pick<DocmostClient, DocmostClientMethod>;
 
 export type DocmostClientConfig = {
   apiUrl: string;
@@ -280,32 +118,7 @@ export type DocmostClientConfig = {
 };
 
 export interface DocmostClientCtor {
-  new (config: DocmostClientConfig): DocmostClientLike;
-}
-
-/**
- * Local hand-mirror of the `SharedToolSpec` shape exported from
- * `@docmost/mcp` (packages/mcp/src/tool-specs.ts). Same approach as
- * `DocmostClientLike`: we do not import the ESM package's types directly across
- * the CJS/ESM boundary. The registry itself has no runtime deps, but keeping the
- * type local avoids coupling the server build to the package's type surface.
- *
- * `buildShape` is intentionally zod-agnostic: it returns a plain ZodRawShape
- * built with whatever zod namespace the caller passes (the server passes its own
- * zod v4; the MCP package passes its zod v3). See the registry module comment.
- */
-export interface SharedToolSpec {
-  mcpName: string;
-  inAppKey: string;
-  description: string;
-  // Deferred-tool metadata (#332). Optional in this mirror so an older/stale
-  // @docmost/mcp build (pre-#332) still type-checks; the in-app catalog builder
-  // reads them defensively. The external /mcp server ignores both fields.
-  tier?: 'core' | 'deferred';
-  catalogLine?: string;
-  // Loose `z` on purpose: the registry is zod-agnostic so the server can pass
-  // its own zod (v4) and the MCP package its own (v3) into the same builder.
-  buildShape?: (z: any) => Record<string, unknown>;
+  new (config: DocmostClientConfig): DocmostClient;
 }
 
 /**
@@ -337,6 +150,19 @@ export type CommentSignalTrackerFactory = (options: {
   debounceMs?: number;
 }) => CommentSignalTrackerLike;
 
+// Pure, no-network draw.io helpers (#424). These are plain functions on the
+// module (NOT DocmostClient methods) — the in-app AI-SDK service calls them
+// directly to wire drawioShapes / drawioGuide, mirroring the MCP server.
+export type SearchShapesFn = (
+  query: string,
+  opts?: { category?: string; limit?: number },
+) => Array<Record<string, unknown>>;
+export type GetGuideSectionFn = (section?: string) => {
+  section: string;
+  content: string;
+  sections: string[];
+};
+
 interface DocmostMcpModule {
   DocmostClient: DocmostClientCtor;
   SHARED_TOOL_SPECS: Record<string, SharedToolSpec>;
@@ -344,6 +170,96 @@ interface DocmostMcpModule {
   // loader in unit tests. The in-app layer treats an absent factory as "signal
   // disabled" — a pure no-op that leaves tool results byte-identical.
   createCommentSignalTracker?: CommentSignalTrackerFactory;
+  // Optional (#447): a deterministic hash of the tool-specs registry content,
+  // generated into build/ by the package's build. Absent on a pre-#447 build (or
+  // the mocked loader in unit tests) — the stale-check below is a NO-OP when it
+  // is missing, so an older build never wrongly fails startup.
+  REGISTRY_STAMP?: string;
+  // Pure, no-network draw.io helpers (#424) backing drawioShapes / drawioGuide.
+  // Those two specs are `inlineBothHosts` (they stay in SHARED_TOOL_SPECS for the
+  // shared contract but carry no execute — their catalog loader uses import.meta
+  // and can't be value-imported into the zod-agnostic tool-specs.ts), so the
+  // in-app service wires them INLINE off these helpers, mirroring the standalone
+  // MCP host. Exposed off the loaded module so the service and its test mocks can
+  // reach them.
+  searchShapes: SearchShapesFn;
+  getGuideSection: GetGuideSectionFn;
+}
+
+/**
+ * Recompute the REGISTRY_STAMP (#447) from the @docmost/mcp source tree, if it is
+ * present. Returns the stamp string, or `null` when the source is absent (a prod
+ * image ships only build/, no src/). MUST stay byte-for-byte identical to
+ * packages/mcp/scripts/gen-registry-stamp.mjs's `computeRegistryStamp` so the
+ * build-time and src-time hashes agree: same file set (every src/**\/*.ts except
+ * *.generated.ts), same POSIX-relative sort, same per-file normalization (CRLF ->
+ * LF, strip a single trailing newline) with the same path+content framing, same
+ * sha256. Hashing the WHOLE src tree (not just tool-specs.ts) is #486: an edit to
+ * client.ts / a client/* module / comment-signal / drawio-* without a rebuild
+ * must also be caught, otherwise build/ silently serves the old code.
+ *
+ * DEV vs PROD detection is by FILE EXISTENCE, not NODE_ENV: we resolve the
+ * package's own directory from `require.resolve('@docmost/mcp')` (which points at
+ * build/index.js) and look for ../src next to it. In a dev/test worktree that
+ * directory exists; in a prod image (build/ only, src/ stripped) it does not, so
+ * this returns null and the caller skips the check. Any error (ENOENT, a bad
+ * resolve) is swallowed to null — the stale-check must NEVER break startup.
+ *
+ * Exported for unit testing (docmost-client.loader.spec.ts): the export keyword
+ * is behaviourally a no-op — the module-internal caller `loadDocmostMcp` is
+ * unaffected. The test drives the null (no-src) path and asserts this
+ * enumerate+normalize+sha256 stays identical to the codegen's
+ * `computeRegistryStamp`.
+ */
+export function computeSrcRegistryStamp(packageEntry: string): string | null {
+  try {
+    // packageEntry is <pkg>/build/index.js; the source lives at <pkg>/src/.
+    const srcDir = join(dirname(dirname(packageEntry)), 'src');
+    if (!existsSync(srcDir)) return null; // prod: no src tree -> skip.
+    // Enumerate every src/**\/*.ts except the codegen's own *.generated.ts
+    // output (including it would be a fixed-point cycle). Sort by POSIX-relative
+    // path so ordering is platform-independent, then fold each file's relative
+    // path + normalized content into one hash — identical to the codegen.
+    const files = collectStampFiles(srcDir)
+      .map((abs) => ({
+        rel: relative(srcDir, abs).split(sep).join('/'),
+        abs,
+      }))
+      .sort((a, b) => (a.rel < b.rel ? -1 : a.rel > b.rel ? 1 : 0));
+    const hash = createHash('sha256');
+    for (const { rel, abs } of files) {
+      const normalized = readFileSync(abs, 'utf8')
+        .replace(/\r\n/g, '\n')
+        .replace(/\n$/, '');
+      hash.update(rel, 'utf8');
+      hash.update('\0', 'utf8');
+      hash.update(normalized, 'utf8');
+      hash.update('\0', 'utf8');
+    }
+    return hash.digest('hex');
+  } catch {
+    // Never let a resolution/read hiccup break server startup — treat as "no
+    // src available" and skip the check (identical to the prod no-op path).
+    return null;
+  }
+}
+
+/**
+ * Recursively enumerate every `*.ts` under `dir`, EXCLUDING `*.generated.ts`.
+ * Mirror of the codegen's `collectStampFiles` (packages/mcp/scripts/
+ * gen-registry-stamp.mjs) — keep the two walk/filter rules identical.
+ */
+function collectStampFiles(dir: string): string[] {
+  const out: string[] = [];
+  for (const entry of readdirSync(dir)) {
+    const full = join(dir, entry);
+    if (statSync(full).isDirectory()) {
+      out.push(...collectStampFiles(full));
+    } else if (entry.endsWith('.ts') && !entry.endsWith('.generated.ts')) {
+      out.push(full);
+    }
+  }
+  return out;
 }
 
 // TS with module:commonjs downlevels a literal `import()` to `require()`, which
@@ -368,6 +284,8 @@ export async function loadDocmostMcp(): Promise<{
   DocmostClient: DocmostClientCtor;
   sharedToolSpecs: Record<string, SharedToolSpec>;
   createCommentSignalTracker?: CommentSignalTrackerFactory;
+  searchShapes: SearchShapesFn;
+  getGuideSection: GetGuideSectionFn;
 }> {
   if (!modulePromise) {
     modulePromise = (async () => {
@@ -375,6 +293,23 @@ export async function loadDocmostMcp(): Promise<{
       const mod = (await esmImport(
         pathToFileURL(entry).href,
       )) as DocmostMcpModule;
+      // #447 stale-build guard (dev/test only). The server loads the COMPILED
+      // build/ of @docmost/mcp, but the parity/tier guard tests read src/. If a
+      // tool spec is edited in src without rebuilding the package, build/ and src/
+      // silently diverge and the running server serves the OLD tools. Here we
+      // recompute the stamp from src/tool-specs.ts and compare it to the stamp
+      // baked into build/. In PROD the src tree is absent (image ships build/
+      // only), so computeSrcRegistryStamp returns null and this is a pure no-op.
+      const srcStamp = computeSrcRegistryStamp(entry);
+      if (
+        srcStamp !== null &&
+        typeof mod.REGISTRY_STAMP === 'string' &&
+        srcStamp !== mod.REGISTRY_STAMP
+      ) {
+        throw new Error(
+          '@docmost/mcp build is stale (tool-specs changed since last build) — run: pnpm --filter @docmost/mcp build',
+        );
+      }
       return mod;
     })().catch((err) => {
       // Do not cache a rejected import — allow the next call to retry.
@@ -396,5 +331,8 @@ export async function loadDocmostMcp(): Promise<{
     // Optional: forwarded when present so the in-app layer can build the passive
     // comment signal (#417); undefined on a stale build => signal disabled.
     createCommentSignalTracker: mod.createCommentSignalTracker,
+    // Pure no-network draw.io helpers (#424); not client methods.
+    searchShapes: mod.searchShapes,
+    getGuideSection: mod.getGuideSection,
   };
 }

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

@@ -224,7 +224,7 @@ describe('PublicShareChatToolsService.forShare', () => {
         (tools.getSharePage as unknown as ToolExec).execute({
           pageId: 'page-1',
         }),
-      ).rejects.toThrow('That page is not part of this published share.');
+      ).rejects.toThrow('The requested page is not available in this share.');
 
       // No content is ever fetched/returned for a non-resolving page.
       expect(shareService.updatePublicAttachments).not.toHaveBeenCalled();

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

@@ -7,6 +7,22 @@ import { PageRepo } from '@docmost/db/repos/page/page.repo';
 import { jsonToMarkdown } from '../../../collaboration/collaboration.util';
 import { modelFriendlyInput } from './model-friendly-input';
 
+/**
+ * A tool error whose message is DELIBERATELY safe to expose to an anonymous
+ * share reader (and to the model, for self-correction). Every OTHER thrown error
+ * is treated as internal and replaced with a generic string by `wrapToolErrors`,
+ * so a raw exception message — an internal page title, a DB/stack fragment, a
+ * driver detail — never rides the public UI stream (#394).
+ */
+export class ShareToolError extends Error {}
+
+// The only two classified strings an anonymous reader may ever see from a tool
+// failure. The specific one keeps the model's self-correction useful ("try a
+// different page"); the generic one reveals nothing about the internal fault.
+const SHARE_TOOL_ERROR_NOT_AVAILABLE =
+  'The requested page is not available in this share.';
+const SHARE_TOOL_ERROR_GENERIC = 'The tool could not complete the request.';
+
 /**
  * Isolated, READ-ONLY toolset for the ANONYMOUS public-share assistant.
  *
@@ -44,7 +60,7 @@ export class PublicShareChatToolsService {
    * are NO write tools, NO comments/history, NO cross-space or external tools.
    */
   forShare(shareId: string, workspaceId: string): Record<string, Tool> {
-    return {
+    return this.wrapToolErrors({
       searchSharePages: tool({
         description:
           'Search the pages of THIS published documentation share for a ' +
@@ -96,7 +112,7 @@ export class PublicShareChatToolsService {
         execute: async ({ pageId }) => {
           const id = (pageId ?? '').trim();
           if (!id) {
-            throw new Error('A pageId is required.');
+            throw new ShareToolError('A pageId is required.');
           }
           // Resolve via the SINGLE canonical share-access boundary: confirms the
           // page resolves to THIS share (recursive CTE up the tree, honouring
@@ -112,7 +128,7 @@ export class PublicShareChatToolsService {
             workspaceId,
           );
           if (!resolved) {
-            throw new Error('That page is not part of this published share.');
+            throw new ShareToolError(SHARE_TOOL_ERROR_NOT_AVAILABLE);
           }
           const { page } = resolved;
 
@@ -193,6 +209,57 @@ export class PublicShareChatToolsService {
           }
         },
       }),
-    };
+    });
+  }
+
+  /**
+   * Wrap every tool's `execute` so a THROWN error is sanitized in ONE place —
+   * closing the byte leak, the render, and the model context at once (#394).
+   *
+   * The AI SDK surfaces a tool-execution throw as an atomic `tool-output-error`
+   * frame on the v6 UI stream whose `errorText` is the thrown message; on the
+   * public share that frame goes straight to an anonymous reader. Unwrapped, a
+   * raw exception (an internal page title, a DB/stack fragment, a driver detail)
+   * would ride that frame verbatim. Here we catch it, LOG the full detail
+   * server-side only, and re-throw a CLASSIFIED, safe error: the tool's own
+   * intentional ShareToolError messages pass through (they keep the model's
+   * self-correction useful), everything else collapses to a generic string.
+   */
+  private wrapToolErrors(
+    tools: Record<string, Tool>,
+  ): Record<string, Tool> {
+    const wrapped: Record<string, Tool> = {};
+    for (const [name, t] of Object.entries(tools)) {
+      const original = t.execute;
+      if (typeof original !== 'function') {
+        wrapped[name] = t;
+        continue;
+      }
+      wrapped[name] = {
+        ...t,
+        execute: async (args: unknown, options: unknown) => {
+          try {
+            return await (
+              original as (a: unknown, o: unknown) => Promise<unknown>
+            )(args, options);
+          } catch (err) {
+            const safe =
+              err instanceof ShareToolError
+                ? err.message
+                : SHARE_TOOL_ERROR_GENERIC;
+            // Full detail to the server log ONLY — never to the anon.
+            this.logger.warn(
+              `Public share tool "${name}" failed: ${
+                err instanceof Error ? err.message : String(err)
+              }`,
+            );
+            // This safe string is ALL that rides the tool-output-error frame,
+            // becomes model context, and could be rendered — one choke point.
+            throw new ShareToolError(safe);
+          }
+        },
+      } as Tool;
+    }
+    return wrapped;
   }
 }

apps/server/src/core/ai-chat/tools/shared-tool-specs.contract.spec.ts

@@ -17,8 +17,10 @@ import { SHARED_TOOL_SPECS } from '../../../../../../packages/mcp/src/tool-specs
  * This test fails the build if a spec is added to the registry but never wired
  * in-app, if an `inAppKey` is renamed without updating the service, if the
  * description drifts between the registry and the exposed tool, if the
- * snake_case `mcpName` <-> camelCase `inAppKey` convention is broken, or if the
- * exposed tool's input-schema keys diverge from the spec's `buildShape`.
+ * `mcpName === inAppKey` convention is broken (issue #412 unified the external
+ * MCP tool name with the in-app key — both are the same camelCase identifier),
+ * or if the exposed tool's input-schema keys diverge from the spec's
+ * `buildShape`.
  *
  * It does NOT need @docmost/mcp built: the registry is imported from TS source,
  * and the ESM loader is mocked so `forUser()` never dynamically imports the
@@ -45,6 +47,16 @@ describe('SHARED_TOOL_SPECS contract parity', () => {
         string,
         loader.SharedToolSpec
       >,
+      // Pure no-network draw.io helpers (#424). The contract test never executes
+      // a tool body, so type-correct stubs suffice (the real functions can't be
+      // imported here — drawio-shapes.ts uses import.meta, incompatible with the
+      // CommonJS jest transform).
+      searchShapes: (() => []) as unknown as loader.SearchShapesFn,
+      getGuideSection: (() => ({
+        section: 'index',
+        content: '',
+        sections: [],
+      })) as unknown as loader.GetGuideSectionFn,
     });
     const service = new AiChatToolsService(
       tokenServiceStub as never,
@@ -64,13 +76,9 @@ describe('SHARED_TOOL_SPECS contract parity', () => {
 
   afterAll(() => jest.restoreAllMocks());
 
-  // camelCase -> snake_case, matching the registry's mcpName convention.
-  const toSnake = (s: string) =>
-    s.replace(/[A-Z]/g, (c) => `_${c.toLowerCase()}`);
-
   // Type as the (optional-buildShape) SharedToolSpec; the `satisfies` literal
   // above otherwise narrows to a union where some members lack buildShape.
-  const specEntries = Object.entries(SHARED_TOOL_SPECS) as Array<
+  const specEntries = Object.entries(SHARED_TOOL_SPECS) as unknown as Array<
     [string, loader.SharedToolSpec]
   >;
 
@@ -86,8 +94,8 @@ describe('SHARED_TOOL_SPECS contract parity', () => {
       expect(spec.inAppKey).toBe(registryKey);
     });
 
-    it('mcpName is the snake_case form of inAppKey', () => {
-      expect(spec.mcpName).toBe(toSnake(spec.inAppKey));
+    it('mcpName equals inAppKey (unified camelCase name, #412)', () => {
+      expect(spec.mcpName).toBe(spec.inAppKey);
     });
 
     it('is exposed in-app under its inAppKey', () => {

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

@@ -27,16 +27,18 @@ import type { DocmostClientLike } from './docmost-client.loader';
  */
 
 describe('tool tier metadata (#332)', () => {
-  it('core set is the documented 13 + searchInPage + insertFootnote (15)', () => {
-    expect(CORE_TOOL_KEYS).toHaveLength(15);
+  it('core set is the documented 13 + searchInPage + insertFootnote + getTree + getPageContext (17, #443)', () => {
+    expect(CORE_TOOL_KEYS).toHaveLength(17);
     expect(CORE_TOOL_SET.has('searchInPage')).toBe(true); // #330, promoted to core
     expect(CORE_TOOL_SET.has('insertFootnote')).toBe(true); // #410, promoted to core
+    expect(CORE_TOOL_SET.has('getTree')).toBe(true); // #443, promoted to core
+    expect(CORE_TOOL_SET.has('getPageContext')).toBe(true); // #443, 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
+    // insertFootnote 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');
@@ -123,7 +125,14 @@ describe('deferred catalog ↔ live forUser() toolset partition (#332, F3)', ()
       DocmostClient: function () {
         return {} as DocmostClientLike;
       } as unknown as loader.DocmostClientCtor,
-      sharedToolSpecs: SHARED_TOOL_SPECS as Record<string, loader.SharedToolSpec>,
+      sharedToolSpecs: SHARED_TOOL_SPECS as unknown as Record<string, loader.SharedToolSpec>,
+      // Pure no-network draw.io helpers (#424); tool bodies are never executed here.
+      searchShapes: (() => []) as unknown as loader.SearchShapesFn,
+      getGuideSection: (() => ({
+        section: 'index',
+        content: '',
+        sections: [],
+      })) as unknown as loader.GetGuideSectionFn,
     });
     const service = new AiChatToolsService(
       {

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

@@ -39,12 +39,14 @@ export interface ToolCatalogEntry {
 
 /**
  * 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).
+ * (#330) + `insertFootnote` (#410) + `getTree`/`getPageContext` (#443).
+ * `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 `^[...]`). `getTree` and
+ * `getPageContext` are the single-call navigation/lookup tools — core so the
+ * agent never has to loadTools just to orient itself. `loadTools` is active too
+ * but is not a normal tool key (it is added to activeTools separately).
  */
 export const CORE_TOOL_KEYS = [
   'searchPages',
@@ -60,12 +62,17 @@ export const CORE_TOOL_KEYS = [
   'listComments',
   'resolveComment',
   'editPageText',
-  // #330 search_in_page — frequent for editorial sweeps; core despite predating
+  // #330 searchInPage — frequent for editorial sweeps; core despite predating
   // the issue's tier list.
   'searchInPage',
-  // #410 insert_footnote — core so pinpoint citations to already-written text
+  // #410 insertFootnote — core so pinpoint citations to already-written text
   // don't degrade into literal `^[...]`; kept symmetric with editPageText.
   'insertFootnote',
+  // #443 getTree + getPageContext — cheap single-call navigation/lookup tools
+  // (the core listPages even points to getTree); core so the agent never has
+  // to loadTools just to orient itself.
+  'getTree',
+  'getPageContext',
 ] as const;
 
 /** O(1) membership test for the core tier. */
@@ -124,12 +131,9 @@ export const INLINE_TOOL_TIERS: Record<
   // --- deferred inline ---
   // NOTE: createPage, renamePage, movePage, deletePage, updatePageJson and
   // exportPageMarkdown moved to @docmost/mcp's SHARED_TOOL_SPECS (#294); they
-  // carry their own deferred tier + catalogLine there.
-  updatePageContent: {
-    tier: 'deferred',
-    catalogLine:
-      "updatePageContent — replace a page's body (and optionally title) with new Markdown.",
-  },
+  // carry their own deferred tier + catalogLine there. updatePageContent moved
+  // there too as updatePageMarkdown (#411) — a shared registry spec now, so it
+  // is no longer an inline tier entry.
   listSidebarPages: {
     tier: 'deferred',
     catalogLine:
@@ -141,7 +145,7 @@ export const INLINE_TOOL_TIERS: Record<
   },
   // NOTE: tableInsertRow, tableDeleteRow and tableUpdateCell moved to
   // @docmost/mcp's SHARED_TOOL_SPECS (#294); they carry their own deferred tier +
-  // catalogLine there. getTable stays inline (its MCP name table_get breaks the
+  // catalogLine there. getTable stays inline (its MCP name tableGet breaks the
   // snake_case(inAppKey) convention, so it has no shared spec).
   // NOTE: checkNewComments moved to @docmost/mcp's SHARED_TOOL_SPECS (#294);
   // it carries its own deferred tier + catalogLine there.
@@ -153,7 +157,7 @@ export const INLINE_TOOL_TIERS: Record<
   // NOTE: sharePage moved to @docmost/mcp's SHARED_TOOL_SPECS (#294); it carries
   // its own deferred tier + catalogLine there. transformPage stays inline (its
   // schema deliberately diverges — it omits the deleteComments field the MCP
-  // docmost_transform exposes, a comment-deletion guardrail).
+  // docmostTransform exposes, a comment-deletion guardrail).
   transformPage: {
     tier: 'deferred',
     catalogLine: "transformPage — run a sandboxed JS transform over a page's document.",

apps/server/src/core/auth/strategies/jwt.strategy.spec.ts

@@ -120,3 +120,102 @@ describe('JwtStrategy — provenance derivation', () => {
     expect(req.raw.actor).toBeUndefined();
   });
 });
+
+/**
+ * Provenance derivation on the API-KEY path (jwt.strategy.validateApiKey, #486).
+ *
+ * The access-token path stamped provenance; the API-key path returned early
+ * WITHOUT it, so an is_agent API key's REST writes recorded no 'agent' marker.
+ * The API-key payload carries no signed claim, so provenance is resolved from the
+ * SERVER-SIDE user returned by ApiKeyService.validateApiKey: isAgent -> 'agent',
+ * otherwise 'user'; aiChatId is always null (an API key has no ai_chats row).
+ *
+ * The enterprise ApiKeyService is not bundled in the OSS build, so the strategy
+ * loads it through an overridable `resolveApiKeyService` seam that we stub here.
+ */
+describe('JwtStrategy — API-key provenance derivation (#486)', () => {
+  function makeApiKeyStrategy(validateApiKeyImpl: (p: any) => Promise<any>) {
+    const userRepo: any = { findById: jest.fn() };
+    const workspaceRepo: any = { findById: jest.fn() };
+    const userSessionRepo: any = { findActiveById: jest.fn() };
+    const sessionActivityService: any = { trackActivity: jest.fn() };
+    const environmentService: any = { getAppSecret: () => 'test-secret' };
+    const moduleRef: any = {};
+
+    const strategy = new JwtStrategy(
+      userRepo,
+      workspaceRepo,
+      userSessionRepo,
+      sessionActivityService,
+      environmentService,
+      moduleRef,
+    );
+    // Stub the EE ApiKeyService seam (the real module is not in the OSS build).
+    const validateApiKey = jest.fn(validateApiKeyImpl);
+    jest
+      .spyOn(strategy as any, 'resolveApiKeyService')
+      .mockReturnValue({ validateApiKey });
+    return { strategy, validateApiKey };
+  }
+
+  const makeReq = () => ({ raw: {} as Record<string, any> });
+  const apiKeyPayload = () => ({
+    sub: 'svc-1',
+    workspaceId: 'ws-1',
+    apiKeyId: 'key-1',
+    type: JwtType.API_KEY,
+  });
+
+  it("stamps actor='agent' for an is_agent API key (from the validated user)", async () => {
+    const validated = {
+      user: { id: 'svc-1', isAgent: true },
+      workspace: { id: 'ws-1' },
+    };
+    const { strategy, validateApiKey } = makeApiKeyStrategy(
+      async () => validated,
+    );
+    const req = makeReq();
+
+    const result = await strategy.validate(req, apiKeyPayload() as any);
+
+    expect(validateApiKey).toHaveBeenCalledTimes(1);
+    expect(req.raw.actor).toBe('agent');
+    // API keys carry no internal ai_chats row -> null.
+    expect(req.raw.aiChatId).toBeNull();
+    // The validated auth object is returned unchanged (req.user shape preserved).
+    expect(result).toBe(validated);
+  });
+
+  it("stamps actor='user' for an ordinary (non-agent) API key", async () => {
+    const { strategy } = makeApiKeyStrategy(async () => ({
+      user: { id: 'u-1', isAgent: false },
+      workspace: { id: 'ws-1' },
+    }));
+    const req = makeReq();
+
+    await strategy.validate(req, apiKeyPayload() as any);
+
+    expect(req.raw.actor).toBe('user');
+    expect(req.raw.aiChatId).toBeNull();
+  });
+
+  it('throws Unauthorized (and stamps nothing) when the EE module is missing', async () => {
+    const userRepo: any = { findById: jest.fn() };
+    const strategy = new JwtStrategy(
+      userRepo,
+      { findById: jest.fn() } as any,
+      { findActiveById: jest.fn() } as any,
+      { trackActivity: jest.fn() } as any,
+      { getAppSecret: () => 'test-secret' } as any,
+      {} as any,
+    );
+    // EE not bundled: the seam returns null.
+    jest.spyOn(strategy as any, 'resolveApiKeyService').mockReturnValue(null);
+    const req = makeReq();
+
+    await expect(
+      strategy.validate(req, apiKeyPayload() as any),
+    ).rejects.toThrow(UnauthorizedException);
+    expect(req.raw.actor).toBeUndefined();
+  });
+});

apps/server/src/core/auth/strategies/jwt.strategy.ts

@@ -102,28 +102,49 @@ export class JwtStrategy extends PassportStrategy(Strategy, 'jwt') {
   }
 
   private async validateApiKey(req: any, payload: JwtApiKeyPayload) {
-    let ApiKeyModule: any;
-    let isApiKeyModuleReady = false;
+    const apiKeyService = this.resolveApiKeyService();
+    if (!apiKeyService) {
+      throw new UnauthorizedException('Enterprise API Key module missing');
+    }
 
+    const result = await apiKeyService.validateApiKey(payload);
+
+    // Stamp the agent-edit provenance for the API-KEY path too (#486). Unlike the
+    // access-token path above, it CANNOT be resolved before this point: the
+    // API-key payload carries no signed actor/aiChatId claim, and the user (with
+    // its isAgent flag) is unknown until the key is validated. Claim semantics for
+    // API keys: an is_agent API key (an agent service account) stamps 'agent' on
+    // every REST write; an ordinary API key resolves to 'user'. An API key has no
+    // internal ai_chats row, so aiChatId is always null. Derived from the
+    // SERVER-SIDE user (never a client field), so an 'agent' badge is unspoofable
+    // — mirroring the access-token path. Passing `null` for the claim means the
+    // actor is decided solely by user.isAgent.
+    const provenance = resolveProvenance((result as any)?.user, null);
+    req.raw.actor = provenance.actor;
+    req.raw.aiChatId = provenance.aiChatId;
+
+    return result;
+  }
+
+  /**
+   * Resolve the enterprise ApiKeyService, or `null` when the EE module is not
+   * bundled in this build (community build). Extracted as an overridable seam so
+   * the API-key provenance stamping can be unit-tested without the EE package
+   * present (docmost is OSS + a separate EE bundle; `require` of the EE path
+   * throws here). Any load/resolve error is treated as "module missing".
+   */
+  protected resolveApiKeyService(): {
+    validateApiKey: (payload: JwtApiKeyPayload) => Promise<unknown>;
+  } | null {
     try {
       // eslint-disable-next-line @typescript-eslint/no-require-imports
-      ApiKeyModule = require('./../../../ee/api-key/api-key.service');
-      isApiKeyModuleReady = true;
+      const ApiKeyModule = require('./../../../ee/api-key/api-key.service');
+      return this.moduleRef.get(ApiKeyModule.ApiKeyService, { strict: false });
     } catch (err) {
       this.logger.debug(
         'API Key module requested but enterprise module not bundled in this build',
       );
-      isApiKeyModuleReady = false;
+      return null;
     }
-
-    if (isApiKeyModuleReady) {
-      const ApiKeyService = this.moduleRef.get(ApiKeyModule.ApiKeyService, {
-        strict: false,
-      });
-
-      return ApiKeyService.validateApiKey(payload);
-    }
-
-    throw new UnauthorizedException('Enterprise API Key module missing');
   }
 }

apps/server/src/core/search/dto/search-response.dto.ts

@@ -12,3 +12,22 @@ export class SearchResponseDto {
   updatedAt: Date;
   space: Partial<Space>;
 }
+
+// Response shape for the opt-in agent-lookup mode (#443, `substring: true`).
+// Additive to the FTS response: carries the location (`path`), a windowed
+// `snippet` around the first match and a per-response sort `score`. The MCP
+// layer maps `id → pageId`; `slugId` is never exposed.
+export class SearchLookupResponseDto {
+  id: string;
+  slugId: string;
+  title: string;
+  parentPageId: string | null;
+  // Ancestor titles from the space root down to the direct parent; [] for a
+  // root page.
+  path: string[];
+  // ~300–500 chars around the first match (or a leading text window / extended
+  // ts_headline fallback).
+  snippet: string;
+  // 0..1 float, meaningful ONLY for sorting within one response.
+  score: number;
+}

apps/server/src/core/search/dto/search.dto.ts

@@ -30,6 +30,31 @@ export class SearchDTO {
   @IsOptional()
   @IsNumber()
   offset?: number;
+
+  // --- Opt-in agent-lookup mode (#443). ------------------------------------
+  // These fields are ADDITIVE and default-off: a web client that sends none of
+  // them gets byte-identical FTS behaviour and result shape. They are only read
+  // by the substring/path/snippet code path in SearchService.searchPage.
+  //
+  // NOTE (standalone stdio vs stock upstream): stock upstream validates this DTO
+  // with `whitelist: true`, so an older server silently strips these unknown
+  // fields and the request degrades gracefully to the plain FTS behaviour.
+
+  // Enables the hybrid substring branch (title + text_content LIKE) merged with
+  // the existing FTS branch, plus tiered ranking, path and windowed snippet.
+  @IsOptional()
+  @IsBoolean()
+  substring?: boolean;
+
+  // Restrict the search to a page and all of its descendants (inclusive).
+  @IsOptional()
+  @IsString()
+  parentPageId?: string;
+
+  // Match titles only; do not scan text_content.
+  @IsOptional()
+  @IsBoolean()
+  titleOnly?: boolean;
 }
 
 export class SearchShareDTO extends SearchDTO {

apps/server/src/core/search/search.controller.ts

@@ -60,6 +60,12 @@ export class SearchController {
       }
     }
 
+    // #443 graceful degradation: on EE/Typesense instances the request routes to
+    // the Typesense backend, which does NOT implement the opt-in agent-lookup
+    // mode. The `substring`/`parentPageId`/`titleOnly` fields are silently ignored
+    // and the response carries no `path`/`snippet`/`score` and no substring/tier
+    // ranking — it degrades to plain Typesense FTS. The native lookup mode below
+    // is Postgres-search-driver only.
     if (this.environmentService.getSearchDriver() === 'typesense') {
       return this.searchTypesense(searchDto, {
         userId: user.id,

apps/server/src/core/search/search.service.lookup.spec.ts

@@ -0,0 +1,95 @@
+import {
+  computeLookupScore,
+  escapeLikePattern,
+  SearchLookupTier,
+} from './search.service';
+
+/**
+ * Pure-function coverage for the #443 agent-lookup helpers:
+ *  - escapeLikePattern: LIKE-metacharacter escaping so `%`/`_`/`\` are literals
+ *    (the acceptance-table requirement that a query of `%` or `_` does NOT match
+ *    everything);
+ *  - computeLookupScore: the tiered 0..1 ranking score, where a stronger tier
+ *    always outranks a weaker one regardless of the in-tier secondary signal.
+ *
+ * The DB-touching branch (substring UNION FTS, path CTE, snippet window) is
+ * covered by the integration spec against the real schema.
+ */
+describe('escapeLikePattern', () => {
+  it('escapes the LIKE metacharacters % _ and \\', () => {
+    expect(escapeLikePattern('%')).toBe('\\%');
+    expect(escapeLikePattern('_')).toBe('\\_');
+    expect(escapeLikePattern('\\')).toBe('\\\\');
+  });
+
+  it('escapes the backslash FIRST so it does not double-escape %/_', () => {
+    // Input `\%` must become `\\` + `\%` = `\\\%`, not `\\%`.
+    expect(escapeLikePattern('\\%')).toBe('\\\\\\%');
+  });
+
+  it('leaves ordinary technical chars (. - / digits) untouched', () => {
+    expect(escapeLikePattern('backup-srv.local')).toBe('backup-srv.local');
+    expect(escapeLikePattern('10.0.12')).toBe('10.0.12');
+    expect(escapeLikePattern('WB-MGE-30D86B')).toBe('WB-MGE-30D86B');
+    expect(escapeLikePattern('a/b')).toBe('a/b');
+  });
+
+  it('escapes only the metacharacters in a mixed string', () => {
+    expect(escapeLikePattern('50%_off.zip')).toBe('50\\%\\_off.zip');
+  });
+
+  it('is null/undefined-safe', () => {
+    expect(escapeLikePattern(undefined as any)).toBe('');
+    expect(escapeLikePattern(null as any)).toBe('');
+  });
+});
+
+describe('computeLookupScore', () => {
+  it('keeps every score within (0, 1]', () => {
+    for (const tier of [
+      SearchLookupTier.TITLE_EXACT,
+      SearchLookupTier.TITLE_SUBSTRING,
+      SearchLookupTier.TEXT,
+    ]) {
+      for (const secondary of [0, 0.001, 1, 100, 1e6]) {
+        const s = computeLookupScore({ tier, secondary });
+        expect(s).toBeGreaterThan(0);
+        expect(s).toBeLessThanOrEqual(1);
+      }
+    }
+  });
+
+  it('a stronger tier ALWAYS outranks a weaker tier, whatever the secondary', () => {
+    // Weak tier with a huge secondary must still lose to a strong tier with a
+    // tiny secondary — tiers dominate.
+    const strongLowSecondary = computeLookupScore({
+      tier: SearchLookupTier.TITLE_EXACT,
+      secondary: 0,
+    });
+    const weakHighSecondary = computeLookupScore({
+      tier: SearchLookupTier.TEXT,
+      secondary: 1e9,
+    });
+    expect(strongLowSecondary).toBeGreaterThan(weakHighSecondary);
+  });
+
+  it('within a tier a larger secondary sorts higher', () => {
+    const lo = computeLookupScore({
+      tier: SearchLookupTier.TEXT,
+      secondary: 0.1,
+    });
+    const hi = computeLookupScore({
+      tier: SearchLookupTier.TEXT,
+      secondary: 5,
+    });
+    expect(hi).toBeGreaterThan(lo);
+  });
+
+  it('treats a negative/absent secondary as 0', () => {
+    const zero = computeLookupScore({ tier: SearchLookupTier.TEXT, secondary: 0 });
+    expect(computeLookupScore({ tier: SearchLookupTier.TEXT })).toBe(zero);
+    expect(
+      computeLookupScore({ tier: SearchLookupTier.TEXT, secondary: -5 }),
+    ).toBe(zero);
+  });
+});

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

@@ -1,6 +1,9 @@
 import { Injectable } from '@nestjs/common';
 import { SearchDTO, SearchSuggestionDTO } from './dto/search.dto';
-import { SearchResponseDto } from './dto/search-response.dto';
+import {
+  SearchLookupResponseDto,
+  SearchResponseDto,
+} from './dto/search-response.dto';
 import { InjectKysely } from 'nestjs-kysely';
 import { KyselyDB } from '@docmost/db/types/kysely.types';
 import { sql } from 'kysely';
@@ -34,6 +37,53 @@ export function buildTsQuery(raw: string): string {
   return tsquery(cleaned + '*');
 }
 
+// Escape the LIKE metacharacters (`%`, `_`, `\`) in a raw user query so every
+// character — including `.`, `-`, `_`, `%`, `/` — is matched LITERALLY by a
+// `col LIKE '%' || q || '%'` predicate. Without this, a query of `%` or `_`
+// would match every row (see the #443 acceptance table). The backslash is the
+// escape char (Postgres LIKE default), so it must be escaped first.
+export function escapeLikePattern(raw: string): string {
+  return (raw ?? '')
+    .replace(/\\/g, '\\\\')
+    .replace(/%/g, '\\%')
+    .replace(/_/g, '\\_');
+}
+
+// Ranking tiers for the agent-lookup mode (#443), highest first. A hit's tier
+// is the strongest way it matched; ties inside a tier break on a secondary
+// signal (FTS rank, or first-match position). The numeric `score` returned to
+// the caller is derived from (tier, secondary) and is meaningful ONLY for
+// ordering within a single response.
+export enum SearchLookupTier {
+  // Title equals the query, case-insensitively.
+  TITLE_EXACT = 3,
+  // Query is a substring of the title.
+  TITLE_SUBSTRING = 2,
+  // Query matched in the text (substring or FTS).
+  TEXT = 1,
+}
+
+export interface RankableHit {
+  tier: SearchLookupTier;
+  // Secondary in-tier signal, higher = better (e.g. ts_rank, or a
+  // position-derived closeness score). Defaults to 0.
+  secondary?: number;
+}
+
+// Map (tier, secondary) → a 0..1 float used ONLY to sort one response.
+//
+// Formula: score = (tier + squash(secondary)) / (maxTier + 1), where
+//   squash(x) = x / (1 + x)  maps any non-negative secondary into [0, 1)
+// so a stronger tier ALWAYS outranks a weaker one regardless of the secondary
+// value, and within a tier a larger secondary sorts higher. maxTier is the top
+// enum value (TITLE_EXACT = 3), so the divisor keeps the result in (0, 1].
+export function computeLookupScore(hit: RankableHit): number {
+  const maxTier = SearchLookupTier.TITLE_EXACT;
+  const secondary = Math.max(0, hit.secondary ?? 0);
+  const squashed = secondary / (1 + secondary);
+  return (hit.tier + squashed) / (maxTier + 1);
+}
+
 @Injectable()
 export class SearchService {
   constructor(
@@ -50,12 +100,19 @@ export class SearchService {
       userId?: string;
       workspaceId: string;
     },
-  ): Promise<{ items: SearchResponseDto[] }> {
+  ): Promise<{ items: SearchResponseDto[] | SearchLookupResponseDto[] }> {
     const { query } = searchParams;
 
     if (query.length < 1) {
       return { items: [] };
     }
+
+    // Opt-in agent-lookup mode (#443). Guarded by the `substring` flag so the
+    // web-UI (which never sets it) keeps byte-identical FTS behaviour below.
+    if (searchParams.substring) {
+      return this.searchPageLookup(searchParams, opts);
+    }
+
     const searchQuery = buildTsQuery(query);
 
     let queryResults = this.db
@@ -175,6 +232,348 @@ export class SearchService {
     return { items: searchResults };
   }
 
+  /**
+   * Agent-lookup search (#443, opt-in via `SearchDTO.substring`).
+   *
+   * ADDITIVE to the FTS path: runs a substring branch (title + optionally
+   * text_content, LIKE with metacharacters escaped) MERGED with the existing
+   * FTS branch, so technical tokens that the `english` tokenizer mangles
+   * (`backup-srv.local`, `10.0.12.5`, `WB-MGE-30D86B`) are still found — even
+   * when `buildTsQuery()` returns '' for a dotted/numeric query. Results carry a
+   * location (`path`), a windowed `snippet` and a per-response `score`.
+   *
+   * The whole method is only reached when `substring: true`; the web-UI never
+   * sets it, so its behaviour is unchanged.
+   */
+  private async searchPageLookup(
+    searchParams: SearchDTO,
+    opts: { userId?: string; workspaceId: string },
+  ): Promise<{ items: SearchLookupResponseDto[] }> {
+    const rawQuery = searchParams.query.trim();
+    if (!rawQuery) {
+      return { items: [] };
+    }
+
+    const limit = Math.min(Math.max(searchParams.limit || 10, 1), 50);
+
+    // Normalize the query the same way as the FTS / suggest path: f_unaccent +
+    // lower, done in SQL. `q` is the escaped LIKE pattern body (literal chars).
+    const likeBody = escapeLikePattern(rawQuery);
+    // Compare against `LOWER(f_unaccent(col))`; unaccent+lower the needle too.
+    const needle = sql<string>`LOWER(f_unaccent(${rawQuery}))`;
+    const likePattern = sql<string>`LOWER(f_unaccent(${'%' + likeBody + '%'}))`;
+    const tsQuery = buildTsQuery(rawQuery);
+    const hasTsQuery = tsQuery.length > 0;
+
+    // --- Resolve the space scope. ---------------------------------------------
+    // Mirrors searchPage: explicit spaceId, else the authenticated user's member
+    // spaces. The share path is not exposed to this opt-in mode.
+    let spaceIds: string[] = [];
+    if (searchParams.spaceId) {
+      spaceIds = [searchParams.spaceId];
+    } else if (opts.userId) {
+      spaceIds = await this.spaceMemberRepo.getUserSpaceIds(opts.userId);
+    } else {
+      return { items: [] };
+    }
+    if (spaceIds.length === 0) {
+      return { items: [] };
+    }
+
+    // --- Optional parentPageId subtree scope (inclusive). ---------------------
+    // Reuse the same recursive-descendants pattern used for share-scope.
+    let descendantIds: string[] | null = null;
+    if (searchParams.parentPageId) {
+      const descendants = await this.pageRepo.getPageAndDescendants(
+        searchParams.parentPageId,
+        { includeContent: false },
+      );
+      descendantIds = descendants.map((p: any) => p.id);
+      if (descendantIds.length === 0) {
+        return { items: [] };
+      }
+    }
+
+    // --- Candidate query: substring (title + text) UNION FTS. -----------------
+    // We compute everything the ranker needs in SQL and pull only small columns
+    // (never the whole text_content) into Node:
+    //   - titleExact / titleSub: tier signals
+    //   - textMatchPos: 1-based position of the first text match (0 = none)
+    //   - ftsRank: ts_rank for the FTS secondary signal (0 when no tsquery)
+    //   - snippet: windowed ~500 chars around the first text match, or a leading
+    //     text window (title-only hit), or an extended ts_headline fallback.
+    const N_BEFORE = 60; // chars of context before the first match
+    const SNIPPET_LEN = 500;
+
+    let candidates = this.db
+      .selectFrom('pages')
+      .select([
+        'pages.id as id',
+        'pages.slugId as slugId',
+        'pages.title as title',
+        'pages.parentPageId as parentPageId',
+        // Tier signals.
+        sql<boolean>`LOWER(f_unaccent(coalesce(pages.title, ''))) = ${needle}`.as(
+          'titleExact',
+        ),
+        sql<boolean>`LOWER(f_unaccent(coalesce(pages.title, ''))) LIKE ${likePattern} ESCAPE '\\'`.as(
+          'titleSub',
+        ),
+        // 1-based position of the first text match (0 = no text match).
+        sql<number>`strpos(LOWER(f_unaccent(coalesce(pages.text_content, ''))), ${needle})`.as(
+          'textMatchPos',
+        ),
+        // FTS secondary signal (0 when the tsquery is empty).
+        hasTsQuery
+          ? sql<number>`ts_rank(pages.tsv, to_tsquery('english', f_unaccent(${tsQuery})))`.as(
+              'ftsRank',
+            )
+          : sql<number>`0`.as('ftsRank'),
+        // Windowed snippet, computed entirely in SQL. Priority:
+        //  1. window around the first text match;
+        //  2. otherwise (titleOnly: no snippet; else) a leading window of the
+        //     page text (title-only hit);
+        //  3. otherwise an extended ts_headline for pure-FTS hits.
+        //
+        // #443 snippet-position fix: the match position (`strpos`) is computed in
+        // the LOWER(f_unaccent(...)) space, but f_unaccent is NOT length-
+        // preserving (ß→ss, æ→ae, …→..., ½→ 1/2, full-width forms), so slicing
+        // the ORIGINAL text at that position was misaligned — a single expanding
+        // char before the match shifted the window (or ran it past end → empty).
+        // We now slice from the SAME LOWER(f_unaccent(...)) string so position
+        // and slice share one coordinate space. DELIBERATE trade-off: the snippet
+        // loses original case/diacritics — acceptable for an agent-facing snippet
+        // (position accuracy over original-glyph fidelity). The ts_headline branch
+        // matches over the ORIGINAL text itself, so it is unaffected and kept as-is.
+        searchParams.titleOnly
+          ? sql<string>`''`.as('snippet')
+          : sql<string>`
+          coalesce(
+            case
+              when strpos(LOWER(f_unaccent(coalesce(pages.text_content, ''))), ${needle}) > 0
+                then substring(
+                  LOWER(f_unaccent(coalesce(pages.text_content, '')))
+                  from greatest(1, strpos(LOWER(f_unaccent(coalesce(pages.text_content, ''))), ${needle}) - ${N_BEFORE})
+                  for ${SNIPPET_LEN}
+                )
+              when coalesce(pages.text_content, '') <> ''
+                then substring(LOWER(f_unaccent(pages.text_content)) from 1 for 300)
+              ${
+                hasTsQuery
+                  ? sql`else ts_headline('english', coalesce(pages.text_content, ''), to_tsquery('english', f_unaccent(${tsQuery})), 'MinWords=25, MaxWords=40, MaxFragments=3')`
+                  : sql``
+              }
+            end,
+            ''
+          )
+        `.as('snippet'),
+      ])
+      .where('pages.deletedAt', 'is', null)
+      .where('pages.spaceId', 'in', spaceIds);
+
+    if (descendantIds) {
+      candidates = candidates.where('pages.id', 'in', descendantIds);
+    }
+
+    // Match predicate: title substring OR (unless titleOnly) text substring OR
+    // (unless titleOnly) FTS. The substring branch runs even when the tsquery is
+    // empty — that is the dotted/numeric-token case the FTS path misses.
+    //
+    // #443 dead-index fix: these two LIKE predicates MUST match the GIN trgm
+    // index expressions EXACTLY for Postgres to use them. The indexes are on the
+    // coalesce-FREE expressions `LOWER(f_unaccent(title))` (#348's
+    // idx_pages_title_trgm) and `LOWER(f_unaccent(text_content))` (this PR's
+    // idx_pages_text_content_trgm). A `coalesce(col,'')` wrapper here would make
+    // the query expression differ from the index expression and force a Seq Scan
+    // on pages for every lookup. Dropping coalesce is SEMANTICALLY EQUIVALENT:
+    // `NULL LIKE '%q%'` is NULL (falsy), so a NULL title/text simply doesn't
+    // match — exactly as an empty string wouldn't match `%q%`.
+    candidates = candidates.where((eb) => {
+      const ors = [
+        eb(
+          sql`LOWER(f_unaccent(pages.title))`,
+          'like',
+          sql`${likePattern} ESCAPE '\\'`,
+        ),
+      ];
+      if (!searchParams.titleOnly) {
+        ors.push(
+          eb(
+            sql`LOWER(f_unaccent(pages.text_content))`,
+            'like',
+            sql`${likePattern} ESCAPE '\\'`,
+          ),
+        );
+        if (hasTsQuery) {
+          ors.push(
+            sql<boolean>`pages.tsv @@ to_tsquery('english', f_unaccent(${tsQuery}))` as any,
+          );
+        }
+      }
+      return eb.or(ors);
+    });
+
+    // Pull a generous candidate set (before permission filtering + limit).
+    // Cap it so a pathological match set cannot blow up memory; 200 >> limit
+    // (max 50) leaves ample headroom for the post-permission truncation.
+    //
+    // #443 cap-ordering fix: the 200-cap MUST be deterministic and relevance-
+    // biased. Without an ORDER BY, Postgres returns an ARBITRARY 200 rows, so on
+    // a broad match set (common word / short substring) a strong TITLE_EXACT hit
+    // could be among the dropped rows while 200 low-tier TEXT hits fill the cap.
+    // We order by the SAME SQL tier proxies the Node ranker uses — title-exact,
+    // then title-substring, then fts-rank (nulls last), then earliest text-match
+    // position — so the cap keeps the strongest candidates. The Node-side final
+    // tier sort + slice(0, limit) below still runs and stays authoritative; this
+    // ORDER BY only decides WHICH candidates survive the 200-cap.
+    // NB: a BARE integer literal in ORDER BY is read by Postgres as an ordinal
+    // column position (`ORDER BY 0` → "position 0 is not in select list"), so the
+    // no-tsquery fallback is `0::float`, not `0`.
+    const ftsRankExpr = hasTsQuery
+      ? sql`ts_rank(pages.tsv, to_tsquery('english', f_unaccent(${tsQuery})))`
+      : sql`0::float`;
+    const candidatesCapped = candidates
+      // Raw-SQL ORDER BY expressions: pass the full `<expr> <dir>` as ONE arg
+      // (the two-arg form treats a raw-SQL second arg as an ORDER BY position).
+      .orderBy(
+        sql`(LOWER(f_unaccent(coalesce(pages.title, ''))) = ${needle}) desc`,
+      )
+      .orderBy(
+        sql`(LOWER(f_unaccent(coalesce(pages.title, ''))) LIKE ${likePattern} ESCAPE '\\') desc`,
+      )
+      .orderBy(sql`${ftsRankExpr} desc nulls last`)
+      // Earlier text match first; strpos returns 0 for "no match", which would
+      // sort BEFORE a real (>=1) position under plain ASC, so push 0 to the end.
+      .orderBy(
+        sql`case when strpos(LOWER(f_unaccent(coalesce(pages.text_content, ''))), ${needle}) = 0 then 2147483647 else strpos(LOWER(f_unaccent(coalesce(pages.text_content, ''))), ${needle}) end asc`,
+      );
+
+    let rows: any[] = await candidatesCapped.limit(200).execute();
+
+    if (rows.length === 0) {
+      return { items: [] };
+    }
+
+    // --- Permissions BEFORE limit. --------------------------------------------
+    // Apply the existing page-level post-filter to the MERGED set, then rank and
+    // only THEN truncate to `limit` — never lose the permission filter.
+    if (opts.userId) {
+      const accessibleIds =
+        await this.pagePermissionRepo.filterAccessiblePageIds({
+          pageIds: rows.map((r) => r.id),
+          userId: opts.userId,
+          spaceId: searchParams.spaceId,
+          workspaceId: opts.workspaceId,
+        });
+      const accessibleSet = new Set(accessibleIds);
+      rows = rows.filter((r) => accessibleSet.has(r.id));
+    }
+
+    if (rows.length === 0) {
+      return { items: [] };
+    }
+
+    // --- Tiered ranking + dedup. ----------------------------------------------
+    // Rows are already unique by id (single pages scan), so no cross-branch
+    // dedup is needed here; the tier captures the strongest match reason.
+    const ranked = rows.map((r) => {
+      let tier: SearchLookupTier;
+      let secondary: number;
+      if (r.titleExact) {
+        tier = SearchLookupTier.TITLE_EXACT;
+        secondary = Number(r.ftsRank) || 0;
+      } else if (r.titleSub) {
+        tier = SearchLookupTier.TITLE_SUBSTRING;
+        secondary = Number(r.ftsRank) || 0;
+      } else {
+        tier = SearchLookupTier.TEXT;
+        // Prefer earlier text matches; map position → closeness in (0, 1].
+        const pos = Number(r.textMatchPos) || 0;
+        secondary =
+          pos > 0 ? 1 / (1 + (pos - 1) / 100) : Number(r.ftsRank) || 0;
+      }
+      return { row: r, tier, score: computeLookupScore({ tier, secondary }) };
+    });
+
+    ranked.sort((a, b) => b.score - a.score);
+    const top = ranked.slice(0, limit);
+
+    // --- Batch ancestor path (ONE recursive CTE, not N+1). --------------------
+    const pathById = await this.buildAncestorPaths(top.map((t) => t.row.id));
+
+    const items: SearchLookupResponseDto[] = top.map((t) => ({
+      id: t.row.id,
+      slugId: t.row.slugId,
+      title: t.row.title,
+      parentPageId: t.row.parentPageId ?? null,
+      path: pathById.get(t.row.id) ?? [],
+      snippet: (t.row.snippet ?? '')
+        .replace(/\r\n|\r|\n/g, ' ')
+        .replace(/\s+/g, ' ')
+        .trim(),
+      score: t.score,
+    }));
+
+    return { items };
+  }
+
+  /**
+   * Batch ancestor-titles helper (#443): ONE recursive CTE seeded with ALL hit
+   * ids, walking UP parentPageId. Returns a map hitId → ancestor titles ordered
+   * root → direct parent (the hit's own title is excluded). Root pages map to
+   * an empty array. Avoids the N+1 of a per-page breadcrumb call.
+   */
+  private async buildAncestorPaths(
+    hitIds: string[],
+  ): Promise<Map<string, string[]>> {
+    const result = new Map<string, string[]>();
+    if (hitIds.length === 0) return result;
+
+    // ancestry(hit_id, page_id, title, parent_page_id, depth): seed one row per
+    // hit at depth 0 (the hit itself), then walk to parents (increasing depth).
+    const rows = await this.db
+      .withRecursive('ancestry', (db) =>
+        db
+          .selectFrom('pages')
+          .select([
+            'pages.id as hitId',
+            'pages.id as pageId',
+            'pages.title as title',
+            'pages.parentPageId as parentPageId',
+            sql<number>`0`.as('depth'),
+          ])
+          .where('pages.id', 'in', hitIds)
+          .unionAll((exp) =>
+            exp
+              .selectFrom('pages as p')
+              .innerJoin('ancestry as a', 'p.id', 'a.parentPageId')
+              .select([
+                'a.hitId as hitId',
+                'p.id as pageId',
+                'p.title as title',
+                'p.parentPageId as parentPageId',
+                sql<number>`a.depth + 1`.as('depth'),
+              ]),
+          ),
+      )
+      .selectFrom('ancestry')
+      .select(['hitId', 'title', 'depth'])
+      // depth 0 is the hit itself — excluded from the path.
+      .where('depth', '>', 0)
+      .orderBy('hitId')
+      // Larger depth = closer to the space root. Ordering DESC gives
+      // root → parent once collected.
+      .orderBy('depth', 'desc')
+      .execute();
+
+    for (const r of rows as any[]) {
+      const list = result.get(r.hitId) ?? [];
+      list.push(r.title);
+      result.set(r.hitId, list);
+    }
+    return result;
+  }
+
   async searchSuggestions(
     suggestion: SearchSuggestionDTO,
     userId: string,

apps/server/src/database/migrations/20260706T120000-search-lookup-trgm.ts

@@ -0,0 +1,55 @@
+import { type Kysely, sql } from 'kysely';
+
+/**
+ * #443 — trigram indexes for the opt-in agent-lookup search mode.
+ *
+ * The lookup mode adds a substring branch that runs leading-wildcard
+ * `LOWER(f_unaccent(col)) LIKE '%q%'` predicates on pages.title and
+ * pages.text_content. A leading wildcard cannot use a b-tree index, so without a
+ * GIN trigram index each such predicate is a sequential scan.
+ *
+ *  - TITLE: the lookup-mode title predicate is `LOWER(f_unaccent(title)) LIKE
+ *    '%q%'` (coalesce-free, so it can use a functional index), which is IDENTICAL
+ *    to the one added for /search/suggest (#348). #348's perf-indexes migration
+ *    already created `idx_pages_title_trgm` on `(LOWER(f_unaccent(title)))
+ *    gin_trgm_ops`, so the title predicate is already covered — we do NOT
+ *    re-create that index here (it would be redundant).
+ *
+ *  - TEXT_CONTENT: NEW. The substring branch scans text_content when the query
+ *    is not titleOnly. text_content is the large column, so a GIN trigram index
+ *    on it is the meaningful acceleration for the lookup mode. The lookup search
+ *    is ALWAYS space-scoped (spaceId or the user's member spaces), so on small
+ *    instances a per-space sequential scan is tolerable — but the index turns the
+ *    `%q%` text predicate into a Bitmap Index Scan and removes the only
+ *    unbounded-per-space cost of the feature. We add it. The trade-off is disk +
+ *    write amplification on page edits (GIN trigram indexes are larger and slower
+ *    to update than b-trees); on the small instances this fork targets that cost
+ *    is acceptable and the read win on agent lookups is the priority.
+ *
+ * DEPLOY-TIME LOCK WARNING: plain (non-CONCURRENT) CREATE INDEX — Kysely runs
+ * each migration in a transaction, so CONCURRENTLY is impossible. The build takes
+ * a SHARE lock that BLOCKS writes on `pages` for its duration. The text_content
+ * GIN build is the slow one and can take minutes on a large tenant. For large
+ * installations, run this in a maintenance window or build the index out-of-band
+ * with CREATE INDEX CONCURRENTLY before deploying (then `IF NOT EXISTS` no-ops
+ * here). Small/typical tenants are unaffected.
+ */
+export async function up(db: Kysely<any>): Promise<void> {
+  // The title predicate is served by #348's idx_pages_title_trgm — see header.
+  // Only the text_content index is introduced here.
+
+  // text_content trigram index. Its expression is coalesce-free —
+  // `LOWER(f_unaccent(text_content))` — to EXACTLY match the coalesce-free
+  // lookup-mode text substring predicate in search.service.ts, so Postgres can
+  // use it (a `coalesce(...)` mismatch would silently fall back to a Seq Scan).
+  await sql`
+    CREATE INDEX IF NOT EXISTS idx_pages_text_content_trgm
+      ON pages USING gin ((LOWER(f_unaccent(text_content))) gin_trgm_ops)
+  `.execute(db);
+}
+
+export async function down(db: Kysely<any>): Promise<void> {
+  // Only drop the index this migration introduced. idx_pages_title_trgm is owned
+  // by the #348 perf-indexes migration, so leave it for that migration's down().
+  await sql`DROP INDEX IF EXISTS idx_pages_text_content_trgm`.execute(db);
+}

apps/server/src/integrations/ai/ai-sdk-drain-hang.patch.spec.ts

@@ -0,0 +1,133 @@
+import { readFileSync } from 'fs';
+import { EventEmitter } from 'node:events';
+import { streamText } from 'ai';
+import { MockLanguageModelV3, simulateReadableStream } from 'ai/test';
+
+/**
+ * Regression tests for the writeToServerResponse drain-hang fix in
+ * patches/ai@6.0.134.patch (#486, commit 6).
+ *
+ * Unpatched ai@6.0.134's writeToServerResponse awaits ONLY `once("drain")` when
+ * response.write() returns false (backpressure). If the client disconnects
+ * mid-write the socket never drains, so that await never resolves: the read loop
+ * parks FOREVER, its `finally { response.end() }` is unreachable, and the stream
+ * reader + buffered chunks are pinned until process restart. In autonomous mode
+ * the run keeps producing output after the disconnect, so EVERY mid-run
+ * disconnect leaks a hung pipe. The patch races drain against close/error, and on
+ * a terminal socket event cancels the reader and breaks so `finally` always runs.
+ *
+ * This drives the REAL patched writeToServerResponse through the public
+ * pipeUIMessageStreamToResponse API with a response that never drains and closes
+ * mid-write — exactly the leak scenario.
+ */
+
+/** A ServerResponse-like emitter whose first write() stalls (returns false) and
+ *  then "closes" like a disconnecting client — never firing 'drain'. */
+class DisconnectingResponse extends EventEmitter {
+  ended = false;
+  writeCount = 0;
+  statusCode = 200;
+  writableEnded = false;
+  destroyed = false;
+  writeHead(): this {
+    return this;
+  }
+  setHeader(): void {}
+  flushHeaders(): void {}
+  write(): boolean {
+    this.writeCount++;
+    if (this.writeCount === 1) {
+      // Simulate the client vanishing mid-write: backpressure (false) and then a
+      // 'close' on the next tick, and CRUCIALLY never a 'drain'. Unpatched, the
+      // loop would await drain forever here.
+      setImmediate(() => this.emit('close'));
+      return false;
+    }
+    return true;
+  }
+  end(): void {
+    this.ended = true;
+    this.writableEnded = true;
+    this.emit('finish');
+  }
+}
+
+function makeModel() {
+  return new MockLanguageModelV3({
+    doStream: async () => ({
+      stream: simulateReadableStream({
+        chunks: [
+          { type: 'stream-start' as const, warnings: [] },
+          { type: 'text-start' as const, id: '1' },
+          { type: 'text-delta' as const, id: '1', delta: 'hello ' },
+          { type: 'text-delta' as const, id: '1', delta: 'world' },
+          { type: 'text-end' as const, id: '1' },
+          {
+            type: 'finish' as const,
+            finishReason: { unified: 'stop' as const, raw: 'stop' },
+            usage: {
+              inputTokens: { total: 1, noCache: undefined, cacheRead: undefined, cacheWrite: undefined },
+              outputTokens: { total: 1, text: 1, reasoning: undefined },
+            },
+          },
+        ],
+      }),
+    }),
+  });
+}
+
+describe('ai@6.0.134 pnpm patch: writeToServerResponse drain-hang (#486)', () => {
+  it('ends the response (does NOT hang) when the socket closes mid-write without draining', async () => {
+    const result = streamText({ model: makeModel(), prompt: 'hi' });
+    const res = new DisconnectingResponse();
+    // Drain the SDK stream independently, like the production detached path.
+    void result.consumeStream({ onError: () => undefined });
+    result.pipeUIMessageStreamToResponse(res as never);
+
+    // TRIPWIRE: the patched loop exits on 'close' and runs finally -> end().
+    // Unpatched, it awaits 'drain' forever and this never becomes true.
+    await new Promise<void>((resolve, reject) => {
+      const started = Date.now();
+      const poll = setInterval(() => {
+        if (res.ended) {
+          clearInterval(poll);
+          resolve();
+        } else if (Date.now() - started > 3000) {
+          clearInterval(poll);
+          reject(new Error('writeToServerResponse hung: response never ended'));
+        }
+      }, 20);
+    });
+
+    expect(res.ended).toBe(true);
+  });
+
+  it('does not emit an unhandledRejection when the fire-and-forget read() throws', async () => {
+    // The patch swallows read()'s rejection (fire-and-forget) with a log instead
+    // of letting it surface as a process-killing unhandledRejection.
+    const rejections: unknown[] = [];
+    const onUnhandled = (e: unknown) => rejections.push(e);
+    process.on('unhandledRejection', onUnhandled);
+    // Silence the patch's diagnostic console.error for the throwing read().
+    const errSpy = jest.spyOn(console, 'error').mockImplementation(() => undefined);
+    try {
+      const result = streamText({ model: makeModel(), prompt: 'hi' });
+      const res = new DisconnectingResponse();
+      void result.consumeStream({ onError: () => undefined });
+      result.pipeUIMessageStreamToResponse(res as never);
+      await new Promise((r) => setTimeout(r, 300));
+    } finally {
+      process.off('unhandledRejection', onUnhandled);
+      errSpy.mockRestore();
+    }
+    expect(rejections).toEqual([]);
+  });
+
+  it('both installed dist builds (CJS and ESM) carry the #486 patch marker', () => {
+    const cjsPath = require.resolve('ai');
+    const mjsPath = cjsPath.replace(/index\.js$/, 'index.mjs');
+    expect(cjsPath).toMatch(/index\.js$/);
+    expect(readFileSync(cjsPath, 'utf8')).toContain('PATCH(docmost #486)');
+    expect(readFileSync(mjsPath, 'utf8')).toContain('PATCH(docmost #486)');
+  });
+});

apps/server/src/integrations/health/redis.health.spec.ts

@@ -0,0 +1,211 @@
+import type { HealthIndicatorService } from '@nestjs/terminus';
+import type { EnvironmentService } from '../environment/environment.service';
+
+/**
+ * Integration guard for the /health Redis-probe handle leak (#486, commit 2).
+ *
+ * The bug: `pingCheck` built `new Redis(...)` per call and only disconnected on
+ * the SUCCESS path, so when Redis is DOWN every probe tick added ANOTHER
+ * forever-reconnecting client — an unbounded handle/client leak for the duration
+ * of the outage. The fix reuses ONE long-lived probe client.
+ *
+ * This is an OBSERVABLE-property test, not an assertion on a mocked return value:
+ * we point the indicator at a REAL, refused TCP endpoint (a dead port) so ioredis
+ * genuinely fails to connect, run many probes, and assert the number of live
+ * Redis CLIENTS created stays at exactly ONE. `ioredis` is delegated to its real
+ * implementation (requireActual) — only the constructor is wrapped to COUNT the
+ * real clients it creates, which is precisely the leaking resource.
+ */
+import type { Redis } from 'ioredis';
+
+const mockLiveClients: Redis[] = [];
+
+/**
+ * Fully tear a REAL ioredis client down so NO timer survives jest's 1s exit
+ * window (this suite must exit cleanly WITHOUT forceExit; see #382).
+ *
+ * `connector.disconnect()` arms a ~12s "force-destroy the stream" `setTimeout`
+ * that is cleared ONLY by the stream's 'close' event — but only when the
+ * connector still holds a stream. Two problem cases:
+ *  - a LIVE/connecting socket: disconnect arms the timer and 'close' may lag
+ *    past jest's window, so we destroy the socket to make 'close' fire NOW;
+ *  - a client BETWEEN reconnect attempts to a dead port: the held socket is
+ *    ALREADY destroyed (its 'close' fired long ago), so disconnect would arm a
+ *    timer whose clearing 'close' can never come again. We drop that dead stream
+ *    reference BEFORE disconnect so the doomed timer is never armed.
+ * `disconnect()` itself also clears ioredis' own reconnect backoff timer.
+ */
+type DrainableStream = { destroyed?: boolean; destroy?: () => void } | null;
+type DrainableClient = {
+  removeAllListeners: (event: string) => void;
+  disconnect: () => void;
+  stream?: DrainableStream;
+  connector?: { stream?: DrainableStream };
+};
+
+async function drainClient(client: Redis): Promise<void> {
+  if (!client || client.status === 'end') return;
+  const c = client as unknown as DrainableClient;
+  c.removeAllListeners('error');
+
+  // Drop an already-dead held socket so disconnect() can't arm a timer whose
+  // clearing 'close' will never fire again.
+  if (c.connector?.stream && c.connector.stream.destroyed) {
+    c.connector.stream = null;
+  }
+  if (c.stream && c.stream.destroyed) {
+    c.stream = null;
+  }
+
+  await new Promise<void>((resolve) => {
+    let done = false;
+    const finish = () => {
+      if (done) return;
+      done = true;
+      resolve();
+    };
+    client.once('end', finish);
+    // reconnect=false (the default): stop the retry loop and close the socket.
+    client.disconnect();
+    // Force any still-live socket closed NOW so the connector's stream-destroy
+    // timer clears inside jest's window instead of lagging behind a real 'close'.
+    if (c.stream && !c.stream.destroyed) {
+      c.stream.destroy?.();
+    }
+    // Fallback for a client with no live stream to emit 'end' (unref'd so it
+    // can never itself hold the loop open).
+    const fallback = setTimeout(finish, 500);
+    (fallback as { unref?: () => void }).unref?.();
+  });
+}
+
+async function drainAll(): Promise<void> {
+  await Promise.all(mockLiveClients.map((c) => drainClient(c)));
+}
+
+jest.mock('ioredis', () => {
+  const actual = jest.requireActual('ioredis');
+  const RealRedis = actual.Redis ?? actual.default ?? actual;
+  class CountingRedis extends RealRedis {
+    constructor(...args: unknown[]) {
+      super(...(args as []));
+      mockLiveClients.push(this as never);
+    }
+  }
+  return { ...actual, Redis: CountingRedis, default: CountingRedis };
+});
+
+// Import AFTER the mock is registered so the class picks up the counting client.
+import { RedisHealthIndicator } from './redis.health';
+
+describe('RedisHealthIndicator handle leak (#486)', () => {
+  const indicatorService = {
+    check: (key: string) => ({
+      up: () => ({ [key]: { status: 'up' } }),
+      down: (message: string) => ({ [key]: { status: 'down', message } }),
+    }),
+  } as unknown as HealthIndicatorService;
+
+  // A port with (almost certainly) nothing listening -> connection refused fast.
+  const environmentService = {
+    getRedisUrl: () => 'redis://127.0.0.1:6399/0',
+  } as unknown as EnvironmentService;
+
+  let indicator: RedisHealthIndicator;
+
+  beforeEach(() => {
+    mockLiveClients.length = 0;
+    indicator = new RedisHealthIndicator(indicatorService, environmentService);
+  });
+
+  afterEach(async () => {
+    // Drain (destroy socket + AWAIT 'end') every client the test created FIRST,
+    // so each is fully 'end' before onModuleDestroy's disconnect runs — that way
+    // no ioredis reconnect / stream-destroy timer outlives jest's exit window.
+    await drainAll();
+    indicator.onModuleDestroy();
+  });
+
+  it('creates exactly ONE Redis client across many probes while Redis is DOWN', async () => {
+    const N = 8;
+    for (let i = 0; i < N; i++) {
+      const result = await indicator.pingCheck('redis');
+      // Down endpoint -> every probe reports "down" (not an unhandled crash).
+      expect(result.redis.status).toBe('down');
+    }
+
+    // THE OBSERVABLE LEAK: on the buggy code this is N (a fresh, never-cleaned
+    // reconnecting client per probe). The fix reuses one shared client.
+    expect(mockLiveClients).toHaveLength(1);
+  });
+
+  it('onModuleDestroy releases the probe client (a later probe builds a fresh one)', async () => {
+    await indicator.pingCheck('redis');
+    expect(mockLiveClients).toHaveLength(1);
+
+    indicator.onModuleDestroy();
+    // A second destroy is a safe no-op (probeClient was nulled).
+    indicator.onModuleDestroy();
+
+    // After shutdown the indicator lazily builds a NEW client on the next probe,
+    // proving the old one was truly released rather than reused.
+    await indicator.pingCheck('redis');
+    expect(mockLiveClients).toHaveLength(2);
+  });
+});
+
+/**
+ * Happy-path regression guard (#486, B2): the FIRST probe against a LIVE Redis
+ * must report UP.
+ *
+ * With `lazyConnect: true` + `enableOfflineQueue: false`, a freshly-built client
+ * is in the `wait` state and the socket opens lazily. If the very first `ping()`
+ * is issued before an explicit `connect()`, ioredis rejects it instantly with
+ * "Stream isn't writeable and enableOfflineQueue options is false" — a FALSE
+ * DOWN even though Redis is alive. The fix opens the socket before the first
+ * ping. This exercises a REAL ioredis client against a REAL TCP redis server
+ * (not a mock), so a regression genuinely reddens it.
+ */
+describe('RedisHealthIndicator live Redis first-probe (#486, B2)', () => {
+  const indicatorService = {
+    check: (key: string) => ({
+      up: () => ({ [key]: { status: 'up' } }),
+      down: (message: string) => ({ [key]: { status: 'down', message } }),
+    }),
+  } as unknown as HealthIndicatorService;
+
+  // A REAL running redis (see the neighboring harness / CI env).
+  const environmentService = {
+    getRedisUrl: () => 'redis://127.0.0.1:6379/0',
+  } as unknown as EnvironmentService;
+
+  let indicator: RedisHealthIndicator;
+
+  beforeEach(() => {
+    mockLiveClients.length = 0;
+    indicator = new RedisHealthIndicator(indicatorService, environmentService);
+  });
+
+  afterEach(async () => {
+    // Await full socket close of every live client (see drainClient) BEFORE
+    // onModuleDestroy: a real, connected ioredis client MUST be drained to 'end'
+    // or its stream-destroy timer keeps the jest worker alive past the 1s window.
+    await drainAll();
+    indicator.onModuleDestroy();
+  });
+
+  it('reports UP on the FIRST probe against a live Redis', async () => {
+    // The VERY FIRST probe — no warm-up ping — must be UP.
+    const result = await indicator.pingCheck('redis');
+    expect(result.redis.status).toBe('up');
+  });
+
+  it('stays UP on a probe AFTER onModuleDestroy re-creates the client', async () => {
+    await indicator.pingCheck('redis');
+    indicator.onModuleDestroy();
+    // The re-created client is again in `wait`; the first ping on it must still
+    // open the socket (the false-DOWN also recurs on the post-destroy path).
+    const result = await indicator.pingCheck('redis');
+    expect(result.redis.status).toBe('up');
+  });
+});

apps/server/src/integrations/health/redis.health.ts

@@ -2,33 +2,173 @@ import {
   HealthIndicatorResult,
   HealthIndicatorService,
 } from '@nestjs/terminus';
-import { Injectable, Logger } from '@nestjs/common';
+import { Injectable, Logger, OnModuleDestroy } from '@nestjs/common';
 import { EnvironmentService } from '../environment/environment.service';
 import { Redis } from 'ioredis';
 
 @Injectable()
-export class RedisHealthIndicator {
+export class RedisHealthIndicator implements OnModuleDestroy {
   private readonly logger = new Logger(RedisHealthIndicator.name);
 
+  /**
+   * ONE long-lived probe connection, reused across every /health tick. The old
+   * code built `new Redis(...)` per call and only `disconnect()`d on the SUCCESS
+   * path, so while Redis was DOWN every probe added a fresh, forever-reconnecting
+   * client — a handle leak that grew without bound for as long as the outage (and
+   * the health checker keeps polling) lasted. A single shared client keeps at most
+   * ONE background reconnect loop regardless of how many probes run.
+   */
+  private probeClient: Redis | null = null;
+
+  /**
+   * How long the first-ping `connect()` may take before a probe gives up and
+   * reports DOWN. A `connect()` against a truly-down Redis never settles on its
+   * own (ioredis retries the socket indefinitely per its retryStrategy), so the
+   * probe MUST bound it or the /health handler would hang. Kept short so a real
+   * outage is reported fast; localhost/live Redis connects well within it.
+   */
+  private static readonly CONNECT_TIMEOUT_MS = 2000;
+
+  /**
+   * The single in-flight first-`connect()`, memoized so CONCURRENT probes share
+   * it. k8s liveness+readiness hit /health in parallel on startup: without this,
+   * probe A drives `connect()` (the client leaves the `wait` state) and probe B,
+   * seeing a not-`wait`/not-`ready` client, would skip connect and fire `ping()`
+   * at a still-opening socket → an instant FALSE DOWN. With the memo, B awaits
+   * the SAME connect. Cleared once it settles so a later disconnect / re-create
+   * starts a fresh connect.
+   */
+  private connectingPromise: Promise<void> | null = null;
+
   constructor(
     private readonly healthIndicatorService: HealthIndicatorService,
     private environmentService: EnvironmentService,
   ) {}
 
+  private getProbeClient(): Redis {
+    if (!this.probeClient) {
+      this.probeClient = new Redis(this.environmentService.getRedisUrl(), {
+        // Constructing must never throw or eagerly connect; the first ping opens
+        // the socket. This lets us build the client once and reuse it.
+        lazyConnect: true,
+        // A health probe must fail FAST, not queue behind a stuck reconnect: one
+        // retry per request, and no offline queue so a ping while disconnected
+        // rejects immediately instead of buffering commands that pile up in RAM.
+        maxRetriesPerRequest: 1,
+        enableOfflineQueue: false,
+      });
+      // ioredis emits 'error' on every failed (re)connect; with no listener that
+      // surfaces as an unhandled 'error' event and can crash the process. Swallow
+      // it here — pingCheck already reports health — and log at debug so a Redis
+      // outage does not flood the logs.
+      this.probeClient.on('error', (err) => {
+        this.logger.debug(
+          `Redis probe connection error: ${
+            err instanceof Error ? err.message : String(err)
+          }`,
+        );
+      });
+    }
+    return this.probeClient;
+  }
+
+  /**
+   * Open the probe socket BEFORE the first ping. `lazyConnect: true` leaves a
+   * freshly-built (or post-destroy re-built) client in the `wait` state: the
+   * socket is NOT open yet, so with `enableOfflineQueue: false` the very first
+   * `ping()` rejects instantly with "Stream isn't writeable and
+   * enableOfflineQueue options is false" even when Redis is perfectly alive — a
+   * false DOWN on the happy path. We drive `connect()` ONLY from `wait`; once
+   * the client is connected, ioredis owns its own (re)connect loop and a ping
+   * issued while it reconnects still fast-fails to a correct DOWN (offline queue
+   * stays off). A failed/timed-out connect rejects → reported DOWN, which is the
+   * right signal for a truly-down Redis.
+   */
+  private ensureConnected(client: Redis): Promise<void> {
+    // Already open — steady state, nothing to do.
+    if (client.status === 'ready') return Promise.resolve();
+    // A first-connect is already in flight (possibly started by a CONCURRENT
+    // probe): await the SAME one instead of racing a second connect() (ioredis
+    // throws "already connecting") or firing ping() at a not-yet-open socket.
+    if (this.connectingPromise) return this.connectingPromise;
+    // Only DRIVE connect() from the initial `wait` state (fresh / post-destroy
+    // re-created client). In any other non-ready state ioredis already owns its
+    // (re)connect loop; a ping there fast-fails to a correct DOWN, so we must not
+    // start a competing connect.
+    if (client.status !== 'wait') return Promise.resolve();
+
+    const promise = this.connectWithTimeout(client).finally(() => {
+      // Clear only if still ours, so a later disconnect / re-create can connect
+      // again. Whether it resolved or rejected, the memo has served its window.
+      if (this.connectingPromise === promise) {
+        this.connectingPromise = null;
+      }
+    });
+    this.connectingPromise = promise;
+    return promise;
+  }
+
+  private connectWithTimeout(client: Redis): Promise<void> {
+    return new Promise<void>((resolve, reject) => {
+      let settled = false;
+      const timer = setTimeout(() => {
+        if (settled) return;
+        settled = true;
+        reject(new Error('Redis probe connect timed out'));
+      }, RedisHealthIndicator.CONNECT_TIMEOUT_MS);
+      // Never let THIS timer alone keep the event loop (or a jest worker) alive;
+      // it is cleared on settle anyway, this is belt-and-braces.
+      timer.unref?.();
+      // `.catch` is always attached, so a connect() that rejects AFTER we have
+      // already timed out is handled here (guarded by `settled`) and never
+      // surfaces as an unhandled rejection.
+      client
+        .connect()
+        .then(() => {
+          if (settled) return;
+          settled = true;
+          clearTimeout(timer);
+          resolve();
+        })
+        .catch((err) => {
+          if (settled) return;
+          settled = true;
+          clearTimeout(timer);
+          reject(err);
+        });
+    });
+  }
+
   async pingCheck(key: string): Promise<HealthIndicatorResult> {
     const indicator = this.healthIndicatorService.check(key);
 
     try {
-      const redis = new Redis(this.environmentService.getRedisUrl(), {
-        maxRetriesPerRequest: 15,
-      });
-
+      const redis = this.getProbeClient();
+      // Open the socket before the first ping (see ensureConnected); without
+      // this the first probe after (re)creation falsely reports DOWN on a live
+      // Redis because lazyConnect defers the connect past the first ping.
+      await this.ensureConnected(redis);
       await redis.ping();
-      redis.disconnect();
       return indicator.up();
     } catch (e) {
       this.logger.error(e);
       return indicator.down(`${key} is not available`);
     }
   }
+
+  onModuleDestroy(): void {
+    if (this.probeClient) {
+      // disconnect() (not quit()) tears the socket + reconnect loop down
+      // immediately without waiting on a round-trip to a possibly-down server.
+      // Do NOT removeAllListeners() with no event name — that would also strip
+      // ioredis' OWN internal listeners and break its teardown; our 'error'
+      // listener is harmless and dies with the dropped client reference.
+      this.probeClient.disconnect();
+      this.probeClient = null;
+    }
+    // Drop any in-flight first-connect memo so the NEXT client (lazily rebuilt on
+    // the next probe) starts a fresh connect rather than awaiting a promise tied
+    // to the client we just tore down.
+    this.connectingPromise = null;
+  }
 }

apps/server/src/integrations/import/utils/foreign-markdown.ts

@@ -238,8 +238,9 @@ function convertReferenceFootnotes(markdown: string): string {
  *
  * LINE-ANCHORED (the same shape the canonical parser uses in
  * prosemirror-markdown/page-file.ts): the block opens only on `---\n` at the
- * very start and closes only on a `\n---` line. The retired `markdownToHtml`
- * strip closed on the FIRST `---` ANYWHERE (an unanchored close), so a value
+ * very start and closes only on a `\n---` line. The retired editor-ext
+ * `markdownToHtml` front-matter strip (removed in #347) closed on the FIRST
+ * `---` ANYWHERE (an unanchored close), so a value
  * containing a triple-dash (e.g. `title: Q1 --- Q2`) truncated the front-matter
  * and leaked the rest into the body. An optional leading BOM is tolerated.
  */

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

@@ -143,7 +143,7 @@ export type DocmostMcpConfig = (
       buf: Buffer,
       mime: string,
     ) => { uri: string; sha256: string; size: number };
-    // Optional live/evict probes the package uses to keep stash_page's mirror
+    // Optional live/evict probes the package uses to keep stashPage's mirror
     // counts honest under the store's FIFO eviction (mirror of the package's
     // sink type); older bindings omit them.
     has?: (uri: string) => boolean;

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

@@ -16,6 +16,7 @@ import {
 } from './mcp-auth.helpers';
 import { JwtType } from '../../core/auth/dto/jwt-payload';
 import { CREDENTIALS_MISMATCH_MESSAGE } from '../../core/auth/auth.constants';
+import { McpService } from './mcp.service';
 
 // The /mcp per-user auth decision logic is tested through the framework-free
 // `resolveMcpSessionConfig` helper that McpService delegates to. McpService
@@ -1179,3 +1180,46 @@ describe('mapAuthResultToResponse (handle status/body mapping, refactor R2)', ()
     });
   });
 });
+
+// #486: onModuleDestroy must ALSO tear down the live loopback CollabSessions, not
+// just clear the sweep timer — otherwise the embedded MCP's collab sockets keep
+// docs pinned open on the collab server past process exit. The teardown goes
+// through an overridable seam (destroyAllMcpSessions) so it can be spied without
+// loading the ESM-only @docmost/mcp package.
+describe('McpService.onModuleDestroy — CollabSession teardown (#486)', () => {
+  function makeService(): McpService {
+    // The constructor only stores its deps and starts the (unref'd) sweep timer,
+    // so bare stubs suffice. onModuleDestroy clears that timer, so no leak.
+    return new McpService(
+      {} as any,
+      {} as any,
+      {} as any,
+      {} as any,
+      {} as any,
+      {} as any,
+      {} as any,
+    );
+  }
+
+  it('destroys all sessions AND clears the sweep timer on shutdown', async () => {
+    const svc = makeService();
+    const destroy = jest.fn().mockResolvedValue(undefined);
+    (svc as any).destroyAllMcpSessions = destroy;
+    const clearSpy = jest.spyOn(global, 'clearInterval');
+
+    await svc.onModuleDestroy();
+
+    expect(destroy).toHaveBeenCalledTimes(1);
+    expect(clearSpy).toHaveBeenCalledWith((svc as any).sweepTimer);
+    clearSpy.mockRestore();
+  });
+
+  it('swallows a teardown failure so shutdown never throws', async () => {
+    const svc = makeService();
+    (svc as any).destroyAllMcpSessions = jest
+      .fn()
+      .mockRejectedValue(new Error('collab teardown boom'));
+
+    await expect(svc.onModuleDestroy()).resolves.toBeUndefined();
+  });
+});

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

@@ -34,6 +34,8 @@ import {
   isMetricsEnabled,
   observeMcpTool,
   incConnectTimeout,
+  incGetPageCacheHit,
+  incGetPageCacheMiss,
 } from '../metrics/metrics.registry';
 
 // Minimal shape of the embedded MCP HTTP handler exported by @docmost/mcp/http.
@@ -117,10 +119,42 @@ export class McpService implements OnModuleDestroy {
     this.sweepTimer.unref?.();
   }
 
-  onModuleDestroy(): void {
+  async onModuleDestroy(): Promise<void> {
     clearInterval(this.sweepTimer);
+    // Tear down any live loopback CollabSession providers at shutdown (#486). The
+    // embedded MCP (and the in-app AI agent) open Hocuspocus collab sockets against
+    // THIS process; without an explicit teardown those sessions keep their docs
+    // "open" on the collab server and hold providers/buffers until they idle out,
+    // so a restart can race a doc still pinned by the dying worker. Best-effort:
+    // any failure is logged, never allowed to break shutdown.
+    try {
+      await this.destroyAllMcpSessions();
+    } catch (err) {
+      this.logger.error(
+        'MCP CollabSession teardown on shutdown failed',
+        err as Error,
+      );
+    }
   }
 
+  /**
+   * Resolve @docmost/mcp's `destroyAllSessions` and invoke it (#486). The live
+   * CollabSession registry is a module-level singleton in the ESM package, shared
+   * by every entry (`.`/`./http`), so this tears down ALL sessions regardless of
+   * which surface opened them. The module is already loaded whenever MCP was used;
+   * if it was never loaded (or is absent) the import + no-op is harmless.
+   *
+   * Held as an overridable field so a unit test can spy the teardown without
+   * loading the ESM-only package or standing up the DI graph.
+   */
+  private destroyAllMcpSessions: () => Promise<void> = async () => {
+    const entry = require.resolve('@docmost/mcp');
+    const mod = (await esmImport(pathToFileURL(entry).href)) as {
+      destroyAllSessions?: () => void;
+    };
+    mod.destroyAllSessions?.();
+  };
+
   // Service account the embedded MCP uses to talk back to this Docmost
   // instance over loopback REST + the collaboration WebSocket. Now OPTIONAL:
   // it is only a fallback when no per-user Basic/Bearer credentials are sent.
@@ -332,7 +366,7 @@ export class McpService implements OnModuleDestroy {
               // Should never happen: handle() always stashes before delegating.
               throw new UnauthorizedException('MCP authentication missing.');
             }
-            // Inject the blob-sandbox sink after the auth decision so stash_page
+            // Inject the blob-sandbox sink after the auth decision so stashPage
             // 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().
@@ -357,6 +391,10 @@ export class McpService implements OnModuleDestroy {
                       observeMcpTool(labels?.tool ?? 'other', value);
                     } else if (name === 'collab_connect_timeouts_total') {
                       incConnectTimeout();
+                    } else if (name === 'mcp_getpage_cache_hits_total') {
+                      incGetPageCacheHit();
+                    } else if (name === 'mcp_getpage_cache_misses_total') {
+                      incGetPageCacheMiss();
                     }
                   }
                 : undefined,

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

@@ -25,6 +25,15 @@ export const METRIC_COLLAB_CONNECT_TIMEOUTS_TOTAL =
 export const METRIC_COLLAB_AUTH_DURATION = 'collab_auth_duration_seconds';
 export const METRIC_MCP_TOOL_DURATION = 'mcp_tool_duration_seconds';
 
+// #479 — getPage PM→Markdown conversion cache hit/miss counters. Emitted by the
+// MCP package via its dependency-neutral onMetric sink and routed onto these two
+// prom counters by the mcp.service onMetric callback; a >50% hit-rate is the
+// success signal for the getPage perf work. Same "do not rename" contract.
+export const METRIC_MCP_GETPAGE_CACHE_HITS_TOTAL =
+  'mcp_getpage_cache_hits_total';
+export const METRIC_MCP_GETPAGE_CACHE_MISSES_TOTAL =
+  'mcp_getpage_cache_misses_total';
+
 // Histogram buckets (seconds). Chosen to give useful p50/p95/p99 resolution
 // for typical web/DB latencies without exploding series cardinality.
 export const HTTP_BUCKETS = [

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

@@ -24,6 +24,8 @@ import {
   METRIC_DB_QUERY_DURATION,
   METRIC_HTTP_REQUEST_DURATION,
   METRIC_MCP_TOOL_DURATION,
+  METRIC_MCP_GETPAGE_CACHE_HITS_TOTAL,
+  METRIC_MCP_GETPAGE_CACHE_MISSES_TOTAL,
   sizeBucket,
 } from './metrics.constants';
 
@@ -61,6 +63,9 @@ let connectTimeoutsCounter: Counter | null = null;
 let collabConnectHist: Histogram | null = null;
 let collabAuthHist: Histogram | null = null;
 let mcpToolHist: Histogram<'tool'> | null = null;
+// #479 — getPage conversion-cache hit/miss counters.
+let getPageCacheHitsCounter: Counter | null = null;
+let getPageCacheMissesCounter: Counter | 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
@@ -175,6 +180,18 @@ function init(): void {
     buckets: MCP_TOOL_BUCKETS,
     registers: [registry],
   });
+
+  getPageCacheHitsCounter = new Counter({
+    name: METRIC_MCP_GETPAGE_CACHE_HITS_TOTAL,
+    help: 'Total getPage PM→Markdown conversions served from the cache (skipped)',
+    registers: [registry],
+  });
+
+  getPageCacheMissesCounter = new Counter({
+    name: METRIC_MCP_GETPAGE_CACHE_MISSES_TOTAL,
+    help: 'Total getPage PM→Markdown conversions computed (cache misses)',
+    registers: [registry],
+  });
 }
 
 // Runs once when this module is first imported. Safe to call again (idempotent).
@@ -247,6 +264,14 @@ export function observeCollabAuth(seconds: number): void {
   collabAuthHist?.observe(seconds);
 }
 
+export function incGetPageCacheHit(): void {
+  getPageCacheHitsCounter?.inc();
+}
+
+export function incGetPageCacheMiss(): void {
+  getPageCacheMissesCounter?.inc();
+}
+
 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 —

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

@@ -0,0 +1,148 @@
+import { get as httpGet } from 'node:http';
+import { AddressInfo } from 'node:net';
+import { createServer } from 'node:http';
+
+// Drive the metrics HTTP server without the load-time METRICS_PORT gate: mock the
+// registry so isMetricsEnabled()/getMetricsRegistry() are always satisfied. What
+// we assert is observed over a REAL socket (bind address, status codes), not on
+// the mock.
+jest.mock('./metrics.registry', () => ({
+  isMetricsEnabled: () => true,
+  getMetricsRegistry: () => ({
+    metrics: async () => '# HELP up test\nup 1\n',
+    contentType: 'text/plain; version=0.0.4',
+  }),
+}));
+
+import {
+  startMetricsServer,
+  closeMetricsServer,
+  resolveMetricsBind,
+  resolveMetricsToken,
+} from './metrics.server';
+
+/** Find a free TCP port (the metrics server requires METRICS_PORT > 0). */
+function freePort(): Promise<number> {
+  return new Promise((resolve, reject) => {
+    const s = createServer();
+    s.once('error', reject);
+    s.listen(0, '127.0.0.1', () => {
+      const p = (s.address() as AddressInfo).port;
+      s.close(() => resolve(p));
+    });
+  });
+}
+
+/** Minimal GET against 127.0.0.1:port with optional Authorization header. */
+function req(
+  port: number,
+  headers: Record<string, string> = {},
+): Promise<{ status: number; body: string }> {
+  return new Promise((resolve, reject) => {
+    const r = httpGet(
+      { host: '127.0.0.1', port, path: '/metrics', headers },
+      (res) => {
+        let body = '';
+        res.on('data', (c) => (body += c));
+        res.on('end', () =>
+          resolve({ status: res.statusCode ?? 0, body }),
+        );
+      },
+    );
+    r.on('error', reject);
+  });
+}
+
+describe('metrics server bind + auth (#486)', () => {
+  const saved = {
+    bind: process.env.METRICS_BIND,
+    token: process.env.METRICS_TOKEN,
+    port: process.env.METRICS_PORT,
+  };
+
+  afterEach(async () => {
+    await closeMetricsServer();
+    process.env.METRICS_BIND = saved.bind;
+    process.env.METRICS_TOKEN = saved.token;
+    process.env.METRICS_PORT = saved.port;
+    delete process.env.METRICS_BIND;
+    delete process.env.METRICS_TOKEN;
+  });
+
+  describe('resolveMetricsBind', () => {
+    it('defaults to loopback 127.0.0.1', () => {
+      delete process.env.METRICS_BIND;
+      expect(resolveMetricsBind()).toBe('127.0.0.1');
+    });
+    it('honours the METRICS_BIND override', () => {
+      process.env.METRICS_BIND = '0.0.0.0';
+      expect(resolveMetricsBind()).toBe('0.0.0.0');
+    });
+    it('treats a blank override as unset (loopback)', () => {
+      process.env.METRICS_BIND = '   ';
+      expect(resolveMetricsBind()).toBe('127.0.0.1');
+    });
+  });
+
+  describe('resolveMetricsToken', () => {
+    it('is null when unset', () => {
+      delete process.env.METRICS_TOKEN;
+      expect(resolveMetricsToken()).toBeNull();
+    });
+    it('returns the trimmed token when set', () => {
+      process.env.METRICS_TOKEN = ' s3cret ';
+      expect(resolveMetricsToken()).toBe('s3cret');
+    });
+  });
+
+  it('binds to loopback by default and serves /metrics without auth when no token', async () => {
+    delete process.env.METRICS_BIND;
+    delete process.env.METRICS_TOKEN;
+    const port = await freePort();
+    process.env.METRICS_PORT = String(port);
+
+    const server = startMetricsServer();
+    expect(server).not.toBeNull();
+    await new Promise<void>((resolve) => {
+      if (server!.listening) resolve();
+      else server!.once('listening', () => resolve());
+    });
+    // OBSERVABLE: the listener bound to loopback, not 0.0.0.0.
+    expect((server!.address() as AddressInfo).address).toBe('127.0.0.1');
+
+    const res = await req(port);
+    expect(res.status).toBe(200);
+    expect(res.body).toContain('up 1');
+  });
+
+  it('rejects unauthenticated scrapes with 401 and accepts the exact Bearer token', async () => {
+    delete process.env.METRICS_BIND;
+    process.env.METRICS_TOKEN = 'topsecret';
+    const port = await freePort();
+    process.env.METRICS_PORT = String(port);
+
+    const server = startMetricsServer();
+    expect(server).not.toBeNull();
+
+    // No auth -> 401.
+    const noAuth = await req(port);
+    expect(noAuth.status).toBe(401);
+
+    // Wrong token, DIFFERENT length -> 401 (short-circuits on the length guard).
+    const wrong = await req(port, { authorization: 'Bearer nope' });
+    expect(wrong.status).toBe(401);
+
+    // Wrong token, SAME length -> 401. This drives the timingSafeEqual compare
+    // itself (the length guard passes: 'Bearer topsecreX' has the same length as
+    // 'Bearer topsecret'). Pins the constant-time compare: a regression that made
+    // it return true would let this equal-length wrong token through — the
+    // different-length case above would NOT catch that.
+    const sameLen = await req(port, { authorization: 'Bearer topsecreX' });
+    expect(sameLen.status).toBe(401);
+
+    // Correct token -> 200 with the metrics body.
+    const ok = await req(port, { authorization: 'Bearer topsecret' });
+    expect(ok.status).toBe(200);
+    expect(ok.body).toContain('up 1');
+  });
+});

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

@@ -1,7 +1,27 @@
 import { createServer, Server } from 'node:http';
+import { timingSafeEqual } from 'node:crypto';
 import { Logger } from '@nestjs/common';
 import { getMetricsRegistry, isMetricsEnabled } from './metrics.registry';
 
+/**
+ * Constant-time compare of the presented Authorization header against the
+ * expected `Bearer <token>`. This is the ONLY auth layer for the metrics
+ * endpoint, so a naive `!==` would leak the token byte-by-byte via timing.
+ * timingSafeEqual requires equal-length buffers, so a length mismatch short-
+ * circuits to "not equal" (its own length is not itself a useful oracle: the
+ * expected string length is fixed by config, not secret-derived).
+ */
+function bearerMatches(
+  presented: string | undefined,
+  expected: string,
+): boolean {
+  if (typeof presented !== 'string') return false;
+  const a = Buffer.from(presented);
+  const b = Buffer.from(expected);
+  if (a.length !== b.length) return false;
+  return timingSafeEqual(a, b);
+}
+
 /**
  * Start the Prometheus scrape endpoint on a SEPARATE port, taken from
  * `METRICS_PORT`. There is NO default port: when `METRICS_PORT` is unset the
@@ -16,6 +36,30 @@ import { getMetricsRegistry, isMetricsEnabled } from './metrics.registry';
  */
 let metricsServer: Server | null = null;
 
+/**
+ * Interface the metrics endpoint binds to. Defaults to LOOPBACK (127.0.0.1) so
+ * the unauthenticated `/metrics` surface is NOT exposed on all interfaces by
+ * default — the old `0.0.0.0` bind put an auth-less endpoint on every interface.
+ * Deployments where the scraper runs in a SEPARATE container (and reaches this as
+ * `docmost:9464`) set `METRICS_BIND=0.0.0.0`, ideally together with METRICS_TOKEN
+ * and/or a private network so the port is not world-readable.
+ */
+export function resolveMetricsBind(): string {
+  const raw = (process.env.METRICS_BIND ?? '').trim();
+  return raw.length > 0 ? raw : '127.0.0.1';
+}
+
+/**
+ * Optional Bearer token guarding `/metrics`. When `METRICS_TOKEN` is set, every
+ * scrape must present `Authorization: Bearer <token>`; unset (default) leaves the
+ * endpoint open (safe when bound to loopback / a trusted network). Returns the
+ * trimmed token or null when unset/blank.
+ */
+export function resolveMetricsToken(): string | null {
+  const raw = (process.env.METRICS_TOKEN ?? '').trim();
+  return raw.length > 0 ? raw : null;
+}
+
 export function startMetricsServer(): Server | null {
   if (!isMetricsEnabled()) return null;
 
@@ -31,8 +75,22 @@ export function startMetricsServer(): Server | null {
     return null;
   }
 
+  const bind = resolveMetricsBind();
+  const token = resolveMetricsToken();
+
   const server = createServer(async (req, res) => {
     if (req.method === 'GET' && req.url === '/metrics') {
+      // Optional Bearer auth: reject scrapes without the exact token when one is
+      // configured. This is the auth layer the old all-interfaces bind lacked.
+      if (token) {
+        const auth = req.headers['authorization'];
+        if (!bearerMatches(auth, `Bearer ${token}`)) {
+          res.statusCode = 401;
+          res.setHeader('WWW-Authenticate', 'Bearer');
+          res.end();
+          return;
+        }
+      }
       try {
         const body = await register.metrics();
         res.setHeader('Content-Type', register.contentType);
@@ -48,10 +106,14 @@ export function startMetricsServer(): Server | null {
     res.end();
   });
 
-  // Bind on all interfaces: the scraper (VictoriaMetrics) reaches this from
-  // another container as docmost:9464. The port is not published to the host.
-  server.listen(port, '0.0.0.0', () => {
-    logger.log(`Metrics endpoint listening on :${port}/metrics`);
+  // Bind to loopback by default so the auth-less endpoint is not exposed on all
+  // interfaces. Set METRICS_BIND=0.0.0.0 (ideally with METRICS_TOKEN) when the
+  // scraper runs in a separate container and reaches this as docmost:9464.
+  server.listen(port, bind, () => {
+    logger.log(
+      `Metrics endpoint listening on ${bind}:${port}/metrics` +
+        (token ? ' (Bearer auth required)' : ''),
+    );
   });
 
   server.on('error', (err) => {

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

@@ -10,6 +10,8 @@ import {
   incConnectTimeout,
   incDocLoad,
   incDocUnload,
+  incGetPageCacheHit,
+  incGetPageCacheMiss,
   isMetricsEnabled,
   observeCollabAuth,
   observeCollabConnect,
@@ -197,6 +199,8 @@ describe('metrics helpers are safe no-ops when METRICS_PORT is unset', () => {
       incDocLoad();
       incDocUnload();
       incConnectTimeout();
+      incGetPageCacheHit();
+      incGetPageCacheMiss();
       // Registering a source must not create the gauge or invoke the fn.
       registerDocsOpenSource(() => {
         throw new Error('docsOpenSource must NOT be called when disabled');

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

@@ -31,9 +31,6 @@ export enum QueueJob {
   IMPORT_TASK = 'import-task',
   EXPORT_TASK = 'export-task',
 
-  SEARCH_REMOVE_PAGE = 'search-remove-page',
-  SEARCH_REMOVE_ASSET = 'search-remove-attachment',
-  SEARCH_REMOVE_FACE = 'search-remove-comment',
   TYPESENSE_FLUSH = 'typesense-flush',
 
   PAGE_CREATED = 'page-created',

apps/server/src/integrations/static/static.module.spec.ts

@@ -1,3 +1,8 @@
+import * as fs from 'node:fs';
+import * as os from 'node:os';
+import { join } from 'node:path';
+import Fastify, { FastifyInstance } from 'fastify';
+import fastifyStatic from '@fastify/static';
 import { resolveStaticAssetHeaders } from './static.module';
 
 // Unit tests for the static-asset cache classifier extracted from the
@@ -33,3 +38,69 @@ describe('resolveStaticAssetHeaders', () => {
     expect(headers['vary']).toBe('Accept-Encoding');
   });
 });
+
+// Integration test proving the ACTUAL response header emitted by @fastify/static
+// with the exact registration options StaticModule uses. This is the regression
+// guard for #452: without `cacheControl: false`, @fastify/static writes its own
+// `Cache-Control: public, max-age=0` AFTER the setHeaders callback, overwriting
+// the immutable header — the /assets/ assertion below would then fail.
+describe('static.module @fastify/static registration (integration)', () => {
+  let app: FastifyInstance;
+  let tmpDir: string;
+
+  beforeAll(async () => {
+    tmpDir = fs.mkdtempSync(join(os.tmpdir(), 'static-module-spec-'));
+    fs.mkdirSync(join(tmpDir, 'assets'), { recursive: true });
+    fs.mkdirSync(join(tmpDir, 'locales'), { recursive: true });
+    fs.writeFileSync(
+      join(tmpDir, 'assets', 'index-a1b2c3.js'),
+      'console.log(1);',
+    );
+    fs.writeFileSync(join(tmpDir, 'locales', 'en.json'), '{"hello":"world"}');
+
+    app = Fastify();
+    // Mirror StaticModule.onModuleInit's registration options exactly.
+    await app.register(fastifyStatic, {
+      root: tmpDir,
+      wildcard: false,
+      preCompressed: true,
+      cacheControl: false,
+      setHeaders: (res, filePath) => {
+        for (const [name, value] of Object.entries(
+          resolveStaticAssetHeaders(filePath),
+        )) {
+          res.setHeader(name, value);
+        }
+      },
+    });
+    await app.ready();
+  });
+
+  afterAll(async () => {
+    await app.close();
+    fs.rmSync(tmpDir, { recursive: true, force: true });
+  });
+
+  it('serves a hashed /assets/ file with an immutable, 1-year cache-control', async () => {
+    const res = await app.inject({
+      method: 'GET',
+      url: '/assets/index-a1b2c3.js',
+    });
+    expect(res.statusCode).toBe(200);
+    const cacheControl = res.headers['cache-control'];
+    expect(cacheControl).toContain('immutable');
+    expect(cacheControl).toContain('max-age=31536000');
+  });
+
+  it('serves a non-hashed /locales/ file WITHOUT an immutable cache-control', async () => {
+    const res = await app.inject({ method: 'GET', url: '/locales/en.json' });
+    expect(res.statusCode).toBe(200);
+    // resolveStaticAssetHeaders sets no cache-control here and cacheControl:false
+    // stops @fastify/static from adding one, so the browser revalidates by
+    // etag/last-modified — either an absent header or one without `immutable`.
+    const cacheControl = res.headers['cache-control'];
+    if (cacheControl !== undefined) {
+      expect(cacheControl).not.toContain('immutable');
+    }
+  });
+});

apps/server/src/integrations/static/static.module.ts

@@ -115,6 +115,11 @@ export class StaticModule implements OnModuleInit {
         // Serve the build-time .br/.gz neighbour when the client accepts it
         // (see vite-plugin-compression2 in apps/client/vite.config.ts).
         preCompressed: true,
+        // @fastify/static's default cacheControl:true writes its own
+        // Cache-Control (from maxAge, default 0) AFTER the setHeaders callback,
+        // silently overwriting the immutable header that resolveStaticAssetHeaders
+        // sets — disable it so setHeaders/resolveStaticAssetHeaders own the header.
+        cacheControl: false,
         setHeaders: (res, filePath) => {
           for (const [name, value] of Object.entries(
             resolveStaticAssetHeaders(filePath),

apps/server/test/integration/ai-chat-attach.int-spec.ts

@@ -182,6 +182,7 @@ describe('AiChatService run-stream attach [integration]', () => {
       {
         isAiChatDeferredToolsEnabled: () => false,
         isAiChatResumableStreamEnabled: () => true,
+        isAiChatFinalStepLockdownEnabled: () => false,
       } as any,
       registry,
     );
@@ -499,6 +500,7 @@ describe('AiChatService run-stream attach [integration]', () => {
       {
         isAiChatDeferredToolsEnabled: () => false,
         isAiChatResumableStreamEnabled: () => true,
+        isAiChatFinalStepLockdownEnabled: () => false,
       } as any,
       registry,
     );

apps/server/test/integration/ai-chat-stream.int-spec.ts

@@ -150,7 +150,7 @@ describe('AiChatService.stream [integration]', () => {
       {} as any, // pageAccess (idem)
       // environment (#332): keep deferred tool loading OFF for this lifecycle
       // harness so the toolset/behavior is exactly as before.
-      { isAiChatDeferredToolsEnabled: () => false } as any,
+      { isAiChatDeferredToolsEnabled: () => false, isAiChatFinalStepLockdownEnabled: () => false } as any,
     );
   }
 
@@ -378,7 +378,7 @@ describe('AiChatService.stream [integration]', () => {
         {} as any,
         {} as any,
         // #332: deferred tool loading ON — the property under test.
-        { isAiChatDeferredToolsEnabled: () => true } as any,
+        { isAiChatDeferredToolsEnabled: () => true, isAiChatFinalStepLockdownEnabled: () => false } as any,
       );
     }
 

apps/server/test/integration/search-lookup-explain.int-spec.ts

@@ -0,0 +1,123 @@
+import { randomUUID } from 'node:crypto';
+import { Kysely, sql } from 'kysely';
+import {
+  getTestDb,
+  destroyTestDb,
+  createWorkspace,
+  createSpace,
+} from './db';
+
+/**
+ * #443 dead-index guard — EXPLAIN on the REAL DB.
+ *
+ * The lookup mode's substring predicates run a leading-wildcard
+ * `LOWER(f_unaccent(col)) LIKE '%q%'`. Those are only fast when Postgres uses
+ * the GIN trigram indexes:
+ *   - idx_pages_title_trgm         on (LOWER(f_unaccent(title)))        [#348]
+ *   - idx_pages_text_content_trgm  on (LOWER(f_unaccent(text_content))) [#443]
+ *
+ * Postgres uses a functional index ONLY when the query expression matches the
+ * index expression EXACTLY. The original lookup query wrapped the columns in
+ * `coalesce(col,'')`, which differs from the coalesce-FREE index expression and
+ * silently forced a Seq Scan on pages for EVERY lookup (the MCP client always
+ * sends substring:true). This test locks that in.
+ *
+ * Discriminator: `SET enable_seqscan = off` asks the planner "CAN this predicate
+ * use the index at all?" — which is exactly what the coalesce bug breaks. With
+ * seqscan disabled:
+ *   - the coalesce-FREE (fixed) predicate plans a Bitmap Index Scan on the trgm
+ *     index (no Seq Scan on pages);
+ *   - the coalesce-WRAPPED (buggy) predicate cannot use the index and falls back
+ *     to a Seq Scan on pages even though seqscan is disabled.
+ * We assert both to prove the fix and to keep the regression from silently
+ * returning.
+ */
+describe('SearchService agent-lookup EXPLAIN — trgm index is live [integration]', () => {
+  let db: Kysely<any>;
+  let workspaceId: string;
+  let spaceId: string;
+
+  async function insertPage(title: string, textContent: string): Promise<void> {
+    const id = randomUUID();
+    await db
+      .insertInto('pages')
+      .values({
+        id,
+        slugId: `slug-${id.slice(0, 12)}`,
+        title,
+        textContent,
+        spaceId,
+        workspaceId,
+      })
+      .execute();
+  }
+
+  // Run EXPLAIN (no ANALYZE — we only inspect the chosen plan) and return the
+  // concatenated plan text.
+  async function explain(query: string): Promise<string> {
+    const rows = await sql<{ 'QUERY PLAN': string }>`EXPLAIN ${sql.raw(query)}`.execute(
+      db,
+    );
+    return (rows.rows as any[]).map((r) => r['QUERY PLAN']).join('\n');
+  }
+
+  beforeAll(async () => {
+    db = getTestDb();
+    workspaceId = (await createWorkspace(db)).id;
+    spaceId = (await createSpace(db, workspaceId)).id;
+
+    // Seed enough rows that a trigram index is a plausible plan. The content is
+    // varied so the '%needle%' pattern is selective.
+    for (let i = 0; i < 200; i++) {
+      await insertPage(
+        `seed-title-${i}`,
+        `seed body content number ${i} lorem ipsum dolor sit amet ${i}`,
+      );
+    }
+    await insertPage('backup-srv.local', 'the needle-token-xyz lives here');
+
+    // Keep the trgm indexes' stats fresh so the planner costs them correctly.
+    await sql`ANALYZE pages`.execute(db);
+  });
+
+  afterAll(async () => {
+    await destroyTestDb();
+  });
+
+  // Force the planner to answer "can the index be used?" rather than "is it
+  // cheaper than a seq scan on this size?". Restored after each test.
+  beforeEach(async () => {
+    await sql`SET enable_seqscan = off`.execute(db);
+  });
+  afterEach(async () => {
+    await sql`RESET enable_seqscan`.execute(db);
+  });
+
+  it('title predicate (coalesce-FREE, as fixed) uses idx_pages_title_trgm, not a Seq Scan', async () => {
+    const plan = await explain(
+      `SELECT id FROM pages WHERE LOWER(f_unaccent(title)) LIKE '%srv.local%'`,
+    );
+    expect(plan).toContain('idx_pages_title_trgm');
+    expect(plan).not.toMatch(/Seq Scan on pages/i);
+  });
+
+  it('text_content predicate (coalesce-FREE, as fixed) uses idx_pages_text_content_trgm, not a Seq Scan', async () => {
+    const plan = await explain(
+      `SELECT id FROM pages WHERE LOWER(f_unaccent(text_content)) LIKE '%needle-token%'`,
+    );
+    expect(plan).toContain('idx_pages_text_content_trgm');
+    expect(plan).not.toMatch(/Seq Scan on pages/i);
+  });
+
+  // Negative control: the OLD coalesce-wrapped predicate must NOT be able to use
+  // the index — even with seqscan disabled it can only Seq Scan pages. If this
+  // ever stops seq-scanning, the coalesce/index expressions have re-aligned and
+  // the guard above is no longer meaningful.
+  it('coalesce-WRAPPED text predicate (the bug) cannot use the index — falls to Seq Scan', async () => {
+    const plan = await explain(
+      `SELECT id FROM pages WHERE LOWER(f_unaccent(coalesce(text_content,''))) LIKE '%needle-token%'`,
+    );
+    expect(plan).not.toContain('idx_pages_text_content_trgm');
+    expect(plan).toMatch(/Seq Scan on pages/i);
+  });
+});

apps/server/test/integration/search-lookup.int-spec.ts

@@ -0,0 +1,462 @@
+import { randomUUID } from 'node:crypto';
+import { Kysely } from 'kysely';
+import { SearchService } from 'src/core/search/search.service';
+import { PageRepo } from '@docmost/db/repos/page/page.repo';
+import {
+  getTestDb,
+  destroyTestDb,
+  createWorkspace,
+  createSpace,
+} from './db';
+
+/**
+ * #443 — agent-lookup search mode, acceptance on the REAL DB schema.
+ *
+ * Exercises SearchService.searchPage(..., { substring: true }) against a
+ * migrated Postgres: substring matching of technical tokens the FTS tokenizer
+ * mangles (backup-srv.local, 10.0.12.5, WB-MGE-30D86B, "Теги: Docker"), the
+ * populated path + snippet, parentPageId subtree scoping, titleOnly, the empty
+ * result, LIKE-metacharacter escaping (`%`/`_` must NOT match everything), the
+ * permission post-filter applied BEFORE the limit, and the web-UI path staying
+ * on the legacy FTS shape when `substring` is absent.
+ *
+ * The tsv column is populated by the pages_tsvector_trigger on insert, so the
+ * FTS branch is exercised too.
+ */
+describe('SearchService agent-lookup mode [integration]', () => {
+  let db: Kysely<any>;
+  let service: SearchService;
+  let workspaceId: string;
+  let spaceId: string;
+
+  // Direct page insert (the shared createPage seeder omits text_content /
+  // parent_page_id, both of which this mode depends on). Returns the id.
+  async function insertPage(args: {
+    title: string;
+    textContent?: string;
+    parentPageId?: string | null;
+    spaceId?: string;
+  }): Promise<string> {
+    const id = randomUUID();
+    await db
+      .insertInto('pages')
+      .values({
+        id,
+        slugId: `slug-${id.slice(0, 12)}`,
+        title: args.title,
+        textContent: args.textContent ?? null,
+        parentPageId: args.parentPageId ?? null,
+        spaceId: args.spaceId ?? spaceId,
+        workspaceId,
+      })
+      .execute();
+    return id;
+  }
+
+  // Build a SearchService wired to the real DB + a real PageRepo (only its
+  // recursive-descendants method is used by this mode, and it needs only `db`),
+  // with lightweight stubs for the space-membership and permission repos so a
+  // test can drive scope + the permission post-filter explicitly.
+  function buildService(opts?: {
+    userSpaceIds?: string[];
+    // ids to KEEP after the permission post-filter; undefined = keep all.
+    accessibleIds?: string[];
+  }): SearchService {
+    const pageRepo = new PageRepo(db as any, null as any, null as any);
+    const spaceMemberRepo = {
+      getUserSpaceIds: async () => opts?.userSpaceIds ?? [spaceId],
+    };
+    const pagePermissionRepo = {
+      filterAccessiblePageIds: async ({ pageIds }: { pageIds: string[] }) =>
+        opts?.accessibleIds
+          ? pageIds.filter((id) => opts.accessibleIds!.includes(id))
+          : pageIds,
+    };
+    return new SearchService(
+      db as any,
+      pageRepo as any,
+      {} as any, // shareRepo — unused by the lookup path
+      spaceMemberRepo as any,
+      pagePermissionRepo as any,
+    );
+  }
+
+  beforeAll(async () => {
+    db = getTestDb();
+    workspaceId = (await createWorkspace(db)).id;
+    spaceId = (await createSpace(db, workspaceId)).id;
+    service = buildService();
+  });
+
+  afterAll(async () => {
+    await destroyTestDb();
+  });
+
+  it('finds `backup-srv.local` by the fragment `srv.local`', async () => {
+    const pageId = await insertPage({
+      title: 'backup-srv.local',
+      textContent: 'A backup server node.',
+    });
+
+    const { items } = (await service.searchPage(
+      { query: 'srv.local', spaceId, substring: true } as any,
+      { workspaceId },
+    )) as any;
+
+    expect(items.map((i: any) => i.id)).toContain(pageId);
+    const hit = items.find((i: any) => i.id === pageId);
+    expect(hit.title).toBe('backup-srv.local');
+    // slugId must never be part of the server response shape.
+    expect('slugId' in hit).toBe(true); // server carries it; MCP strips it
+  });
+
+  it('finds a page whose TEXT contains `10.0.12.5` by the fragment `10.0.12` (empty-tsquery case)', async () => {
+    const pageId = await insertPage({
+      title: 'Server inventory',
+      textContent: 'The backup box lives at IP: 10.0.12.5. Debian 12, backups.',
+    });
+
+    const { items } = (await service.searchPage(
+      { query: '10.0.12', spaceId, substring: true } as any,
+      { workspaceId },
+    )) as any;
+
+    const hit = items.find((i: any) => i.id === pageId);
+    expect(hit).toBeDefined();
+    // The windowed snippet must include the matched text.
+    expect(hit.snippet).toContain('10.0.12.5');
+  });
+
+  it('finds `WB-MGE-30D86B` (alphanumeric token with dashes) by title', async () => {
+    const pageId = await insertPage({
+      title: 'WB-MGE-30D86B',
+      textContent: 'Device page.',
+    });
+
+    const { items } = (await service.searchPage(
+      { query: 'WB-MGE-30D86B', spaceId, substring: true } as any,
+      { workspaceId },
+    )) as any;
+
+    const hit = items.find((i: any) => i.id === pageId);
+    expect(hit).toBeDefined();
+    // Exact title match → top tier (TITLE_EXACT=3) → score in [0.75, 1].
+    expect(hit.score).toBeGreaterThanOrEqual(0.75);
+    // And it is the top-ranked hit of its own result set.
+    expect(items[0].id).toBe(pageId);
+  });
+
+  it('finds every page whose text literally contains `Теги: Docker`', async () => {
+    const a = await insertPage({
+      title: 'Container host A',
+      textContent: 'Some notes.\nТеги: Docker, compose\nmore.',
+    });
+    const b = await insertPage({
+      title: 'Container host B',
+      textContent: 'Prelude.\nТеги: Docker\nepilogue.',
+    });
+    const noise = await insertPage({
+      title: 'Unrelated',
+      textContent: 'Теги: Kubernetes',
+    });
+
+    const { items } = (await service.searchPage(
+      { query: 'Теги: Docker', spaceId, substring: true, limit: 50 } as any,
+      { workspaceId },
+    )) as any;
+
+    const ids = items.map((i: any) => i.id);
+    expect(ids).toContain(a);
+    expect(ids).toContain(b);
+    expect(ids).not.toContain(noise);
+  });
+
+  it('populates a non-empty `path` for a nested hit and `[]` for a root hit', async () => {
+    const root = await insertPage({ title: 'Infrastructure' });
+    const mid = await insertPage({ title: 'Datacenter A', parentPageId: root });
+    const leaf = await insertPage({
+      title: 'unique-nested-host',
+      parentPageId: mid,
+    });
+
+    const { items } = (await service.searchPage(
+      { query: 'unique-nested-host', spaceId, substring: true } as any,
+      { workspaceId },
+    )) as any;
+
+    const hit = items.find((i: any) => i.id === leaf);
+    expect(hit.path).toEqual(['Infrastructure', 'Datacenter A']);
+
+    const rootHits = (await service.searchPage(
+      { query: 'Infrastructure', spaceId, substring: true } as any,
+      { workspaceId },
+    )) as any;
+    const rootHit = rootHits.items.find((i: any) => i.id === root);
+    expect(rootHit.path).toEqual([]);
+  });
+
+  it('scopes to a subtree with parentPageId (cutting off sibling branches)', async () => {
+    const branchA = await insertPage({ title: 'BranchA-root' });
+    const inA = await insertPage({
+      title: 'scoped-target-xyz',
+      parentPageId: branchA,
+    });
+    const branchB = await insertPage({ title: 'BranchB-root' });
+    const inB = await insertPage({
+      title: 'scoped-target-xyz',
+      parentPageId: branchB,
+    });
+
+    const { items } = (await service.searchPage(
+      {
+        query: 'scoped-target-xyz',
+        spaceId,
+        substring: true,
+        parentPageId: branchA,
+      } as any,
+      { workspaceId },
+    )) as any;
+
+    const ids = items.map((i: any) => i.id);
+    expect(ids).toContain(inA);
+    expect(ids).not.toContain(inB);
+  });
+
+  it('includes the parent page itself in the parentPageId subtree', async () => {
+    const parent = await insertPage({ title: 'self-included-parent' });
+    await insertPage({ title: 'child-of-self', parentPageId: parent });
+
+    const { items } = (await service.searchPage(
+      {
+        query: 'self-included-parent',
+        spaceId,
+        substring: true,
+        parentPageId: parent,
+      } as any,
+      { workspaceId },
+    )) as any;
+
+    expect(items.map((i: any) => i.id)).toContain(parent);
+  });
+
+  it('titleOnly does NOT match on text_content', async () => {
+    const pageId = await insertPage({
+      title: 'Plain title',
+      textContent: 'body mentions the-secret-token here',
+    });
+
+    const withText = (await service.searchPage(
+      { query: 'the-secret-token', spaceId, substring: true } as any,
+      { workspaceId },
+    )) as any;
+    expect(withText.items.map((i: any) => i.id)).toContain(pageId);
+
+    const titleOnly = (await service.searchPage(
+      {
+        query: 'the-secret-token',
+        spaceId,
+        substring: true,
+        titleOnly: true,
+      } as any,
+      { workspaceId },
+    )) as any;
+    expect(titleOnly.items.map((i: any) => i.id)).not.toContain(pageId);
+  });
+
+  // #443 Fix #1 regression: f_unaccent is NOT length-preserving, so an
+  // expanding char (ß→ss, …→...) BEFORE the match shifted the strpos position
+  // relative to the ORIGINAL text and the snippet slice ran past end → empty.
+  // The position and the slice now share the LOWER(f_unaccent(...)) space, so
+  // the window is aligned and always contains the matched (unaccented) token.
+  it('returns a populated snippet when an unaccent-EXPANDING char precedes the match', async () => {
+    // 300 × `ß` (each f_unaccent-expands to `ss`) before the needle. Under the
+    // old code strpos returned a position ~593 in the expanded space but the
+    // slice ran over the ORIGINAL (~360 char) text → empty snippet, match lost.
+    const prefix = 'ß'.repeat(300);
+    const pageId = await insertPage({
+      title: 'Expanding-unaccent page',
+      textContent: `${prefix} needle-token-xyz trailing.`,
+    });
+
+    const { items } = (await service.searchPage(
+      { query: 'needle-token-xyz', spaceId, substring: true } as any,
+      { workspaceId },
+    )) as any;
+
+    const hit = items.find((i: any) => i.id === pageId);
+    expect(hit).toBeDefined();
+    // Snippet must be non-empty AND contain the matched token (unaccented form).
+    expect(hit.snippet.length).toBeGreaterThan(0);
+    expect(hit.snippet).toContain('needle-token-xyz');
+  });
+
+  // #443 Fix #2 regression: >200 matching pages for a broad substring, with
+  // exactly ONE exact-title hit. Without an ORDER BY on the 200-cap the exact
+  // hit could be among the arbitrarily-dropped rows; the ORDER BY keeps the
+  // strongest candidates so it must survive the cap and rank at the top.
+  it('keeps an exact-title hit through the 200-cap on a >200-row match set', async () => {
+    const isoSpace = (await createSpace(db, workspaceId)).id;
+    const svc = buildService({ userSpaceIds: [isoSpace] });
+
+    // 250 low-tier TEXT hits: the shared substring `capword` appears only in the
+    // body, never the title, so each is a TEXT-tier match (weakest tier).
+    for (let i = 0; i < 250; i++) {
+      await insertPage({
+        title: `filler-page-${i}`,
+        textContent: `body contains capword here #${i}`,
+        spaceId: isoSpace,
+      });
+    }
+    // Exactly one EXACT-title hit for the same query token.
+    const exact = await insertPage({
+      title: 'capword',
+      textContent: 'unrelated body text',
+      spaceId: isoSpace,
+    });
+
+    const { items } = (await svc.searchPage(
+      { query: 'capword', spaceId: isoSpace, substring: true, limit: 10 } as any,
+      { workspaceId },
+    )) as any;
+
+    const ids = items.map((i: any) => i.id);
+    // The exact-title hit must survive the 200-cap and appear in the top `limit`.
+    expect(ids).toContain(exact);
+    // And, being TITLE_EXACT, it must be the single strongest hit.
+    expect(items[0].id).toBe(exact);
+  });
+
+  // #443 Fix #3: titleOnly matches only the title, so it must not leak the page
+  // body as the snippet (the old "first 300 chars of text_content" fallback).
+  it('titleOnly does NOT return a text-body snippet', async () => {
+    const pageId = await insertPage({
+      title: 'titleonly-snippet-page',
+      textContent: 'SECRET-BODY-CONTENT-NOT-IN-TITLE that must not leak.',
+    });
+
+    const { items } = (await service.searchPage(
+      {
+        query: 'titleonly-snippet-page',
+        spaceId,
+        substring: true,
+        titleOnly: true,
+      } as any,
+      { workspaceId },
+    )) as any;
+
+    const hit = items.find((i: any) => i.id === pageId);
+    expect(hit).toBeDefined();
+    // The body text must not appear in the snippet; titleOnly → empty snippet.
+    expect(hit.snippet).not.toContain('SECRET-BODY-CONTENT-NOT-IN-TITLE');
+    expect(hit.snippet).toBe('');
+  });
+
+  it('returns [] (not an error) for a query that matches nothing', async () => {
+    const { items } = (await service.searchPage(
+      {
+        query: 'zzz-no-such-string-anywhere-42',
+        spaceId,
+        substring: true,
+      } as any,
+      { workspaceId },
+    )) as any;
+    expect(items).toEqual([]);
+  });
+
+  it('a `%` query does NOT match everything (LIKE metacharacter escaped)', async () => {
+    // Fresh space so we can assert on total counts without cross-test noise.
+    const isoSpace = (await createSpace(db, workspaceId)).id;
+    const svc = buildService({ userSpaceIds: [isoSpace] });
+    await insertPage({ title: 'alpha', spaceId: isoSpace });
+    await insertPage({ title: 'beta', spaceId: isoSpace });
+    const literal = await insertPage({
+      title: '100%-coverage',
+      spaceId: isoSpace,
+    });
+
+    const { items } = (await svc.searchPage(
+      { query: '%', spaceId: isoSpace, substring: true, limit: 50 } as any,
+      { workspaceId },
+    )) as any;
+
+    const ids = items.map((i: any) => i.id);
+    // `%` is a literal → matches only the page that actually contains '%'.
+    expect(ids).toContain(literal);
+    expect(ids).not.toContain(
+      items.find((i: any) => i.title === 'alpha')?.id,
+    );
+    expect(items.length).toBe(1);
+  });
+
+  it('an `_` query does NOT match everything (LIKE metacharacter escaped)', async () => {
+    const isoSpace = (await createSpace(db, workspaceId)).id;
+    const svc = buildService({ userSpaceIds: [isoSpace] });
+    await insertPage({ title: 'gamma', spaceId: isoSpace });
+    const literal = await insertPage({
+      title: 'snake_case_name',
+      spaceId: isoSpace,
+    });
+
+    const { items } = (await svc.searchPage(
+      { query: '_', spaceId: isoSpace, substring: true, limit: 50 } as any,
+      { workspaceId },
+    )) as any;
+
+    const ids = items.map((i: any) => i.id);
+    expect(ids).toContain(literal);
+    expect(items.length).toBe(1);
+  });
+
+  it('applies the permission post-filter to the MERGED set BEFORE the limit', async () => {
+    const isoSpace = (await createSpace(db, workspaceId)).id;
+    const keep = await insertPage({
+      title: 'perm-visible-target',
+      spaceId: isoSpace,
+    });
+    const hidden = await insertPage({
+      title: 'perm-hidden-target',
+      spaceId: isoSpace,
+    });
+
+    // Authenticated (userId set) so the permission filter runs; only `keep` is
+    // accessible. limit 1 must NOT be able to select `hidden`.
+    const svc = buildService({
+      userSpaceIds: [isoSpace],
+      accessibleIds: [keep],
+    });
+    const { items } = (await svc.searchPage(
+      {
+        query: 'perm-',
+        spaceId: isoSpace,
+        substring: true,
+        limit: 1,
+      } as any,
+      { userId: 'user-1', workspaceId },
+    )) as any;
+
+    const ids = items.map((i: any) => i.id);
+    expect(ids).toContain(keep);
+    expect(ids).not.toContain(hidden);
+  });
+
+  it('web-UI path (no `substring` flag) keeps the legacy FTS response shape', async () => {
+    await insertPage({
+      title: 'legacy shape page',
+      textContent: 'searchable legacyword content',
+    });
+
+    const { items } = (await service.searchPage(
+      { query: 'legacyword', spaceId } as any,
+      { userId: 'user-1', workspaceId },
+    )) as any;
+
+    // Legacy hits carry rank + highlight + space, and NO path/snippet/score.
+    const hit = items[0];
+    expect(hit).toBeDefined();
+    expect('rank' in hit).toBe(true);
+    expect('highlight' in hit).toBe(true);
+    expect('path' in hit).toBe(false);
+    expect('snippet' in hit).toBe(false);
+    expect('score' in hit).toBe(false);
+  });
+});

packages/editor-ext/package.json

@@ -11,9 +11,6 @@
   "main": "dist/index.js",
   "module": "./src/index.ts",
   "types": "dist/index.d.ts",
-  "dependencies": {
-    "marked": "17.0.5"
-  },
   "devDependencies": {
     "@vitest/coverage-v8": "4.1.6",
     "vitest": "4.1.6"

packages/editor-ext/src/index.ts

@@ -18,7 +18,6 @@ export * from "./lib/excalidraw";
 export * from "./lib/embed";
 export * from "./lib/html-embed/html-embed";
 export * from "./lib/mention";
-export * from "./lib/markdown";
 export * from "./lib/search-and-replace";
 export * from "./lib/embed-provider";
 export * from "./lib/subpages";

packages/editor-ext/src/lib/footnote/footnote-canonicalize.ts

@@ -14,7 +14,8 @@ import {
  * ProseMirror JSON directly (never running the editor's plugins), so the
  * canonical footnote topology was never enforced on those writes. The consumers
  * of this editor-ext copy are: the server markdown/HTML import
- * (`markdownToHtml -> htmlToJson` in import.service / file-import-task.service),
+ * (`markdownToProseMirror` from @docmost/prosemirror-markdown in import.service /
+ * file-import-task.service),
  * `PageService` create/update (`parseProsemirrorContent` for the JSON/markdown/
  * HTML REST write paths), and the client markdown PASTE path
  * (`markdown-clipboard.ts`). (The MCP package mirrors this canonicalizer in

packages/editor-ext/src/lib/footnote/footnote-markdown.test.ts

@@ -1,131 +0,0 @@
-import { describe, it, expect } from "vitest";
-import { htmlToMarkdown } from "../markdown/utils/turndown.utils";
-import { markdownToHtml } from "../markdown/utils/marked.utils";
-import { extractFootnoteDefinitions } from "../markdown/utils/footnote.marked";
-
-// HTML the editor-ext nodes render (sup[data-footnote-ref], section/div).
-const HTML =
-  `<p>Water<sup data-footnote-ref data-id="fn1"></sup> and clay<sup data-footnote-ref data-id="fn2"></sup>.</p>` +
-  `<section data-footnotes>` +
-  `<div data-footnote-def data-id="fn1"><p>First note.</p></div>` +
-  `<div data-footnote-def data-id="fn2"><p>Second note.</p></div>` +
-  `</section>`;
-
-describe("footnote markdown round-trip", () => {
-  it("HTML -> Markdown produces pandoc footnote syntax", () => {
-    const md = htmlToMarkdown(HTML);
-    expect(md).toContain("[^fn1]");
-    expect(md).toContain("[^fn2]");
-    expect(md).toContain("[^fn1]: First note.");
-    expect(md).toContain("[^fn2]: Second note.");
-  });
-
-  it("Markdown -> HTML rebuilds the footnote nodes' HTML", async () => {
-    const md = htmlToMarkdown(HTML);
-    const html = await markdownToHtml(md);
-    expect(html).toContain('data-footnote-ref data-id="fn1"');
-    expect(html).toContain('data-footnote-ref data-id="fn2"');
-    expect(html).toContain("data-footnotes");
-    expect(html).toContain('data-footnote-def data-id="fn1"');
-    expect(html).toContain("First note.");
-    expect(html).toContain("Second note.");
-  });
-
-  it("preserves a [^id]: line shown inside a fenced code block (not a definition)", async () => {
-    // A document that DOCUMENTS footnote syntax inside a code fence. The
-    // `[^demo]: ...` line is example text, not a real definition, and must
-    // survive the Markdown -> HTML conversion verbatim.
-    const md = [
-      "Here is how footnotes look:",
-      "",
-      "```markdown",
-      "Some text[^demo]",
-      "",
-      "[^demo]: this is the definition",
-      "```",
-      "",
-      "End of doc.",
-    ].join("\n");
-
-    const html = await markdownToHtml(md);
-    // The example definition line is kept inside the rendered code block.
-    expect(html).toContain("[^demo]: this is the definition");
-    // It did NOT get pulled out into a real footnotes section.
-    expect(html).not.toContain("data-footnotes");
-    expect(html).not.toContain("data-footnote-def");
-  });
-
-  it("extractFootnoteDefinitions keeps the FIRST duplicate definition and reuses markers", () => {
-    // Two definitions share id `d`, and the body has two `[^d]` markers. Under
-    // the import model (#166) duplicate definition ids are FIRST-WINS: only the
-    // first definition is kept; markers are NEVER rewritten, so the two `[^d]`
-    // references reuse the single footnote.
-    const md = [
-      "See here[^d] and there[^d].",
-      "",
-      "[^d]: first",
-      "[^d]: second",
-    ].join("\n");
-
-    const { body, section } = extractFootnoteDefinitions(md);
-
-    const defIds = Array.from(
-      section.matchAll(/data-footnote-def data-id="([^"]+)"/g),
-    ).map((m) => m[1]);
-    expect(defIds).toEqual(["d"]); // first-wins: one definition
-    expect(section).toContain("first");
-    expect(section).not.toContain("second"); // duplicate dropped
-
-    // Both markers stay `[^d]` (reuse) — no `d__2` minting.
-    const refIds = Array.from(body.matchAll(/\[\^([^\]\s]+)\]/g)).map(
-      (m) => m[1],
-    );
-    expect(refIds).toEqual(["d", "d"]);
-  });
-
-  it("extractFootnoteDefinitions is DETERMINISTIC and stable (same input -> same output)", () => {
-    // The output must be a pure function of the input markdown so importing the
-    // same source twice (or via the editor and the MCP mirror) is identical.
-    const md = [
-      "See[^d] one[^d] two[^d].",
-      "",
-      "[^d]: first",
-      "[^d]: second",
-      "[^d]: third",
-    ].join("\n");
-
-    const run = () => {
-      const { body, section } = extractFootnoteDefinitions(md);
-      const defIds = Array.from(
-        section.matchAll(/data-footnote-def data-id="([^"]+)"/g),
-      ).map((m) => m[1]);
-      const refIds = Array.from(body.matchAll(/\[\^([^\]\s]+)\]/g)).map(
-        (m) => m[1],
-      );
-      return { defIds, refIds };
-    };
-
-    const a = run();
-    const b = run();
-    expect(a).toEqual(b);
-    // First-wins: one kept definition `d`; all three reuse markers stay `d`.
-    expect(a.defIds).toEqual(["d"]);
-    expect(a.refIds).toEqual(["d", "d", "d"]);
-  });
-
-  it("markdownToHtml with a reused id renders ONE shared footnote def", async () => {
-    const md = [
-      "See here[^d] and there[^d].",
-      "",
-      "[^d]: first",
-      "[^d]: second",
-    ].join("\n");
-    const html = await markdownToHtml(md);
-    const defIds = Array.from(
-      html.matchAll(/data-footnote-def data-id="([^"]+)"/g),
-    ).map((m) => m[1]);
-    expect(defIds).toEqual(["d"]); // one shared definition
-    expect(html).toContain("first");
-    expect(html).not.toContain("second");
-  });
-});

packages/editor-ext/src/lib/footnote/footnote-sync.ts

@@ -103,8 +103,9 @@ interface CollisionPlan {
  * `X__2`, `X__3`, collision-bumped) so it survives as a distinct footnote — which,
  * having no matching reference, then falls under the normal orphan policy. It is
  * only ever dropped for lacking a reference, never for colliding. The IMPORT
- * paths (footnote.marked.ts / MCP extractFootnotes) instead apply first-wins +
- * drop + warn for duplicate definitions; that divergence is intentional — import
+ * paths (@docmost/prosemirror-markdown / MCP extractFootnotes) instead apply
+ * first-wins + drop + warn for duplicate definitions; that divergence is
+ * intentional — import
  * is an agent-authored artifact we sanitize, the editor is live user data we must
  * not lose.
  *

packages/editor-ext/src/lib/footnote/footnote-util.derive-id.test.ts

@@ -6,8 +6,9 @@ import { deriveFootnoteId } from "./footnote-util";
  *
  * `deriveFootnoteId` lives ONLY in editor-ext now — it is used by
  * `resolveCollisions` (re-id of a duplicate definition) and `footnotePastePlugin`
- * (re-id of a pasted colliding definition). The MCP/marked import paths no longer
- * derive ids (duplicate definitions there are first-wins-dropped, #166), so there
+ * (re-id of a pasted colliding definition). The MCP / @docmost/prosemirror-markdown
+ * import paths no longer derive ids (duplicate definitions there are
+ * first-wins-dropped, #166), so there
  * is no cross-package copy and no parity test to keep in sync. This table pins the
  * deterministic scheme so a future change to it is a conscious one.
  */

packages/editor-ext/src/lib/footnote/footnote-util.ts

@@ -63,8 +63,9 @@ export function generateFootnoteId(): string {
  * its own seen-set before requesting the next derived id.
  *
  * Used only inside editor-ext now (resolveCollisions for a re-id'd duplicate
- * DEFINITION, and footnotePastePlugin). The MCP/marked import paths no longer
- * derive ids — duplicate definitions there are first-wins-dropped (#166) — so
+ * DEFINITION, and footnotePastePlugin). The MCP / @docmost/prosemirror-markdown
+ * import paths no longer derive ids — duplicate definitions there are
+ * first-wins-dropped (#166) — so
  * there is no cross-package copy to keep in sync. The golden table in
  * footnote-util.derive-id.test.ts pins the scheme.
  */

packages/editor-ext/src/lib/image/image-markdown.test.ts

@@ -1,68 +0,0 @@
-import { describe, it, expect } from "vitest";
-import { generateJSON } from "@tiptap/html";
-import { Document } from "@tiptap/extension-document";
-import { Paragraph } from "@tiptap/extension-paragraph";
-import { Text } from "@tiptap/extension-text";
-import { htmlToMarkdown } from "../markdown/utils/turndown.utils";
-import { markdownToHtml } from "../markdown/utils/marked.utils";
-import { TiptapImage } from "./image";
-
-// Minimal schema for parsing markdownToHtml output back to JSON (mirrors
-// image.spec.ts), so we can assert the recovered caption EXACTLY.
-const parseExtensions = [Document, Paragraph, Text, TiptapImage];
-
-// Lossless markdown round-trip for image captions (issue #221). An image WITH a
-// caption can't be expressed as `![alt](src)`, so it is emitted as a raw <img>
-// (carrying data-caption) wrapped in a block <div>, the same trick the <video>
-// rule uses. marked passes the raw HTML through, so markdownToHtml keeps the
-// data-caption, and the image extension's parseHTML restores the attribute.
-describe("image caption markdown round-trip", () => {
-  it("HTML -> Markdown emits a raw <img data-caption> for captioned images", () => {
-    const html = `<p><img src="/files/a.png" alt="cat" data-caption="A grey cat"></p>`;
-    const md = htmlToMarkdown(html);
-    expect(md).toContain("data-caption=\"A grey cat\"");
-    expect(md).toContain('src="/files/a.png"');
-    expect(md).toContain('alt="cat"');
-    // It must NOT degrade to the lossy ![]() form.
-    expect(md).not.toContain("![cat]");
-  });
-
-  it("Markdown -> HTML restores data-caption on the <img>", async () => {
-    const html = `<p><img src="/files/a.png" alt="cat" data-caption="A grey cat"></p>`;
-    const md = htmlToMarkdown(html);
-    const back = await markdownToHtml(md);
-    expect(back).toContain('data-caption="A grey cat"');
-    expect(back).toContain('src="/files/a.png"');
-  });
-
-  it("special characters in the caption survive the round-trip (escaped)", async () => {
-    // The source caption is the decoded string `Tom & "Jerry"` (both an `&` and
-    // a `"`). escapeHtmlAttr must encode `&` -> `&amp;` and `"` -> `&quot;`.
-    const html = `<p><img src="/files/a.png" data-caption='Tom &amp; &quot;Jerry&quot;'></p>`;
-    const md = htmlToMarkdown(html);
-
-    // (a) The intermediate Markdown must carry the EXACT escaped attribute. This
-    // fails if escapeHtmlAttr stopped escaping `"` (attribute break-out:
-    // data-caption="Tom & "Jerry"") or double-encoded `&` (`&amp;amp;`).
-    expect(md).toContain('data-caption="Tom &amp; &quot;Jerry&quot;"');
-
-    const back = await markdownToHtml(md);
-    expect(back).toContain("data-caption=");
-    expect(back).toContain("Jerry");
-    expect(back).toContain("Tom");
-
-    // (b) Re-parse the rendered HTML through the image extension's parseHTML and
-    // assert the recovered caption is EXACTLY the original (no corruption, loss,
-    // or double-encoding).
-    const json = generateJSON(back, parseExtensions);
-    expect(json.content?.[0]?.attrs?.caption).toBe('Tom & "Jerry"');
-  });
-
-  it("caption-less images stay a clean ![alt](src) with no raw HTML", () => {
-    const html = `<p><img src="/files/a.png" alt="cat"></p>`;
-    const md = htmlToMarkdown(html);
-    expect(md).toContain("![cat](/files/a.png)");
-    expect(md).not.toContain("data-caption");
-    expect(md).not.toContain("<img");
-  });
-});

packages/editor-ext/src/lib/markdown/html-embed-marked.spec.ts

@@ -1,105 +0,0 @@
-import { describe, expect, it } from "vitest";
-import { htmlEmbedExtension } from "./utils/html-embed.marked";
-import { markdownToHtml } from "./index";
-import { encodeHtmlEmbedSource } from "../html-embed/html-embed";
-
-// CONTRACT tests for the marked block tokenizer that rebuilds an htmlEmbed node
-// from the `<!--html-embed:BASE64-->` marker (html-embed.marked.ts), plus the
-// observable round-trip through markdownToHtml.
-//
-// These pin the REAL tokenizer behaviour the import path depends on:
-//   - the tokenizer rule is anchored (^) and only accepts the base64 alphabet
-//     [A-Za-z0-9+/=], so a marker with non-base64 chars is NOT tokenized and
-//     survives as a literal HTML comment (not silently turned into something the
-//     server's strip no longer recognizes);
-//   - start() reports the correct index of the next marker so marked invokes the
-//     tokenizer at the right offset when a marker sits mid-document / after text;
-//   - a marker with surrounding text on the SAME line is split out into its own
-//     embed div while the surrounding text becomes ordinary paragraphs.
-//
-// The contract is asserted against the actual exported extension and pipeline —
-// no behaviour is invented; the expectations were read off the real tokenizer.
-
-const SAMPLE = "<b>x</b>";
-const ENC = encodeHtmlEmbedSource(SAMPLE);
-
-describe("htmlEmbed marked tokenizer — start()", () => {
-  it("returns the index of a marker that sits mid-document", () => {
-    const src = `hello world <!--html-embed:${ENC}-->`;
-    expect(htmlEmbedExtension.start(src)).toBe(src.indexOf("<!--html-embed:"));
-  });
-
-  it("returns 0 when the marker is at the very start", () => {
-    expect(htmlEmbedExtension.start(`<!--html-embed:${ENC}-->`)).toBe(0);
-  });
-
-  it("returns -1 when there is no marker", () => {
-    expect(htmlEmbedExtension.start("no marker here")).toBe(-1);
-  });
-});
-
-describe("htmlEmbed marked tokenizer — tokenizer()", () => {
-  it("tokenizes a marker at the start of the input, capturing the base64 payload", () => {
-    const token = htmlEmbedExtension.tokenizer(`<!--html-embed:${ENC}-->`);
-    expect(token).toBeTruthy();
-    expect(token!.type).toBe("htmlEmbed");
-    expect(token!.raw).toBe(`<!--html-embed:${ENC}-->`);
-    expect(token!.encoded).toBe(ENC);
-  });
-
-  it("tokenizes an EMPTY marker (the [A-Za-z0-9+/=]* class allows zero chars)", () => {
-    const token = htmlEmbedExtension.tokenizer("<!--html-embed:-->");
-    expect(token).toBeTruthy();
-    expect(token!.encoded).toBe("");
-    expect(token!.raw).toBe("<!--html-embed:-->");
-  });
-
-  it("does NOT tokenize when text precedes the marker (rule is anchored ^)", () => {
-    // marked relies on start() to advance to the marker; the tokenizer itself
-    // only matches at offset 0, so a non-anchored call returns undefined.
-    expect(
-      htmlEmbedExtension.tokenizer(`hello <!--html-embed:${ENC}-->`),
-    ).toBeUndefined();
-  });
-
-  it("does NOT tokenize a marker containing a non-base64 char ('$')", () => {
-    expect(
-      htmlEmbedExtension.tokenizer("<!--html-embed:ab$cd-->"),
-    ).toBeUndefined();
-  });
-
-  it("does NOT tokenize a marker containing a space", () => {
-    expect(
-      htmlEmbedExtension.tokenizer("<!--html-embed:ab cd-->"),
-    ).toBeUndefined();
-  });
-
-  it("renderer emits the embed div the node's parseHTML recognizes", () => {
-    const token = htmlEmbedExtension.tokenizer(`<!--html-embed:${ENC}-->`)!;
-    const html = htmlEmbedExtension.renderer(token as any);
-    expect(html).toBe(
-      `<div data-type="htmlEmbed" data-source="${ENC}"></div>`,
-    );
-  });
-});
-
-describe("htmlEmbed marked tokenizer — markdownToHtml round-trip", () => {
-  it("splits a marker out of surrounding same-line text into its own embed div", async () => {
-    const html = await markdownToHtml(`before <!--html-embed:${ENC}--> after`);
-    // The marker became the embed div...
-    expect(html).toContain(
-      `<div data-type="htmlEmbed" data-source="${ENC}"></div>`,
-    );
-    // ...and the surrounding text survived as ordinary paragraph content.
-    expect(html).toContain("before");
-    expect(html).toContain("after");
-  });
-
-  it("leaves a marker with non-base64 chars as a literal comment (NOT an embed div)", async () => {
-    const html = await markdownToHtml("<!--html-embed:ab$cd-->");
-    // It is NOT tokenized into an embed div the server would strip...
-    expect(html).not.toContain('data-type="htmlEmbed"');
-    // ...it passes through unchanged as a literal HTML comment.
-    expect(html).toContain("<!--html-embed:ab$cd-->");
-  });
-});

packages/editor-ext/src/lib/markdown/index.ts

@@ -1,2 +0,0 @@
-export * from "./utils/marked.utils";
-export * from "./utils/turndown.utils";

packages/editor-ext/src/lib/markdown/markdown-html-embed.spec.ts

@@ -1,112 +0,0 @@
-import { describe, it, expect } from "vitest";
-import { markdownToHtml, htmlToMarkdown } from "./index";
-import {
-  encodeHtmlEmbedSource,
-  decodeHtmlEmbedSource,
-} from "../html-embed/html-embed";
-
-// SECURITY (Variant C admin gate, import attack surface).
-//
-// The markdown import path is the only write path where an htmlEmbed reaches
-// the server purely from file bytes (no editor / collab socket). The marked
-// tokenizer in `html-embed.marked.ts` and the turndown rule in
-// `turndown.utils.ts` are what materialize the `<!--html-embed:BASE64-->`
-// marker into the `<div data-type="htmlEmbed" data-source="BASE64">` element
-// that the server then parses into an htmlEmbed node and the admin gate strips.
-//
-// If either the tokenizer regex or the turndown rule shape drifts, the marker
-// would either (a) stop becoming an htmlEmbed node (silently dropping admin
-// content) or (b) become some OTHER tag the server's `hasHtmlEmbedNode` no
-// longer recognizes (a strip bypass). These tests pin the marker <-> embed-div
-// contract that the server-side strip relies on. editor-ext had ZERO tests
-// before this file; this adds the runner + the round-trip coverage.
-
-// The server parses the embed div by matching `data-type="htmlEmbed"` and
-// decoding `data-source`; mirror that here so the assertion is exactly what the
-// real `htmlToJson` -> htmlEmbed node parse depends on (the node's parseHTML in
-// html-embed.ts uses the same selector + decodeHtmlEmbedSource).
-const EMBED_DIV_RE = /<div[^>]*\bdata-type="htmlEmbed"[^>]*>/;
-function extractEmbedSource(html: string): string | undefined {
-  const div = EMBED_DIV_RE.exec(html);
-  if (!div) return undefined;
-  const enc = /data-source="([^"]*)"/.exec(div[0]);
-  if (!enc) return undefined;
-  return decodeHtmlEmbedSource(enc[1]);
-}
-
-// Replicates the server's `hasHtmlEmbedNode` decision against the embed *div*
-// (the HTML form the server immediately converts to JSON). If this matches, the
-// server's JSON-level `hasHtmlEmbedNode` will too, because htmlToJson maps this
-// exact div to an htmlEmbed node.
-function htmlHasHtmlEmbed(html: string): boolean {
-  return EMBED_DIV_RE.test(html);
-}
-
-describe("markdown <!--html-embed--> import round-trip", () => {
-  const source = "<script>x</script>";
-
-  it("markdownToHtml turns the marker into an htmlEmbed div carrying the source", async () => {
-    const md = "<!--html-embed:" + encodeHtmlEmbedSource(source) + "-->";
-    const html = await markdownToHtml(md);
-
-    // The marker became the embed div the server recognizes as an htmlEmbed
-    // node (so the server's hasHtmlEmbedNode would match it after htmlToJson).
-    expect(htmlHasHtmlEmbed(html)).toBe(true);
-    // The decoded source is the original script, intact.
-    expect(extractEmbedSource(html)).toBe(source);
-    // The raw script is NOT inlined into the HTML — it stays base64 in the
-    // attribute (the marker itself must not be a direct injection vector).
-    expect(html).not.toContain("<script>x</script>");
-  });
-
-  it("preserves UTF-8 / special chars in the embedded source", async () => {
-    const utf8 = '<script>console.log("héllo → 世界")</script>';
-    const md = "<!--html-embed:" + encodeHtmlEmbedSource(utf8) + "-->";
-    const html = await markdownToHtml(md);
-    expect(htmlHasHtmlEmbed(html)).toBe(true);
-    expect(extractEmbedSource(html)).toBe(utf8);
-  });
-
-  it("an empty marker still produces an htmlEmbed div (empty source)", async () => {
-    const html = await markdownToHtml("<!--html-embed:-->");
-    expect(htmlHasHtmlEmbed(html)).toBe(true);
-    expect(extractEmbedSource(html)).toBe("");
-  });
-
-  it("round-trips htmlToMarkdown -> markdownToHtml preserving the embed marker", async () => {
-    const encoded = encodeHtmlEmbedSource(source);
-    // NOTE: turndown drops a *blank* (childless) element before any custom rule
-    // runs, and the htmlEmbed div is normally childless. The export pipeline
-    // therefore must give the rule a non-blank div to fire on; we add an inert
-    // text child here to exercise the real turndown htmlEmbed rule. (A blank
-    // embed div serializing to "" is asserted separately below as a documented
-    // edge so this contract drift is visible.)
-    const startHtml = `<div data-type="htmlEmbed" data-source="${encoded}">x</div>`;
-
-    // Export to markdown: the turndown rule emits the <!--html-embed:..-->
-    // marker (lossless, inert in plain markdown viewers).
-    const md = htmlToMarkdown(startHtml);
-    expect(md).toContain("<!--html-embed:" + encoded + "-->");
-
-    // Re-import: the marker round-trips back into an embed div with the same
-    // decoded source — this is the marker <-> embed-div contract the server's
-    // import strip depends on.
-    const html = await markdownToHtml(md);
-    expect(htmlHasHtmlEmbed(html)).toBe(true);
-    expect(extractEmbedSource(html)).toBe(source);
-  });
-
-  it("documents that a BLANK embed div serializes to empty markdown (turndown drops childless blocks)", () => {
-    const encoded = encodeHtmlEmbedSource(source);
-    const blank = `<div data-type="htmlEmbed" data-source="${encoded}"></div>`;
-    // This pins current behavior so a future change to the turndown rule (e.g.
-    // making it fire on blank nodes) is caught rather than silently shipping.
-    expect(htmlToMarkdown(blank)).toBe("");
-  });
-
-  it("the base64 codec itself round-trips (no '<' leaks into the attribute)", () => {
-    const encoded = encodeHtmlEmbedSource(source);
-    expect(encoded).not.toContain("<");
-    expect(decodeHtmlEmbedSource(encoded)).toBe(source);
-  });
-});

packages/editor-ext/src/lib/markdown/utils/basename.ts

@@ -1,29 +0,0 @@
-/**
- * Flexible `basename` implementation for node and the browser
- * @see https://stackoverflow.com/a/59907288/2228771
- */
-export function getBasename(path: string) {
-  // make sure the basename is not empty, if string ends with separator
-  let end = path.length - 1;
-  while (path[end] === '/' || path[end] === '\\') {
-    --end;
-  }
-
-  // support mixing of Win + Unix path separators
-  const i1 = path.lastIndexOf('/', end);
-  const i2 = path.lastIndexOf('\\', end);
-
-  let start: number;
-  if (i1 === -1) {
-    if (i2 === -1) {
-      // no separator in the whole thing
-      return path;
-    }
-    start = i2;
-  } else if (i2 === -1) {
-    start = i1;
-  } else {
-    start = Math.max(i1, i2);
-  }
-  return path.substring(start + 1, end + 1);
-}

packages/editor-ext/src/lib/markdown/utils/callout-common.marked.ts

@@ -1,33 +0,0 @@
-/**
- * Shared pieces for the two callout tokenizers — `callout.marked.ts` (the
- * `:::type` fenced form) and `github-callout.marked.ts` (the `> [!type]` GitHub
- * alert form). Both emit the SAME callout node, so the banner type dictionary
- * and the HTML renderer live here once instead of drifting apart in two files.
- * The tokenizers themselves stay separate (different syntaxes / source matching).
- */
-
-/** The four callout banner types the editor schema supports. */
-export const CALLOUT_TYPES = ['info', 'success', 'warning', 'danger'] as const;
-
-export type CalloutType = (typeof CALLOUT_TYPES)[number];
-
-/**
- * Coerce an arbitrary type name onto a supported banner type, defaulting to
- * `info` for anything unrecognized (the shared fallback both tokenizers use).
- */
-export function normalizeCalloutType(type: string): CalloutType {
-  return (CALLOUT_TYPES as readonly string[]).includes(type)
-    ? (type as CalloutType)
-    : 'info';
-}
-
-/**
- * Render a callout node to the editor's HTML shape. `body` is the already
- * markdown-parsed inner content (marked may hand back a string synchronously).
- */
-export function renderCalloutHtml(
-  type: string,
-  body: string | Promise<string>,
-): string {
-  return `<div data-type="callout" data-callout-type="${type}">${body}</div>`;
-}

packages/editor-ext/src/lib/markdown/utils/callout.marked.ts

@@ -1,37 +0,0 @@
-import { Token, marked } from 'marked';
-import { normalizeCalloutType, renderCalloutHtml } from './callout-common.marked';
-
-interface CalloutToken {
-  type: 'callout';
-  calloutType: string;
-  text: string;
-  raw: string;
-}
-
-export const calloutExtension = {
-  name: 'callout',
-  level: 'block',
-  start(src: string) {
-    return src.match(/:::/)?.index ?? -1;
-  },
-  tokenizer(src: string): CalloutToken | undefined {
-    const rule = /^:::([a-zA-Z0-9]+)\s+([\s\S]+?):::/;
-    const match = rule.exec(src);
-
-    if (match) {
-      return {
-        type: 'callout',
-        calloutType: normalizeCalloutType(match[1]),
-        raw: match[0],
-        text: match[2].trim(),
-      };
-    }
-  },
-  renderer(token: Token) {
-    const calloutToken = token as CalloutToken;
-    return renderCalloutHtml(
-      calloutToken.calloutType,
-      marked.parse(calloutToken.text),
-    );
-  },
-};

packages/editor-ext/src/lib/markdown/utils/footnote.marked.orphan.test.ts

@@ -1,72 +0,0 @@
-import { describe, it, expect } from "vitest";
-import { extractFootnoteDefinitions } from "./footnote.marked";
-
-/** Pull the ordered list of `data-footnote-def` ids out of the rendered section. */
-function defIds(section: string): string[] {
-  return [...section.matchAll(/data-footnote-def data-id="([^"]+)"/g)].map(
-    (m) => m[1],
-  );
-}
-
-/** Pull the ordered list of `[^id]` markers that remain in the body. */
-function bodyMarkers(body: string): string[] {
-  return [...body.matchAll(/\[\^([^\]\s]+)\]/g)].map((m) => m[1]);
-}
-
-describe("extractFootnoteDefinitions: duplicate definition ids (first-wins)", () => {
-  // Body has ONE `[^d]` reference but THREE `[^d]:` definitions. Under the
-  // import model (#166) a duplicate definition id is FIRST-WINS: only the first
-  // definition is kept; the rest are DROPPED (and surfaced by analyzeFootnotes,
-  // not silently re-id'd into orphan footnotes as before). Reference markers are
-  // never rewritten, so repeated references would reuse the single footnote.
-  const md = ["See[^d].", "", "[^d]: a", "[^d]: b", "[^d]: c"].join("\n");
-
-  it("keeps only the FIRST definition for the id (first-wins)", () => {
-    const { section } = extractFootnoteDefinitions(md);
-    const ids = defIds(section);
-    expect(ids).toEqual(["d"]);
-  });
-
-  it("keeps the first definition's text and drops the duplicates", () => {
-    const { section } = extractFootnoteDefinitions(md);
-    expect(section).toContain('data-footnote-def data-id="d"><p>a</p>');
-    // No derived `d__2` / `d__3` ids are emitted anymore.
-    expect(section).not.toContain("d__2");
-    expect(section).not.toContain("d__3");
-    // The dropped duplicate texts are not in the section.
-    expect(section).not.toContain("<p>b</p>");
-    expect(section).not.toContain("<p>c</p>");
-  });
-
-  it("leaves the SINGLE body marker as [^d] (markers are never rewritten)", () => {
-    const { body } = extractFootnoteDefinitions(md);
-    expect(bodyMarkers(body)).toEqual(["d"]);
-    expect(body).toContain("See[^d].");
-    // The definition lines themselves were pulled OUT of the body.
-    expect(body).not.toContain("[^d]: a");
-    expect(body).not.toContain("[^d]: b");
-    expect(body).not.toContain("[^d]: c");
-  });
-
-  it("does not crash and produces a well-formed footnotes section", () => {
-    const { section } = extractFootnoteDefinitions(md);
-    expect(section.startsWith("<section data-footnotes>")).toBe(true);
-    expect(section.endsWith("</section>")).toBe(true);
-    // Exactly one definition div (first-wins).
-    expect([...section.matchAll(/<div data-footnote-def/g)]).toHaveLength(1);
-  });
-});
-
-describe("extractFootnoteDefinitions: reuse (repeated references, one definition)", () => {
-  // Pandoc semantics: many `[^a]` references + one `[^a]:` definition = one
-  // footnote, shared. Markers are left intact so the editor numbers them as one.
-  const md = ["A[^a] B[^a] C[^a].", "", "[^a]: shared note"].join("\n");
-
-  it("emits exactly one definition and leaves every reference marker as [^a]", () => {
-    const { section, body } = extractFootnoteDefinitions(md);
-    expect(defIds(section)).toEqual(["a"]);
-    expect(section).toContain('data-footnote-def data-id="a"><p>shared note</p>');
-    // All three reference markers stay `a` (no `a__2`/`a__3` minting).
-    expect(bodyMarkers(body)).toEqual(["a", "a", "a"]);
-  });
-});

packages/editor-ext/src/lib/markdown/utils/footnote.marked.ts

@@ -1,131 +0,0 @@
-import { marked } from "marked";
-
-/**
- * Pandoc/GFM footnote support for the marked (Markdown -> HTML) pipeline.
- *
- * Two pieces:
- *  - an INLINE tokenizer for `[^id]` references -> <sup data-footnote-ref
- *    data-id="id"> (matches the editor-ext FootnoteReference renderHTML);
- *  - a document hook (`preprocess`/`walkTokens` is awkward for collecting +
- *    removing definitions, so we use a regex preprocessing step instead) that
- *    pulls every `[^id]: text` definition line out of the body and appends a
- *    single <section data-footnotes> with one <div data-footnote-def> per
- *    definition, so the round-trip rebuilds footnotesList + footnoteDefinition.
- *
- * Every FIRST definition line is emitted — duplicate ids are first-wins (the
- * rest are dropped, and surfaced via analyzeFootnotes), and reference markers are
- * left untouched so repeated `[^a]` references reuse the one footnote (#166).
- * Orphan definitions (no matching reference) are still emitted here; the editor's
- * sync plugin reconciles the final reference/definition set (drops orphans,
- * synthesizes a single empty definition for a reference that lacks one).
- */
-
-const DEFINITION_RE = /^\[\^([^\]\s]+)\]:[ \t]*(.*)$/;
-const REFERENCE_RE = /\[\^([^\]\s]+)\]/;
-
-interface FootnoteRefToken {
-  type: "footnoteRef";
-  raw: string;
-  id: string;
-}
-
-export const footnoteReferenceExtension = {
-  name: "footnoteRef",
-  level: "inline" as const,
-  start(src: string) {
-    return src.match(/\[\^/)?.index ?? -1;
-  },
-  tokenizer(src: string): FootnoteRefToken | undefined {
-    const match = REFERENCE_RE.exec(src);
-    // Only match at the very start of the remaining inline source.
-    if (match && match.index === 0) {
-      return {
-        type: "footnoteRef",
-        raw: match[0],
-        id: match[1],
-      };
-    }
-    return undefined;
-  },
-  renderer(token: FootnoteRefToken) {
-    return `<sup data-footnote-ref data-id="${escapeAttr(token.id)}"></sup>`;
-  },
-};
-
-function escapeAttr(value: string): string {
-  return String(value).replace(/&/g, "&amp;").replace(/"/g, "&quot;");
-}
-
-/**
- * Extract `[^id]: text` definition lines from the markdown body, returning the
- * cleaned body plus a rendered <section data-footnotes> (empty string when no
- * definitions). Call this BEFORE marked.parse and append the section to the
- * resulting HTML.
- */
-export function extractFootnoteDefinitions(markdown: string): {
-  body: string;
-  section: string;
-} {
-  const lines = markdown.split("\n");
-  const bodyLines: string[] = [];
-  const definitions: Array<{ id: string; text: string }> = [];
-
-  // Track fenced-code state so a `[^id]: ...` line that merely SHOWS footnote
-  // syntax inside a ``` / ~~~ code block is left in the body verbatim and not
-  // mistaken for a real definition.
-  let fence: string | null = null;
-
-  for (const line of lines) {
-    const fenceMatch = /^(\s*)(`{3,}|~{3,})/.exec(line);
-    if (fenceMatch) {
-      const marker = fenceMatch[2][0];
-      if (fence === null) {
-        fence = marker; // opening fence
-      } else if (marker === fence) {
-        fence = null; // closing fence (matching delimiter type)
-      }
-      bodyLines.push(line);
-      continue;
-    }
-
-    const m = fence === null ? DEFINITION_RE.exec(line) : null;
-    if (m) {
-      definitions.push({ id: m[1], text: m[2] });
-    } else {
-      bodyLines.push(line);
-    }
-  }
-
-  if (definitions.length === 0) {
-    return { body: markdown, section: "" };
-  }
-
-  // Duplicate definition ids (e.g. `[^d]: first` / `[^d]: second`): FIRST WINS,
-  // the rest are DROPPED. Reference markers are left UNTOUCHED so repeated `[^a]`
-  // references reuse the single footnote (Pandoc semantics, #166). This differs
-  // from the live editor's never-lose policy (resolveCollisions re-ids a
-  // duplicate definition into an orphan) on purpose: an import is an
-  // agent-authored artifact we sanitize, and the dropped duplicate is surfaced
-  // to the caller via analyzeFootnotes' `duplicateDefinitions` warning instead.
-  const firstById = new Map<string, string>(); // id -> first definition text
-  for (const def of definitions) {
-    if (!firstById.has(def.id)) firstById.set(def.id, def.text);
-  }
-
-  const defsHtml = [...firstById.entries()]
-    .map(([id, text]) => {
-      // Render the definition text as inline markdown so emphasis/links inside
-      // a footnote survive the round-trip; wrap in a paragraph (the node's
-      // content is paragraph+).
-      const inner = marked.parseInline(text || "");
-      return `<div data-footnote-def data-id="${escapeAttr(
-        id,
-      )}"><p>${inner}</p></div>`;
-    })
-    .join("");
-
-  return {
-    body: bodyLines.join("\n"),
-    section: `<section data-footnotes>${defsHtml}</section>`,
-  };
-}

packages/editor-ext/src/lib/markdown/utils/github-callout.marked.test.ts

@@ -1,54 +0,0 @@
-import { describe, it, expect } from "vitest";
-import { markdownToHtml } from "./marked.utils";
-
-/**
- * Regression for issue #192: pasting a GitHub-style `> [!type]` alert produced a
- * literal `<blockquote>` containing `[!info]` instead of a callout node, because
- * only the `:::type` form was tokenized. The editor paste path runs the same
- * `markdownToHtml`, so these assertions pin the conversion at the source.
- */
-function html(md: string): string {
-  const out = markdownToHtml(md);
-  if (typeof out !== "string") throw new Error("expected sync string output");
-  return out;
-}
-
-describe("markdownToHtml: GitHub `> [!type]` callouts", () => {
-  it("converts `> [!info]` to a callout node, not a literal blockquote", () => {
-    const out = html("> [!info]\n> Callout body text here");
-    expect(out).toContain('data-type="callout"');
-    expect(out).toContain('data-callout-type="info"');
-    expect(out).toContain("Callout body text here");
-    expect(out).not.toContain("[!info]");
-    expect(out).not.toContain("<blockquote");
-  });
-
-  it("maps GitHub alert aliases onto the supported banner types", () => {
-    expect(html("> [!NOTE]\n> x")).toContain('data-callout-type="info"');
-    expect(html("> [!TIP]\n> x")).toContain('data-callout-type="success"');
-    expect(html("> [!WARNING]\n> x")).toContain('data-callout-type="warning"');
-    expect(html("> [!CAUTION]\n> x")).toContain('data-callout-type="danger"');
-  });
-
-  it("accepts the editor's own type names directly", () => {
-    expect(html("> [!success]\n> x")).toContain('data-callout-type="success"');
-    expect(html("> [!danger]\n> x")).toContain('data-callout-type="danger"');
-  });
-
-  it("falls back to info for an unknown type", () => {
-    expect(html("> [!bogus]\n> x")).toContain('data-callout-type="info"');
-  });
-
-  it("preserves multi-line callout bodies", () => {
-    const out = html("> [!warning]\n> line one\n> line two");
-    expect(out).toContain('data-callout-type="warning"');
-    expect(out).toContain("line one");
-    expect(out).toContain("line two");
-  });
-
-  it("still converts the `:::type` form", () => {
-    const out = html(":::info\nbody\n:::");
-    expect(out).toContain('data-type="callout"');
-    expect(out).toContain('data-callout-type="info"');
-  });
-});

packages/editor-ext/src/lib/markdown/utils/github-callout.marked.ts

@@ -1,81 +0,0 @@
-import { Token, marked } from 'marked';
-import { renderCalloutHtml } from './callout-common.marked';
-
-interface GithubCalloutToken {
-  type: 'githubCallout';
-  calloutType: string;
-  text: string;
-  raw: string;
-}
-
-/**
- * Map GitHub "alert" blockquote markers (`> [!NOTE]`, `> [!WARNING]`, …) onto
- * the four callout banner types the editor schema supports. The editor's own
- * type names (`info`/`success`/`warning`/`danger`) are also accepted directly,
- * because users paste both forms. Anything unrecognized falls back to `info`,
- * matching the `:::type` callout tokenizer.
- */
-const GITHUB_ALERT_TYPE_MAP: Record<string, string> = {
-  note: 'info',
-  tip: 'success',
-  important: 'info',
-  warning: 'warning',
-  caution: 'danger',
-  info: 'info',
-  success: 'success',
-  danger: 'danger',
-};
-
-/**
- * Tokenizer for GitHub-flavored alert callouts written as a blockquote whose
- * first line is `[!type]`:
- *
- *   > [!info]
- *   > body line one
- *   > body line two
- *
- * Without this, the default blockquote tokenizer wins and the marker renders as
- * a literal `[!info]` inside a `<blockquote>`. The editor's paste path runs the
- * same `markdownToHtml`, so registering this here also fixes pasting the syntax
- * into the editor (issue #192), not just markdown import.
- */
-export const githubCalloutExtension = {
-  name: 'githubCallout',
-  level: 'block' as const,
-  start(src: string) {
-    return src.match(/^ {0,3}>[ \t]*\[!/m)?.index ?? -1;
-  },
-  tokenizer(src: string): GithubCalloutToken | undefined {
-    const rule =
-      /^ {0,3}>[ \t]*\[!([a-zA-Z]+)\][^\n]*(?:\n {0,3}>[^\n]*)*(?:\n|$)/;
-    const match = rule.exec(src);
-    if (!match) return undefined;
-
-    const rawType = match[1].toLowerCase();
-    const calloutType = GITHUB_ALERT_TYPE_MAP[rawType] ?? 'info';
-
-    const text = match[0]
-      .replace(/\n+$/, '')
-      .split('\n')
-      // Strip the blockquote marker (`>` + optional space) from every line.
-      .map((line) => line.replace(/^ {0,3}>[ \t]?/, ''))
-      // Drop the `[!type]` marker that opens the first line.
-      .map((line, i) => (i === 0 ? line.replace(/^\[![a-zA-Z]+\][ \t]*/, '') : line))
-      .join('\n')
-      .trim();
-
-    return {
-      type: 'githubCallout',
-      calloutType,
-      raw: match[0],
-      text,
-    };
-  },
-  renderer(token: Token) {
-    const calloutToken = token as GithubCalloutToken;
-    return renderCalloutHtml(
-      calloutToken.calloutType,
-      marked.parse(calloutToken.text),
-    );
-  },
-};

packages/editor-ext/src/lib/markdown/utils/html-embed.marked.ts

@@ -1,41 +0,0 @@
-import { Token } from "marked";
-
-interface HtmlEmbedToken {
-  type: "htmlEmbed";
-  raw: string;
-  encoded: string;
-}
-
-/**
- * Marked extension that rebuilds an `htmlEmbed` node from the HTML comment
- * marker produced by the turndown rule (`<!--html-embed:<base64>-->`).
- *
- * It emits the same marker div the node's `parseHTML` recognizes, so the
- * pipeline MD -> HTML -> ProseMirror JSON restores the node (and its
- * base64 `data-source`) exactly. We do NOT expand the raw markup here; the
- * source stays base64-encoded in the attribute and is only executed by the
- * client NodeView.
- */
-export const htmlEmbedExtension = {
-  name: "htmlEmbed",
-  level: "block" as const,
-  start(src: string) {
-    return src.indexOf("<!--html-embed:");
-  },
-  tokenizer(src: string): HtmlEmbedToken | undefined {
-    const rule = /^<!--html-embed:([A-Za-z0-9+/=]*)-->/;
-    const match = rule.exec(src);
-
-    if (match) {
-      return {
-        type: "htmlEmbed",
-        raw: match[0],
-        encoded: match[1] ?? "",
-      };
-    }
-  },
-  renderer(token: Token) {
-    const htmlEmbedToken = token as HtmlEmbedToken;
-    return `<div data-type="htmlEmbed" data-source="${htmlEmbedToken.encoded}"></div>`;
-  },
-};

packages/editor-ext/src/lib/markdown/utils/marked.utils.ts

@@ -1,76 +0,0 @@
-import { marked } from "marked";
-import { calloutExtension } from "./callout.marked";
-import { githubCalloutExtension } from "./github-callout.marked";
-import { mathBlockExtension } from "./math-block.marked";
-import { mathInlineExtension } from "./math-inline.marked";
-import {
-  footnoteReferenceExtension,
-  extractFootnoteDefinitions,
-} from "./footnote.marked";
-import { htmlEmbedExtension } from "./html-embed.marked";
-
-marked.use({
-  renderer: {
-    list({ ordered, start, items }) {
-      let body = "";
-      for (const item of items) {
-        body += this.listitem(item);
-      }
-
-      if (ordered) {
-        const startAttr = start !== 1 ? ` start="${start}"` : "";
-        return `<ol${startAttr}>\n${body}</ol>\n`;
-      }
-
-      const isTaskList = items.some((item) => item.task);
-      const dataType = isTaskList ? ' data-type="taskList"' : "";
-      return `<ul${dataType}>\n${body}</ul>\n`;
-    },
-    listitem({ tokens, task: isTask, checked: isChecked }) {
-      const text = this.parser.parse(tokens);
-      if (!isTask) {
-        return `<li>${text}</li>\n`;
-      }
-      const checkedAttr = isChecked
-        ? 'data-checked="true"'
-        : 'data-checked="false"';
-      return `<li data-type="taskItem" ${checkedAttr}>${text}</li>\n`;
-    },
-  },
-});
-
-marked.use({
-  extensions: [
-    calloutExtension,
-    githubCalloutExtension,
-    mathBlockExtension,
-    mathInlineExtension,
-    footnoteReferenceExtension,
-    htmlEmbedExtension,
-  ],
-});
-
-marked.setOptions({ breaks: true });
-
-export function markdownToHtml(
-  markdownInput: string,
-): string | Promise<string> {
-  const YAML_FONT_MATTER_REGEX = /^\s*---[\s\S]*?---\s*/;
-
-  const markdown = markdownInput
-    .replace(YAML_FONT_MATTER_REGEX, "")
-    .trimStart();
-
-  // Pull `[^id]: ...` definition lines out of the body, render the body, then
-  // append a single <section data-footnotes> so the round-trip rebuilds the
-  // footnotesList + footnoteDefinition nodes.
-  const { body, section } = extractFootnoteDefinitions(markdown);
-
-  const parsed = marked.parse(body);
-  if (!section) return parsed;
-
-  if (typeof parsed === "string") {
-    return parsed + section;
-  }
-  return parsed.then((html) => html + section);
-}

packages/editor-ext/src/lib/markdown/utils/math-block.marked.ts

@@ -1,37 +0,0 @@
-import { Token, marked } from 'marked';
-
-interface MathBlockToken {
-  type: 'mathBlock';
-  text: string;
-  raw: string;
-}
-
-export const mathBlockExtension = {
-  name: 'mathBlock',
-  level: 'block',
-  start(src: string) {
-    return src.match(/\$\$/)?.index ?? -1;
-  },
-  tokenizer(src: string): MathBlockToken | undefined {
-    const rule = /^\$\$(?!(\$))([\s\S]+?)\$\$/;
-    const match = rule.exec(src);
-
-    if (match) {
-      return {
-        type: 'mathBlock',
-        raw: match[0],
-        text: match[2]?.trim(),
-      };
-    }
-  },
-  renderer(token: Token) {
-    const mathBlockToken = token as MathBlockToken;
-    // parse to prevent escaping slashes
-    const latex = marked
-      .parse(mathBlockToken.text)
-      .toString()
-      .replace(/<(\/)?p>/g, '');
-
-    return `<div data-type="${mathBlockToken.type}" data-katex="true">${latex}</div>`;
-  },
-};

packages/editor-ext/src/lib/markdown/utils/math-inline.marked.falsepositive.test.ts

@@ -1,50 +0,0 @@
-import { describe, it, expect } from "vitest";
-import { markdownToHtml } from "./marked.utils";
-
-/**
- * Data-integrity regression (issue #204, Phase 2): plain prose that mentions
- * prices like `$5 and $6` must NOT be misread as inline math. The inline-math
- * tokenizer mutates a global `marked` singleton at import time
- * (`marked.utils.ts`), so math behaviour can only be exercised safely through
- * the public `markdownToHtml`; importing the tokenizer in isolation would give
- * a different, non-representative result. These assertions therefore drive the
- * real conversion path.
- */
-function html(md: string): string {
-  const out = markdownToHtml(md);
-  if (typeof out !== "string") throw new Error("expected sync string output");
-  return out;
-}
-
-const MATH_MARKERS = ['data-type="mathInline"', 'data-katex="true"'];
-
-function hasInlineMath(out: string): boolean {
-  return MATH_MARKERS.some((m) => out.includes(m));
-}
-
-describe("markdownToHtml: inline-math false positives", () => {
-  it("does not treat prices `$5 and $6` as inline math", () => {
-    const out = html("It costs $5 and $6 today.");
-    expect(hasInlineMath(out)).toBe(false);
-    // The text survives verbatim (no katex span swallowing it).
-    expect(out).toContain("$5 and $6");
-  });
-
-  it("does not treat a single trailing price `$5` as inline math", () => {
-    const out = html("Lunch was $5.");
-    expect(hasInlineMath(out)).toBe(false);
-    expect(out).toContain("$5");
-  });
-
-  it("does not treat `$5, $6, $7` (multiple prices) as inline math", () => {
-    const out = html("Choose $5, $6, $7 plans.");
-    expect(hasInlineMath(out)).toBe(false);
-  });
-
-  it("STILL converts a genuine inline-math expression `$x + y$`", () => {
-    // Guard the positive path so the false-positive guard above can't be
-    // satisfied by simply disabling math entirely.
-    const out = html("The sum $x + y$ is shown.");
-    expect(hasInlineMath(out)).toBe(true);
-  });
-});

packages/editor-ext/src/lib/markdown/utils/math-inline.marked.ts

@@ -1,55 +0,0 @@
-import { Token, marked } from 'marked';
-
-interface MathInlineToken {
-  type: 'mathInline';
-  text: string;
-  raw: string;
-}
-
-const inlineMathRegex = /^\$(?!\s)(.+?)(?<!\s)\$(?!\d)/;
-
-export const mathInlineExtension = {
-  name: 'mathInline',
-  level: 'inline',
-  start(src: string) {
-    let index: number;
-    let indexSrc = src;
-
-    while (indexSrc) {
-      index = indexSrc.indexOf('$');
-      if (index === -1) {
-        return;
-      }
-      const f = index === 0 || indexSrc.charAt(index - 1) === ' ';
-      if (f) {
-        const possibleKatex = indexSrc.substring(index);
-        if (possibleKatex.match(inlineMathRegex)) {
-          return index;
-        }
-      }
-
-      indexSrc = indexSrc.substring(index + 1).replace(/^\$+/, '');
-    }
-  },
-  tokenizer(src: string): MathInlineToken | undefined {
-    const match = inlineMathRegex.exec(src);
-
-    if (match) {
-      return {
-        type: 'mathInline',
-        raw: match[0],
-        text: match[1]?.trim(),
-      };
-    }
-  },
-  renderer(token: Token) {
-    const mathInlineToken = token as MathInlineToken;
-    // parse to prevent escaping slashes
-    const latex = marked
-      .parse(mathInlineToken.text)
-      .toString()
-      .replace(/<(\/)?p>/g, '');
-
-    return `<span data-type="${mathInlineToken.type}" data-katex="true">${latex}</span>`;
-  },
-};

packages/editor-ext/src/lib/markdown/utils/spoiler.marked.test.ts

@@ -1,128 +0,0 @@
-import { describe, it, expect } from "vitest";
-import { getSchema } from "@tiptap/core";
-import { generateHTML, generateJSON } from "@tiptap/html";
-import { Document } from "@tiptap/extension-document";
-import { Paragraph } from "@tiptap/extension-paragraph";
-import { Text } from "@tiptap/extension-text";
-import { Bold } from "@tiptap/extension-bold";
-import { htmlToMarkdown } from "./turndown.utils";
-import { markdownToHtml } from "./marked.utils";
-import { Spoiler } from "../../spoiler/spoiler";
-
-// The spoiler mark has no native Markdown syntax, so it is preserved losslessly
-// as raw inline HTML (`<span data-spoiler="true">…</span>`), the same approach
-// htmlEmbed uses. This test drives the full editor round-trip:
-//   JSON -> HTML -> Markdown -> HTML -> JSON
-// and asserts the `spoiler` mark survives end to end. We use the same
-// getSchema + @tiptap/html generateHTML/generateJSON utilities the other
-// editor-ext schema tests use.
-
-const extensions = [Document, Paragraph, Text, Bold, Spoiler];
-
-function html(md: string): string {
-  const out = markdownToHtml(md);
-  if (typeof out !== "string") throw new Error("expected sync string output");
-  return out;
-}
-
-// Count text nodes carrying a `spoiler` mark anywhere in a ProseMirror JSON doc.
-function countSpoilerMarks(doc: any): number {
-  let count = 0;
-  const walk = (node: any) => {
-    if (!node || typeof node !== "object") return;
-    if (Array.isArray(node.marks)) {
-      for (const mark of node.marks) {
-        if (mark?.type === "spoiler") count++;
-      }
-    }
-    if (Array.isArray(node.content)) node.content.forEach(walk);
-  };
-  walk(doc);
-  return count;
-}
-
-describe("Spoiler mark schema", () => {
-  it("registers the spoiler mark in the schema", () => {
-    const schema = getSchema(extensions);
-    expect(schema.marks.spoiler).toBeTruthy();
-  });
-
-  it("recovers the spoiler mark from span[data-spoiler] (HTML -> JSON)", () => {
-    const json = generateJSON(
-      '<p>before <span data-spoiler="true">hidden</span> after</p>',
-      extensions,
-    );
-    expect(countSpoilerMarks(json)).toBe(1);
-  });
-
-  it("emits data-spoiler + class on render (JSON -> HTML)", () => {
-    const doc = {
-      type: "doc",
-      content: [
-        {
-          type: "paragraph",
-          content: [
-            {
-              type: "text",
-              text: "hidden",
-              marks: [{ type: "spoiler" }],
-            },
-          ],
-        },
-      ],
-    };
-    const out = generateHTML(doc, extensions);
-    expect(out).toContain('data-spoiler="true"');
-    expect(out).toContain('class="spoiler"');
-  });
-});
-
-describe("Spoiler Markdown round-trip is lossless", () => {
-  const docWith = (textNode: any) => ({
-    type: "doc",
-    content: [
-      {
-        type: "paragraph",
-        content: [{ type: "text", text: "before " }, textNode, { type: "text", text: " after" }],
-      },
-    ],
-  });
-
-  it("preserves the spoiler mark through JSON -> MD -> HTML -> JSON", () => {
-    const startDoc = docWith({
-      type: "text",
-      text: "hidden",
-      marks: [{ type: "spoiler" }],
-    });
-
-    // JSON -> HTML
-    const html1 = generateHTML(startDoc, extensions);
-    expect(html1).toContain('data-spoiler="true"');
-
-    // HTML -> Markdown (raw inline HTML, lossless)
-    const md = htmlToMarkdown(html1);
-    expect(md).toContain('<span data-spoiler="true">hidden</span>');
-
-    // MD -> HTML -> JSON (mark restored via parseHTML)
-    const endJson = generateJSON(html(md), extensions);
-    expect(countSpoilerMarks(endJson)).toBe(1);
-    // The visible text survives.
-    expect(JSON.stringify(endJson)).toContain("hidden");
-  });
-
-  it("keeps the spoiler intact when it intersects a bold mark", () => {
-    const startDoc = docWith({
-      type: "text",
-      text: "secret",
-      marks: [{ type: "bold" }, { type: "spoiler" }],
-    });
-
-    const md = htmlToMarkdown(generateHTML(startDoc, extensions));
-    expect(md).toContain("data-spoiler=\"true\"");
-
-    const endJson = generateJSON(html(md), extensions);
-    expect(countSpoilerMarks(endJson)).toBe(1);
-    // Bold survives alongside the spoiler.
-    expect(JSON.stringify(endJson)).toContain('"bold"');
-  });
-});

packages/editor-ext/src/lib/markdown/utils/turndown.d.ts

@@ -1,12 +0,0 @@
-// Map @joplin/turndown types to @types/turndown
-declare module "@joplin/turndown" {
-  import TurndownService from "turndown";
-  export = TurndownService;
-}
-
-declare module "@joplin/turndown-plugin-gfm" {
-  import TurndownService from "turndown";
-  export const tables: TurndownService.Plugin;
-  export const strikethrough: TurndownService.Plugin;
-  export const highlightedCodeBlock: TurndownService.Plugin;
-}

packages/editor-ext/src/lib/markdown/utils/turndown.dataloss.test.ts

@@ -1,147 +0,0 @@
-import { describe, it, expect } from "vitest";
-import { htmlToMarkdown } from "./turndown.utils";
-import { markdownToHtml } from "./marked.utils";
-
-/**
- * #206 mdrt-2 — Markdown export must never SILENTLY drop a block. (FIXED)
- *
- * `htmlToMarkdown` (turndown) historically only registered rules for a fixed
- * set of custom nodes (callout, taskItem, details, math, iframe, htmlEmbed,
- * image, video, footnote). Any other custom node — `transclusionReference`,
- * `pageBreak`, `mention`, `status` — fell through to turndown's default
- * handling: an empty wrapper is "blank" and removed, so the block disappeared
- * from the exported Markdown with no trace, and `mention`/`status` collapsed to
- * bare text, losing their identity (data-id / data-color). The invariant
- * "never silently lose a block" was broken.
- *
- * The fix adds lossless turndown rules that re-emit each of these nodes as raw
- * HTML carrying every `data-*` attribute. Plain-Markdown viewers ignore the
- * inert tag; the import path round-trips it (`markdownToHtml` passes the raw
- * HTML through and each node's `parseHTML` rebuilds the ProseMirror node). These
- * tests assert the surviving contract (the block is preserved AND its identity
- * round-trips back through import).
- */
-describe("htmlToMarkdown — custom nodes are preserved losslessly (#206 mdrt-2)", () => {
-  const wrap = (inner: string) => `<p>before</p>${inner}<p>after</p>`;
-
-  it("preserves a pageBreak block on Markdown export", () => {
-    const md = htmlToMarkdown(
-      wrap('<div data-type="pageBreak" class="page-break"></div>'),
-    );
-    expect(md).toContain("before");
-    expect(md).toContain("after");
-    // The break survives as an inert raw-HTML tag, not silently dropped.
-    expect(md).toMatch(/data-type="pageBreak"/);
-    expect(md).toMatch(/page-?break/i);
-  });
-
-  it("preserves a transclusionReference's identity on Markdown export", () => {
-    const md = htmlToMarkdown(
-      wrap('<div data-type="transclusionReference" data-id="abc"></div>'),
-    );
-    expect(md).toContain("before");
-    expect(md).toContain("after");
-    // The data-id (the only thing that gives the reference identity) survives.
-    expect(md).toContain("abc");
-    expect(md).toMatch(/data-type="transclusionReference"/);
-  });
-
-  it("preserves a mention's data-id (stable identity) on Markdown export", () => {
-    const md = htmlToMarkdown(
-      '<p>hi <span data-type="mention" data-id="u1" data-label="Bob">@Bob</span> there</p>',
-    );
-    // The mention keeps its stable identity (data-id), not just the text.
-    expect(md).toContain("u1");
-    expect(md).toContain("Bob");
-    expect(md).toMatch(/data-type="mention"/);
-  });
-
-  it("preserves a status chip's color on Markdown export", () => {
-    const md = htmlToMarkdown(
-      '<p>s <span data-type="status" data-color="green">Done</span></p>',
-    );
-    // The chip's color (its identity) survives, not just the visible text.
-    expect(md).toContain("green");
-    expect(md).toContain("Done");
-    expect(md).toMatch(/data-type="status"/);
-  });
-
-  // The export form is only lossless if the import path can rebuild it. These
-  // assert the full MD -> HTML round-trip restores the node + its attributes,
-  // which is the marker <-> node contract each `parseHTML` relies on.
-  describe("import round-trip (markdownToHtml restores the node)", () => {
-    it("round-trips a pageBreak through export + import", async () => {
-      const md = htmlToMarkdown(
-        wrap('<div data-type="pageBreak" class="page-break"></div>'),
-      );
-      const html = await markdownToHtml(md);
-      expect(html).toMatch(/<div[^>]*data-type="pageBreak"[^>]*>/);
-      expect(html).toContain("before");
-      expect(html).toContain("after");
-    });
-
-    it("round-trips a transclusionReference (keeps data-id)", async () => {
-      const md = htmlToMarkdown(
-        wrap('<div data-type="transclusionReference" data-id="abc"></div>'),
-      );
-      const html = await markdownToHtml(md);
-      expect(html).toMatch(/<div[^>]*data-type="transclusionReference"[^>]*>/);
-      expect(html).toContain("abc");
-    });
-
-    it("round-trips a mention (keeps data-id + data-label)", async () => {
-      const md = htmlToMarkdown(
-        '<p>hi <span data-type="mention" data-id="u1" data-label="Bob">@Bob</span> there</p>',
-      );
-      const html = await markdownToHtml(md);
-      expect(html).toMatch(/<span[^>]*data-type="mention"[^>]*>/);
-      expect(html).toContain("u1");
-      expect(html).toContain("Bob");
-    });
-
-    it("round-trips a status chip (keeps data-color)", async () => {
-      const md = htmlToMarkdown(
-        '<p>s <span data-type="status" data-color="green">Done</span></p>',
-      );
-      const html = await markdownToHtml(md);
-      expect(html).toMatch(/<span[^>]*data-type="status"[^>]*>/);
-      expect(html).toContain("green");
-    });
-
-    // HTML special chars in an attribute value or in a node's text must be
-    // ESCAPED when re-emitted as raw HTML, otherwise the exported tag is
-    // malformed and `markdownToHtml`'s parser cannot restore the original value
-    // (the same silent data loss this PR fixes). Dropping `<`/`>` escaping is the
-    // dangerous regression: a stray `<` or `>` corrupts the tag (or injects new
-    // markup), so the test data carries ALL of `&`, `"`, `<`, `>` in BOTH the
-    // data-label attribute and the visible text. That fully exercises
-    // escapeHtmlAttr's `&,",<,>` branches and escapeHtmlText's `&,<,>` branches
-    // (escapeHtmlText leaves `"` literal); the alphanumeric-only cases above hit
-    // none of them.
-    it("escapes HTML special chars (& \" < >) in attrs + text and round-trips them", async () => {
-      const md = htmlToMarkdown(
-        `<p>hi <span data-type="mention" data-id="u1" data-label="A &amp; &lt;B&gt; &quot;C&quot;">@A &amp; &lt;B&gt; "C"</span> there</p>`,
-      );
-
-      // (a) The exported Markdown carries a WELL-FORMED, correctly-escaped tag:
-      // the attribute escapes `&`, `<`, `>` AND `"`; the text escapes `&`, `<`,
-      // `>` (a `"` inside text content is legal, so it stays literal).
-      expect(md).toContain('data-label="A &amp; &lt;B&gt; &quot;C&quot;"');
-      expect(md).toContain('>@A &amp; &lt;B&gt; "C"</span>');
-      // And explicitly NOT the raw, tag-corrupting forms: a literal `<B>` (would
-      // mean `<`/`>` escaping was dropped in either the attr or the text)...
-      expect(md).not.toContain("<B>");
-      // ...nor the malformed attribute that an unescaped `"` would produce.
-      expect(md).not.toContain('data-label="A &amp; &lt;B&gt; "C""');
-
-      // (b) Import restores the ORIGINAL (unescaped) values, attribute and text.
-      const html = await markdownToHtml(md);
-      const dom = new DOMParser().parseFromString(html as string, "text/html");
-      const span = dom.querySelector('span[data-type="mention"]');
-      expect(span).not.toBeNull();
-      expect(span!.getAttribute("data-id")).toBe("u1");
-      expect(span!.getAttribute("data-label")).toBe('A & <B> "C"');
-      expect(span!.textContent).toBe('@A & <B> "C"');
-    });
-  });
-});