fix(#345): normalize CRLF before front-matter strip (review round 3)

F9 [WARNING] The line-anchored front-matter regex from round 2 requires a bare
LF after the opening `---`, so a Windows/CRLF foreign file (`---\r\n...`) slips
past the strip and leaks its front-matter into the body (where `title: Foo`
renders as a setext heading that title extraction hijacks). The canonical parser
whose regex shape this copied (page-file.ts) normalizes CRLF -> LF BEFORE its
FRONTMATTER_RE; the import path copied the regex but missed the normalization.
normalizeForeignMarkdown now replaces CRLF with LF first (which also makes
convertReferenceFootnotes' split('\n') consistent). Adds a CRLF fixture.

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

.env.example

@@ -209,6 +209,20 @@ MCP_DOCMOST_PASSWORD=
 # active" behavior.
 # AI_CHAT_DEFERRED_TOOLS=true
 
+# --- Autonomous / detached agent runs (settings.ai.autonomousRuns) ---
+# Opt-in per workspace (AI settings; off by default). When on, a chat turn becomes
+# a server-side RUN that survives a browser disconnect — only an explicit Stop ends
+# it, and a client reconnects/live-follows the run.
+#
+# DEPLOY CONSTRAINT — SINGLE-INSTANCE ONLY in phase 1: Stop and the in-process
+# AbortController that backs it are process-local, so a Stop only aborts a run
+# executing on the SAME replica that owns it (cross-instance pub/sub stop is phase
+# 2 and not yet reliable). Do NOT enable autonomousRuns on a horizontally-scaled
+# deployment (multiple replicas behind a load balancer, or Docmost cloud
+# CLOUD=true) — run a single instance instead. The server logs a startup WARNING
+# when it detects a multi-instance deployment (CLOUD=true) so the constraint is
+# visible, and a startup sweep settles any run left dangling by a restart.
+
 # --- Anonymous public-share AI assistant ---
 # Opt-in per workspace (AI settings -> "public share assistant"; off by default).
 # When enabled, anonymous visitors of a published share can ask an AI about that
@@ -242,3 +256,27 @@ MCP_DOCMOST_PASSWORD=
 # FAILS CLOSED if Redis is unavailable (default: 1,000,000 tokens per workspace
 # per rolling day).
 # SHARE_AI_WORKSPACE_TOKEN_BUDGET_PER_DAY=1000000
+
+# --- Observability / perf metrics (#355) ---
+#
+# Two INDEPENDENT toggles, both OFF by default:
+#
+# 1) METRICS_PORT — the server-side Prometheus scrape endpoint.
+#    UNSET (default) => the whole prom subsystem is OFF: no registry, no
+#    collectors, and NOTHING is exposed on the main app port. There is NO
+#    default port — leaving it blank disables it. When set to a port (e.g.
+#    9464), a SEPARATE bare node:http listener serves GET /metrics on that port
+#    only (never on the main :3000 app listener), for a scraper such as
+#    VictoriaMetrics/Prometheus reaching it as <host>:<port>/metrics.
+# METRICS_PORT=9464
+#
+# 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
+#    metrics into the `client_metrics` table (read directly by Grafana, separate
+#    from METRICS_PORT). Leave OFF unless you actually consume this data: the
+#    endpoint is public and the table has NO app-side retention, so enabling it
+#    requires an EXTERNAL pruner to bound `client_metrics` growth (the deployed
+#    infra prunes rows >90d via a maintenance container). When off, the endpoint
+#    does not exist and the client installs no observers.
+# CLIENT_TELEMETRY_ENABLED=false

.github/workflows/develop.yml

@@ -18,12 +18,48 @@ env:
   IMAGE: ghcr.io/vvzvlad/gitmost
 
 jobs:
-  # Run the reusable test suite first so a failing test blocks the image build.
+  # Run the reusable test suite. Together with the e2e jobs below it gates the
+  # publish job (the image push), not the build itself — build runs in parallel.
   test:
     uses: ./.github/workflows/test.yml
 
+  # Runs in parallel with the test/e2e jobs and only warms the buildx cache
+  # (GHA cache, scope develop-amd64). No push happens here — the publish job
+  # below is the only one that pushes the image.
   build:
-    needs: test
+    runs-on: ubuntu-latest
+    timeout-minutes: 30
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v4
+        with:
+          fetch-depth: 0
+
+      - name: Set up Docker Buildx
+        uses: docker/setup-buildx-action@v3
+
+      - name: Resolve version
+        id: version
+        run: echo "value=$(git describe --tags --always)" >> "$GITHUB_OUTPUT"
+
+      - name: Build develop image (warm cache, no push)
+        uses: docker/build-push-action@v6
+        with:
+          context: .
+          platforms: linux/amd64
+          build-args: |
+            APP_VERSION=${{ steps.version.outputs.value }}
+            AI_AGENT_ROLES_CATALOG_URL=https://raw.githubusercontent.com/vvzvlad/gitmost/develop/agent-roles-catalog
+          push: false
+          cache-from: type=gha,scope=develop-amd64
+          cache-to: type=gha,scope=develop-amd64,mode=max,ignore-error=true
+
+  # The gate: rebuilds from the cache the build job just wrote (near-instant on
+  # a cache hit; worst case — cache eviction — a full rebuild, which matches the
+  # old sequential timing) and pushes :develop only when unit tests AND both
+  # e2e suites AND the build are green.
+  publish:
+    needs: [test, e2e-server, e2e-mcp, build]
     runs-on: ubuntu-latest
     timeout-minutes: 30
     steps:
@@ -57,13 +93,10 @@ jobs:
           push: true
           tags: ${{ env.IMAGE }}:develop
           cache-from: type=gha,scope=develop-amd64
-          cache-to: type=gha,scope=develop-amd64,mode=max,ignore-error=true
 
-  # e2e jobs run on every develop push but DO NOT gate the build/publish above:
-  # `build` stays `needs: test` only, so the :develop image still ships even if
-  # e2e fails. A failing e2e job turns the run red and triggers GitHub's email
-  # to the pusher — that red run + email is the intended notification, not a
-  # deploy block.
+  # e2e jobs gate the publish (image push), not the build: the :develop image
+  # is pushed only when unit tests AND both e2e suites pass (publish.needs
+  # lists them all).
   e2e-server:
     runs-on: ubuntu-latest
     # Hard cap: the full-AppModule e2e leaks open handles and hung jest to the 6h max.
@@ -124,9 +157,7 @@ jobs:
       - name: Run server e2e
         run: pnpm --filter ./apps/server test:e2e
 
-  # Same rationale as e2e-server: this job is intentionally NOT in
-  # `build.needs`. Deploy of the :develop image must not be blocked by e2e;
-  # a red run plus GitHub's email to the pusher is the notification mechanism.
+  # Gates the publish too — see the comment above e2e-server.
   e2e-mcp:
     runs-on: ubuntu-latest
     timeout-minutes: 20

AGENTS.md

@@ -201,7 +201,7 @@ 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` and `git-sync`; there is exactly ONE copy of the converter now |
+| `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 |
 
 `build` targets are Nx-cached and dependency-ordered (`dependsOn: ["^build"]`), so `editor-ext` builds before the apps. `nx.json` sets `affected.defaultBase: main`.
 
@@ -279,11 +279,12 @@ The API server is a Fastify app with a global `/api` prefix (`main.ts` excludes
    - `core/ai-chat/tools/` — the agent's ~40 read+write tools. Every tool runs under the **calling user's** CASL permissions via a per-user loopback access token (`docmost-client.loader.ts`), so the agent can never exceed what the user could do. Only **reversible** operations are exposed (page history + trash; no permanent delete). Agent edits get an "AI agent" provenance badge in page history (`20260616T130000-agent-provenance` migration).
    - `core/ai-chat/embedding/` — RAG indexer + a BullMQ consumer on `AI_QUEUE` that embeds pages into `page_embeddings` (vector search), complementing Postgres full-text search. Pages are (re)indexed on edit; `AI_EMBEDDING_TIMEOUT_MS` bounds a hung embeddings endpoint.
    - `core/ai-chat/external-mcp/` — admins can attach external MCP servers (e.g. Tavily) to give the agent web access. **`ssrf-guard.ts` validates outbound MCP URLs against SSRF** — keep that guard in the path when touching external-MCP connection logic.
+   - `core/ai-chat/ai-chat-run.service.ts` + `ai_chat_runs` — **detached/autonomous agent runs** (`#184`), behind the per-workspace `settings.ai.autonomousRuns` flag (off by default). When on, a turn becomes a server-side RUN that survives a browser disconnect; only an explicit `POST /ai-chat/stop` ends it, and a client reconnects/live-follows via `POST /ai-chat/run`. **DEPLOY CONSTRAINT — single-instance only in phase 1:** Stop and the AbortController that backs it are process-local, so a Stop only aborts a run executing on the **same** replica that owns it (cross-instance pub/sub stop is phase 2). Do **not** enable `autonomousRuns` on a horizontally-scaled deployment (multiple replicas behind a load balancer, or Docmost cloud `CLOUD=true`) — run a single instance instead. The server logs a startup WARNING when it detects a multi-instance deployment (`CLOUD=true`) so the constraint is visible. The startup sweep settles any run left dangling by a restart.
 
 ### 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, import/export) — editor schema changes often need to be made in `editor-ext`, not just the client. The ProseMirror↔Markdown converter and its Docmost schema mirror now live in a SINGLE package, `@docmost/prosemirror-markdown` (#293), consumed by both `mcp` and `git-sync` — 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.
+- 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.
 - 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`.
 

CHANGELOG.md

@@ -72,6 +72,19 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   append/prepend fragments, nor to COMMENT bodies — a comment may legitimately
   contain a standalone footnote definition, which canonicalization would drop.
   (#228)
+- **Detached, autonomous agent runs that survive a browser disconnect.** When the
+  new `settings.ai.autonomousRuns` workspace flag is on (off by default), an
+  AI-chat turn becomes a first-class, server-side RUN tracked in a new
+  `ai_chat_runs` table instead of a socket-bound stream: closing the tab or
+  losing the connection no longer aborts the turn — it keeps executing and
+  persisting server-side, and only an explicit Stop ends it. A client can
+  reconnect and live-follow (or stop) an in-flight run via `POST /ai-chat/run`
+  (resolve the latest run + its assistant message for a chat) and
+  `POST /ai-chat/stop` (stop by `runId` or `chatId`). A partial unique index
+  enforces one active run per chat, and a startup sweep settles any run left
+  dangling by a restart. Phase 1 is single-instance-only (cross-instance Stop is
+  not yet reliable); the server warns at startup on a horizontally-scaled
+  deployment. (#184)
 - **Out-of-band page transfer via an in-RAM blob sandbox (`stash_page`).** A
   new MCP tool serializes a whole page (its full ProseMirror JSON, with every
   internal image/file mirrored) into an ephemeral in-RAM blob and returns only

Dockerfile

@@ -5,6 +5,13 @@ RUN npm install -g pnpm@10.4.0
 
 FROM base AS builder
 
+# re2 (packages/mcp) always compiles from source under pnpm (the prebuilt-binary
+# download cannot identify the GitHub repo), so node-gyp needs python3/make/g++.
+# This stage is discarded, so the toolchain can stay installed.
+RUN apt-get update \
+  && apt-get install -y --no-install-recommends python3 make g++ \
+  && rm -rf /var/lib/apt/lists/*
+
 WORKDIR /app
 
 COPY . .
@@ -57,9 +64,16 @@ COPY --from=builder /app/patches /app/patches
 
 RUN chown -R node:node /app
 
-USER node
+# Toolchain is needed transiently to compile re2 during the prod install; install
+# and purge it in one layer to keep the final image slim. The install itself runs
+# as the node user via su to keep node_modules ownership without a costly chown layer.
+RUN apt-get update \
+  && apt-get install -y --no-install-recommends python3 make g++ \
+  && su node -c "pnpm install --frozen-lockfile --prod" \
+  && apt-get purge -y --auto-remove python3 make g++ \
+  && rm -rf /var/lib/apt/lists/*
 
-RUN pnpm install --frozen-lockfile --prod
+USER node
 
 RUN mkdir -p /app/data/storage
 

apps/client/package.json

@@ -61,6 +61,7 @@
     "react-clear-modal": "^2.0.18",
     "react-dom": "^18.3.1",
     "react-drawio": "1.0.7",
+    "web-vitals": "^5.1.0",
     "react-error-boundary": "6.1.1",
     "react-helmet-async": "3.0.0",
     "react-i18next": "16.5.8",
@@ -97,7 +98,6 @@
     "typescript": "5.9.3",
     "typescript-eslint": "8.57.1",
     "vite": "8.0.5",
-    "vite-plugin-compression2": "2.5.3",
     "vitest": "4.1.6"
   }
 }

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

@@ -19,7 +19,7 @@ import {
   IconPlus,
   IconX,
 } from "@tabler/icons-react";
-import { useAtom, useSetAtom } from "jotai";
+import { useAtom, useAtomValue, useSetAtom } from "jotai";
 import { useLocation, useMatch } from "react-router-dom";
 import { useTranslation } from "react-i18next";
 import { useQueryClient } from "@tanstack/react-query";
@@ -41,13 +41,24 @@ import { extractPageSlugId } from "@/lib";
 import {
   AI_CHATS_RQ_KEY,
   AI_CHAT_MESSAGES_RQ_KEY,
+  AI_CHAT_RUN_RQ_KEY,
   useAiChatMessagesQuery,
+  useAiChatRunQuery,
   useAiChatsQuery,
   useAiRolesQuery,
 } from "@/features/ai-chat/queries/ai-chat-query.ts";
+import {
+  shouldClearLatchOnQueryError,
+  shouldClearStoppingLatch,
+  shouldObserveRun,
+} from "@/features/ai-chat/utils/run-polling.ts";
+import { workspaceAtom } from "@/features/user/atoms/current-user-atom";
 import ConversationList from "@/features/ai-chat/components/conversation-list.tsx";
 import ChatThread from "@/features/ai-chat/components/chat-thread.tsx";
-import { exportAiChat } from "@/features/ai-chat/services/ai-chat-service.ts";
+import {
+  exportAiChat,
+  stopRun,
+} from "@/features/ai-chat/services/ai-chat-service.ts";
 import { useChatSession } from "@/features/ai-chat/hooks/use-chat-session.ts";
 import {
   shouldCollapseOnOutsidePointer,
@@ -234,6 +245,147 @@ export default function AiChatWindow() {
   const { data: messageRows, isLoading: messagesLoading } =
     useAiChatMessagesQuery(activeChatId ?? undefined);
 
+  // #184 reconnect-and-live-follow. Whether detached agent runs are enabled for
+  // this workspace. The reconnect endpoint itself is NOT flag-gated server-side
+  // (it is only owner-gated and returns `{ run: null }` when the chat has no
+  // run); but when the feature is off no runs are ever created, so polling it
+  // would always come back empty — we gate it off here to avoid pointless polls.
+  const workspace = useAtomValue(workspaceAtom);
+  const autonomousRunsEnabled =
+    workspace?.settings?.ai?.autonomousRuns === true;
+
+  // Whether THIS tab is the one actively streaming the open chat's run locally
+  // (it started the run here and holds the SSE). Reported up from ChatThread. We
+  // are the STREAMER while true and a passive OBSERVER while false — the basis of
+  // the observer-vs-streamer detection. Reset to false by the fresh ChatThread's
+  // mount effect on every chat switch.
+  const [localStreaming, setLocalStreaming] = useState(false);
+  const onStreamingChange = useCallback((streaming: boolean) => {
+    setLocalStreaming(streaming);
+  }, []);
+
+  // #184 Stop wiring. While a detached run is being stopped we SUPPRESS the
+  // observer merge so the stopping run's still-persisting output does not
+  // re-stream back into view between the moment the user pressed Stop and the run
+  // actually settling as 'aborted' server-side. Polling itself keeps running (so
+  // the terminal transition is still detected) — only the visual merge is gated.
+  // Cleared when the run is observed terminal (below) or the chat is switched.
+  const [stoppingRun, setStoppingRun] = useState(false);
+  // Reset the stopping latch whenever the open chat changes: it is scoped to the
+  // run of the previously-open chat.
+  useEffect(() => {
+    setStoppingRun(false);
+  }, [activeChatId]);
+
+  // Authoritative stop of the open chat's detached run (the Stop button in
+  // autonomous mode). Latch "stopping" first (suppresses the re-stream flash),
+  // then request the server stop — the ONLY thing that ends a detached run; a mere
+  // local SSE abort is a client disconnect the server ignores. On failure we
+  // release the latch so the observer resumes (better to show the live run than to
+  // freeze the view) and surface the error.
+  const handleServerStop = useCallback(
+    (chatId: string): void => {
+      setStoppingRun(true);
+      // #234 F4: drop the PREVIOUS turn's run from the cache so `run` becomes null
+      // until the CURRENT turn's run is fetched fresh. Without this, once the local
+      // stream aborts (localStreaming -> false) the run query re-enables and
+      // react-query SYNCHRONOUSLY returns the still-cached prior terminal run; the
+      // terminal effect would then clear the stopping latch against that STALE run
+      // before the current turn's (still-running, detached, growing) run is ever
+      // observed — re-opening the observer merge and flashing the growing output
+      // over the frozen row. With the cache cleared the terminal effect's
+      // `if (!run) return` holds the latch until the current run itself is observed
+      // terminal (see shouldClearStoppingLatch).
+      queryClient.removeQueries({ queryKey: AI_CHAT_RUN_RQ_KEY(chatId) });
+      void stopRun(chatId).catch(() => {
+        setStoppingRun(false);
+        notifications.show({
+          message: t("Failed to stop the run"),
+          color: "red",
+        });
+      });
+    },
+    [t, queryClient],
+  );
+
+  // Poll the latest run of the open chat ONLY when we are a passive observer:
+  // feature on, a chat is open, and we are NOT the local streamer (the streamer
+  // already has the live SSE — polling/merging too would double-render). The
+  // query's own status-keyed refetchInterval stops once the run is terminal.
+  const { data: runData, isError: runQueryFailed } = useAiChatRunQuery(
+    activeChatId ?? undefined,
+    autonomousRunsEnabled && !localStreaming,
+  );
+  const run = runData?.run ?? null;
+
+  // Safety net (#234 F4 review): after handleServerStop clears the run cache,
+  // `run` is null until the current turn's run is fetched fresh, and the terminal
+  // effect below holds the latch via `if (!run) return`. If that refetch instead
+  // ERRORS PERMANENTLY (the GET-run keeps failing) while we are no longer the
+  // streamer, the run stays null, its status-keyed refetchInterval is off, and
+  // nothing would ever observe a terminal run — freezing the view with the
+  // observer merge suppressed. Release the latch on that error so the live view
+  // resumes rather than stays stuck (the local stopRun may already have succeeded
+  // independently).
+  //
+  // #234 F7: this must NOT fire on a TRANSIENT error while `run` is still an
+  // ACTIVE held run. In TanStack Query v5 (retry:false) the query's `data` is
+  // RETAINED on error, so `runQueryFailed` can be true while `run` is still
+  // pending/running — releasing then would re-open the observer merge and flash
+  // the growing detached run over the frozen row (the very flash F4 prevents). The
+  // decision is the pure, unit-tested `shouldClearLatchOnQueryError`, which gates
+  // on the run NOT being active: it cures only the genuine permanent-null-freeze
+  // (`run === null`) and never releases against an active run.
+  useEffect(() => {
+    if (
+      shouldClearLatchOnQueryError({
+        stoppingRun,
+        isLocalStreaming: localStreaming,
+        runQueryFailed,
+        run,
+      })
+    )
+      setStoppingRun(false);
+  }, [stoppingRun, localStreaming, runQueryFailed, run]);
+  // The run's incrementally-persisted assistant message to merge into the thread,
+  // but only while we are an observer (never when we are the streamer — guards
+  // against a stale poll fighting the live stream). Includes a terminal run so the
+  // final persisted output is shown on reopen.
+  const observedRow =
+    shouldObserveRun(run, localStreaming) && !stoppingRun
+      ? (runData?.message ?? null)
+      : null;
+
+  // When the observed run reaches a terminal status, do a final messages refetch
+  // so the persisted final state (token/context badge, export source) is shown,
+  // then the query's refetchInterval has already stopped polling. Deduped per run
+  // id so it fires exactly once per run, not on every subsequent poll-less render.
+  const finalizedRunIdRef = useRef<string | null>(null);
+  useEffect(() => {
+    if (!run || !activeChatId) return;
+    if (run.status === "pending" || run.status === "running") {
+      // Active again (a new run) — re-arm so its terminal transition fires once.
+      finalizedRunIdRef.current = null;
+      return;
+    }
+    // Terminal: a stop we requested has landed (or the run finished on its own),
+    // so release the stopping latch — the observer merge can now show the final
+    // persisted (aborted/finished) output without any live re-stream. The decision
+    // is the pure, unit-tested `shouldClearStoppingLatch` (run-polling.ts): release
+    // ONLY when we requested a stop, this tab is no longer the streamer, AND the
+    // CURRENT run is terminal. The #234 F4 cache removal in handleServerStop makes
+    // `run` null (this branch's `if (!run) return` above holds) until the current
+    // turn's run is fetched fresh, so the latch can never clear against a stale
+    // cached run.
+    if (shouldClearStoppingLatch({ stoppingRun, run, isLocalStreaming: localStreaming }))
+      setStoppingRun(false);
+    if (finalizedRunIdRef.current === run.id) return;
+    finalizedRunIdRef.current = run.id;
+    queryClient.invalidateQueries({
+      queryKey: AI_CHAT_MESSAGES_RQ_KEY(activeChatId),
+    });
+  }, [run, activeChatId, queryClient, stoppingRun, localStreaming]);
+
   // The page the user is currently viewing. AiChatWindow lives in a pathless
   // parent layout route, so useParams() can't see :pageSlug. Match the full
   // pathname against the authenticated page route instead so "the current page"
@@ -882,6 +1034,18 @@ export default function AiChatWindow() {
               assistantName={currentRole?.name}
               onTurnFinished={onTurnFinished}
               onServerChatId={onServerChatId}
+              // #184: live-follow a still-running run when we reopened the chat as
+              // a passive observer; null when there is nothing to observe or this
+              // tab is the streamer. onStreamingChange lets the window stop polling
+              // while we are the streamer.
+              observedRow={observedRow}
+              onStreamingChange={onStreamingChange}
+              // #184: in autonomous mode the Stop button must hit the authoritative
+              // server stop (a local SSE abort is a client disconnect the server
+              // ignores). onServerStop also arms the "stopping" latch above so the
+              // stopped run's output does not re-stream via the observer merge.
+              autonomousRunsEnabled={autonomousRunsEnabled}
+              onServerStop={handleServerStop}
             />
           )}
         </div>

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

@@ -11,6 +11,7 @@ const h = vi.hoisted(() => ({
     onFinish: null as null | ((arg: Record<string, unknown>) => void),
     sendMessage: vi.fn(),
     stop: vi.fn(),
+    setMessages: vi.fn(),
     transport: null as null | {
       prepareSendMessagesRequest: (arg: {
         messages: unknown[];
@@ -30,6 +31,8 @@ vi.mock("@ai-sdk/react", () => ({
       status: h.state.status,
       stop: h.state.stop,
       error: null,
+      // #184: ChatThread reads setMessages to merge a polled observer run.
+      setMessages: h.state.setMessages,
     };
   },
 }));
@@ -228,3 +231,56 @@ describe("ChatThread — turn-end decision (onFinish)", () => {
     }
   });
 });
+
+// #184 passive-observer merge: when reconnecting to a still-running run, the
+// parent feeds the polled run message via `observedRow`; ChatThread merges it via
+// setMessages — but ONLY when this tab is NOT itself streaming (the streamer's
+// SSE owns the view, so a stale observedRow must never overwrite it).
+describe("ChatThread — observer run merge (#184)", () => {
+  beforeEach(() => {
+    h.state.onFinish = null;
+    h.state.setMessages.mockReset();
+  });
+
+  const observedRow = {
+    id: "a-run",
+    role: "assistant",
+    content: "step 1\nstep 2",
+    metadata: {
+      parts: [{ type: "text", text: "step 1\nstep 2" }],
+    },
+    createdAt: "2026-01-01T00:00:00Z",
+  } as const;
+
+  function renderObserver(status: string) {
+    h.state.status = status;
+    render(
+      <MantineProvider>
+        <ChatThread
+          chatId="c1"
+          initialRows={[]}
+          onTurnFinished={vi.fn()}
+          observedRow={observedRow as never}
+        />
+      </MantineProvider>,
+    );
+  }
+
+  it("merges the polled run message when this tab is a passive observer", () => {
+    renderObserver("ready");
+    expect(h.state.setMessages).toHaveBeenCalledTimes(1);
+    // The updater replaces/append the observed assistant row by id.
+    const updater = h.state.setMessages.mock.calls[0][0] as (
+      prev: { id: string; parts: { text: string }[] }[],
+    ) => { id: string; parts: { text: string }[] }[];
+    const merged = updater([{ id: "u1", parts: [{ text: "hi" }] }]);
+    expect(merged).toHaveLength(2);
+    expect(merged[1].id).toBe("a-run");
+    expect(merged[1].parts[0].text).toBe("step 1\nstep 2");
+  });
+
+  it("does NOT merge while THIS tab is the streamer (no double-render)", () => {
+    renderObserver("streaming");
+    expect(h.state.setMessages).not.toHaveBeenCalled();
+  });
+});

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

@@ -24,6 +24,7 @@ import {
 } from "@/features/ai-chat/utils/role-launch.ts";
 import { describeChatError } from "@/features/ai-chat/utils/error-message.ts";
 import { extractServerChatId } from "@/features/ai-chat/utils/adopt-chat-id.ts";
+import { mergeObservedMessage } from "@/features/ai-chat/utils/run-polling.ts";
 import {
   dequeue,
   enqueueMessage,
@@ -86,6 +87,29 @@ interface ChatThreadProps {
    *  Copy/export button available mid-stream). Distinct from onTurnFinished,
    *  which fires only at the terminal outcome. */
   onServerChatId?: (serverChatId?: string) => void;
+  /** #184 reconnect-and-live-follow. When THIS tab reopened a chat whose agent
+   *  run is still going (it is a PASSIVE OBSERVER — it did not start the run here),
+   *  the parent polls the reconnect endpoint and feeds the run's incrementally-
+   *  persisted assistant message here; we merge it into the live list so new
+   *  steps/tool-calls appear as they are persisted. Null when there is nothing to
+   *  observe (no run, feature off, or this tab IS the streamer). The merge is
+   *  ADDITIONALLY guarded by our own `isStreaming`, so a stale value can never
+   *  fight the local stream when we are the streamer. */
+  observedRow?: IAiChatMessageRow | null;
+  /** Report this tab's live streaming status up to the parent, so it can stop
+   *  polling the run while WE are the active streamer (the SSE owns the view) and
+   *  resume once we go idle. Called from an effect on every transition. */
+  onStreamingChange?: (streaming: boolean) => void;
+  /** #184: whether detached/autonomous agent runs are enabled for this workspace.
+   *  When true the Stop button must additionally hit the AUTHORITATIVE server stop
+   *  (via onServerStop) — aborting only the local SSE is just a client disconnect,
+   *  which the server deliberately ignores, so the detached run would keep going. */
+  autonomousRunsEnabled?: boolean;
+  /** #184: request the server-side stop of this chat's active run (the parent owns
+   *  the endpoint call + the "stopping" latch that keeps observer-polling from
+   *  immediately re-streaming the stopping run's output). Called with the resolved
+   *  chat id when the user presses Stop in autonomous mode. */
+  onServerStop?: (chatId: string) => void;
 }
 
 /**
@@ -131,6 +155,10 @@ export default function ChatThread({
   assistantName,
   onTurnFinished,
   onServerChatId,
+  observedRow,
+  onStreamingChange,
+  autonomousRunsEnabled,
+  onServerStop,
 }: ChatThreadProps) {
   const { t } = useTranslation();
 
@@ -216,6 +244,16 @@ export default function ChatThread({
   const flushOnAbortRef = useRef(false);
   const interruptNextSendRef = 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
+  // autonomous run — it keeps burning tokens and WRITING TO PAGES — so we cannot
+  // just no-op. We latch the stop as PENDING and fire the authoritative server
+  // stop the moment onServerChatId adopts the id (below). Read-and-cleared there;
+  // also defused on every new turn start so it can never fire against a later,
+  // unrelated turn's run.
+  const stopPendingRef = useRef(false);
+
   // FIFO dequeue + send the next queued message (no-op when the queue is empty).
   // Returns whether a message was actually sent, so callers can tell an empty
   // dequeue (nothing to flush) from a real send.
@@ -274,7 +312,7 @@ export default function ChatThread({
     [],
   );
 
-  const { messages, sendMessage, status, stop, error } = useChat({
+  const { messages, sendMessage, status, stop, error, setMessages } = useChat({
     // Stable per-mount key. Existing chats use their real id; new chats use a
     // generated client id (never `undefined`) so the store is NOT re-created on
     // every render mid-stream (see `chatStoreId` above).
@@ -365,7 +403,14 @@ export default function ChatThread({
       return;
     lastForwardedChatIdRef.current = serverChatId;
     onServerChatId(serverChatId);
-  }, [messages, onServerChatId]);
+    // #234 F5: if Stop was pressed before the id was known, the authoritative
+    // server stop was deferred to this adoption point — fire it now with the
+    // just-adopted id. One-shot (read-and-clear) so it can't fire twice.
+    if (stopPendingRef.current) {
+      stopPendingRef.current = false;
+      onServerStop?.(serverChatId);
+    }
+  }, [messages, onServerChatId, onServerStop]);
 
   // Live "turn was interrupted" marker for the CURRENT session. The red error
   // banner (driven by `error`) covers the error case; this covers an aborted
@@ -378,6 +423,27 @@ export default function ChatThread({
 
   const isStreaming = status === "submitted" || status === "streaming";
 
+  // #184: report our live streaming status up so the parent stops polling the run
+  // while WE are the streamer (the SSE owns the view) and resumes once we go idle.
+  // Effect (not render) so it never updates parent state during our own render;
+  // fires on mount with `false`, which also re-syncs the parent after a chat
+  // switch remounts this thread (a fresh mount is idle until the user sends).
+  useEffect(() => {
+    onStreamingChange?.(isStreaming);
+  }, [isStreaming, onStreamingChange]);
+
+  // #184 passive-observer merge: when the parent feeds a polled run message (we
+  // reopened a chat whose run is still going and did NOT start it here), merge it
+  // into the live list so new steps/tool-calls appear as they are persisted. Hard-
+  // gated by `!isStreaming`: if THIS tab is actually the streamer, the local SSE
+  // owns the view and a stale observedRow must never overwrite it. `observedRow`
+  // is a stable per-poll object, so this runs once per poll, not per render.
+  useEffect(() => {
+    if (isStreaming || !observedRow) return;
+    const observed = rowToUiMessage(observedRow);
+    setMessages((prev) => mergeObservedMessage(prev, observed));
+  }, [observedRow, isStreaming, setMessages]);
+
   // "Send now" on a queued message: interrupt the current turn and immediately
   // send THIS message, keeping the agent's partial output. Other queued messages
   // stay queued and flush normally after the new turn. Reuses the existing
@@ -409,6 +475,40 @@ export default function ChatThread({
     [setQueue, stop],
   );
 
+  // Stop the current turn. ALWAYS abort the local SSE (`stop()`) so the composer
+  // returns to idle immediately. In AUTONOMOUS mode the turn is a DETACHED run:
+  // aborting the local SSE is only a client disconnect, which the server ignores,
+  // so the run would keep executing — we ADDITIONALLY request the authoritative
+  // server-side stop (the parent owns that call + the "stopping" latch that keeps
+  // observer-polling from re-streaming the stopping run's output). The chat id is
+  // read live from chatIdRef (adopted early at the stream's `start` chunk); if it
+  // is not known yet — a brand-new chat in the first moment of its first turn —
+  // only the local abort happens (there is no server-side run handle to stop yet).
+  const handleStop = useCallback(() => {
+    stop();
+    if (!autonomousRunsEnabled) return;
+    if (chatIdRef.current) {
+      onServerStop?.(chatIdRef.current);
+    } else {
+      // #234 F5: no chat id yet (brand-new chat in the first moment of its first
+      // turn, before the `start` chunk adopted the id). Latch the stop as pending;
+      // the onServerChatId adoption effect fires the deferred server stop as soon
+      // as the id appears, so the detached run is still authoritatively stopped
+      // instead of left running by a silent local-only abort.
+      //
+      // KNOWN LIMITATION (#234 F5 review): `stop()` above has already aborted the
+      // local SSE reader. In the rare sub-window where Stop is pressed while still
+      // `submitted` (request sent, not one chunk read yet), that abort can cancel
+      // the reader BEFORE the `start` chunk is applied to `messages`, so the
+      // adoption effect never runs and this pending stop never fires. The detached
+      // run then keeps going for that turn. This is not a regression (the pre-fix
+      // behavior sent no server stop at all); closing it fully would require
+      // deferring the local abort until adoption, which is riskier and out of scope
+      // for this fix. Documented so a future change can address the abort-ordering.
+      stopPendingRef.current = true;
+    }
+  }, [stop, autonomousRunsEnabled, onServerStop]);
+
   // Clear the stopped marker as soon as a new turn begins streaming, and drop any
   // stale "Send now" interrupt flags. On the legit interrupt path both refs are
   // already consumed synchronously (onFinish + prepareSendMessagesRequest) before
@@ -420,6 +520,11 @@ export default function ChatThread({
       setStopNotice(null);
       flushOnAbortRef.current = false;
       interruptNextSendRef.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
+      // set AFTER this effect (on the Stop click), so this does not clobber it.
+      stopPendingRef.current = false;
     }
   }, [isStreaming]);
 
@@ -539,7 +644,7 @@ export default function ChatThread({
         <ChatInput
           onSend={(text) => sendMessage({ text })}
           onQueue={enqueue}
-          onStop={stop}
+          onStop={handleStop}
           isStreaming={isStreaming}
         />
       </Stack>

apps/client/src/features/ai-chat/queries/ai-chat-query.ts

@@ -12,6 +12,7 @@ import {
   deleteAiChat,
   deleteAiRole,
   getAiChatMessages,
+  getAiChatRun,
   getAiChats,
   getAiRoleCatalog,
   getAiRoleCatalogBundle,
@@ -24,6 +25,7 @@ import {
 import {
   IAiChat,
   IAiChatMessageRow,
+  IAiChatRunResponse,
   IAiRole,
   IAiRoleCatalog,
   IAiRoleCatalogBundle,
@@ -34,6 +36,7 @@ import {
   IAiRoleUpdateFromCatalogResult,
 } from "@/features/ai-chat/types/ai-chat.types.ts";
 import { IPagination } from "@/lib/types.ts";
+import { runPollInterval } from "@/features/ai-chat/utils/run-polling.ts";
 
 export const AI_CHATS_RQ_KEY = ["ai-chats"];
 export const AI_ROLES_RQ_KEY = ["ai-roles"];
@@ -51,16 +54,18 @@ export const AI_CHAT_MESSAGES_RQ_KEY = (chatId: string) => [
   "ai-chat-messages",
   chatId,
 ];
+export const AI_CHAT_RUN_RQ_KEY = (chatId: string) => ["ai-chat-run", chatId];
 
 /** Paginated list of the current user's chats (auto-loads further pages). */
 export function useAiChatsQuery() {
   const query = useInfiniteQuery({
     queryKey: AI_CHATS_RQ_KEY,
-    queryFn: ({ pageParam }) =>
-      getAiChats({ cursor: pageParam, limit: 50 }),
+    queryFn: ({ pageParam }) => getAiChats({ cursor: pageParam, limit: 50 }),
     initialPageParam: undefined as string | undefined,
     getNextPageParam: (lastPage) =>
-      lastPage.meta.hasNextPage ? (lastPage.meta.nextCursor ?? undefined) : undefined,
+      lastPage.meta.hasNextPage
+        ? (lastPage.meta.nextCursor ?? undefined)
+        : undefined,
   });
 
   const data = useMemo<IPagination<IAiChat> | undefined>(() => {
@@ -90,7 +95,9 @@ export function useAiChatMessagesQuery(chatId: string | undefined) {
       getAiChatMessages({ chatId: chatId as string, cursor: pageParam }),
     initialPageParam: undefined as string | undefined,
     getNextPageParam: (lastPage) =>
-      lastPage.meta.hasNextPage ? (lastPage.meta.nextCursor ?? undefined) : undefined,
+      lastPage.meta.hasNextPage
+        ? (lastPage.meta.nextCursor ?? undefined)
+        : undefined,
     enabled: !!chatId,
   });
 
@@ -131,6 +138,34 @@ export function useAiChatMessagesQuery(chatId: string | undefined) {
   };
 }
 
+/**
+ * Reconnect to a chat's latest agent run and LIVE-FOLLOW it (#184). While the run
+ * is active the query re-polls every {@link runPollInterval} ms (driven off the
+ * fetched `run.status`, the same status-keyed refetchInterval pattern as the
+ * embeddings reindex polling); once the run reaches a terminal status — or there
+ * is no run — the interval returns `false` and polling stops on its own. Polling
+ * is thus naturally bounded by the run terminating; no separate timeout cap.
+ *
+ * `enabled` gates the whole thing: callers pass `false` when the autonomous-runs
+ * feature is off (the endpoint is NOT flag-gated server-side, but with the feature
+ * off the chat has no runs, so polling would only ever return `{ run: null }`) OR
+ * when THIS tab is the one actively streaming the run (the live SSE owns the view,
+ * so we must not also poll/merge). The global `retry: false` means a failed fetch
+ * leaves `data` undefined, so refetchInterval(undefined run) returns false — a
+ * failed fetch can never spin a tight loop.
+ */
+export function useAiChatRunQuery(
+  chatId: string | undefined,
+  enabled: boolean,
+) {
+  return useQuery<IAiChatRunResponse, Error>({
+    queryKey: AI_CHAT_RUN_RQ_KEY(chatId ?? ""),
+    queryFn: () => getAiChatRun(chatId as string),
+    enabled: !!chatId && enabled,
+    refetchInterval: (query) => runPollInterval(query.state.data?.run),
+  });
+}
+
 export function useRenameAiChatMutation() {
   const queryClient = useQueryClient();
   const { t } = useTranslation();
@@ -280,11 +315,14 @@ export function useImportAiRolesFromCatalogMutation() {
     mutationFn: (payload) => importAiRolesFromCatalog(payload),
     onSuccess: (result) => {
       notifications.show({
-        message: t("Imported {{created}}, renamed {{renamed}}, skipped {{skipped}}", {
-          created: result.created,
-          renamed: result.renamed,
-          skipped: result.skipped,
-        }),
+        message: t(
+          "Imported {{created}}, renamed {{renamed}}, skipped {{skipped}}",
+          {
+            created: result.created,
+            renamed: result.renamed,
+            skipped: result.skipped,
+          },
+        ),
       });
       // Surface partial failures (e.g. unique-name races) as a red warning.
       if (result.errors.length > 0) {

apps/client/src/features/ai-chat/queries/ai-chat-run-query.test.tsx

@@ -0,0 +1,92 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import React from "react";
+import { renderHook, waitFor } from "@testing-library/react";
+import { QueryClient, QueryClientProvider } from "@tanstack/react-query";
+import type { IAiChatRunResponse } from "@/features/ai-chat/types/ai-chat.types.ts";
+
+// react-i18next is pulled in transitively by ai-chat-query.ts (the mutation hooks
+// use it); stub it so the module imports cleanly in this hook test.
+vi.mock("react-i18next", () => ({
+  useTranslation: () => ({ t: (key: string) => key }),
+}));
+
+vi.mock("@mantine/notifications", () => ({
+  notifications: { show: vi.fn() },
+}));
+
+// Mock the whole service module; only getAiChatRun is exercised here, but the
+// other named exports must exist so ai-chat-query.ts imports resolve.
+vi.mock("@/features/ai-chat/services/ai-chat-service.ts", () => ({
+  getAiChatRun: vi.fn(),
+  getAiChatMessages: vi.fn(),
+  getAiChats: vi.fn(),
+  getAiRoleCatalog: vi.fn(),
+  getAiRoleCatalogBundle: vi.fn(),
+  getAiRoles: vi.fn(),
+  importAiRolesFromCatalog: vi.fn(),
+  createAiRole: vi.fn(),
+  deleteAiChat: vi.fn(),
+  deleteAiRole: vi.fn(),
+  renameAiChat: vi.fn(),
+  updateAiRole: vi.fn(),
+  updateAiRoleFromCatalog: vi.fn(),
+}));
+
+import { getAiChatRun } from "@/features/ai-chat/services/ai-chat-service.ts";
+import { useAiChatRunQuery } from "@/features/ai-chat/queries/ai-chat-query.ts";
+
+function createWrapper() {
+  const queryClient = new QueryClient({
+    defaultOptions: { queries: { retry: false } },
+  });
+  return function Wrapper({ children }: { children: React.ReactNode }) {
+    return (
+      <QueryClientProvider client={queryClient}>{children}</QueryClientProvider>
+    );
+  };
+}
+
+const runningResponse: IAiChatRunResponse = {
+  run: { id: "run-1", chatId: "c1", status: "running" },
+  message: {
+    id: "a1",
+    role: "assistant",
+    content: "working...",
+    createdAt: "2026-01-01T00:00:00Z",
+  },
+};
+
+describe("useAiChatRunQuery — enable gating", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+  });
+
+  it("fetches the run when enabled (passive observer, feature on)", async () => {
+    vi.mocked(getAiChatRun).mockResolvedValue(runningResponse);
+    const { result } = renderHook(() => useAiChatRunQuery("c1", true), {
+      wrapper: createWrapper(),
+    });
+    await waitFor(() => expect(result.current.isSuccess).toBe(true));
+    expect(getAiChatRun).toHaveBeenCalledWith("c1");
+    expect(result.current.data?.run?.status).toBe("running");
+  });
+
+  it("does NOT fetch when disabled (this tab is the streamer / feature off)", async () => {
+    vi.mocked(getAiChatRun).mockResolvedValue(runningResponse);
+    renderHook(() => useAiChatRunQuery("c1", false), {
+      wrapper: createWrapper(),
+    });
+    // Give any errant fetch a chance to fire, then assert none did.
+    await new Promise((r) => setTimeout(r, 20));
+    expect(getAiChatRun).not.toHaveBeenCalled();
+  });
+
+  it("does NOT fetch when there is no chat id", async () => {
+    vi.mocked(getAiChatRun).mockResolvedValue(runningResponse);
+    renderHook(() => useAiChatRunQuery(undefined, true), {
+      wrapper: createWrapper(),
+    });
+    await new Promise((r) => setTimeout(r, 20));
+    expect(getAiChatRun).not.toHaveBeenCalled();
+  });
+});

apps/client/src/features/ai-chat/services/ai-chat-service.ts

@@ -5,6 +5,7 @@ import {
   IAiChatListParams,
   IAiChatMessageRow,
   IAiChatMessagesParams,
+  IAiChatRunResponse,
   IAiRole,
   IAiRoleCatalog,
   IAiRoleCatalogBundle,
@@ -42,6 +43,38 @@ export async function getAiChatMessages(
   return req.data;
 }
 
+/**
+ * Reconnect to the latest agent run of a chat (#184). Returns the run's
+ * persisted lifecycle state and the assistant message it materializes (the
+ * partial output while the run is in-flight, the final output once it finished).
+ * The DB is the source of truth, so this works for an in-flight run (the browser
+ * dropped, the run kept going) and a finished one alike; `{ run: null }` when the
+ * chat has never had a run. Owner-gated server-side (the requesting user must own
+ * the chat); it is NOT flag-gated — when the feature is off the chat simply has no
+ * runs, so the endpoint returns `{ run: null }`.
+ */
+export async function getAiChatRun(
+  chatId: string,
+): Promise<IAiChatRunResponse> {
+  const req = await api.post<IAiChatRunResponse>("/ai-chat/run", { chatId });
+  return req.data;
+}
+
+/**
+ * Explicitly STOP the active agent run of a chat (#184). This is the ONLY thing
+ * that ends a DETACHED run — a mere browser disconnect (aborting the local SSE)
+ * is deliberately ignored server-side, so the client must call this to actually
+ * stop an autonomous run. Targeted by `chatId` (the server resolves whatever run
+ * is active on it); owner-gated server-side. Returns `{ stopped }` — false when
+ * there was nothing active to stop.
+ */
+export async function stopRun(
+  chatId: string,
+): Promise<{ stopped: boolean }> {
+  const req = await api.post<{ stopped: boolean }>("/ai-chat/stop", { chatId });
+  return req.data;
+}
+
 /**
  * Resolve the chat bound to a document (the current user's most-recent chat
  * created on that page), or null when there is none. Drives auto-open-on-page.

apps/client/src/features/ai-chat/types/ai-chat.types.ts

@@ -200,6 +200,38 @@ export interface IAiChatMessageRow {
   createdAt: string;
 }
 
+/**
+ * A persisted agent-run row (#184), mirroring the `ai_chat_runs` fields the
+ * client reads from `POST /ai-chat/run`. Only `status` is load-bearing for the
+ * reconnect-and-live-update UX (it drives the poll cadence); the rest are carried
+ * for display/diagnostics. The DB is the source of truth, so this resolves for an
+ * in-flight run (the browser dropped, the run kept going) and a finished one.
+ */
+export interface IAiChatRun {
+  id: string;
+  chatId: string;
+  // 'pending' | 'running' | 'succeeded' | 'failed' | 'aborted'. The first two are
+  // ACTIVE (keep polling); the rest are TERMINAL (stop polling).
+  status: "pending" | "running" | "succeeded" | "failed" | "aborted" | string;
+  error?: string | null;
+  stepCount?: number;
+  assistantMessageId?: string | null;
+  startedAt?: string | null;
+  finishedAt?: string | null;
+  createdAt?: string;
+  updatedAt?: string;
+}
+
+/**
+ * Response of `POST /ai-chat/run` (#184): the latest run of a chat and the
+ * assistant message it materializes (the partial/final output, projected from the
+ * persisted rows). Both are `null` when the chat has never had a run.
+ */
+export interface IAiChatRunResponse {
+  run: IAiChatRun | null;
+  message: IAiChatMessageRow | null;
+}
+
 export interface IAiChatListParams extends QueryParams {}
 
 export interface IAiChatMessagesParams {

apps/client/src/features/ai-chat/utils/run-polling.test.ts

@@ -0,0 +1,303 @@
+import { describe, it, expect } from "vitest";
+import type { UIMessage } from "@ai-sdk/react";
+import type { IAiChatRun } from "@/features/ai-chat/types/ai-chat.types.ts";
+import {
+  RUN_POLL_INTERVAL_MS,
+  isRunActive,
+  runPollInterval,
+  shouldObserveRun,
+  shouldClearStoppingLatch,
+  shouldClearLatchOnQueryError,
+  mergeObservedMessage,
+} from "./run-polling.ts";
+
+function makeRun(status: string): IAiChatRun {
+  return { id: "run-1", chatId: "c1", status };
+}
+
+function makeMsg(id: string, text: string): UIMessage {
+  return {
+    id,
+    role: "assistant",
+    parts: [{ type: "text", text }],
+  } as UIMessage;
+}
+
+describe("isRunActive", () => {
+  it("treats pending and running as active", () => {
+    expect(isRunActive(makeRun("pending"))).toBe(true);
+    expect(isRunActive(makeRun("running"))).toBe(true);
+  });
+
+  it("treats terminal / unknown / nullish as not active", () => {
+    expect(isRunActive(makeRun("succeeded"))).toBe(false);
+    expect(isRunActive(makeRun("failed"))).toBe(false);
+    expect(isRunActive(makeRun("aborted"))).toBe(false);
+    expect(isRunActive(makeRun("weird-future-status"))).toBe(false);
+    expect(isRunActive(null)).toBe(false);
+    expect(isRunActive(undefined)).toBe(false);
+  });
+});
+
+describe("runPollInterval (the refetchInterval helper)", () => {
+  it("returns 2000ms while the run is pending/running", () => {
+    expect(runPollInterval(makeRun("pending"))).toBe(RUN_POLL_INTERVAL_MS);
+    expect(runPollInterval(makeRun("running"))).toBe(RUN_POLL_INTERVAL_MS);
+    expect(RUN_POLL_INTERVAL_MS).toBe(2000);
+  });
+
+  it("returns false (stop polling) once the run is terminal", () => {
+    expect(runPollInterval(makeRun("succeeded"))).toBe(false);
+    expect(runPollInterval(makeRun("failed"))).toBe(false);
+    expect(runPollInterval(makeRun("aborted"))).toBe(false);
+  });
+
+  it("returns false (no polling) when there is no run", () => {
+    expect(runPollInterval(null)).toBe(false);
+    expect(runPollInterval(undefined)).toBe(false);
+  });
+});
+
+describe("shouldObserveRun (observer-vs-streamer decision)", () => {
+  it("observes an active run when this tab is NOT the local streamer", () => {
+    expect(shouldObserveRun(makeRun("running"), false)).toBe(true);
+    expect(shouldObserveRun(makeRun("pending"), false)).toBe(true);
+  });
+
+  it("observes a terminal run too (so the final output shows on reopen)", () => {
+    expect(shouldObserveRun(makeRun("succeeded"), false)).toBe(true);
+  });
+
+  it("does NOT observe when this tab IS the streamer (no double-render)", () => {
+    expect(shouldObserveRun(makeRun("running"), true)).toBe(false);
+    expect(shouldObserveRun(makeRun("succeeded"), true)).toBe(false);
+  });
+
+  it("does NOT observe when there is no run", () => {
+    expect(shouldObserveRun(null, false)).toBe(false);
+    expect(shouldObserveRun(undefined, false)).toBe(false);
+  });
+});
+
+describe("shouldClearStoppingLatch (#234 latch-release decision)", () => {
+  // The one case the latch SHOULD clear: we requested a stop, we are the passive
+  // observer (not streaming), and the CURRENT run is terminal.
+  it("clears only when stopping, observing, and the run is terminal", () => {
+    expect(
+      shouldClearStoppingLatch({
+        stoppingRun: true,
+        run: makeRun("aborted"),
+        isLocalStreaming: false,
+      }),
+    ).toBe(true);
+    expect(
+      shouldClearStoppingLatch({
+        stoppingRun: true,
+        run: makeRun("succeeded"),
+        isLocalStreaming: false,
+      }),
+    ).toBe(true);
+    expect(
+      shouldClearStoppingLatch({
+        stoppingRun: true,
+        run: makeRun("failed"),
+        isLocalStreaming: false,
+      }),
+    ).toBe(true);
+  });
+
+  // Round-3 regression: clearing while THIS tab is still the local streamer would
+  // re-open the flash for the current turn the moment we switch to observer role.
+  // A predicate lacking the streaming gate would (wrongly) return true here.
+  it("does NOT clear while this tab is the local streamer", () => {
+    expect(
+      shouldClearStoppingLatch({
+        stoppingRun: true,
+        run: makeRun("aborted"),
+        isLocalStreaming: true,
+      }),
+    ).toBe(false);
+    expect(
+      shouldClearStoppingLatch({
+        stoppingRun: true,
+        run: makeRun("succeeded"),
+        isLocalStreaming: true,
+      }),
+    ).toBe(false);
+  });
+
+  // The detached run keeps growing after a local abort — while it is still
+  // active the latch MUST hold so the observer merge stays suppressed.
+  it("does NOT clear while the run is still active", () => {
+    expect(
+      shouldClearStoppingLatch({
+        stoppingRun: true,
+        run: makeRun("running"),
+        isLocalStreaming: false,
+      }),
+    ).toBe(false);
+    expect(
+      shouldClearStoppingLatch({
+        stoppingRun: true,
+        run: makeRun("pending"),
+        isLocalStreaming: false,
+      }),
+    ).toBe(false);
+  });
+
+  // #234 F4: on Stop the stale PREVIOUS-turn run is removed from the cache, so the
+  // observed `run` is null until the current turn's run is fetched fresh. A null
+  // run HOLDS the latch — it can never clear against the just-removed stale run,
+  // only against the current turn's own terminal run once observed.
+  it("does NOT clear against a removed/absent run (F4 stale-run guard)", () => {
+    expect(
+      shouldClearStoppingLatch({
+        stoppingRun: true,
+        run: null,
+        isLocalStreaming: false,
+      }),
+    ).toBe(false);
+    expect(
+      shouldClearStoppingLatch({
+        stoppingRun: true,
+        run: undefined,
+        isLocalStreaming: false,
+      }),
+    ).toBe(false);
+  });
+
+  it("does NOT clear when no stop was requested", () => {
+    expect(
+      shouldClearStoppingLatch({
+        stoppingRun: false,
+        run: makeRun("aborted"),
+        isLocalStreaming: false,
+      }),
+    ).toBe(false);
+  });
+});
+
+describe("shouldClearLatchOnQueryError (#234 F7 error-safety-net decision)", () => {
+  // This guards the REAL anti-flash decision the component's run-query-error
+  // safety-net effect uses (ai-chat-window.tsx wires the effect to THIS helper,
+  // not a copy — so the test is non-vacuous vs the live code).
+
+  // (b) The F7 hole: a TRANSIENT run-query error while `run` is STILL ACTIVE must
+  // NOT clear the latch. TanStack Query v5 retains `data` on error, so
+  // runQueryFailed can be true while the held run is still pending/running.
+  // Against the PRE-F7 condition (without `!isRunActive(run)`) this would return
+  // true — so this assertion fails on the buggy code (non-vacuous).
+  it("does NOT clear on a transient error while the run is still ACTIVE (F7)", () => {
+    expect(
+      shouldClearLatchOnQueryError({
+        stoppingRun: true,
+        isLocalStreaming: false,
+        runQueryFailed: true,
+        run: makeRun("running"),
+      }),
+    ).toBe(false);
+    expect(
+      shouldClearLatchOnQueryError({
+        stoppingRun: true,
+        isLocalStreaming: false,
+        runQueryFailed: true,
+        run: makeRun("pending"),
+      }),
+    ).toBe(false);
+  });
+
+  // (a) The genuine permanent-null-freeze: run cache cleared by removeQueries +
+  // the refetch keeps ERRORING, so `run === null`. This is the ONLY case the
+  // safety-net exists to cure — it MUST clear so the frozen view resumes.
+  it("clears on a permanent error when the run is null (permanent-null-freeze)", () => {
+    expect(
+      shouldClearLatchOnQueryError({
+        stoppingRun: true,
+        isLocalStreaming: false,
+        runQueryFailed: true,
+        run: null,
+      }),
+    ).toBe(true);
+    expect(
+      shouldClearLatchOnQueryError({
+        stoppingRun: true,
+        isLocalStreaming: false,
+        runQueryFailed: true,
+        run: undefined,
+      }),
+    ).toBe(true);
+  });
+
+  // A TERMINAL run also satisfies `!isRunActive`; clearing then is harmless — the
+  // terminal effect (shouldClearStoppingLatch) already clears for a terminal run,
+  // so this only ever agrees with it. Asserted so the (c) reasoning is pinned.
+  it("clears on an error when the run is terminal (harmless, agrees with terminal effect)", () => {
+    expect(
+      shouldClearLatchOnQueryError({
+        stoppingRun: true,
+        isLocalStreaming: false,
+        runQueryFailed: true,
+        run: makeRun("aborted"),
+      }),
+    ).toBe(true);
+  });
+
+  it("does NOT clear without an actual query error", () => {
+    expect(
+      shouldClearLatchOnQueryError({
+        stoppingRun: true,
+        isLocalStreaming: false,
+        runQueryFailed: false,
+        run: null,
+      }),
+    ).toBe(false);
+  });
+
+  it("does NOT clear while this tab is the local streamer", () => {
+    expect(
+      shouldClearLatchOnQueryError({
+        stoppingRun: true,
+        isLocalStreaming: true,
+        runQueryFailed: true,
+        run: null,
+      }),
+    ).toBe(false);
+  });
+
+  it("does NOT clear when no stop was requested", () => {
+    expect(
+      shouldClearLatchOnQueryError({
+        stoppingRun: false,
+        isLocalStreaming: false,
+        runQueryFailed: true,
+        run: null,
+      }),
+    ).toBe(false);
+  });
+});
+
+describe("mergeObservedMessage", () => {
+  it("replaces the message with the same id in place (per-step growth)", () => {
+    const prev = [makeMsg("u1", "hi"), makeMsg("a1", "step 1")];
+    const observed = makeMsg("a1", "step 1\nstep 2");
+    const next = mergeObservedMessage(prev, observed);
+    expect(next).toHaveLength(2);
+    expect(next[1]).toBe(observed);
+    expect(next[0]).toBe(prev[0]); // untouched
+    expect(next).not.toBe(prev); // new array (never mutates input)
+  });
+
+  it("appends when the observed message is not yet present", () => {
+    const prev = [makeMsg("u1", "hi")];
+    const observed = makeMsg("a1", "first token");
+    const next = mergeObservedMessage(prev, observed);
+    expect(next).toHaveLength(2);
+    expect(next[1]).toBe(observed);
+  });
+
+  it("returns the original list unchanged when there is nothing to merge", () => {
+    const prev = [makeMsg("u1", "hi")];
+    expect(mergeObservedMessage(prev, null)).toBe(prev);
+    expect(mergeObservedMessage(prev, undefined)).toBe(prev);
+  });
+});

apps/client/src/features/ai-chat/utils/run-polling.ts

@@ -0,0 +1,151 @@
+import type { UIMessage } from "@ai-sdk/react";
+import type { IAiChatRun } from "@/features/ai-chat/types/ai-chat.types.ts";
+
+/**
+ * Reconnect-and-live-follow helpers (#184). When a chat is reopened while its
+ * agent run is STILL going, this tab is a PASSIVE OBSERVER: it did not start the
+ * run here (no local SSE stream), so it catches up by POLLING the reconnect
+ * endpoint (`POST /ai-chat/run`) and merging the run's incrementally-persisted
+ * assistant message into the rendered thread. These are the small pure decisions
+ * that machinery hangs off, extracted so they can be unit-tested in isolation
+ * (mirrors how reindex polling / editor-sync-state are tested).
+ */
+
+/** How often to re-poll the reconnect endpoint while a run is ACTIVE. */
+export const RUN_POLL_INTERVAL_MS = 2000;
+
+// 'pending' and 'running' are the two ACTIVE statuses; 'succeeded' | 'failed' |
+// 'aborted' are TERMINAL (and any unknown future status is treated as terminal,
+// so a stale/odd value never polls forever).
+const ACTIVE_STATUSES = new Set(["pending", "running"]);
+
+/** Whether a run is still going (worth polling / merging live updates from). */
+export function isRunActive(run: IAiChatRun | null | undefined): boolean {
+  return !!run && ACTIVE_STATUSES.has(run.status);
+}
+
+/**
+ * The TanStack Query `refetchInterval` value for the run query: poll every
+ * {@link RUN_POLL_INTERVAL_MS} while the run is active, and `false` (stop) once
+ * it is terminal or there is no run. Polling is thus naturally bounded by the run
+ * reaching a terminal status — no separate timeout cap is needed.
+ */
+export function runPollInterval(
+  run: IAiChatRun | null | undefined,
+): number | false {
+  return isRunActive(run) ? RUN_POLL_INTERVAL_MS : false;
+}
+
+/**
+ * Observer-vs-streamer decision. We render the polled run message (catch up +
+ * keep advancing) ONLY when this tab is a passive observer: there IS a run AND
+ * this tab is NOT the one locally streaming it (we reconnected, we didn't start
+ * it here). When this tab is the streamer, the live SSE stream owns the view, so
+ * we neither poll nor merge — avoiding a double-render fight. Terminal runs still
+ * merge (so the final persisted output is shown on reopen); the poll itself is
+ * stopped separately by {@link runPollInterval}.
+ */
+export function shouldObserveRun(
+  run: IAiChatRun | null | undefined,
+  localStreaming: boolean,
+): boolean {
+  return !!run && !localStreaming;
+}
+
+/**
+ * Should the "stopping" latch — which suppresses the observer re-stream flash
+ * after the user pressed Stop — be RELEASED now? All three must hold:
+ *  - `stoppingRun`: we actually requested a stop (otherwise nothing to release);
+ *  - `!isLocalStreaming`: this tab is NOT the local streamer. While we are the
+ *    streamer the run query is disabled, so the observed `run` is not the run we
+ *    are following — releasing the latch then would re-open the flash for the
+ *    current turn the instant we switch to observer role;
+ *  - the observed `run` EXISTS and has reached a TERMINAL status.
+ *
+ * The null / still-active `run` case is the #234 F4 invariant. On Stop the stale
+ * PREVIOUS-turn run is removed from the query cache (`removeQueries`), so `run`
+ * is null until the CURRENT turn's run is re-fetched fresh; a null or active run
+ * therefore HOLDS the latch, so it can only ever clear against the current turn's
+ * OWN terminal run — never a stale cached one. (The cache removal itself is
+ * integration-level in AiChatWindow; this predicate encodes the decision given
+ * whatever run is currently observed, and a stale terminal run is
+ * indistinguishable from a current terminal run at the predicate level — hence
+ * the cache removal is what guarantees only the current run is ever passed here.)
+ */
+export function shouldClearStoppingLatch(args: {
+  stoppingRun: boolean;
+  run: IAiChatRun | null | undefined;
+  isLocalStreaming: boolean;
+}): boolean {
+  const { stoppingRun, run, isLocalStreaming } = args;
+  if (!stoppingRun || isLocalStreaming) return false;
+  return !!run && !isRunActive(run);
+}
+
+/**
+ * Should the "stopping" latch be RELEASED by the run-query ERROR safety-net?
+ * (#234 F7 — a NEW path of the same re-stream flash the F4 latch exists to
+ * prevent.) After Stop, `handleServerStop` clears the run cache; the terminal
+ * effect then holds the latch via `if (!run) return` until the CURRENT turn's run
+ * is fetched fresh. If that refetch instead ERRORS permanently, `run` stays null,
+ * its status-keyed refetchInterval is off, and nothing would ever observe a
+ * terminal run — freezing the view with the observer merge suppressed. This
+ * safety-net cures ONLY that genuine permanent-null-freeze.
+ *
+ * All four must hold:
+ *  - `stoppingRun`: we actually requested a stop (otherwise nothing to release);
+ *  - `!isLocalStreaming`: this tab is NOT the local streamer (same reason as
+ *    {@link shouldClearStoppingLatch});
+ *  - `runQueryFailed`: the run query is in its error state (TanStack Query v5 with
+ *    retry:false — isError);
+ *  - `!isRunActive(run)`: the observed `run` is NOT an active (pending/running)
+ *    held run. This is the F7 gate. In TanStack Query v5 the query's `data` is
+ *    RETAINED on error, so `runQueryFailed` can be true while `run` is STILL an
+ *    ACTIVE run (a single transient GET-run failure in the window between Stop and
+ *    settle). Without this gate a transient error would release the latch early —
+ *    re-opening the observer merge and flashing the growing detached run over the
+ *    frozen row (exactly the F4 flash). Gating on the run NOT being active means we
+ *    only ever cure the permanent-null-freeze (`run === null`, so
+ *    `isRunActive(null)` is false), never release against an active run.
+ *
+ * (A terminal `run` also satisfies `!isRunActive(run)`; clearing then is harmless
+ * — the terminal effect's {@link shouldClearStoppingLatch} already clears the
+ * latch for a terminal run, so this only ever agrees with it, never conflicts.)
+ *
+ * INVARIANT (do not break): clearing the latch on the `run === null` branch is safe
+ * ONLY because the run query's `refetchInterval` (see {@link runPollInterval}) stops
+ * polling when the data is empty — so after we clear on null+error there is no
+ * subsequent auto-poll that could return a still-active detached run and re-open the
+ * merge. If `refetchInterval` is ever changed to keep polling on `run === null`/on
+ * error, this null-branch clear would re-open the F7 flash through the null path.
+ * Do not change the run query's refetchInterval without re-checking this path.
+ */
+export function shouldClearLatchOnQueryError(args: {
+  stoppingRun: boolean;
+  isLocalStreaming: boolean;
+  runQueryFailed: boolean;
+  run: IAiChatRun | null | undefined;
+}): boolean {
+  const { stoppingRun, isLocalStreaming, runQueryFailed, run } = args;
+  return (
+    stoppingRun && !isLocalStreaming && runQueryFailed && !isRunActive(run)
+  );
+}
+
+/**
+ * Merge an observed assistant message into the rendered list: replace the message
+ * with the same id in place (the in-progress assistant row is already seeded from
+ * history, so per-step growth replaces it), or append it when absent. Returns a
+ * new array; the input is never mutated.
+ */
+export function mergeObservedMessage(
+  messages: UIMessage[],
+  observed: UIMessage | null | undefined,
+): UIMessage[] {
+  if (!observed) return messages;
+  const idx = messages.findIndex((m) => m.id === observed.id);
+  if (idx === -1) return [...messages, observed];
+  const next = messages.slice();
+  next[idx] = observed;
+  return next;
+}

apps/client/src/features/editor/page-editor.tsx

@@ -93,6 +93,11 @@ import {
   isBodyEditable,
   isCollabSynced,
 } from "@/features/editor/editor-sync-state";
+import {
+  isVitalsActive,
+  measurePageOpen,
+  reportEditorTx,
+} from "@/lib/telemetry/vitals";
 
 interface PageEditorProps {
   pageId: string;
@@ -351,6 +356,40 @@ export default function PageEditor({
           editor.storage.pageId = pageId;
           handleScrollTo(editor);
           editorRef.current = editor;
+
+          // #355 — perf instrumentation. Skip ALL of it when telemetry is
+          // disabled (F1 flag off) or this session isn't sampled: no page-open
+          // measure, and crucially NO dispatch wrapping, so a non-collecting
+          // session pays zero per-transaction cost.
+          if (isVitalsActive()) {
+            // page_open_ms: this is the first editor-content render, so measure
+            // against any page-open mark set on the tree-row/link click.
+            measurePageOpen();
+
+            // editor_tx_ms: time the SYNCHRONOUS part of applying each
+            // transaction (state.apply + updateState) by wrapping the view's
+            // dispatch. Only slow syncs (>8ms) are reported (see reportEditorTx),
+            // so the common path adds just one performance.now() pair. Passive:
+            // the original dispatch still runs unchanged.
+            try {
+              const view = editor.view as unknown as {
+                dispatch: (tr: unknown) => void;
+              };
+              const originalDispatch = view.dispatch.bind(view);
+              view.dispatch = (tr: unknown) => {
+                const started = performance.now();
+                originalDispatch(tr);
+                const elapsed = performance.now() - started;
+                try {
+                  reportEditorTx(elapsed, editor.state.doc.content.size);
+                } catch {
+                  // never let telemetry break editing
+                }
+              };
+            } catch {
+              // if the view shape changes, skip editor_tx instrumentation
+            }
+          }
         }
       },
       onUpdate({ editor }) {

apps/client/src/features/workspace/components/settings/components/ai-provider-settings.tsx

@@ -394,6 +394,10 @@ export default function AiProviderSettings() {
     useState<boolean>(
       workspace?.settings?.ai?.publicShareAssistant ?? false,
     );
+  // #184: detached/autonomous agent runs (settings.ai.autonomousRuns).
+  const [autonomousRunsEnabled, setAutonomousRunsEnabled] = useState<boolean>(
+    workspace?.settings?.ai?.autonomousRuns ?? false,
+  );
   const [chatToggleLoading, setChatToggleLoading] = useState(false);
   const [searchToggleLoading, setSearchToggleLoading] = useState(false);
   const [dictationToggleLoading, setDictationToggleLoading] = useState(false);
@@ -403,6 +407,8 @@ export default function AiProviderSettings() {
     publicShareAssistantToggleLoading,
     setPublicShareAssistantToggleLoading,
   ] = useState(false);
+  const [autonomousRunsToggleLoading, setAutonomousRunsToggleLoading] =
+    useState(false);
 
   // Whether a key is currently stored server-side (drives the placeholder).
   const [hasApiKey, setHasApiKey] = useState(false);
@@ -730,6 +736,37 @@ export default function AiProviderSettings() {
     }
   }
 
+  // Optimistic toggle for detached/autonomous agent runs
+  // (settings.ai.autonomousRuns). When on, a chat turn becomes a server-side run
+  // that survives a browser disconnect and can be reconnected to / live-followed;
+  // only an explicit Stop ends it. Off by default; single-instance-only in phase 1.
+  async function handleToggleAutonomousRuns(value: boolean) {
+    setAutonomousRunsToggleLoading(true);
+    const previous = autonomousRunsEnabled;
+    setAutonomousRunsEnabled(value);
+    try {
+      const updated = await updateWorkspace({ autonomousRuns: value });
+      setWorkspace({
+        ...updated,
+        settings: {
+          ...updated.settings,
+          ai: { ...updated.settings?.ai, autonomousRuns: value },
+        },
+      });
+      notifications.show({ message: t("Updated successfully") });
+    } catch (err) {
+      setAutonomousRunsEnabled(previous);
+      const message = (err as { response?: { data?: { message?: string } } })
+        ?.response?.data?.message;
+      notifications.show({
+        message: message ?? t("Failed to update data"),
+        color: "red",
+      });
+    } finally {
+      setAutonomousRunsToggleLoading(false);
+    }
+  }
+
   // Admins only — match the previous behavior.
   if (!isAdmin) {
     return (
@@ -960,6 +997,31 @@ export default function AiProviderSettings() {
           {...form.getInputProps("publicShareAssistantRoleId")}
         />
 
+        {/* Detached/autonomous agent runs: a chat turn becomes a server-side run
+            that survives a browser disconnect; only an explicit Stop ends it.
+            Single-instance-only in phase 1. */}
+        <Group justify="space-between" align="center" wrap="nowrap" mt="md">
+          <Stack gap={0}>
+            <Text fw={600} size="sm">
+              {t("Autonomous agent runs")}
+            </Text>
+            <Text size="xs" c="dimmed">
+              {t(
+                "Keep an agent turn running server-side even if the browser disconnects; reconnect and follow it on reopen. Single-instance deployments only.",
+              )}
+            </Text>
+          </Stack>
+          <Switch
+            label={t("Enabled")}
+            labelPosition="left"
+            checked={autonomousRunsEnabled}
+            disabled={autonomousRunsToggleLoading}
+            onChange={(e) =>
+              handleToggleAutonomousRuns(e.currentTarget.checked)
+            }
+          />
+        </Group>
+
         <Group mt="md" align="center">
           <Button
             variant="default"

apps/client/src/features/workspace/types/workspace.types.ts

@@ -26,6 +26,9 @@ export interface IWorkspace {
   aiDictation?: boolean;
   aiDictationStreaming?: boolean;
   aiPublicShareAssistant?: boolean;
+  // Write-only field for updateWorkspace({ autonomousRuns }). Read state lives at
+  // settings.ai.autonomousRuns.
+  autonomousRuns?: boolean;
   trashRetentionDays?: number;
   // Default lifetime (HOURS) for new temporary notes; frozen per-note at creation.
   temporaryNoteHours?: number;
@@ -65,6 +68,9 @@ export interface IWorkspaceAiSettings {
   dictation?: boolean;
   dictationStreaming?: boolean;
   publicShareAssistant?: boolean;
+  // #184: detached agent runs (a run survives a browser disconnect and can be
+  // reconnected to / live-followed on reopen). Gates the run-reconnect polling.
+  autonomousRuns?: boolean;
 }
 
 export interface IWorkspaceSharingSettings {

apps/client/src/lib/config.ts

@@ -47,6 +47,13 @@ export function isCompactPageTreeEnabled(): boolean {
   return castToBoolean(getConfigValue("COMPACT_PAGE_TREE", "true"));
 }
 
+// #355 — operator toggle for client perf-telemetry. DEFAULT OFF: the server
+// mirrors CLIENT_TELEMETRY_ENABLED into window.CONFIG; when off the client
+// installs no observers and sends nothing (the sink endpoint doesn't exist).
+export function isClientTelemetryEnabled(): boolean {
+  return castToBoolean(getConfigValue("CLIENT_TELEMETRY_ENABLED", "false"));
+}
+
 export function getAvatarUrl(
   avatarUrl: string,
   type: AvatarIconType = AvatarIconType.AVATAR,

apps/client/src/lib/telemetry/route-template.test.ts

@@ -0,0 +1,35 @@
+import { describe, it, expect } from "vitest";
+import { templateRoute } from "./route-template";
+
+describe("templateRoute", () => {
+  it("templates a space page path (never leaks slugs)", () => {
+    const t = templateRoute("/s/engineering/p/design-doc-abc123");
+    expect(t).toBe("/s/:space/p/:slug");
+    expect(t).not.toContain("engineering");
+    expect(t).not.toContain("design-doc");
+  });
+
+  it("templates share, redirect and space paths", () => {
+    expect(templateRoute("/share/abc/p/xyz")).toBe("/share/:shareId/p/:slug");
+    expect(templateRoute("/share/p/xyz")).toBe("/share/p/:slug");
+    expect(templateRoute("/p/some-slug")).toBe("/p/:slug");
+    expect(templateRoute("/s/team")).toBe("/s/:space");
+    expect(templateRoute("/s/team/trash")).toBe("/s/:space/trash");
+    expect(templateRoute("/labels/urgent")).toBe("/labels/:label");
+  });
+
+  it("keeps known static routes verbatim", () => {
+    expect(templateRoute("/home")).toBe("/home");
+    expect(templateRoute("/settings/members")).toBe("/settings/members");
+    expect(templateRoute("/")).toBe("/");
+  });
+
+  it("normalises a trailing slash", () => {
+    expect(templateRoute("/s/team/p/slug/")).toBe("/s/:space/p/:slug");
+  });
+
+  it("collapses unknown paths to 'other' (bounded cardinality)", () => {
+    expect(templateRoute("/weird/unknown/thing")).toBe("other");
+    expect(templateRoute("/s/team/p/slug/extra/segments")).toBe("other");
+  });
+});

apps/client/src/lib/telemetry/route-template.ts

@@ -0,0 +1,70 @@
+/**
+ * Map a raw pathname to a BOUNDED route TEMPLATE (#355).
+ *
+ * Perf metrics must be labelled by route template only — never a raw path with
+ * slugs/ids — so the server-side `route` column and any downstream aggregation
+ * stay low-cardinality and carry NO page slugs/titles (privacy). Anything that
+ * does not match a known pattern collapses to `other`.
+ *
+ * The template vocabulary mirrors the issue's example (`/s/:space/p/:slug`).
+ */
+const ROUTE_PATTERNS: { re: RegExp; template: string }[] = [
+  // Share pages (public).
+  { re: /^\/share\/[^/]+\/p\/[^/]+$/, template: '/share/:shareId/p/:slug' },
+  { re: /^\/share\/p\/[^/]+$/, template: '/share/p/:slug' },
+  { re: /^\/share\/[^/]+$/, template: '/share/:shareId' },
+  // Page redirect.
+  { re: /^\/p\/[^/]+$/, template: '/p/:slug' },
+  // Space + page.
+  { re: /^\/s\/[^/]+\/p\/[^/]+$/, template: '/s/:space/p/:slug' },
+  { re: /^\/s\/[^/]+\/trash$/, template: '/s/:space/trash' },
+  { re: /^\/s\/[^/]+$/, template: '/s/:space' },
+  // Misc dynamic.
+  { re: /^\/labels\/[^/]+$/, template: '/labels/:label' },
+  { re: /^\/invites\/[^/]+$/, template: '/invites/:invitationId' },
+  { re: /^\/settings\/groups\/[^/]+$/, template: '/settings/groups/:groupId' },
+];
+
+// Static routes we accept verbatim (finite set).
+const STATIC_ROUTES = new Set<string>([
+  '/home',
+  '/spaces',
+  '/favorites',
+  '/login',
+  '/forgot-password',
+  '/password-reset',
+  '/setup/register',
+  '/settings/account/profile',
+  '/settings/account/preferences',
+  '/settings/workspace',
+  '/settings/ai',
+  '/settings/members',
+  '/settings/groups',
+  '/settings/spaces',
+  '/settings/sharing',
+]);
+
+export function templateRoute(pathname: string): string {
+  // Normalise a trailing slash (except root).
+  const path =
+    pathname.length > 1 && pathname.endsWith('/')
+      ? pathname.slice(0, -1)
+      : pathname;
+
+  if (path === '' || path === '/') return '/';
+  if (STATIC_ROUTES.has(path)) return path;
+
+  for (const { re, template } of ROUTE_PATTERNS) {
+    if (re.test(path)) return template;
+  }
+  return 'other';
+}
+
+/** Template for the current window location. */
+export function currentRouteTemplate(): string {
+  try {
+    return templateRoute(window.location.pathname);
+  } catch {
+    return 'other';
+  }
+}

apps/client/src/lib/telemetry/vitals.ts

@@ -0,0 +1,290 @@
+import {
+  onCLS,
+  onINP,
+  onLCP,
+  onTTFB,
+  type CLSMetricWithAttribution,
+  type INPMetricWithAttribution,
+  type LCPMetricWithAttribution,
+  type TTFBMetricWithAttribution,
+} from "web-vitals/attribution";
+import { isClientTelemetryEnabled } from "@/lib/config";
+import { currentRouteTemplate } from "./route-template";
+
+/**
+ * Client perf-telemetry (#355): web-vitals + custom metrics buffered and posted
+ * to POST /api/telemetry/vitals via sendBeacon.
+ *
+ * Design constraints from the issue:
+ *  - Sampling is decided ONCE per session (25%), cached in sessionStorage,
+ *    BEFORE any observer is subscribed. Non-sampled sessions send nothing.
+ *  - Route labels are TEMPLATES only; attr is truncated to 120 chars; no page
+ *    titles/slugs/text ever leave the browser.
+ *  - Observers are passive and reporting is best-effort — telemetry must not
+ *    degrade the perf it measures.
+ */
+
+const ENDPOINT = "/api/telemetry/vitals";
+const SAMPLE_RATE = 0.25;
+const SAMPLE_KEY = "gm_vitals_sampled";
+const FLUSH_INTERVAL_MS = 15_000;
+const MAX_BUFFER = 40; // flush early if the buffer fills between timers
+const MAX_ATTR_LENGTH = 120;
+const EDITOR_TX_MIN_MS = 8; // only report editor transactions slower than this
+
+const ALLOWED_NAMES = new Set([
+  "INP",
+  "LCP",
+  "CLS",
+  "TTFB",
+  "editor_tx_ms",
+  "page_open_ms",
+  "longtask_ms",
+]);
+
+interface VitalEvent {
+  name: string;
+  value: number;
+  rating?: string;
+  route?: string;
+  attr?: string;
+  docSize?: number;
+}
+
+let sampledCache: boolean | null = null;
+let initialised = false;
+let buffer: VitalEvent[] = [];
+let longtaskSum = 0; // accumulated longtask duration (ms) for the current window
+
+/**
+ * Decide once per session whether this session is sampled. Cached in
+ * sessionStorage so the choice is stable across reloads within the session and
+ * identical for every observer/custom-metric caller.
+ */
+export function isVitalsSampled(): boolean {
+  if (sampledCache !== null) return sampledCache;
+  try {
+    const stored = sessionStorage.getItem(SAMPLE_KEY);
+    if (stored === "1") return (sampledCache = true);
+    if (stored === "0") return (sampledCache = false);
+    const sampled = Math.random() < SAMPLE_RATE;
+    sessionStorage.setItem(SAMPLE_KEY, sampled ? "1" : "0");
+    return (sampledCache = sampled);
+  } catch {
+    // sessionStorage unavailable (private mode / SSR): default to not sampled.
+    return (sampledCache = false);
+  }
+}
+
+/**
+ * True only when telemetry is BOTH enabled by the operator (F1 flag) AND this
+ * session is sampled. Callers outside initVitals (e.g. the editor dispatch
+ * wrapper) use this to skip ALL instrumentation cost on disabled/non-sampled
+ * sessions — no observers, no per-transaction timing.
+ */
+export function isVitalsActive(): boolean {
+  return isClientTelemetryEnabled() && isVitalsSampled();
+}
+
+function truncateAttr(value: unknown): string | undefined {
+  if (typeof value !== "string" || value.length === 0) return undefined;
+  return value.slice(0, MAX_ATTR_LENGTH);
+}
+
+function enqueue(event: VitalEvent): void {
+  if (!ALLOWED_NAMES.has(event.name)) return;
+  if (!Number.isFinite(event.value)) return;
+  buffer.push(event);
+  if (buffer.length >= MAX_BUFFER) flush();
+}
+
+function flush(): void {
+  // Fold any pending longtask total into the batch first.
+  if (longtaskSum > 0) {
+    buffer.push({
+      name: "longtask_ms",
+      value: Math.round(longtaskSum),
+      route: currentRouteTemplate(),
+    });
+    longtaskSum = 0;
+  }
+  if (buffer.length === 0) return;
+
+  const payload = JSON.stringify({ events: buffer });
+  buffer = [];
+
+  try {
+    const blob = new Blob([payload], { type: "application/json" });
+    if (navigator.sendBeacon && navigator.sendBeacon(ENDPOINT, blob)) return;
+    // Fallback for browsers without sendBeacon: keepalive fetch.
+    void fetch(ENDPOINT, {
+      method: "POST",
+      body: payload,
+      headers: { "Content-Type": "application/json" },
+      keepalive: true,
+    }).catch(() => undefined);
+  } catch {
+    // Best-effort: never throw out of telemetry.
+  }
+}
+
+/**
+ * Report a custom client metric (editor_tx_ms, page_open_ms). No-op unless the
+ * session is sampled. Route is always the current TEMPLATE.
+ */
+export function reportClientMetric(
+  name: "editor_tx_ms" | "page_open_ms",
+  value: number,
+  extra?: { docSize?: number },
+): void {
+  if (!isVitalsActive()) return;
+  if (!Number.isFinite(value)) return;
+  enqueue({
+    name,
+    value,
+    route: currentRouteTemplate(),
+    docSize: extra?.docSize,
+  });
+}
+
+/** Threshold-gated editor transaction reporter (only reports slow syncs). */
+export function reportEditorTx(ms: number, docSize: number): void {
+  if (ms <= EDITOR_TX_MIN_MS) return;
+  reportClientMetric("editor_tx_ms", ms, { docSize });
+}
+
+const PAGE_OPEN_MARK = "gm_page_open_start";
+
+/** Mark the start of a page-open interaction (tree-row / link click). */
+export function markPageOpenStart(): void {
+  try {
+    performance.clearMarks(PAGE_OPEN_MARK);
+    performance.mark(PAGE_OPEN_MARK);
+  } catch {
+    // ignore
+  }
+}
+
+/**
+ * Measure page_open_ms at first editor-content render, if a start mark exists.
+ * Consumes the mark so a later render doesn't double-count.
+ */
+export function measurePageOpen(): void {
+  try {
+    const marks = performance.getEntriesByName(PAGE_OPEN_MARK, "mark");
+    if (marks.length === 0) return;
+    const started = marks[0].startTime;
+    const elapsed = performance.now() - started;
+    performance.clearMarks(PAGE_OPEN_MARK);
+    if (elapsed > 0 && Number.isFinite(elapsed)) {
+      reportClientMetric("page_open_ms", elapsed);
+    }
+  } catch {
+    // ignore
+  }
+}
+
+function attrTarget(
+  metric:
+    | INPMetricWithAttribution
+    | LCPMetricWithAttribution
+    | CLSMetricWithAttribution,
+): string | undefined {
+  const a = metric.attribution as Record<string, unknown> | undefined;
+  if (!a) return undefined;
+  // Different vitals expose their culprit element under different keys; only a
+  // CSS-selector-ish target string is taken (no text content / titles).
+  return (
+    truncateAttr(a.interactionTarget) ??
+    truncateAttr(a.element) ??
+    truncateAttr(a.largestShiftTarget) ??
+    undefined
+  );
+}
+
+/**
+ * Initialise client telemetry. Safe to call multiple times (idempotent). Returns
+ * immediately without subscribing when the session is not sampled — so a
+ * non-sampled session subscribes to NO observers and sends nothing.
+ */
+export function initVitals(): void {
+  if (initialised) return;
+  initialised = true;
+
+  // Operator flag gate (F1, default OFF): when telemetry is disabled the sink
+  // endpoint does not even exist server-side, so install ZERO observers.
+  if (!isClientTelemetryEnabled()) return;
+
+  // Sampling gate is evaluated BEFORE any observer subscription.
+  if (!isVitalsSampled()) return;
+
+  const report = (
+    metric:
+      | INPMetricWithAttribution
+      | LCPMetricWithAttribution
+      | CLSMetricWithAttribution
+      | TTFBMetricWithAttribution,
+  ) => {
+    enqueue({
+      name: metric.name,
+      value: metric.value,
+      rating: metric.rating,
+      route: currentRouteTemplate(),
+      attr:
+        metric.name === "TTFB"
+          ? undefined
+          : attrTarget(
+              metric as
+                | INPMetricWithAttribution
+                | LCPMetricWithAttribution
+                | CLSMetricWithAttribution,
+            ),
+    });
+  };
+
+  onINP(report);
+  onLCP(report);
+  onCLS(report);
+  onTTFB(report);
+
+  // Long tasks: aggregate the total blocking time per flush window (a passive
+  // observer; individual entries are summed, never stored/sent individually).
+  try {
+    if (typeof PerformanceObserver !== "undefined") {
+      const observer = new PerformanceObserver((list) => {
+        for (const entry of list.getEntries()) {
+          longtaskSum += entry.duration;
+        }
+      });
+      observer.observe({ type: "longtask", buffered: true });
+    }
+  } catch {
+    // longtask entry type unsupported: skip silently.
+  }
+
+  // page_open_ms start: mark when the user clicks a page link/tree-row (any
+  // anchor navigating to a page URL). Passive capture listener; the matching
+  // measure fires at first editor-content render (measurePageOpen). No page
+  // titles/slugs are read — only the click timing is marked.
+  document.addEventListener(
+    "click",
+    (event) => {
+      const target = event.target as Element | null;
+      const anchor = target?.closest?.("a[href]") as HTMLAnchorElement | null;
+      if (!anchor) return;
+      const href = anchor.getAttribute("href") ?? "";
+      // A page link is `/s/:space/p/:slug`, `/p/:slug` or a share page path.
+      if (/\/p\//.test(href)) markPageOpenStart();
+    },
+    { capture: true, passive: true },
+  );
+
+  // Flush on tab hide (most reliable delivery point) and periodically.
+  const onHidden = () => {
+    if (document.visibilityState === "hidden") flush();
+  };
+  document.addEventListener("visibilitychange", onHidden);
+  window.addEventListener("pagehide", flush);
+
+  setInterval(flush, FLUSH_INTERVAL_MS);
+}

apps/client/src/main.tsx

@@ -22,6 +22,7 @@ import {
   isPostHogEnabled,
 } from "@/lib/config.ts";
 import posthog from "posthog-js";
+import { initVitals } from "@/lib/telemetry/vitals";
 
 export const queryClient = new QueryClient({
   defaultOptions: {
@@ -43,6 +44,10 @@ if (isCloud() && isPostHogEnabled) {
   });
 }
 
+// #355 — client perf-telemetry. Decides sampling ONCE (25%/session) before
+// subscribing to any observer; non-sampled sessions send nothing.
+initVitals();
+
 const container = document.getElementById("root") as HTMLElement;
 const root = (container as any).__reactRoot ??= ReactDOM.createRoot(container);
 

apps/client/vite.config.ts

@@ -1,6 +1,5 @@
 import { defineConfig, loadEnv } from "vite";
 import react from "@vitejs/plugin-react";
-import { compression } from "vite-plugin-compression2";
 import * as path from "path";
 import { execSync } from "node:child_process";
 
@@ -54,25 +53,7 @@ export default defineConfig(({ mode }) => {
       },
       APP_VERSION: JSON.stringify(resolveAppVersion(envPath)),
     },
-    plugins: [
-      react(),
-      // Emit .br and .gz next to every built asset so the server can serve the
-      // precompressed copy (see @fastify/static preCompressed in static.module.ts).
-      compression({
-        algorithms: ["brotliCompress", "gzip"],
-        // vite-plugin-compression2's default `include` only covers text-ish
-        // bundle output (js/mjs/json/css/html/svg/…). Extend it with the large
-        // VAD binaries copied from public/vad (.wasm ~26MB, .onnx ~2.3MB) so
-        // they are brotli/gzip'd once at build time and served via
-        // @fastify/static preCompressed — otherwise @fastify/compress would
-        // re-brotli them on EVERY request. The default types are repeated here
-        // because setting `include` replaces (does not extend) the default.
-        include: /\.(html|xml|css|json|js|mjs|svg|yaml|yml|toml|wasm|onnx)$/,
-        // index.html is rewritten at server boot (window.CONFIG injection); a
-        // precompressed copy would go stale — NEVER precompress it.
-        exclude: [/index\.html$/],
-      }),
-    ],
+    plugins: [react()],
     build: {
       rolldownOptions: {
         output: {

apps/server/package.json

@@ -23,7 +23,7 @@
     "migration:reset": "tsx src/database/migrate.ts down-to NO_MIGRATIONS",
     "migration:codegen": "kysely-codegen --dialect=postgres --camel-case --env-file=../../.env --out-file=./src/database/types/db.d.ts",
     "lint": "eslint \"{src,apps,libs,test}/**/*.ts\" --fix",
-    "pretest": "pnpm --filter @docmost/editor-ext build",
+    "pretest": "pnpm --filter @docmost/editor-ext build && pnpm --filter @docmost/prosemirror-markdown build",
     "test": "jest",
     "test:int": "jest --config test/jest-integration.json",
     "test:watch": "jest --watch",
@@ -43,7 +43,7 @@
     "@clickhouse/client": "^1.18.2",
     "@docmost/mcp": "workspace:*",
     "@docmost/pdf-inspector": "1.9.6",
-    "@fastify/compress": "^9.0.0",
+    "@docmost/prosemirror-markdown": "workspace:*",
     "@fastify/cookie": "^11.0.2",
     "@fastify/multipart": "^10.0.0",
     "@fastify/static": "^9.1.3",
@@ -112,6 +112,7 @@
     "pino-pretty": "^13.1.3",
     "postgres": "^3.4.8",
     "postmark": "^4.0.7",
+    "prom-client": "^15.1.3",
     "react": "^18.3.1",
     "react-email": "6.0.8",
     "reflect-metadata": "^0.2.2",
@@ -175,7 +176,7 @@
       "/node_modules/"
     ],
     "transform": {
-      "happy-dom.+\\.js$": [
+      "(happy-dom.+|prosemirror-markdown/build/.+)\\.js$": [
         "babel-jest",
         {
           "presets": [
@@ -193,7 +194,7 @@
       "^.+\\.(t|j)sx?$": "ts-jest"
     },
     "transformIgnorePatterns": [
-      "/node_modules/(?!(\\.pnpm/)?(nanoid|uuid|image-dimensions|marked|happy-dom|lib0)(@|/))"
+      "/node_modules/(?!(\\.pnpm/)?(nanoid|uuid|image-dimensions|marked|happy-dom|lib0|@docmost/prosemirror-markdown)(@|/))"
     ],
     "collectCoverageFrom": [
       "**/*.(t|j)s"
@@ -204,7 +205,8 @@
       "^@docmost/db/(.*)$": "<rootDir>/database/$1",
       "^@docmost/transactional/(.*)$": "<rootDir>/integrations/transactional/$1",
       "^@docmost/ee/(.*)$": "<rootDir>/ee/$1",
-      "^src/(.*)$": "<rootDir>/$1"
+      "^src/(.*)$": "<rootDir>/$1",
+      "^@tiptap/react$": "<rootDir>/../test/stubs/tiptap-react.js"
     }
   }
 }

apps/server/src/app.module.ts

@@ -31,6 +31,8 @@ import { McpModule } from './integrations/mcp/mcp.module';
 import { SandboxModule } from './integrations/sandbox/sandbox.module';
 import { AiModule } from './integrations/ai/ai.module';
 import { AiChatModule } from './core/ai-chat/ai-chat.module';
+import { MetricsModule } from './integrations/metrics/metrics.module';
+import { ClientTelemetryModule } from './core/telemetry/client-telemetry.module';
 
 const enterpriseModules = [];
 try {
@@ -93,6 +95,10 @@ try {
     SandboxModule,
     AiModule,
     AiChatModule,
+    MetricsModule,
+    // Gated OFF by default: only registers the public vitals sink controller
+    // when CLIENT_TELEMETRY_ENABLED=true (maintainer decision E1=B).
+    ClientTelemetryModule.register(),
     ...enterpriseModules,
   ],
   controllers: [AppController],

apps/server/src/collaboration/collaboration.util.ts

@@ -43,7 +43,6 @@ import {
   Column,
   Status,
   addUniqueIdsToDoc,
-  htmlToMarkdown,
   TransclusionSource,
   TransclusionReference,
   FootnoteReference,
@@ -51,6 +50,7 @@ import {
   FootnoteDefinition,
   PageEmbed,
 } from '@docmost/editor-ext';
+import { convertProseMirrorToMarkdown } from '@docmost/prosemirror-markdown';
 import { generateText, getSchema, JSONContent } from '@tiptap/core';
 import { generateHTML, generateJSON } from '../common/helpers/prosemirror/html';
 // @tiptap/html library works best for generating prosemirror json state but not HTML
@@ -239,6 +239,10 @@ export function prosemirrorNodeToYElement(node: any): Y.XmlElement | Y.XmlText {
 }
 
 export function jsonToMarkdown(tiptapJson: any): string {
-  const html = jsonToHtml(tiptapJson);
-  return htmlToMarkdown(html);
+  // Direct ProseMirror JSON -> Markdown via the canonical converter
+  // (`@docmost/prosemirror-markdown`) — no HTML intermediate, no second
+  // editor-ext markdown layer. Same serializer as the page/space export and the
+  // git-sync vault writer, so every server PM->MD path emits identical canonical
+  // markdown (issue #345).
+  return convertProseMirrorToMarkdown(tiptapJson);
 }

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

@@ -41,6 +41,7 @@ import {
   HISTORY_INTERVAL,
 } from '../constants';
 import { TransclusionService } from '../../core/page/transclusion/transclusion.service';
+import { observeCollabStore } from '../../integrations/metrics/metrics.registry';
 
 /**
  * #251 — wire format of the client→server stateless message that signals a
@@ -192,6 +193,17 @@ export class PersistenceExtension implements Extension {
   }
 
   async onStoreDocument(data: onStoreDocumentPayload) {
+    // #355 — time the full store (persist + post-store side effects) into
+    // collab_store_duration_seconds. No-op when METRICS_PORT is unset.
+    const startedAt = performance.now();
+    try {
+      await this.storeDocument(data);
+    } finally {
+      observeCollabStore((performance.now() - startedAt) / 1000);
+    }
+  }
+
+  private async storeDocument(data: onStoreDocumentPayload) {
     const { documentName, document, context } = data;
 
     const pageId = getPageId(documentName);

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

@@ -0,0 +1,527 @@
+import { Logger } from '@nestjs/common';
+import {
+  AiChatRunService,
+  RunAlreadyActiveError,
+  ONE_ACTIVE_RUN_PER_CHAT_INDEX,
+  mapTurnStatusToRun,
+} from './ai-chat-run.service';
+
+/** Shape a Postgres unique-violation the way the postgres.js driver surfaces it:
+ *  SQLSTATE 23505 + the offending index in `constraint_name`. */
+function uniqueViolation(constraintName: string): Error & {
+  code: string;
+  constraint_name: string;
+} {
+  return Object.assign(
+    new Error('duplicate key value violates unique constraint'),
+    {
+      code: '23505',
+      constraint_name: constraintName,
+    },
+  );
+}
+
+/**
+ * Unit coverage for the #184 phase-1 run lifecycle (AiChatRunService) with a
+ * hand-rolled mock repo — no Nest graph, no DB. The invariant under test is the
+ * one that makes a run "autonomous": a run keeps going when its SUBSCRIBER (the
+ * browser) detaches, and ONLY an explicit stop aborts it. We assert that at the
+ * abort-signal level (the signal the agent loop actually consumes).
+ */
+
+/** Minimal EnvironmentService stub. Single-instance (CLOUD unset) by default. */
+function makeEnv(isCloud = false) {
+  return { isCloud: () => isCloud };
+}
+
+function makeRepo(overrides: Record<string, jest.Mock> = {}) {
+  return {
+    insert: jest.fn(async (v: any) => ({
+      id: 'run-1',
+      status: v.status ?? 'running',
+      chatId: v.chatId,
+      workspaceId: v.workspaceId,
+    })),
+    update: jest.fn(async () => ({ id: 'run-1' })),
+    markStopRequested: jest.fn(async () => ({ id: 'run-1' })),
+    findActiveByChat: jest.fn(async () => undefined),
+    findLatestByChat: jest.fn(async () => undefined),
+    findById: jest.fn(async () => undefined),
+    sweepRunning: jest.fn(async () => 0),
+    ...overrides,
+  };
+}
+
+describe('mapTurnStatusToRun', () => {
+  it('maps the turn terminal status to the run terminal status', () => {
+    expect(mapTurnStatusToRun('completed')).toBe('succeeded');
+    expect(mapTurnStatusToRun('error')).toBe('failed');
+    expect(mapTurnStatusToRun('aborted')).toBe('aborted');
+  });
+});
+
+describe('AiChatRunService.onModuleInit (startup sweep)', () => {
+  afterEach(() => jest.restoreAllMocks());
+
+  it('calls sweepRunning and resolves; logs when > 0', async () => {
+    const repo = makeRepo({ sweepRunning: jest.fn(async () => 2) });
+    const logSpy = jest
+      .spyOn(Logger.prototype, 'log')
+      .mockImplementation(() => undefined);
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await expect(svc.onModuleInit()).resolves.toBeUndefined();
+    expect(repo.sweepRunning).toHaveBeenCalledTimes(1);
+    expect(logSpy).toHaveBeenCalledTimes(1);
+    expect(String(logSpy.mock.calls[0][0])).toContain('2');
+  });
+
+  it('a sweep failure is swallowed (never blocks startup)', async () => {
+    const repo = makeRepo({
+      sweepRunning: jest.fn(async () => {
+        throw new Error('db down');
+      }),
+    });
+    const warnSpy = jest
+      .spyOn(Logger.prototype, 'warn')
+      .mockImplementation(() => undefined);
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await expect(svc.onModuleInit()).resolves.toBeUndefined();
+    // The first warn is the sweep failure (the multi-instance warn never fires
+    // single-instance), so the message is the db error.
+    expect(String(warnSpy.mock.calls[0][0])).toContain('db down');
+  });
+
+  it('F1 (DECISION C): the boot sweep is UNCONDITIONAL — sweepRunning is called with NO staleness window, so a fresh running run (updatedAt = now) is settled, not skipped', async () => {
+    // The bug: a fast restart (deploy/OOM within minutes of the last step) left a
+    // run stuck 'running' under the old 10-min window, 409ing every later turn in
+    // the chat. The fix settles ALL pending|running on boot. We assert the service
+    // invokes sweepRunning with no `staleMs` (the unconditional path); the repo's
+    // own spec proves no-window => no updatedAt filter.
+    const repo = makeRepo({ sweepRunning: jest.fn(async () => 1) });
+    jest.spyOn(Logger.prototype, 'log').mockImplementation(() => undefined);
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await svc.onModuleInit();
+    expect(repo.sweepRunning).toHaveBeenCalledTimes(1);
+    const callArgs = repo.sweepRunning.mock.calls[0] as unknown[];
+    const firstArg = callArgs[0] as { staleMs?: number } | undefined;
+    // Either no opts at all, or opts without a staleMs window => unconditional.
+    expect(firstArg?.staleMs).toBeUndefined();
+  });
+
+  it('F2 (DECISION A): warns at startup that autonomousRuns is single-instance-only when a horizontally-scaled deployment (CLOUD) is detected', async () => {
+    const repo = makeRepo();
+    const warnSpy = jest
+      .spyOn(Logger.prototype, 'warn')
+      .mockImplementation(() => undefined);
+    const svc = new AiChatRunService(repo as never, makeEnv(true) as never);
+    await svc.onModuleInit();
+    const warned = warnSpy.mock.calls.some((c) =>
+      /single-instance-only/i.test(String(c[0])),
+    );
+    expect(warned).toBe(true);
+  });
+
+  it('F2: does NOT warn about multi-instance on a single-instance (CLOUD unset) deployment', async () => {
+    const repo = makeRepo();
+    const warnSpy = jest
+      .spyOn(Logger.prototype, 'warn')
+      .mockImplementation(() => undefined);
+    const svc = new AiChatRunService(repo as never, makeEnv(false) as never);
+    await svc.onModuleInit();
+    const warned = warnSpy.mock.calls.some((c) =>
+      /single-instance-only/i.test(String(c[0])),
+    );
+    expect(warned).toBe(false);
+  });
+});
+
+describe('AiChatRunService run lifecycle', () => {
+  it('beginRun inserts a running row and registers a live abort controller', async () => {
+    const repo = makeRepo();
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    const handle = await svc.beginRun({
+      chatId: 'chat-1',
+      workspaceId: 'ws-1',
+      userId: 'user-1',
+    });
+    expect(repo.insert).toHaveBeenCalledWith(
+      expect.objectContaining({
+        chatId: 'chat-1',
+        workspaceId: 'ws-1',
+        createdBy: 'user-1',
+        status: 'running',
+        trigger: 'user',
+      }),
+    );
+    expect(handle.runId).toBe('run-1');
+    expect(handle.signal.aborted).toBe(false);
+    expect(svc.isLocallyActive('run-1')).toBe(true);
+  });
+
+  it('beginRun REJECTS the racer: a 23505 on the one-active-per-chat index throws RunAlreadyActiveError (not swallowed) and registers no controller', async () => {
+    // The race: the controller's cheap pre-check passed for BOTH concurrent
+    // turns, so the loser's INSERT hits the partial unique index. That rejection
+    // is the authoritative gate — it must surface, not be swallowed into an
+    // untracked turn.
+    const repo = makeRepo({
+      insert: jest.fn(async () => {
+        throw uniqueViolation(ONE_ACTIVE_RUN_PER_CHAT_INDEX);
+      }),
+    });
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await expect(
+      svc.beginRun({ chatId: 'chat-1', workspaceId: 'ws-1', userId: 'user-1' }),
+    ).rejects.toBeInstanceOf(RunAlreadyActiveError);
+    // No controller leaked for a rejected start.
+    expect(svc.isLocallyActive('run-1')).toBe(false);
+  });
+
+  it('beginRun does NOT mask an unrelated unique violation as already-active', async () => {
+    // A 23505 on some OTHER constraint is a real bug, not the race — it must
+    // propagate unchanged so it is never silently treated as "already active".
+    const other = uniqueViolation('ai_chat_runs_pkey');
+    const repo = makeRepo({
+      insert: jest.fn(async () => {
+        throw other;
+      }),
+    });
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await expect(
+      svc.beginRun({ chatId: 'chat-1', workspaceId: 'ws-1', userId: 'user-1' }),
+    ).rejects.toBe(other);
+  });
+
+  it('beginRun propagates a non-unique insert failure unchanged', async () => {
+    const boom = new Error('connection reset');
+    const repo = makeRepo({
+      insert: jest.fn(async () => {
+        throw boom;
+      }),
+    });
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await expect(
+      svc.beginRun({ chatId: 'chat-1', workspaceId: 'ws-1', userId: 'user-1' }),
+    ).rejects.toBe(boom);
+  });
+
+  it('two concurrent begins on one chat: exactly one wins, the other is rejected as already-active', async () => {
+    // Integration-style: model the DB partial unique index with a one-shot slot.
+    // The first insert claims it; the second hits a 23505 on the active index.
+    let slotTaken = false;
+    const repo = makeRepo({
+      insert: jest.fn(async (v: any) => {
+        if (slotTaken) throw uniqueViolation(ONE_ACTIVE_RUN_PER_CHAT_INDEX);
+        slotTaken = true;
+        return { id: 'run-win', status: v.status, chatId: v.chatId };
+      }),
+    });
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    const results = await Promise.allSettled([
+      svc.beginRun({ chatId: 'chat-1', workspaceId: 'ws-1', userId: 'user-1' }),
+      svc.beginRun({ chatId: 'chat-1', workspaceId: 'ws-1', userId: 'user-1' }),
+    ]);
+    const fulfilled = results.filter((r) => r.status === 'fulfilled');
+    const rejected = results.filter((r) => r.status === 'rejected');
+    expect(fulfilled).toHaveLength(1);
+    expect(rejected).toHaveLength(1);
+    expect((rejected[0] as PromiseRejectedResult).reason).toBeInstanceOf(
+      RunAlreadyActiveError,
+    );
+    // Exactly the winner is locally active.
+    expect(svc.isLocallyActive('run-win')).toBe(true);
+  });
+
+  it('a SUBSCRIBER detaching does NOT abort the run (only an explicit stop does)', async () => {
+    const repo = makeRepo();
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    const handle = await svc.beginRun({
+      chatId: 'chat-1',
+      workspaceId: 'ws-1',
+      userId: 'user-1',
+    });
+    // Model a browser disconnect: nothing in the run service is told to stop.
+    // The signal the agent loop consumes must stay un-aborted and the run stays
+    // locally active — i.e. it keeps running server-side.
+    expect(handle.signal.aborted).toBe(false);
+    expect(svc.isLocallyActive('run-1')).toBe(true);
+    // markStopRequested was never called by a mere detach.
+    expect(repo.markStopRequested).not.toHaveBeenCalled();
+  });
+
+  it('requestStop aborts the live controller, marks the row, and reports true', async () => {
+    const repo = makeRepo();
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    const handle = await svc.beginRun({
+      chatId: 'chat-1',
+      workspaceId: 'ws-1',
+      userId: 'user-1',
+    });
+    const aborted = jest.fn();
+    handle.signal.addEventListener('abort', aborted);
+
+    const result = await svc.requestStop('run-1', 'ws-1');
+
+    expect(result).toBe(true);
+    expect(handle.signal.aborted).toBe(true);
+    expect(aborted).toHaveBeenCalledTimes(1);
+    expect(repo.markStopRequested).toHaveBeenCalledWith('run-1', 'ws-1');
+  });
+
+  it('requestStop on a run this replica does NOT hold still marks the row (true)', async () => {
+    // e.g. after a restart, or a sibling replica owns the controller. The row is
+    // marked so the owning replica/sweep settles it; we report a stop took effect.
+    const repo = makeRepo({
+      markStopRequested: jest.fn(async () => ({ id: 'run-9' })),
+    });
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    const result = await svc.requestStop('run-9', 'ws-1');
+    expect(result).toBe(true);
+    expect(svc.isLocallyActive('run-9')).toBe(false);
+  });
+
+  it('requestStop still aborts the live controller when markStopRequested rejects (transient DB error)', async () => {
+    // F15: the in-memory abort is the ONLY thing that stops a run and must not be
+    // hostage to the audit write of stop_requested_at. A transient failure on
+    // markStopRequested must NOT prevent abort() nor make requestStop throw.
+    const warnSpy = jest
+      .spyOn(Logger.prototype, 'warn')
+      .mockImplementation(() => undefined);
+    const repo = makeRepo({
+      markStopRequested: jest.fn(async () => {
+        throw new Error('pool exhausted');
+      }),
+    });
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    const handle = await svc.beginRun({
+      chatId: 'chat-1',
+      workspaceId: 'ws-1',
+      userId: 'user-1',
+    });
+    const aborted = jest.fn();
+    handle.signal.addEventListener('abort', aborted);
+
+    // Does NOT throw despite the DB write rejecting.
+    const result = await svc.requestStop('run-1', 'ws-1');
+
+    // The live turn was aborted even though the audit write failed...
+    expect(handle.signal.aborted).toBe(true);
+    expect(aborted).toHaveBeenCalledTimes(1);
+    expect(repo.markStopRequested).toHaveBeenCalledWith('run-1', 'ws-1');
+    // ...the catch branch logged the swallowed failure...
+    expect(warnSpy).toHaveBeenCalledTimes(1);
+    // ...and a stop is reported as having taken effect (the entry existed).
+    expect(result).toBe(true);
+    warnSpy.mockRestore();
+  });
+
+  it('requestStop on an already-settled run (nothing active) reports false', async () => {
+    const repo = makeRepo({
+      markStopRequested: jest.fn(async () => undefined),
+    });
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    const result = await svc.requestStop('run-done', 'ws-1');
+    expect(result).toBe(false);
+  });
+
+  it('finalizeRun settles the row to the mapped status with finishedAt and drops the in-memory entry', async () => {
+    const repo = makeRepo();
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await svc.beginRun({
+      chatId: 'chat-1',
+      workspaceId: 'ws-1',
+      userId: 'user-1',
+    });
+    expect(svc.isLocallyActive('run-1')).toBe(true);
+
+    await svc.finalizeRun('run-1', 'ws-1', 'error', 'provider blew up');
+
+    expect(svc.isLocallyActive('run-1')).toBe(false);
+    expect(repo.update).toHaveBeenCalledWith(
+      'run-1',
+      'ws-1',
+      expect.objectContaining({
+        status: 'failed',
+        error: 'provider blew up',
+        finishedAt: expect.any(Date),
+      }),
+    );
+  });
+
+  it('finalizeRun is IDEMPOTENT: a second settle no-ops (single terminal write)', async () => {
+    // The #184 review fix: AiChatService.stream wraps the turn in a safety-net
+    // catch that settles a failed turn AND streamText's terminal callback may
+    // also settle — both routes call finalizeRun. Only the FIRST may write the
+    // terminal row; the second must no-op so a late settle can never clobber the
+    // real terminal status or double-write the row.
+    const repo = makeRepo();
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await svc.beginRun({
+      chatId: 'chat-1',
+      workspaceId: 'ws-1',
+      userId: 'user-1',
+    });
+
+    await svc.finalizeRun('run-1', 'ws-1', 'error', 'first');
+    expect(svc.isLocallyActive('run-1')).toBe(false);
+    // A second settle (e.g. a streamText callback firing after the catch) no-ops.
+    await svc.finalizeRun('run-1', 'ws-1', 'completed', undefined);
+
+    expect(repo.update).toHaveBeenCalledTimes(1);
+    expect(repo.update).toHaveBeenCalledWith(
+      'run-1',
+      'ws-1',
+      expect.objectContaining({ status: 'failed', error: 'first' }),
+    );
+  });
+
+  it('CONCURRENCY: two simultaneous finalizeRun on the same run write the terminal row EXACTLY ONCE (the 2nd caller exits synchronously at the atomic claim)', async () => {
+    // The CRITICAL race: AiChatService.stream's safety-net catch settles the turn
+    // to 'error' while a streamText terminal callback also settles it — both call
+    // finalizeRun for the SAME runId. The once-gate must close ATOMICALLY: a
+    // `settled.has` check alone is read BEFORE the awaited UPDATE, so both callers
+    // would pass it and BOTH write the row (last-write-wins clobber + double
+    // write). The fix claims the run with a SYNCHRONOUS `active.delete` before any
+    // await, so the second caller returns in the same tick, before the UPDATE.
+    //
+    // We force the two calls to overlap by making `update` return a promise we
+    // resolve only AFTER both finalizeRun calls have run their synchronous bodies.
+    let resolveUpdate!: (v: unknown) => void;
+    const updateGate = new Promise((res) => {
+      resolveUpdate = res;
+    });
+    const update = jest.fn(() => updateGate);
+    const repo = makeRepo({ update });
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await svc.beginRun({
+      chatId: 'chat-1',
+      workspaceId: 'ws-1',
+      userId: 'user-1',
+    });
+
+    // Fire both before the (pending) update resolves. The first synchronously
+    // claims the entry (active.delete) and awaits update; the second, started in
+    // the same macrotask, finds the entry already gone and returns at the claim
+    // WITHOUT ever calling update.
+    const p1 = svc.finalizeRun('run-1', 'ws-1', 'completed');
+    const p2 = svc.finalizeRun('run-1', 'ws-1', 'error', 'safety-net');
+
+    // The decisive assertion: exactly one caller reached the terminal UPDATE.
+    expect(update).toHaveBeenCalledTimes(1);
+
+    // Let the single in-flight update land; both calls resolve cleanly.
+    resolveUpdate({ id: 'run-1' });
+    await Promise.all([p1, p2]);
+
+    expect(update).toHaveBeenCalledTimes(1);
+    // The winner is the FIRST caller ('completed' -> 'succeeded'); the late
+    // 'error' settle never wrote, so it could not clobber the real status.
+    expect(update).toHaveBeenCalledWith(
+      'run-1',
+      'ws-1',
+      expect.objectContaining({ status: 'succeeded' }),
+    );
+    expect(svc.isLocallyActive('run-1')).toBe(false);
+  });
+
+  it('F6: a TRANSIENT terminal-write failure is ridden out by the bounded retry — the run is settled, not stranded', async () => {
+    // The bug: finalizeRun used to DROP the in-memory entry BEFORE the terminal
+    // UPDATE, then only warn-log a failure. A single transient blip (pool
+    // exhaustion / deadlock / connection hiccup) on that PK UPDATE left the row
+    // 'running' with nothing left to recover it -> every later turn in that chat
+    // 409s until a restart. The fix updates FIRST and retries.
+    let calls = 0;
+    const repo = makeRepo({
+      update: jest.fn(async () => {
+        calls += 1;
+        if (calls === 1) throw new Error('deadlock detected');
+        return { id: 'run-1' };
+      }),
+    });
+    jest.spyOn(Logger.prototype, 'warn').mockImplementation(() => undefined);
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await svc.beginRun({
+      chatId: 'chat-1',
+      workspaceId: 'ws-1',
+      userId: 'user-1',
+    });
+
+    await svc.finalizeRun('run-1', 'ws-1', 'completed');
+
+    // The retry landed the terminal write: the entry is dropped (slot freed) and
+    // the row carries the real terminal status — NOT stranded at 'running'.
+    expect(svc.isLocallyActive('run-1')).toBe(false);
+    expect(repo.update).toHaveBeenCalledTimes(2);
+    expect(repo.update).toHaveBeenLastCalledWith(
+      'run-1',
+      'ws-1',
+      expect.objectContaining({ status: 'succeeded' }),
+    );
+  });
+
+  it('F6: if the terminal write keeps failing, the entry is RETAINED and a LATER settle completes it (chat not permanently 409d)', async () => {
+    // Worst case: the DB is down for the whole first finalize (all attempts fail).
+    // The run must NOT be silently lost — the entry stays so a subsequent settle
+    // (a streamText callback, requestStop -> onAbort, or a future sweep) can retry.
+    let healthy = false;
+    const repo = makeRepo({
+      update: jest.fn(async () => {
+        if (!healthy) throw new Error('pool exhausted');
+        return { id: 'run-1' };
+      }),
+    });
+    jest.spyOn(Logger.prototype, 'warn').mockImplementation(() => undefined);
+    const errorSpy = jest
+      .spyOn(Logger.prototype, 'error')
+      .mockImplementation(() => undefined);
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await svc.beginRun({
+      chatId: 'chat-1',
+      workspaceId: 'ws-1',
+      userId: 'user-1',
+    });
+
+    // First settle: every bounded attempt fails -> entry retained, NOT settled.
+    await svc.finalizeRun('run-1', 'ws-1', 'completed');
+    expect(svc.isLocallyActive('run-1')).toBe(true);
+    // F12: the give-up emits ONE explicit, greppable ERROR (run + chat context)
+    // so an operator can tell "gave up, run held in memory" from a per-attempt
+    // blip — distinct from the per-attempt warns.
+    const gaveUp = errorSpy.mock.calls.some(
+      (c) =>
+        /NON-TERMINAL/.test(String(c[0])) &&
+        /run-1/.test(String(c[0])) &&
+        /chat-1/.test(String(c[0])),
+    );
+    expect(gaveUp).toBe(true);
+
+    // The DB recovers; a later settle now succeeds and frees the slot.
+    healthy = true;
+    await svc.finalizeRun('run-1', 'ws-1', 'completed');
+    expect(svc.isLocallyActive('run-1')).toBe(false);
+    expect(repo.update).toHaveBeenLastCalledWith(
+      'run-1',
+      'ws-1',
+      expect.objectContaining({ status: 'succeeded' }),
+    );
+
+    // And it is now idempotent: a further settle no-ops (terminal row already
+    // written), so a double-settle can never clobber the real status.
+    const callsBefore = repo.update.mock.calls.length;
+    await svc.finalizeRun('run-1', 'ws-1', 'error', 'late');
+    expect(repo.update).toHaveBeenCalledTimes(callsBefore);
+  });
+
+  it('recordStep / linkAssistantMessage are best-effort: a repo failure is swallowed', async () => {
+    const repo = makeRepo({
+      update: jest.fn(async () => {
+        throw new Error('transient');
+      }),
+    });
+    jest.spyOn(Logger.prototype, 'warn').mockImplementation(() => undefined);
+    const svc = new AiChatRunService(repo as never, makeEnv() as never);
+    await expect(svc.recordStep('run-1', 'ws-1', 3)).resolves.toBeUndefined();
+    await expect(
+      svc.linkAssistantMessage('run-1', 'ws-1', 'msg-1'),
+    ).resolves.toBeUndefined();
+  });
+});

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

@@ -0,0 +1,452 @@
+import { Injectable, Logger, OnModuleInit } from '@nestjs/common';
+import { AiChatRunRepo } from '@docmost/db/repos/ai-chat/ai-chat-run.repo';
+import { AiChatRun } from '@docmost/db/types/entity.types';
+import { isUniqueViolation, violatedConstraint } from '@docmost/db/utils';
+import { EnvironmentService } from '../../integrations/environment/environment.service';
+
+/** Name of the partial unique index enforcing "one active run per chat" (see the
+ *  ai_chat_runs migration). A 23505 on THIS constraint is the race-safe signal
+ *  that a concurrent turn already owns the chat — distinct from any other unique
+ *  collision, which must NOT be silently treated as "already active". */
+export const ONE_ACTIVE_RUN_PER_CHAT_INDEX = 'ai_chat_runs_one_active_per_chat';
+
+/**
+ * Thrown by {@link AiChatRunService.beginRun} when the run-row INSERT loses the
+ * race for a chat's single active slot (the partial unique index rejects it with
+ * a 23505). This is the AUTHORITATIVE concurrency gate: the controller's cheap
+ * pre-check is only a fast-path, and a request that slips past it must NOT run
+ * untracked. The caller (AiChatService.stream) translates this into a 409 and
+ * aborts the turn BEFORE any AI/provider call.
+ */
+export class RunAlreadyActiveError extends Error {
+  constructor(public readonly chatId: string) {
+    super(`An agent run is already in progress for chat ${chatId}`);
+    this.name = 'RunAlreadyActiveError';
+  }
+}
+
+/**
+ * The terminal status of a TURN (the #183 assistant-row lifecycle) maps onto the
+ * terminal status of a RUN (#184). A turn that completed -> the run succeeded; a
+ * turn that errored -> the run failed; a turn aborted (explicit user stop) -> the
+ * run aborted. Pure + unit-testable.
+ */
+export type TurnTerminalStatus = 'completed' | 'error' | 'aborted';
+export type RunTerminalStatus = 'succeeded' | 'failed' | 'aborted';
+
+export function mapTurnStatusToRun(
+  status: TurnTerminalStatus,
+): RunTerminalStatus {
+  switch (status) {
+    case 'completed':
+      return 'succeeded';
+    case 'error':
+      return 'failed';
+    case 'aborted':
+      return 'aborted';
+  }
+}
+
+/** An in-flight run held in process memory: its AbortController is the ONLY thing
+ *  that can stop the turn (an explicit user stop), independent of the browser
+ *  socket. A mere disconnect never touches it, so the run keeps going. */
+interface ActiveRun {
+  controller: AbortController;
+  chatId: string;
+  workspaceId: string;
+}
+
+/** The live handle the streaming path drives a run through (returned by
+ *  {@link AiChatRunService.beginRun}). The `signal` governs the agent loop's
+ *  abort — wired to the run, NOT to the HTTP socket. */
+export interface RunHandle {
+  runId: string;
+  signal: AbortSignal;
+}
+
+/**
+ * AiChatRunService (#184 phase 1) — owns the agent RUN as a first-class,
+ * server-side lifecycle object detached from the HTTP request / browser window.
+ *
+ * Responsibilities:
+ *  - create a run row when a turn starts (inserted directly as 'running'; the
+ *    'pending' status is only the column default + a reserved value, never
+ *    written by code in phase 1) and register an in-memory AbortController for it
+ *    (the explicit-stop lever);
+ *  - finalize the run row (succeeded / failed / aborted) and unregister it;
+ *  - service an EXPLICIT user stop (`requestStop`) — the ONLY thing that aborts a
+ *    run; a browser disconnect deliberately does NOT;
+ *  - crash-recovery sweep of dangling runs on startup.
+ *
+ * The agent loop itself still runs in AiChatService.stream (reusing #183's
+ * step-granular durable write path, `consumeStream` already drains it independent
+ * of the socket); this service only wraps it in a durable lifecycle and an
+ * abort handle that outlives the subscriber.
+ */
+@Injectable()
+export class AiChatRunService implements OnModuleInit {
+  private readonly logger = new Logger(AiChatRunService.name);
+
+  // runId -> ActiveRun. Process-local on purpose (phase 1 is single-process /
+  // in-memory transport; a cross-process BullMQ runner + Redis stop-signal is
+  // deferred to phase 2). A stop for a runId not in this map (e.g. after a
+  // restart) still records `stop_requested_at` on the row.
+  private readonly active = new Map<string, ActiveRun>();
+
+  // runIds whose TERMINAL row write has SUCCEEDED — the idempotency once-gate
+  // (F6). A finalize must short-circuit only AFTER the terminal write has landed,
+  // NOT merely after the in-memory entry was dropped: a transient UPDATE failure
+  // has to stay retryable, so "already settled" means "row already terminal", not
+  // "entry already gone". Grows by one short UUID per finished run over process
+  // uptime — negligible in phase 1's single process.
+  private readonly settled = new Set<string>();
+
+  // Bounded retry for the terminal write (F6): a single PK UPDATE can fail
+  // transiently under many fire-and-forget writes (pool exhaustion, deadlock, a
+  // brief connection blip). Riding out that blip in-place matters because the
+  // dominant success path (streamText onFinish) settles exactly ONCE — if that
+  // write is dropped and never retried, the row is stranded 'running' and the
+  // one-active-run gate 409s every future turn in the chat until a restart (no
+  // periodic sweep in phase 1).
+  private static readonly FINALIZE_MAX_ATTEMPTS = 3;
+  private static readonly FINALIZE_RETRY_BASE_MS = 50;
+
+  constructor(
+    private readonly runRepo: AiChatRunRepo,
+    private readonly environment: EnvironmentService,
+  ) {}
+
+  /**
+   * Crash-recovery sweep on server start: settle EVERY run still left
+   * pending/running to 'aborted' (F1 / DECISION C). The boot sweep is
+   * UNCONDITIONAL — no staleness window — because phase 1 is single-process: on a
+   * fresh boot any pending|running run is definitionally hung (no live runner owns
+   * it), so even a fast restart (deploy/OOM within minutes of the last step) can
+   * no longer leave a run stuck 'running' forever (which would make the
+   * one-active-run gate 409 every future turn in that chat). The staleness window
+   * is reintroduced only for the phase-2 multi-instance timer sweep, where a
+   * booting replica must not abort a run another replica is actively executing.
+   * Best-effort — a sweep failure is logged but MUST NOT block startup (mirrors
+   * AiChatService.onModuleInit for #183).
+   */
+  async onModuleInit(): Promise<void> {
+    this.warnIfMultiInstance();
+    try {
+      // No `staleMs`: unconditional boot sweep (F1). See AiChatRunRepo.sweepRunning.
+      const swept = await this.runRepo.sweepRunning();
+      if (swept > 0) {
+        this.logger.log(
+          `Startup sweep: marked ${swept} dangling agent run(s) as 'aborted'.`,
+        );
+      }
+    } catch (err) {
+      this.logger.warn(
+        `Startup sweep of dangling runs failed: ${
+          err instanceof Error ? err.message : 'unknown error'
+        }`,
+      );
+    }
+  }
+
+  /**
+   * F2 (DECISION A): autonomous runs are SINGLE-INSTANCE-ONLY in phase 1. An
+   * explicit Stop, and the in-memory AbortController that backs it, are
+   * process-local: a Stop only aborts the live turn if it lands on the SAME
+   * replica that owns the run (it still stamps `stop_requested_at` cross-instance,
+   * but nothing reads that flag during an active run yet). Cross-instance pub/sub
+   * stop is phase 2. So if the deployment is horizontally scaled, warn loudly at
+   * startup that a Stop may not reach a run executing on another replica.
+   *
+   * DETECTION: this codebase always wires the socket.io Redis adapter (REDIS_URL
+   * is mandatory), so the adapter alone is NOT a horizontal-scaling signal. The
+   * authoritative signal the codebase has is `CLOUD=true` (EnvironmentService
+   * .isCloud()), the Docmost-cloud multi-replica deployment. We warn whenever that
+   * is set, because any workspace could enable settings.ai.autonomousRuns. A
+   * self-hosted operator running multiple replicas behind a load balancer is also
+   * multi-instance; the deploy docs (.env.example / AGENTS.md) spell out the
+   * single-instance constraint for that case.
+   */
+  private warnIfMultiInstance(): void {
+    if (this.environment.isCloud()) {
+      this.logger.warn(
+        'Autonomous agent runs (settings.ai.autonomousRuns) are SINGLE-INSTANCE-ONLY ' +
+          'in phase 1: a horizontally-scaled deployment was detected (CLOUD=true). ' +
+          'An explicit Stop only aborts a run executing on the same replica that owns ' +
+          'it (cross-instance Stop is not yet reliable — phase 2). Run a single ' +
+          'instance if you enable autonomousRuns, or keep the flag off.',
+      );
+    }
+  }
+
+  /**
+   * Start a run for a turn: insert the run row (status 'running', startedAt now),
+   * register a fresh AbortController for it, and return a {@link RunHandle} whose
+   * `signal` the agent loop uses. The DB partial unique index guarantees at most
+   * one active run per chat — a second concurrent start on the same chat REJECTS
+   * at the insert (a 23505 on {@link ONE_ACTIVE_RUN_PER_CHAT_INDEX}). That
+   * rejection is the AUTHORITATIVE race gate: it is surfaced as a distinct
+   * {@link RunAlreadyActiveError} (NOT swallowed), so the caller turns it into a
+   * 409 and never streams an untracked turn. The controller is registered AFTER a
+   * successful insert so a rejected start leaks nothing.
+   */
+  async beginRun(args: {
+    chatId: string;
+    workspaceId: string;
+    userId: string;
+    trigger?: string;
+  }): Promise<RunHandle> {
+    let run: AiChatRun;
+    try {
+      run = await this.runRepo.insert({
+        chatId: args.chatId,
+        workspaceId: args.workspaceId,
+        createdBy: args.userId,
+        trigger: args.trigger ?? 'user',
+        status: 'running',
+        startedAt: new Date(),
+      });
+    } catch (err) {
+      // The race backstop: a concurrent turn already holds this chat's single
+      // active slot, so the partial unique index rejected our insert. Surface a
+      // distinct signal — the caller MUST reject this turn (409), not run it
+      // untracked. Any OTHER error propagates unchanged.
+      if (
+        isUniqueViolation(err) &&
+        violatedConstraint(err) === ONE_ACTIVE_RUN_PER_CHAT_INDEX
+      ) {
+        throw new RunAlreadyActiveError(args.chatId);
+      }
+      throw err;
+    }
+    const controller = new AbortController();
+    this.active.set(run.id, {
+      controller,
+      chatId: args.chatId,
+      workspaceId: args.workspaceId,
+    });
+    return { runId: run.id, signal: controller.signal };
+  }
+
+  /** Link the assistant message (the #183 projection) to its run. Best-effort. */
+  async linkAssistantMessage(
+    runId: string,
+    workspaceId: string,
+    assistantMessageId: string,
+  ): Promise<void> {
+    try {
+      await this.runRepo.update(runId, workspaceId, { assistantMessageId });
+    } catch (err) {
+      this.logger.warn(
+        `Failed to link assistant message to run ${runId}: ${
+          err instanceof Error ? err.message : 'unknown error'
+        }`,
+      );
+    }
+  }
+
+  /** Persist progress: bump the run's finished-step count. Best-effort (never
+   *  blocks or breaks the stream). */
+  async recordStep(
+    runId: string,
+    workspaceId: string,
+    stepCount: number,
+  ): Promise<void> {
+    try {
+      await this.runRepo.update(runId, workspaceId, { stepCount });
+    } catch (err) {
+      this.logger.warn(
+        `Failed to record step for run ${runId}: ${
+          err instanceof Error ? err.message : 'unknown error'
+        }`,
+      );
+    }
+  }
+
+  /**
+   * Finalize a run to its terminal status (succeeded / failed / aborted),
+   * stamping finishedAt + any error. Best-effort, but ROBUST against a transient
+   * terminal-write failure (F6) AND atomically safe against a concurrent settle.
+   *
+   * ATOMIC ONCE-CLAIM (the gate must close in ONE synchronous tick): two
+   * finalizeRun calls for the SAME run can race — the documented real path is
+   * AiChatService.stream's safety-net catch settling the turn to 'error' while a
+   * streamText terminal callback (onFinish/onAbort/onError) ALSO settles it. The
+   * `settled.has` check alone is NOT a gate: it is read BEFORE the awaited UPDATE,
+   * so two callers can both see `false` and both write the row (last-write-wins
+   * clobbers the real terminal status, and the bounded retry only widens that
+   * window). The claim therefore happens via `active.delete`, a SYNCHRONOUS
+   * check-and-clear with NO await between the gate and the entry removal: the
+   * second concurrent caller finds the entry already gone and returns in the same
+   * tick, before any UPDATE. The transition "nobody is finalizing" -> "I am
+   * finalizing" is thus a single atomic step.
+   *
+   * ORDER MATTERS (F6): once we own the claim, the terminal UPDATE happens FIRST;
+   * only once it SUCCEEDS do we record the run as settled. If the UPDATE fails on
+   * every bounded attempt we RESTORE the in-memory entry, leave the run UNsettled,
+   * and emit an ERROR signal that the row is left non-terminal 'running' (which
+   * would 409 every future turn in the chat until recovery). An in-process retry
+   * by a LATER settle is only POSSIBLE, never guaranteed: it needs (a) the entry
+   * to have been restored at the give-up path AND (b) a fresh settler to arrive
+   * AFTER that restore. A concurrent settler that arrives DURING the retry window
+   * — while the entry is deleted for backoff and not yet restored — is consumed at
+   * the synchronous `active.delete` claim (it finds nothing to delete and returns
+   * a no-op), so it does NOT become an in-process retrier. The NO-streamText path
+   * (the turn threw before streamText was wired, so ONLY the safety-net ever
+   * settles) likewise has no second in-process settler at all. The UNCONDITIONAL
+   * backstop in every case is the boot sweep on the next restart (phase 1 has no
+   * periodic in-process sweep); the retained entry is bounded (cleared on restart)
+   * and harmless meanwhile.
+   *
+   * IDEMPOTENT on SUCCESS (#184 review): the terminal write happens AT MOST ONCE
+   * per run. After a successful write the once-gate keys off {@link settled} (the
+   * terminal row already written) so a settle arriving AFTER the entry was already
+   * dropped-and-settled returns early; a settle racing the in-flight write is
+   * stopped earlier still, by the `active.delete` claim. Either way a genuine
+   * double-settle collapses to a single write and a late settle can never clobber
+   * the real terminal status or double-write the row.
+   */
+  async finalizeRun(
+    runId: string,
+    workspaceId: string,
+    turnStatus: TurnTerminalStatus,
+    error?: string,
+  ): Promise<void> {
+    // ---- Atomic once-claim (synchronous; NO await before the gate closes) ----
+    // Already terminally written -> idempotent no-op.
+    if (this.settled.has(runId)) return;
+    // Capture the entry BEFORE the delete so a total-failure path can restore it.
+    const entry = this.active.get(runId);
+    // SYNCHRONOUS check-and-clear: the FIRST caller deletes (claims) the entry;
+    // any concurrent SECOND caller finds nothing to delete and returns HERE, in
+    // the same tick, before any await — so it can never reach the UPDATE.
+    if (!this.active.delete(runId)) return;
+
+    let lastError: unknown;
+    for (
+      let attempt = 1;
+      attempt <= AiChatRunService.FINALIZE_MAX_ATTEMPTS;
+      attempt++
+    ) {
+      try {
+        await this.runRepo.update(runId, workspaceId, {
+          status: mapTurnStatusToRun(turnStatus),
+          finishedAt: new Date(),
+          error: error ?? null,
+        });
+        // Terminal write landed: arm the once-gate. The entry is already gone
+        // (claimed above); we do NOT restore it. The slot is now free.
+        this.settled.add(runId);
+        return;
+      } catch (err) {
+        lastError = err;
+        this.logger.warn(
+          `Failed to finalize run ${runId} (attempt ${attempt}/${
+            AiChatRunService.FINALIZE_MAX_ATTEMPTS
+          }): ${err instanceof Error ? err.message : 'unknown error'}`,
+        );
+        if (attempt < AiChatRunService.FINALIZE_MAX_ATTEMPTS) {
+          await this.delay(AiChatRunService.FINALIZE_RETRY_BASE_MS * attempt);
+        }
+      }
+    }
+    // Every attempt failed: this is a give-up, materially worse than a per-attempt
+    // blip — the row is left NON-TERMINAL ('running'), so emit ONE explicit,
+    // greppable ERROR so an operator can tell "survived a blip" from "gave up, run
+    // held in memory until recovery" (the last warn alone says only "attempt 3/3").
+    this.logger.error(
+      `Run ${runId} (chat ${entry?.chatId ?? 'unknown'}) left NON-TERMINAL ` +
+        `('running'): terminal write failed after ${
+          AiChatRunService.FINALIZE_MAX_ATTEMPTS
+        } attempts; entry retained in memory, recovery deferred to next settle / ` +
+        `boot sweep`,
+      lastError,
+    );
+    // RESTORE the claimed entry (and leave the run UNsettled) so a LATER settle
+    // that arrives AFTER this restore MAY retry the terminal write — but that
+    // in-process retry is NOT guaranteed (a concurrent settler caught in the retry
+    // window above is consumed at the `active.delete` claim, and the no-streamText
+    // path has no second settler at all). The UNCONDITIONAL backstop in every case
+    // is the boot sweep on the next restart; the restored entry is bounded and
+    // cleared on restart.
+    if (entry) this.active.set(runId, entry);
+  }
+
+  /** Small async backoff between terminal-write retries (F6). Isolated so it is
+   *  trivial to stub/fake-time in tests. */
+  private delay(ms: number): Promise<void> {
+    return new Promise((resolve) => setTimeout(resolve, ms));
+  }
+
+  /**
+   * Request an EXPLICIT stop of a run (the user pressed Stop). This is the ONLY
+   * thing that aborts a run — distinct from a browser disconnect, which leaves
+   * the run going. Aborts the in-process controller FIRST (the only thing that
+   * actually stops the run, if this replica owns it), then makes a best-effort
+   * attempt to stamp `stop_requested_at` — that audit write stamps only while the
+   * row is active and may be skipped on a DB error or lost to the finalize race,
+   * which is acceptable since the row still settles as 'aborted'. Returns true
+   * when a stop took effect (row marked and/or controller aborted), false when
+   * there was nothing active to stop.
+   */
+  async requestStop(runId: string, workspaceId: string): Promise<boolean> {
+    const entry = this.active.get(runId);
+    if (entry) {
+      // Abort the live turn FIRST -> streamText onAbort fires -> the partial is
+      // persisted (#183) and finalizeRun settles the row as 'aborted'. This is
+      // the ONLY thing that aborts a run, so it MUST NOT be hostage to the audit
+      // write below: a transient failure on `markStopRequested` (pool exhaustion,
+      // deadlock, dropped connection) must never leave the run executing despite
+      // an explicit Stop. At worst only the `stop_requested_at` timestamp is lost.
+      entry.controller.abort();
+    }
+    // Record `stop_requested_at` (best-effort). A transient DB failure here is
+    // logged and treated as `marked = false`; the abort above already took
+    // effect, so we never rethrow and skip stopping the run. Note: because
+    // markStopRequested only stamps while the row is active, aborting first means
+    // even a healthy write can lose the race against the resulting finalize and
+    // skip the stamp — acceptable, as the row still settles as 'aborted' and only
+    // this audit timestamp may be lost.
+    let marked: unknown;
+    try {
+      marked = await this.runRepo.markStopRequested(runId, workspaceId);
+    } catch (err) {
+      marked = undefined;
+      this.logger.warn(
+        `requestStop: markStopRequested failed for run ${runId} ` +
+          `(stop_requested_at not recorded); abort already issued: ` +
+          `${err instanceof Error ? err.message : String(err)}`,
+      );
+    }
+    return Boolean(marked) || Boolean(entry);
+  }
+
+  /** Latest persisted run for a chat — the reconnect target (an in-flight or
+   *  finished run). Pure read-through to the repo. */
+  getLatestForChat(
+    chatId: string,
+    workspaceId: string,
+  ): Promise<AiChatRun | undefined> {
+    return this.runRepo.findLatestByChat(chatId, workspaceId);
+  }
+
+  /** Fetch a run by id (workspace-scoped). Used to resolve + ownership-check an
+   *  explicit stop targeting a runId. */
+  getRun(runId: string, workspaceId: string): Promise<AiChatRun | undefined> {
+    return this.runRepo.findById(runId, workspaceId);
+  }
+
+  /** The active run on a chat, if any (used to reject a concurrent start with a
+   *  clean 409 before committing to the stream). */
+  getActiveForChat(
+    chatId: string,
+    workspaceId: string,
+  ): Promise<AiChatRun | undefined> {
+    return this.runRepo.findActiveByChat(chatId, workspaceId);
+  }
+
+  /** Test/diagnostic seam: whether this replica is holding a live controller for
+   *  the run. */
+  isLocallyActive(runId: string): boolean {
+    return this.active.has(runId);
+  }
+}

apps/server/src/core/ai-chat/ai-chat.controller.bound-chat.spec.ts

@@ -25,6 +25,7 @@ describe('AiChatController.boundChat', () => {
     };
     const controller = new AiChatController(
       {} as never,
+      {} as never, // aiChatRunService
       aiChatRepo as never,
       {} as never,
       {} as never,

apps/server/src/core/ai-chat/ai-chat.controller.export.spec.ts

@@ -53,6 +53,7 @@ describe('AiChatController.export', () => {
     };
     const controller = new AiChatController(
       {} as never,
+      {} as never, // aiChatRunService
       aiChatRepo as never,
       aiChatMessageRepo as never,
       {} as never,

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

@@ -0,0 +1,164 @@
+import { BadRequestException, ForbiddenException } from '@nestjs/common';
+import { AiChatController } from './ai-chat.controller';
+import type { User, Workspace } from '@docmost/db/types/entity.types';
+
+/**
+ * Wiring spec for the #184 run-reconnect / run-stop endpoints
+ * (`POST /ai-chat/run` and `POST /ai-chat/stop`). Both are OWNER-gated via
+ * assertOwnedChat (the requesting user must own the chat) and NOT flag-gated.
+ * Exercised with hand-rolled mocks — no Nest graph, no DB. The controller's
+ * constructor order is (aiChatService, aiChatRunService, aiChatRepo,
+ * aiChatMessageRepo, aiTranscription).
+ */
+describe('AiChatController run endpoints (#184)', () => {
+  const user = { id: 'u1' } as User;
+  const workspace = { id: 'ws1' } as Workspace;
+
+  function makeController(opts: {
+    chat?: unknown; // what aiChatRepo.findById returns (owner-gate)
+    run?: unknown; // getLatestForChat / getRun result
+    activeRun?: unknown; // getActiveForChat result
+    message?: unknown; // aiChatMessageRepo.findById result
+    stopped?: boolean; // requestStop result
+  }) {
+    const aiChatRunService = {
+      getLatestForChat: jest.fn().mockResolvedValue(opts.run),
+      getRun: jest.fn().mockResolvedValue(opts.run),
+      getActiveForChat: jest.fn().mockResolvedValue(opts.activeRun),
+      requestStop: jest.fn().mockResolvedValue(opts.stopped ?? false),
+    };
+    const aiChatRepo = {
+      findById: jest.fn().mockResolvedValue(opts.chat),
+    };
+    const aiChatMessageRepo = {
+      findById: jest.fn().mockResolvedValue(opts.message),
+    };
+    const controller = new AiChatController(
+      {} as never, // aiChatService
+      aiChatRunService as never,
+      aiChatRepo as never,
+      aiChatMessageRepo as never,
+      {} as never, // aiTranscription
+      {} as never, // pageRepo
+    );
+    return { controller, aiChatRunService, aiChatRepo, aiChatMessageRepo };
+  }
+
+  describe('POST /ai-chat/run (getRun)', () => {
+    it('owner-gates: a chat the user does not own throws ForbiddenException', async () => {
+      const { controller, aiChatRunService } = makeController({
+        chat: { id: 'c1', creatorId: 'someone-else' },
+      });
+      await expect(
+        controller.getRun({ chatId: 'c1' }, user, workspace),
+      ).rejects.toBeInstanceOf(ForbiddenException);
+      // It must NOT reach the run lookup once the owner-gate fails.
+      expect(aiChatRunService.getLatestForChat).not.toHaveBeenCalled();
+    });
+
+    it('returns { run: null, message: null } when the chat has never had a run', async () => {
+      const { controller, aiChatRunService } = makeController({
+        chat: { id: 'c1', creatorId: 'u1' },
+        run: undefined,
+      });
+      const res = await controller.getRun({ chatId: 'c1' }, user, workspace);
+      expect(res).toEqual({ run: null, message: null });
+      expect(aiChatRunService.getLatestForChat).toHaveBeenCalledWith(
+        'c1',
+        'ws1',
+      );
+    });
+
+    it('returns the run and its projected assistant message', async () => {
+      const run = { id: 'run-1', chatId: 'c1', assistantMessageId: 'm1' };
+      const message = { id: 'm1', role: 'assistant' };
+      const { controller, aiChatMessageRepo } = makeController({
+        chat: { id: 'c1', creatorId: 'u1' },
+        run,
+        message,
+      });
+      const res = await controller.getRun({ chatId: 'c1' }, user, workspace);
+      expect(res).toEqual({ run, message });
+      expect(aiChatMessageRepo.findById).toHaveBeenCalledWith('m1', 'ws1');
+    });
+
+    it('returns message: null when the run has no linked assistant message', async () => {
+      const run = { id: 'run-1', chatId: 'c1', assistantMessageId: null };
+      const { controller, aiChatMessageRepo } = makeController({
+        chat: { id: 'c1', creatorId: 'u1' },
+        run,
+      });
+      const res = await controller.getRun({ chatId: 'c1' }, user, workspace);
+      expect(res).toEqual({ run, message: null });
+      expect(aiChatMessageRepo.findById).not.toHaveBeenCalled();
+    });
+  });
+
+  describe('POST /ai-chat/stop (stopRun)', () => {
+    it('throws BadRequestException when neither runId nor chatId is given', async () => {
+      const { controller } = makeController({});
+      await expect(
+        controller.stopRun({}, user, workspace),
+      ).rejects.toBeInstanceOf(BadRequestException);
+    });
+
+    it('stops by runId: owner-gates via the run’s chat, then requests the stop', async () => {
+      const { controller, aiChatRunService, aiChatRepo } = makeController({
+        run: { id: 'run-1', chatId: 'c1' },
+        chat: { id: 'c1', creatorId: 'u1' },
+        stopped: true,
+      });
+      const res = await controller.stopRun({ runId: 'run-1' }, user, workspace);
+      expect(res).toEqual({ stopped: true });
+      expect(aiChatRunService.getRun).toHaveBeenCalledWith('run-1', 'ws1');
+      expect(aiChatRepo.findById).toHaveBeenCalledWith('c1', 'ws1');
+      expect(aiChatRunService.requestStop).toHaveBeenCalledWith('run-1', 'ws1');
+    });
+
+    it('stops by runId: a foreign run’s chat throws ForbiddenException (no stop)', async () => {
+      const { controller, aiChatRunService } = makeController({
+        run: { id: 'run-1', chatId: 'c1' },
+        chat: { id: 'c1', creatorId: 'someone-else' },
+      });
+      await expect(
+        controller.stopRun({ runId: 'run-1' }, user, workspace),
+      ).rejects.toBeInstanceOf(ForbiddenException);
+      expect(aiChatRunService.requestStop).not.toHaveBeenCalled();
+    });
+
+    it('stops by runId: an unknown run reports { stopped: false }', async () => {
+      const { controller, aiChatRunService } = makeController({
+        run: undefined,
+      });
+      const res = await controller.stopRun({ runId: 'gone' }, user, workspace);
+      expect(res).toEqual({ stopped: false });
+      expect(aiChatRunService.requestStop).not.toHaveBeenCalled();
+    });
+
+    it('stops by chatId: owner-gates, resolves the active run, requests the stop', async () => {
+      const { controller, aiChatRunService, aiChatRepo } = makeController({
+        chat: { id: 'c1', creatorId: 'u1' },
+        activeRun: { id: 'run-9' },
+        stopped: true,
+      });
+      const res = await controller.stopRun({ chatId: 'c1' }, user, workspace);
+      expect(res).toEqual({ stopped: true });
+      expect(aiChatRepo.findById).toHaveBeenCalledWith('c1', 'ws1');
+      expect(aiChatRunService.getActiveForChat).toHaveBeenCalledWith(
+        'c1',
+        'ws1',
+      );
+      expect(aiChatRunService.requestStop).toHaveBeenCalledWith('run-9', 'ws1');
+    });
+
+    it('stops by chatId: reports { stopped: false } when no run is active', async () => {
+      const { controller, aiChatRunService } = makeController({
+        chat: { id: 'c1', creatorId: 'u1' },
+        activeRun: undefined,
+      });
+      const res = await controller.stopRun({ chatId: 'c1' }, user, workspace);
+      expect(res).toEqual({ stopped: false });
+      expect(aiChatRunService.requestStop).not.toHaveBeenCalled();
+    });
+  });
+});

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

@@ -1,6 +1,7 @@
 import {
   BadRequestException,
   Body,
+  ConflictException,
   Controller,
   ForbiddenException,
   HttpCode,
@@ -20,7 +21,13 @@ import { JwtAuthGuard } from '../../common/guards/jwt-auth.guard';
 import { AuthUser } from '../../common/decorators/auth-user.decorator';
 import { AuthWorkspace } from '../../common/decorators/auth-workspace.decorator';
 import { SkipTransform } from '../../common/decorators/skip-transform.decorator';
-import { AiChat, User, Workspace } from '@docmost/db/types/entity.types';
+import {
+  AiChat,
+  AiChatMessage,
+  AiChatRun,
+  User,
+  Workspace,
+} from '@docmost/db/types/entity.types';
 import { PaginationOptions } from '@docmost/db/pagination/pagination-options';
 import { AiChatRepo } from '@docmost/db/repos/ai-chat/ai-chat.repo';
 import { AiChatMessageRepo } from '@docmost/db/repos/ai-chat/ai-chat-message.repo';
@@ -28,7 +35,12 @@ import { PageRepo } from '@docmost/db/repos/page/page.repo';
 import { UserThrottlerGuard } from '../../integrations/throttle/user-throttler.guard';
 import { AI_CHAT_THROTTLER } from '../../integrations/throttle/throttler-names';
 import { FileInterceptor } from '../../common/interceptors/file.interceptor';
-import { AiChatService, AiChatStreamBody } from './ai-chat.service';
+import {
+  AiChatRunHooks,
+  AiChatService,
+  AiChatStreamBody,
+} from './ai-chat.service';
+import { AiChatRunService } from './ai-chat-run.service';
 import { AiTranscriptionService } from './ai-transcription.service';
 import {
   BoundChatDto,
@@ -36,7 +48,9 @@ import {
   ExportChatDto,
   GeneratePageTitleDto,
   GetChatMessagesDto,
+  GetRunDto,
   RenameChatDto,
+  StopRunDto,
 } from './dto/ai-chat.dto';
 import { describeProviderError } from '../../integrations/ai/ai-error.util';
 import { buildChatMarkdown } from './chat-markdown.util';
@@ -53,6 +67,7 @@ export class AiChatController {
 
   constructor(
     private readonly aiChatService: AiChatService,
+    private readonly aiChatRunService: AiChatRunService,
     private readonly aiChatRepo: AiChatRepo,
     private readonly aiChatMessageRepo: AiChatMessageRepo,
     private readonly aiTranscription: AiTranscriptionService,
@@ -149,6 +164,75 @@ export class AiChatController {
     return { markdown };
   }
 
+  /**
+   * Reconnect to the latest run of a chat (#184 phase 1). Returns the run's
+   * persisted lifecycle state ({ status, error, stepCount, timings, ... }) plus
+   * the assistant message it projects (the partial/final output) — the DB is the
+   * source of truth, so this works for an in-flight run (the browser dropped, the
+   * run kept going) and a finished one alike. Owner-gated via assertOwnedChat.
+   * `{ run: null }` when the chat has never had a run.
+   */
+  @HttpCode(HttpStatus.OK)
+  @Post('run')
+  async getRun(
+    @Body() dto: GetRunDto,
+    @AuthUser() user: User,
+    @AuthWorkspace() workspace: Workspace,
+  ): Promise<{ run: AiChatRun | null; message: AiChatMessage | null }> {
+    await this.assertOwnedChat(dto.chatId, user, workspace);
+    const run = await this.aiChatRunService.getLatestForChat(
+      dto.chatId,
+      workspace.id,
+    );
+    if (!run) return { run: null, message: null };
+    const message = run.assistantMessageId
+      ? await this.aiChatMessageRepo.findById(
+          run.assistantMessageId,
+          workspace.id,
+        )
+      : undefined;
+    return { run, message: message ?? null };
+  }
+
+  /**
+   * Explicitly STOP an agent run (#184 phase 1) — the user pressed Stop. This is
+   * the ONLY thing that ends a detached run; a browser disconnect deliberately
+   * does not. Target by `runId` (from the streamed start metadata) or by `chatId`
+   * (stop whatever run is active on it). Owner-gated. Returns
+   * `{ stopped }` — false when there was nothing active to stop.
+   */
+  @HttpCode(HttpStatus.OK)
+  @Post('stop')
+  async stopRun(
+    @Body() dto: StopRunDto,
+    @AuthUser() user: User,
+    @AuthWorkspace() workspace: Workspace,
+  ): Promise<{ stopped: boolean }> {
+    let runId = dto.runId;
+    if (!runId && !dto.chatId) {
+      throw new BadRequestException('runId or chatId is required');
+    }
+    if (runId) {
+      // Resolve the run to its chat and owner-gate via that chat.
+      const run = await this.aiChatRunService.getRun(runId, workspace.id);
+      if (!run) return { stopped: false };
+      await this.assertOwnedChat(run.chatId, user, workspace);
+    } else {
+      await this.assertOwnedChat(dto.chatId!, user, workspace);
+      const active = await this.aiChatRunService.getActiveForChat(
+        dto.chatId!,
+        workspace.id,
+      );
+      if (!active) return { stopped: false };
+      runId = active.id;
+    }
+    const stopped = await this.aiChatRunService.requestStop(
+      runId,
+      workspace.id,
+    );
+    return { stopped };
+  }
+
   /** Rename a chat. */
   @HttpCode(HttpStatus.OK)
   @Post('rename')
@@ -200,11 +284,20 @@ export class AiChatController {
     @AuthWorkspace() workspace: Workspace,
   ): Promise<void> {
     // A7 gate: the workspace must have AI chat explicitly enabled.
-    const settings = (workspace.settings ?? {}) as { ai?: { chat?: boolean } };
+    const settings = (workspace.settings ?? {}) as {
+      ai?: { chat?: boolean; autonomousRuns?: boolean };
+    };
     if (settings.ai?.chat !== true) {
       throw new ForbiddenException('AI chat is disabled');
     }
 
+    // #184 phase 1 flag: when ON, the turn becomes a detached, durable RUN — its
+    // lifecycle is tracked in ai_chat_runs, a browser disconnect no longer aborts
+    // it, and only an explicit /ai-chat/stop ends it. When OFF (the default) the
+    // turn is socket-bound exactly as before, so existing deployments are
+    // unaffected.
+    const autonomousRuns = settings.ai?.autonomousRuns === true;
+
     const sessionId = (req.raw as { sessionId?: string }).sessionId;
     if (!sessionId) {
       // The chat requires an interactive session to mint loopback tokens
@@ -228,6 +321,58 @@ export class AiChatController {
     // HttpException) instead of breaking mid-stream.
     const model = await this.aiChatService.getChatModel(workspace.id, role);
 
+    // #184: one active run per chat. For an EXISTING chat reject a concurrent
+    // start with a clean 409 BEFORE hijack (the common double-submit / second-tab
+    // case), so the user gets JSON, not a mid-stream error. A brand-new chat
+    // (no chatId) cannot have a prior run, and the DB partial unique index is the
+    // backstop against any race that slips past this check.
+    if (autonomousRuns && body.chatId) {
+      const active = await this.aiChatRunService.getActiveForChat(
+        body.chatId,
+        workspace.id,
+      );
+      if (active) {
+        throw new ConflictException({
+          message: 'An agent run is already in progress for this chat',
+          code: 'A_RUN_ALREADY_ACTIVE',
+        });
+      }
+    }
+
+    // Run-lifecycle hooks (#184), only when the flag is on. They wrap the turn in
+    // a durable run whose abort is governed by the run (explicit stop), persist
+    // its progress, and settle its terminal status — see AiChatRunService.
+    const runHooks: AiChatRunHooks | undefined = autonomousRuns
+      ? {
+          begin: (chatId) =>
+            this.aiChatRunService.beginRun({
+              chatId,
+              workspaceId: workspace.id,
+              userId: user.id,
+              trigger: 'user',
+            }),
+          onAssistantSeeded: (runId, messageId) =>
+            this.aiChatRunService.linkAssistantMessage(
+              runId,
+              workspace.id,
+              messageId,
+            ),
+          onStep: (runId, stepCount) =>
+            void this.aiChatRunService.recordStep(
+              runId,
+              workspace.id,
+              stepCount,
+            ),
+          onSettled: (runId, status, error) =>
+            this.aiChatRunService.finalizeRun(
+              runId,
+              workspace.id,
+              status,
+              error,
+            ),
+        }
+      : undefined;
+
     // Abort the agent loop when the client disconnects. `close` also fires on
     // normal completion, so only abort when the response has not finished
     // writing (a genuine disconnect). `once` fires at most once and self-removes;
@@ -242,18 +387,44 @@ export class AiChatController {
       // A genuine disconnect leaves the response unfinished (unlike a normal
       // completion, which also fires `close`). Such a drop — e.g. a reverse
       // proxy cutting the SSE mid-answer — is otherwise invisible server-side,
-      // so log it here before aborting the agent loop.
+      // so log it here.
       if (!res.raw.writableEnded) {
-        this.logger.warn(
-          `AI chat stream: client disconnected before completion; aborting turn ` +
-            `(elapsed=${Date.now() - reqStartedAt}ms since request received)`,
-        );
-        controller.abort();
+        if (autonomousRuns) {
+          // #184: the turn is a DETACHED run. A disconnect must NOT abort it —
+          // the run keeps executing and persisting server-side; the client
+          // reconnects via /ai-chat/run (or re-stops via /ai-chat/stop). Log only.
+          this.logger.log(
+            `AI chat stream: client disconnected; run continues server-side ` +
+              `(elapsed=${Date.now() - reqStartedAt}ms since request received)`,
+          );
+        } else {
+          this.logger.warn(
+            `AI chat stream: client disconnected before completion; aborting turn ` +
+              `(elapsed=${Date.now() - reqStartedAt}ms since request received)`,
+          );
+          controller.abort();
+        }
       }
     };
     req.raw.once('close', onClose);
     res.raw.once('finish', () => req.raw.off('close', onClose));
 
+    // #184: in detached mode the turn is NOT aborted on disconnect, so the SDK's
+    // pipe keeps writing to a socket the client may have dropped — for the rest of
+    // the (continuing) run. A write to the dead socket can emit an 'error' on the
+    // raw response; without a listener that surfaces as an unhandled error event.
+    // Swallow it (the run continues server-side regardless). Legacy mode aborts on
+    // disconnect, so it does not need this and keeps its exact prior behavior.
+    if (autonomousRuns) {
+      res.raw.on('error', (err) => {
+        this.logger.debug(
+          `AI chat detached stream: post-disconnect socket error swallowed: ${
+            err instanceof Error ? err.message : String(err)
+          }`,
+        );
+      });
+    }
+
     // Commit to streaming: hijack so Fastify stops managing the response and
     // the AI SDK can write the UI-message stream directly to the Node socket.
     res.hijack();
@@ -268,15 +439,32 @@ export class AiChatController {
         signal: controller.signal,
         model,
         role,
+        // #184: present only when the flag is on; wraps the turn in a durable run.
+        runHooks,
       });
     } catch (err) {
-      // Any failure AFTER hijack can no longer send a clean JSON error, so emit
-      // a minimal error on the raw socket if nothing has been written yet.
-      this.logger.error('AI chat stream failed', err as Error);
+      // Any failure AFTER hijack can no longer go through Nest's exception
+      // filter, so emit the error on the raw socket if nothing has been written
+      // yet. The lost-the-race 409 (RunAlreadyActiveError -> ConflictException)
+      // is raised by stream() BEFORE it writes a byte, so headers are still
+      // unsent here: honor the HttpException's real status + body (a clean 409),
+      // not a blanket 500. Everything else stays a 500.
+      const isHttp = err instanceof HttpException;
+      if (!isHttp) {
+        this.logger.error('AI chat stream failed', err as Error);
+      }
       if (!res.raw.headersSent) {
-        res.raw.statusCode = 500;
+        const status = isHttp ? err.getStatus() : 500;
+        const payload = isHttp
+          ? err.getResponse()
+          : { error: 'Internal server error' };
+        res.raw.statusCode = status;
         res.raw.setHeader('Content-Type', 'application/json');
-        res.raw.end(JSON.stringify({ error: 'Internal server error' }));
+        res.raw.end(
+          JSON.stringify(
+            typeof payload === 'string' ? { message: payload } : payload,
+          ),
+        );
       } else if (!res.raw.writableEnded) {
         res.raw.end();
       }

apps/server/src/core/ai-chat/ai-chat.generate-page-title.spec.ts

@@ -57,6 +57,7 @@ describe('AiChatController.generatePageTitle', () => {
     const aiChatService = { generatePageTitle: generate };
     const controller = new AiChatController(
       aiChatService as never,
+      {} as never, // aiChatRunService
       {} as never,
       {} as never,
       {} as never,

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

@@ -3,6 +3,7 @@ import { AiModule } from '../../integrations/ai/ai.module';
 import { TokenModule } from '../auth/token.module';
 import { AiChatController } from './ai-chat.controller';
 import { AiChatService } from './ai-chat.service';
+import { AiChatRunService } from './ai-chat-run.service';
 import { AiTranscriptionService } from './ai-transcription.service';
 import { AiChatToolsService } from './tools/ai-chat-tools.service';
 import { EmbeddingModule } from './embedding/embedding.module';
@@ -42,6 +43,7 @@ import { PublicShareChatToolsService } from './tools/public-share-chat-tools.ser
   controllers: [AiChatController, PublicShareChatController],
   providers: [
     AiChatService,
+    AiChatRunService,
     AiTranscriptionService,
     AiChatToolsService,
     PublicShareChatService,

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

@@ -1,5 +1,7 @@
 import { Logger } from '@nestjs/common';
-import { AiChatService } from './ai-chat.service';
+import { AiChatService, AiChatRunHooks } from './ai-chat.service';
+import { AiChatRunService } from './ai-chat-run.service';
+import type { User, Workspace } from '@docmost/db/types/entity.types';
 
 /**
  * Lifecycle unit tests for AiChatService.onModuleInit (#183 crash-recovery
@@ -61,3 +63,99 @@ describe('AiChatService.onModuleInit (startup sweep)', () => {
     expect(String(warnSpy.mock.calls[0][0])).toContain('db unavailable');
   });
 });
+
+/**
+ * #184 CRITICAL run-lifecycle safety net (review fix). A transient failure
+ * AFTER a successful beginRun but BEFORE streamText's terminal callbacks own the
+ * lifecycle must STILL settle the run — otherwise the run row is stuck 'running'
+ * forever (sweepRunning only runs at startup) and the partial unique index + the
+ * controller pre-check 409 every future turn in that chat until a restart. Here
+ * we model the very first bare await after beginRun (the user-message insert)
+ * throwing, wiring the run hooks to a REAL AiChatRunService (mock repo) exactly
+ * as the controller does, and assert the run is settled to 'error' and its
+ * in-memory entry dropped (so a follow-up turn would NOT be 409'd).
+ */
+describe('AiChatService.stream run-lifecycle safety net (#184)', () => {
+  const user = { id: 'u1' } as User;
+  const workspace = { id: 'ws1' } as Workspace;
+
+  afterEach(() => jest.restoreAllMocks());
+
+  it('an exception after beginRun settles the run to error and drops the in-memory entry', async () => {
+    jest.spyOn(Logger.prototype, 'error').mockImplementation(() => undefined);
+
+    // Real run service over a mock repo, so finalizeRun's in-memory bookkeeping
+    // (active.delete) is exercised for real.
+    const runRepo = {
+      insert: jest.fn().mockResolvedValue({ id: 'run-1', status: 'running' }),
+      update: jest.fn().mockResolvedValue({ id: 'run-1' }),
+    };
+    const runService = new AiChatRunService(runRepo as never, { isCloud: () => false } as never);
+
+    // The user-message insert (the first bare await after beginRun) throws.
+    const aiChatMessageRepo = {
+      insert: jest.fn().mockRejectedValue(new Error('insert boom')),
+    };
+    const aiChatRepo = {
+      // Existing chat -> chatId stays, no new-chat insert path.
+      findById: jest.fn().mockResolvedValue({ id: 'chat-1', creatorId: 'u1' }),
+    };
+
+    const service = new AiChatService(
+      {} as never, // ai
+      aiChatRepo as never,
+      aiChatMessageRepo as never,
+      {} as never, // aiChatPageSnapshotRepo
+      {} as never, // aiSettings
+      {} as never, // tools
+      {} as never, // mcpClients
+      {} as never, // aiAgentRoleRepo
+      {} as never, // pageRepo
+      {} as never, // pageAccess
+      {} as never, // environment
+    );
+
+    const runHooks: AiChatRunHooks = {
+      begin: (chatId) =>
+        runService.beginRun({
+          chatId,
+          workspaceId: workspace.id,
+          userId: user.id,
+          trigger: 'user',
+        }),
+      onSettled: (runId, status, error) =>
+        runService.finalizeRun(runId, workspace.id, status, error),
+    };
+
+    await expect(
+      service.stream({
+        user,
+        workspace,
+        sessionId: 'sess',
+        body: {
+          chatId: 'chat-1',
+          messages: [
+            { id: 'm', role: 'user', parts: [{ type: 'text', text: 'hi' }] },
+          ],
+        },
+        res: {} as never,
+        signal: new AbortController().signal,
+        model: {} as never,
+        role: null,
+        runHooks,
+      }),
+    ).rejects.toThrow('insert boom');
+
+    // The run was begun...
+    expect(runRepo.insert).toHaveBeenCalledTimes(1);
+    // ...then settled to a terminal FAILED status by the safety net...
+    expect(runRepo.update).toHaveBeenCalledTimes(1);
+    expect(runRepo.update).toHaveBeenCalledWith(
+      'run-1',
+      'ws1',
+      expect.objectContaining({ status: 'failed' }),
+    );
+    // ...and the in-memory entry is gone, so a follow-up turn is NOT 409'd.
+    expect(runService.isLocallyActive('run-1')).toBe(false);
+  });
+});

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

@@ -0,0 +1,489 @@
+import { ConflictException, Logger } 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
+// any streamText/generateText, so these never resolve a real model.
+jest.mock('ai', () => ({
+  streamText: jest.fn(),
+  generateText: jest.fn(),
+  convertToModelMessages: jest.fn(() => []),
+  stepCountIs: jest.fn(() => () => false),
+}));
+
+import { streamText, generateText } from 'ai';
+import { AiChatService } from './ai-chat.service';
+import { RunAlreadyActiveError } from './ai-chat-run.service';
+
+/**
+ * Race-closure coverage for the "one active run per chat" guard (#184).
+ *
+ * THE BUG: two simultaneous POST /ai-chat/stream on the same chat both pass the
+ * controller's cheap pre-check (TOCTOU), so the loser's run-row INSERT hits the
+ * partial unique index. Previously that 23505 was SWALLOWED and the second turn
+ * streamed UNTRACKED (no runId, not stoppable). THE FIX: beginRun surfaces a
+ * RunAlreadyActiveError and stream() turns it into a 409 BEFORE any AI call —
+ * the second turn never runs.
+ */
+describe('AiChatService.stream — concurrent-run race rejection (#184)', () => {
+  const streamTextMock = streamText as unknown as jest.Mock;
+  const generateTextMock = generateText as unknown as jest.Mock;
+
+  beforeEach(() => {
+    streamTextMock.mockReset();
+    generateTextMock.mockReset();
+  });
+
+  // Minimal service whose only reachable deps before begin() are aiChatRepo
+  // (resolve the existing chat) — everything past begin must remain untouched.
+  function makeService(beginImpl: () => Promise<unknown>) {
+    const aiChatMessageRepo = { insert: jest.fn() };
+    const aiChatRepo = {
+      // An existing chat: stream keeps the supplied chatId and skips creation.
+      findById: jest.fn(async () => ({ id: 'chat-1', workspaceId: 'ws-1' })),
+      insert: jest.fn(),
+    };
+    const svc = new AiChatService(
+      {} as never, // ai
+      aiChatRepo as never,
+      aiChatMessageRepo as never,
+      {} as never, // aiChatPageSnapshotRepo
+      {} as never, // aiSettings
+      {} as never, // tools
+      {} as never, // mcpClients
+      {} as never, // aiAgentRoleRepo
+      {} as never, // pageRepo
+      {} as never, // pageAccess
+      { isAiChatDeferredToolsEnabled: () => false } as never, // environment
+    );
+    const begin = jest.fn(beginImpl);
+    return { svc, begin, aiChatRepo, aiChatMessageRepo };
+  }
+
+  const baseArgs = (begin: jest.Mock) => ({
+    user: { id: 'user-1' } as never,
+    workspace: { id: 'ws-1' } as never,
+    sessionId: 'sess-1',
+    body: { chatId: 'chat-1', messages: [] } as never,
+    res: { raw: {} } as never,
+    signal: new AbortController().signal,
+    model: {} as never,
+    role: null,
+    runHooks: {
+      begin,
+      onAssistantSeeded: jest.fn(),
+      onStep: jest.fn(),
+      onSettled: jest.fn(),
+    } as never,
+  });
+
+  it('rejects the racer with a 409 ConflictException BEFORE any AI call, and never persists an untracked turn', async () => {
+    // begin loses the unique-index race -> RunAlreadyActiveError.
+    const { svc, begin, aiChatMessageRepo } = makeService(() => {
+      throw new RunAlreadyActiveError('chat-1');
+    });
+
+    const promise = svc.stream(baseArgs(begin));
+
+    await expect(promise).rejects.toBeInstanceOf(ConflictException);
+    await promise.catch((err: ConflictException) => {
+      expect(err.getStatus()).toBe(409);
+      expect((err.getResponse() as { code?: string }).code).toBe(
+        'A_RUN_ALREADY_ACTIVE',
+      );
+    });
+
+    // The decisive assertions: the rejected racer spent NO tokens and left NO
+    // untracked turn behind.
+    expect(begin).toHaveBeenCalledTimes(1);
+    expect(streamTextMock).not.toHaveBeenCalled();
+    expect(generateTextMock).not.toHaveBeenCalled();
+    expect(aiChatMessageRepo.insert).not.toHaveBeenCalled();
+  });
+});
+
+/**
+ * F3 — the LOAD-BEARING run-detach wiring: `effectiveSignal = handle.signal`
+ * after runHooks.begin, then `abortSignal: effectiveSignal` passed to streamText.
+ * That single line is what makes a run survive a browser disconnect (the agent
+ * loop's abort is governed by the RUN's signal, not the socket): a regression to
+ * the socket-bound signal would still pass every other test green while silently
+ * breaking Stop + durability. These two tests pin the exact signal streamText
+ * consumes on both paths.
+ */
+describe('AiChatService.stream — abortSignal wiring (#184 F3)', () => {
+  const streamTextMock = streamText as unknown as jest.Mock;
+
+  // A streamText result stub: the post-call drain + pipe are no-ops here; we only
+  // care WHICH abortSignal streamText was handed.
+  function makeStreamResult() {
+    return {
+      consumeStream: jest.fn(),
+      pipeUIMessageStreamToResponse: jest.fn(),
+    };
+  }
+
+  // A raw-response stub sufficient for the post-streamText wiring
+  // (stripStreamingHopByHopHeaders binds writeHead; startSseHeartbeat registers
+  // close/finish listeners; flushHeaders is belt-and-braces).
+  function makeRes() {
+    return {
+      raw: {
+        writeHead: jest.fn(),
+        write: jest.fn(),
+        once: jest.fn(),
+        on: jest.fn(),
+        flushHeaders: jest.fn(),
+        writableEnded: false,
+        destroyed: false,
+      },
+    };
+  }
+
+  // Wire only the deps reached on the way to streamText: resolve the existing
+  // chat, persist the user + seed the assistant row, load (empty) history, the
+  // admin settings, an empty external toolset + Docmost toolset.
+  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: [],
+      })),
+    };
+    const svc = new AiChatService(
+      {} as never, // ai
+      aiChatRepo as never,
+      aiChatMessageRepo as never,
+      {} as never, // aiChatPageSnapshotRepo
+      aiSettings as never,
+      tools as never,
+      mcpClients as never,
+      {} as never, // aiAgentRoleRepo
+      {} as never, // pageRepo (openPage undefined -> never touched)
+      {} as never, // pageAccess
+      { isAiChatDeferredToolsEnabled: () => false } as never, // environment
+    );
+    return { svc };
+  }
+
+  const body = {
+    chatId: 'chat-1',
+    messages: [
+      { id: 'm1', role: 'user', parts: [{ type: 'text', text: 'hi' }] },
+    ],
+  };
+
+  beforeEach(() => {
+    streamTextMock.mockReset();
+    streamTextMock.mockImplementation(() => makeStreamResult());
+    jest
+      .spyOn(Logger.prototype, 'log')
+      .mockImplementation(() => undefined as never);
+  });
+
+  afterEach(() => jest.restoreAllMocks());
+
+  it('happy path (run-wrapped): streamText is driven with abortSignal === handle.signal (the RUN signal, NOT the socket)', async () => {
+    const { svc } = makeService();
+    const runController = new AbortController();
+    const runSignal = runController.signal;
+    const socketSignal = new AbortController().signal;
+
+    const begin = jest.fn(async () => ({ runId: 'run-1', signal: runSignal }));
+    await svc.stream({
+      user: { id: 'user-1' } as never,
+      workspace: { id: 'ws-1' } as never,
+      sessionId: 'sess-1',
+      body: body as never,
+      res: makeRes() as never,
+      signal: socketSignal,
+      model: {} as never,
+      role: null,
+      runHooks: {
+        begin,
+        onAssistantSeeded: jest.fn(),
+        onStep: jest.fn(),
+        onSettled: jest.fn(),
+      } as never,
+    });
+
+    expect(begin).toHaveBeenCalledTimes(1);
+    expect(streamTextMock).toHaveBeenCalledTimes(1);
+    // THE assertion: the agent loop's abort is wired to the RUN, so a browser
+    // disconnect (which aborts only `socketSignal`) cannot end the turn.
+    expect(streamTextMock.mock.calls[0][0].abortSignal).toBe(runSignal);
+    expect(streamTextMock.mock.calls[0][0].abortSignal).not.toBe(socketSignal);
+  });
+
+  it('legacy path (no runHooks): streamText is driven with the SOCKET signal', async () => {
+    const { svc } = makeService();
+    const socketSignal = new AbortController().signal;
+
+    await svc.stream({
+      user: { id: 'user-1' } as never,
+      workspace: { id: 'ws-1' } as never,
+      sessionId: 'sess-1',
+      body: body as never,
+      res: makeRes() as never,
+      signal: socketSignal,
+      model: {} as never,
+      role: null,
+      // No runHooks -> the turn stays socket-bound (flag off / default).
+    });
+
+    expect(streamTextMock).toHaveBeenCalledTimes(1);
+    expect(streamTextMock.mock.calls[0][0].abortSignal).toBe(socketSignal);
+  });
+
+  /**
+   * F9 — streamText's TERMINAL callbacks carry the #184 run lifecycle:
+   *   onStepFinish -> runHooks.onStep(runId, stepCount)
+   *   onFinish     -> runHooks.onSettled(runId, 'completed')   (dominant path)
+   *   onAbort      -> runHooks.onSettled(runId, 'aborted')
+   *   onError      -> runHooks.onSettled(runId, 'error', cause)
+   * makeStreamResult() ignores the streamText options, so these callbacks never
+   * fire on their own — a regression in this wiring (esp. the success path) would
+   * strand the run with NO test catching it. Here we CAPTURE the options streamText
+   * was handed and invoke each callback with the real wiring, asserting the run
+   * hooks fire with the right args.
+   */
+  // Drive stream() to the point streamText is called, capturing the options object
+  // (which carries onStepFinish/onFinish/onError/onAbort) and the run hooks.
+  async function captureStreamCallbacks() {
+    const { svc } = makeService();
+    let capturedOpts: any;
+    streamTextMock.mockImplementation((opts: any) => {
+      capturedOpts = opts;
+      return makeStreamResult();
+    });
+    const runHooks = {
+      begin: jest.fn(async () => ({
+        runId: 'run-1',
+        signal: new AbortController().signal,
+      })),
+      onAssistantSeeded: jest.fn(),
+      onStep: jest.fn(),
+      onSettled: jest.fn(),
+    };
+    await svc.stream({
+      user: { id: 'user-1' } as never,
+      workspace: { id: 'ws-1' } as never,
+      sessionId: 'sess-1',
+      body: body as never,
+      res: makeRes() as never,
+      signal: new AbortController().signal,
+      model: {} as never,
+      role: null,
+      runHooks: runHooks as never,
+    });
+    expect(capturedOpts).toBeDefined();
+    return { capturedOpts, runHooks };
+  }
+
+  it('F9: onStepFinish bumps the run step count, onFinish settles the run "completed" (the dominant autonomous-run path)', async () => {
+    const { capturedOpts, runHooks } = await captureStreamCallbacks();
+
+    // A finished step -> onStep(runId, finishedStepCount).
+    capturedOpts.onStepFinish({ text: 'step one', toolCalls: [], content: [] });
+    expect(runHooks.onStep).toHaveBeenCalledWith('run-1', 1);
+    capturedOpts.onStepFinish({ text: 'step two', toolCalls: [], content: [] });
+    expect(runHooks.onStep).toHaveBeenLastCalledWith('run-1', 2);
+
+    // The success terminal callback settles the run.
+    await capturedOpts.onFinish({
+      text: 'done',
+      finishReason: 'stop',
+      totalUsage: {},
+      usage: {},
+      steps: [],
+    });
+    expect(runHooks.onSettled).toHaveBeenCalledWith('run-1', 'completed');
+  });
+
+  it('F9: onAbort settles the run "aborted"', async () => {
+    jest
+      .spyOn(Logger.prototype, 'warn')
+      .mockImplementation(() => undefined as never);
+    const { capturedOpts, runHooks } = await captureStreamCallbacks();
+
+    await capturedOpts.onAbort({ steps: [] });
+    expect(runHooks.onSettled).toHaveBeenCalledWith('run-1', 'aborted');
+  });
+
+  it('F9: onError settles the run "error" carrying the provider cause', async () => {
+    jest
+      .spyOn(Logger.prototype, 'error')
+      .mockImplementation(() => undefined as never);
+    jest
+      .spyOn(Logger.prototype, 'warn')
+      .mockImplementation(() => undefined as never);
+    const { capturedOpts, runHooks } = await captureStreamCallbacks();
+
+    await capturedOpts.onError({ error: new Error('provider exploded') });
+    expect(runHooks.onSettled).toHaveBeenCalledWith(
+      'run-1',
+      'error',
+      expect.stringContaining('provider exploded'),
+    );
+  });
+});
+
+/**
+ * F14 — the begin-failure RESILIENCE 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.
+ *
+ * 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.
+ */
+describe('AiChatService.stream — begin-failure resilience / legacy fallback (#184 F14)', () => {
+  const streamTextMock = streamText as unknown as jest.Mock;
+
+  function makeStreamResult() {
+    return {
+      consumeStream: jest.fn(),
+      pipeUIMessageStreamToResponse: jest.fn(),
+    };
+  }
+
+  function makeRes() {
+    return {
+      raw: {
+        writeHead: jest.fn(),
+        write: jest.fn(),
+        once: jest.fn(),
+        on: jest.fn(),
+        flushHeaders: jest.fn(),
+        writableEnded: false,
+        destroyed: false,
+      },
+    };
+  }
+
+  // Same harness as the F3 abortSignal block, but it also exposes
+  // aiChatMessageRepo so we can assert the user turn IS persisted (the turn really
+  // streamed) despite begin() blowing up.
+  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: [],
+      })),
+    };
+    const svc = new AiChatService(
+      {} as never, // ai
+      aiChatRepo as never,
+      aiChatMessageRepo as never,
+      {} as never, // aiChatPageSnapshotRepo
+      aiSettings as never,
+      tools as never,
+      mcpClients as never,
+      {} as never, // aiAgentRoleRepo
+      {} as never, // pageRepo
+      {} as never, // pageAccess
+      { isAiChatDeferredToolsEnabled: () => false } as never, // environment
+    );
+    return { svc, aiChatMessageRepo };
+  }
+
+  const body = {
+    chatId: 'chat-1',
+    messages: [
+      { id: 'm1', role: 'user', parts: [{ type: 'text', text: 'hi' }] },
+    ],
+  };
+
+  beforeEach(() => {
+    streamTextMock.mockReset();
+    streamTextMock.mockImplementation(() => makeStreamResult());
+    jest
+      .spyOn(Logger.prototype, 'log')
+      .mockImplementation(() => undefined as never);
+  });
+
+  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 () => {
+    const errorSpy = jest
+      .spyOn(Logger.prototype, 'error')
+      .mockImplementation(() => undefined as never);
+
+    const { svc, aiChatMessageRepo } = makeService();
+    const socketSignal = new AbortController().signal;
+
+    // A transient, NON-race begin failure (e.g. a non-unique DB error inserting
+    // the run row). This is the `else` branch of the begin try/catch.
+    const begin = jest.fn(async () => {
+      throw new Error('insert failed');
+    });
+
+    const promise = svc.stream({
+      user: { id: 'user-1' } as never,
+      workspace: { id: 'ws-1' } as never,
+      sessionId: 'sess-1',
+      body: body as never,
+      res: makeRes() as never,
+      signal: socketSignal,
+      model: {} as never,
+      role: null,
+      runHooks: {
+        begin,
+        onAssistantSeeded: jest.fn(),
+        onStep: jest.fn(),
+        onSettled: jest.fn(),
+      } as never,
+    });
+
+    // The turn proceeds: NO throw at all (in particular NOT a 409).
+    await expect(promise).resolves.toBeUndefined();
+
+    expect(begin).toHaveBeenCalledTimes(1);
+
+    // The resilience branch logged the legacy-fallback warning.
+    expect(errorSpy).toHaveBeenCalledWith(
+      expect.stringContaining('streaming without run tracking'),
+      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.
+    expect(streamTextMock.mock.calls[0][0].abortSignal).toBe(socketSignal);
+  });
+});

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

@@ -453,6 +453,12 @@ describe('chatStreamMetadata', () => {
     });
   });
 
+  it('attaches the runId on the start part when a run wraps the turn (#184)', () => {
+    expect(
+      chatStreamMetadata({ type: 'start' }, 'chat-1', undefined, 'run-1'),
+    ).toEqual({ chatId: 'chat-1', runId: 'run-1' });
+  });
+
   it('returns the CUMULATIVE step usage passed in for the finish-step part', () => {
     // finish-step usage is per-step in v6; the caller accumulates and passes the
     // running sum, which this just wraps.

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

@@ -43,6 +43,30 @@ export class BoundChatDto {
   pageId: string;
 }
 
+/**
+ * Reconnect to the latest run of a chat (#184): fetch its persisted lifecycle
+ * state (and the assistant message it projects) for an in-flight or finished run.
+ */
+export class GetRunDto {
+  @IsString()
+  chatId: string;
+}
+
+/**
+ * Explicitly STOP an agent run (#184): the user pressed Stop — distinct from a
+ * browser disconnect, which never stops a run. Either the run id (preferred, from
+ * the streamed start metadata) or the chat id (stop whatever run is active on it).
+ */
+export class StopRunDto {
+  @IsOptional()
+  @IsString()
+  runId?: string;
+
+  @IsOptional()
+  @IsString()
+  chatId?: string;
+}
+
 /** Export a chat to Markdown (#183). `lang` localizes the few fixed
  *  role/tool-action labels; defaults to English server-side. */
 export class ExportChatDto {

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

@@ -474,19 +474,6 @@ export class AttachmentController {
     const fileSize = Number(attachment.fileSize);
     const rangeHeader = req.headers.range;
 
-    // Opt this download route out of the global @fastify/compress hook.
-    // Attachment bytes are final and mostly binary, so on-the-fly compression
-    // only burns CPU — and on the 206/Range branch it is actively corrupting:
-    // compress decides purely by Content-Type, so for a compressible mime
-    // (application/octet-stream fallback, image/svg+xml, text/*) it would gzip
-    // the byte slice and drop Content-Length while Content-Range still
-    // describes the RAW offsets and the status stays 206. A resuming client
-    // (`curl -C -`, download managers) then appends the encoded bytes as if
-    // raw and ends up with a broken file. @fastify/compress skips whenever the
-    // request carries `x-no-compression` (see its onSend hook), so setting it
-    // here covers both the 200 (full file) and 206 (range) responses.
-    req.headers['x-no-compression'] = 'true';
-
     res.header('Accept-Ranges', 'bytes');
     res.header(
       'Content-Security-Policy',

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

@@ -16,6 +16,7 @@ import {
   AUTH_THROTTLER,
   PAGE_TEMPLATE_THROTTLER,
   PUBLIC_SHARE_AI_THROTTLER,
+  VITALS_THROTTLER,
 } from '../../integrations/throttle/throttler-names';
 import { LoginDto } from './dto/login.dto';
 import { AuthService } from './services/auth.service';
@@ -184,16 +185,21 @@ export class AuthController {
   }
 
   // The global ThrottlerGuard applies ALL named throttlers to every route by
-  // default, so each non-AUTH bucket (AI chat, page template, public-share AI)
-  // is explicitly skipped here. collab-token is auth-guarded (JwtAuthGuard),
-  // per-user and client-cached, so those feature buckets are irrelevant to it;
-  // skipping them avoids spurious 429s when a user opens many pages in a short
-  // window. The AUTH bucket is skipped too for the same per-user, cached reason.
+  // default, so each non-AUTH bucket (AI chat, page template, public-share AI,
+  // client vitals) is explicitly skipped here. collab-token is auth-guarded
+  // (JwtAuthGuard), per-user and client-cached, so those feature buckets are
+  // irrelevant to it; skipping them avoids spurious 429s when a user opens many
+  // pages in a short window. The VITALS bucket must be skipped too: it is a
+  // process-wide named throttler, so without this skip its per-IP limit would
+  // silently cap collab-token (the one route that opts out of every other
+  // bucket) and break editing behind shared/NAT IPs. The AUTH bucket is skipped
+  // for the same per-user, cached reason.
   @SkipThrottle({
     [AUTH_THROTTLER]: true,
     [AI_CHAT_THROTTLER]: true,
     [PAGE_TEMPLATE_THROTTLER]: true,
     [PUBLIC_SHARE_AI_THROTTLER]: true,
+    [VITALS_THROTTLER]: true,
   })
   @UseGuards(JwtAuthGuard)
   @HttpCode(HttpStatus.OK)

apps/server/src/core/page/services/page.service.ts

@@ -52,7 +52,9 @@ import {
   INTERNAL_LINK_REGEX,
   extractPageSlugId,
 } from '../../../integrations/export/utils';
-import { markdownToHtml, canonicalizeFootnotes } from '@docmost/editor-ext';
+import { canonicalizeFootnotes } from '@docmost/editor-ext';
+import { markdownToProseMirror } from '@docmost/prosemirror-markdown';
+import { normalizeForeignMarkdown } from '../../../integrations/import/utils/foreign-markdown';
 import { WatcherService } from '../../watcher/watcher.service';
 import { sql } from 'kysely';
 import { TransclusionService } from '../transclusion/transclusion.service';
@@ -1301,8 +1303,14 @@ export class PageService {
 
     switch (format) {
       case 'markdown': {
-        const html = await markdownToHtml(content as string);
-        prosemirrorJson = htmlToJson(html as string);
+        // Canonical markdown -> ProseMirror JSON directly via
+        // `@docmost/prosemirror-markdown` (issue #345) — no HTML intermediate,
+        // no editor-ext markdown layer. Foreign markdown surfaces the strict
+        // parser rejects (GFM `[^id]` reference footnotes) are normalized to the
+        // canonical inline form first.
+        prosemirrorJson = await markdownToProseMirror(
+          normalizeForeignMarkdown(content as string),
+        );
         break;
       }
       case 'html': {

apps/server/src/core/telemetry/client-metrics.constants.ts

@@ -0,0 +1,105 @@
+/**
+ * Server-side whitelist + limits for POST /api/telemetry/vitals (#355).
+ *
+ * The endpoint is PUBLIC (browsers post it, no auth) so it is a privacy and
+ * abuse surface: everything not on these lists is silently DROPPED and the
+ * request still returns 200 (never 400 — a 400 would make browsers retry).
+ */
+
+// The only metric names accepted. Anything else is dropped.
+export const ALLOWED_METRIC_NAMES = new Set<string>([
+  'INP',
+  'LCP',
+  'CLS',
+  'TTFB',
+  'editor_tx_ms',
+  'page_open_ms',
+  'longtask_ms',
+]);
+
+// The only rating values accepted (web-vitals). Anything else -> null.
+export const ALLOWED_RATINGS = new Set<string>([
+  'good',
+  'needs-improvement',
+  'poor',
+]);
+
+// Max events accepted per batch; the rest are ignored.
+export const MAX_EVENTS_PER_BATCH = 50;
+
+// Defence-in-depth body cap (~16KB). Fastify's global bodyLimit is far larger,
+// so we re-check the parsed payload size here and drop oversized batches.
+export const MAX_BODY_BYTES = 16 * 1024;
+
+// attr is truncated to this many characters (attribution target only, no PII).
+export const MAX_ATTR_LENGTH = 120;
+
+// route label sanity cap (client sends a template like /s/:space/p/:slug).
+export const MAX_ROUTE_LENGTH = 200;
+
+// `client_metrics.doc_size` is a Postgres `int` (int4). A garbage/huge docSize
+// on a single event would overflow int4 and make Postgres reject the WHOLE
+// batch INSERT, losing every event in it. Values outside this range are DROPPED
+// to null (the event is still kept) so one bad field never loses the batch.
+export const DOC_SIZE_MAX = 2147483647; // 2^31 - 1 (int4 max)
+
+export interface ClientMetricRow {
+  name: string;
+  value: number;
+  rating: string | null;
+  route: string | null;
+  attr: string | null;
+  docSize: number | null;
+  workspaceId: string | null;
+}
+
+/**
+ * Validate + normalise a single incoming event into a DB row, or return null to
+ * DROP it. Pure so it is directly unit-testable. Enforces the name whitelist,
+ * numeric value, rating whitelist, attr truncation and doc_size (int) coercion.
+ */
+export function sanitizeVitalEvent(
+  raw: unknown,
+  workspaceId: string | null,
+): ClientMetricRow | null {
+  if (!raw || typeof raw !== 'object') return null;
+  const e = raw as Record<string, unknown>;
+
+  const name = e.name;
+  if (typeof name !== 'string' || !ALLOWED_METRIC_NAMES.has(name)) return null;
+
+  const value =
+    typeof e.value === 'number' && Number.isFinite(e.value) ? e.value : null;
+  if (value === null) return null;
+
+  const rating =
+    typeof e.rating === 'string' && ALLOWED_RATINGS.has(e.rating)
+      ? e.rating
+      : null;
+
+  let route: string | null = null;
+  if (typeof e.route === 'string' && e.route.length > 0) {
+    route = e.route.slice(0, MAX_ROUTE_LENGTH);
+  }
+
+  let attr: string | null = null;
+  if (typeof e.attr === 'string' && e.attr.length > 0) {
+    attr = e.attr.slice(0, MAX_ATTR_LENGTH);
+  }
+
+  let docSize: number | null = null;
+  if (typeof e.docSize === 'number' && Number.isFinite(e.docSize)) {
+    docSize = Math.trunc(e.docSize);
+  } else if (typeof e.doc_size === 'number' && Number.isFinite(e.doc_size)) {
+    // Accept snake_case too, in case a client sends the raw column name.
+    docSize = Math.trunc(e.doc_size as number);
+  }
+  // Guard the int4 column: an out-of-range docSize would overflow int4 and make
+  // Postgres reject the whole batch INSERT. Drop the field (keep the event)
+  // rather than lose every other event in the batch.
+  if (docSize !== null && (docSize < 0 || docSize > DOC_SIZE_MAX)) {
+    docSize = null;
+  }
+
+  return { name, value, rating, route, attr, docSize, workspaceId };
+}

apps/server/src/core/telemetry/client-telemetry.module.spec.ts

@@ -0,0 +1,47 @@
+import { ClientTelemetryModule } from './client-telemetry.module';
+import { VitalsController } from './vitals.controller';
+import { VitalsService } from './vitals.service';
+
+// The register() gate is the CORE of the maintainer's E1=B decision: the public,
+// unauthenticated /api/telemetry/vitals endpoint must be OFF by default, so a
+// self-host deploy has no anonymous disk-fill surface into `client_metrics`. A
+// regression that inverts the flag (or a truthiness bug where "" / "false"
+// registers the route) would silently reopen that surface — pin it here.
+describe('ClientTelemetryModule.register (E1=B gate)', () => {
+  const original = process.env.CLIENT_TELEMETRY_ENABLED;
+  afterEach(() => {
+    if (original === undefined) delete process.env.CLIENT_TELEMETRY_ENABLED;
+    else process.env.CLIENT_TELEMETRY_ENABLED = original;
+  });
+
+  it('OFF by default (flag unset) — no controller, no provider (endpoint absent)', () => {
+    delete process.env.CLIENT_TELEMETRY_ENABLED;
+    const mod = ClientTelemetryModule.register();
+    expect(mod.controllers).toEqual([]);
+    expect(mod.providers).toEqual([]);
+  });
+
+  it.each(['false', 'False', '0', '', 'yes', '1'])(
+    'stays OFF for non-"true" value %p (no route)',
+    (val) => {
+      process.env.CLIENT_TELEMETRY_ENABLED = val;
+      const mod = ClientTelemetryModule.register();
+      expect(mod.controllers).toEqual([]);
+      expect(mod.providers).toEqual([]);
+    },
+  );
+
+  it('ON only for "true" — registers VitalsController + VitalsService', () => {
+    process.env.CLIENT_TELEMETRY_ENABLED = 'true';
+    const mod = ClientTelemetryModule.register();
+    expect(mod.controllers).toContain(VitalsController);
+    expect(mod.providers).toContain(VitalsService);
+  });
+
+  it('ON is case-insensitive ("TRUE")', () => {
+    process.env.CLIENT_TELEMETRY_ENABLED = 'TRUE';
+    const mod = ClientTelemetryModule.register();
+    expect(mod.controllers).toContain(VitalsController);
+    expect(mod.providers).toContain(VitalsService);
+  });
+});

apps/server/src/core/telemetry/client-telemetry.module.ts

@@ -0,0 +1,32 @@
+import { DynamicModule, Module } from '@nestjs/common';
+import { VitalsController } from './vitals.controller';
+import { VitalsService } from './vitals.service';
+
+/**
+ * Client perf-telemetry (#355): the public /api/telemetry/vitals sink that
+ * persists web-vitals + custom client metrics into `client_metrics`.
+ * Named ClientTelemetryModule to avoid confusion with the unrelated
+ * integrations/telemetry (product usage ping) module.
+ *
+ * GATED OFF BY DEFAULT (maintainer decision E1=B). The public, unauthenticated
+ * endpoint is only registered when CLIENT_TELEMETRY_ENABLED=true — otherwise the
+ * route does NOT exist at all (no anonymous disk-fill surface, and no unbounded
+ * `client_metrics` growth on a self-host deploy without an external pruner). The
+ * client is told the same flag via window.CONFIG and skips sending when off.
+ */
+@Module({})
+export class ClientTelemetryModule {
+  static register(): DynamicModule {
+    // Read process.env directly (not EnvironmentService) so the toggle is
+    // resolved at module-registration time, identical to how the metrics
+    // subsystem reads METRICS_PORT. Absent/anything-but-"true" => OFF.
+    const enabled =
+      (process.env.CLIENT_TELEMETRY_ENABLED ?? '').toLowerCase() === 'true';
+
+    return {
+      module: ClientTelemetryModule,
+      controllers: enabled ? [VitalsController] : [],
+      providers: enabled ? [VitalsService] : [],
+    };
+  }
+}

apps/server/src/core/telemetry/vitals.controller.ts

@@ -0,0 +1,64 @@
+import {
+  Body,
+  Controller,
+  HttpCode,
+  Post,
+  Req,
+  UseGuards,
+} from '@nestjs/common';
+import { SkipThrottle, Throttle, ThrottlerGuard } from '@nestjs/throttler';
+import { FastifyRequest } from 'fastify';
+import { Public } from '../../common/decorators/public.decorator';
+import {
+  AI_CHAT_THROTTLER,
+  AUTH_THROTTLER,
+  PAGE_TEMPLATE_THROTTLER,
+  PUBLIC_SHARE_AI_THROTTLER,
+  VITALS_THROTTLER,
+} from '../../integrations/throttle/throttler-names';
+import { VitalsService } from './vitals.service';
+
+/**
+ * POST /api/telemetry/vitals (#355) — public client perf-metrics sink.
+ *
+ * PUBLIC (browsers post via sendBeacon, no session) but IP-throttled. Always
+ * returns 200 with no body of interest: invalid/foreign/oversized payloads are
+ * silently dropped by the service rather than 400'd, so browsers never retry.
+ */
+@Controller('telemetry')
+export class VitalsController {
+  constructor(private readonly vitalsService: VitalsService) {}
+
+  @Public()
+  @UseGuards(ThrottlerGuard)
+  // The global ThrottlerGuard applies ALL named throttlers to every route, so
+  // every OTHER bucket must be skipped here — otherwise the strictest of them
+  // (public-share AI at 5/min) would override the intended vitals limit and cap
+  // this route at 5/min instead of 120/min. Skip them all so ONLY the VITALS
+  // bucket below applies.
+  @SkipThrottle({
+    [AUTH_THROTTLER]: true,
+    [AI_CHAT_THROTTLER]: true,
+    [PAGE_TEMPLATE_THROTTLER]: true,
+    [PUBLIC_SHARE_AI_THROTTLER]: true,
+  })
+  @Throttle({ [VITALS_THROTTLER]: { limit: 120, ttl: 60_000 } })
+  @Post('vitals')
+  @HttpCode(200)
+  async vitals(
+    @Body() body: unknown,
+    @Req() req: FastifyRequest,
+  ): Promise<{ ok: true }> {
+    // workspaceId is resolved by the workspace-host middleware onto req.raw when
+    // the browser posts from a workspace host; null otherwise. No other PII.
+    const workspaceId =
+      ((req.raw as unknown as { workspaceId?: string })?.workspaceId ?? null) ||
+      null;
+    try {
+      await this.vitalsService.ingest(body, workspaceId);
+    } catch {
+      // Never surface storage errors to the browser; telemetry is best-effort.
+    }
+    return { ok: true };
+  }
+}

apps/server/src/core/telemetry/vitals.service.spec.ts

@@ -0,0 +1,149 @@
+import { VitalsService } from './vitals.service';
+import { MAX_ATTR_LENGTH } from './client-metrics.constants';
+
+// buildRows is pure (no DB access), so a null db is fine here.
+const svc = new VitalsService(null as any);
+
+describe('VitalsService.buildRows', () => {
+  const WS = 'ws-uuid';
+
+  it('accepts a valid batch and maps whitelisted fields to rows', () => {
+    const body = {
+      events: [
+        { name: 'INP', value: 123.4, rating: 'good', route: '/s/:space/p/:slug' },
+        { name: 'editor_tx_ms', value: 12, route: '/s/:space/p/:slug', docSize: 4096 },
+      ],
+    };
+    const rows = svc.buildRows(body, WS);
+    expect(rows).toHaveLength(2);
+    expect(rows[0]).toEqual({
+      name: 'INP',
+      value: 123.4,
+      rating: 'good',
+      route: '/s/:space/p/:slug',
+      attr: null,
+      docSize: null,
+      workspaceId: WS,
+    });
+    expect(rows[1].name).toBe('editor_tx_ms');
+    expect(rows[1].docSize).toBe(4096);
+    expect(rows[1].workspaceId).toBe(WS);
+  });
+
+  it('accepts a bare array body', () => {
+    const rows = svc.buildRows([{ name: 'LCP', value: 1 }], WS);
+    expect(rows).toHaveLength(1);
+    expect(rows[0].name).toBe('LCP');
+  });
+
+  it('drops events with foreign metric names', () => {
+    const rows = svc.buildRows(
+      { events: [{ name: 'evil_metric', value: 1 }, { name: 'LCP', value: 2 }] },
+      WS,
+    );
+    expect(rows).toHaveLength(1);
+    expect(rows[0].name).toBe('LCP');
+  });
+
+  it('drops events with a non-numeric or missing value', () => {
+    const rows = svc.buildRows(
+      {
+        events: [
+          { name: 'CLS', value: 'nan' },
+          { name: 'CLS' },
+          { name: 'CLS', value: 0.1 },
+        ],
+      },
+      WS,
+    );
+    expect(rows).toHaveLength(1);
+    expect(rows[0].value).toBe(0.1);
+  });
+
+  it('strips foreign fields and only keeps whitelisted columns', () => {
+    const rows = svc.buildRows(
+      { events: [{ name: 'TTFB', value: 5, secret: 'drop-me', title: 'my page' }] },
+      WS,
+    );
+    expect(rows).toHaveLength(1);
+    expect(Object.keys(rows[0]).sort()).toEqual(
+      ['attr', 'docSize', 'name', 'rating', 'route', 'value', 'workspaceId'].sort(),
+    );
+    expect((rows[0] as any).secret).toBeUndefined();
+    expect((rows[0] as any).title).toBeUndefined();
+  });
+
+  it('rejects a rating outside the allowed set (-> null)', () => {
+    const rows = svc.buildRows(
+      { events: [{ name: 'INP', value: 1, rating: 'terrible' }] },
+      WS,
+    );
+    expect(rows[0].rating).toBeNull();
+  });
+
+  it('truncates attr to 120 chars', () => {
+    const longAttr = 'a'.repeat(500);
+    const rows = svc.buildRows(
+      { events: [{ name: 'INP', value: 1, attr: longAttr }] },
+      WS,
+    );
+    expect(rows[0].attr).toHaveLength(MAX_ATTR_LENGTH);
+  });
+
+  it('caps the batch at 50 events', () => {
+    const events = Array.from({ length: 200 }, () => ({ name: 'CLS', value: 1 }));
+    const rows = svc.buildRows({ events }, WS);
+    expect(rows).toHaveLength(50);
+  });
+
+  it('drops an oversized (>16KB) payload wholesale', () => {
+    const events = Array.from({ length: 50 }, () => ({
+      name: 'INP',
+      value: 1,
+      attr: 'x'.repeat(400),
+      route: '/s/:space/p/:slug',
+    }));
+    // Serialised body far exceeds 16KB.
+    const rows = svc.buildRows({ events }, WS);
+    expect(rows).toHaveLength(0);
+  });
+
+  it('returns [] for malformed bodies', () => {
+    expect(svc.buildRows(null, WS)).toEqual([]);
+    expect(svc.buildRows('nope', WS)).toEqual([]);
+    expect(svc.buildRows({ notEvents: 1 }, WS)).toEqual([]);
+    expect(svc.buildRows(42, WS)).toEqual([]);
+  });
+
+  it('carries a null workspaceId through', () => {
+    const rows = svc.buildRows({ events: [{ name: 'LCP', value: 1 }] }, null);
+    expect(rows[0].workspaceId).toBeNull();
+  });
+
+  it('drops an out-of-int4-range docSize to null without losing the batch', () => {
+    const rows = svc.buildRows(
+      {
+        events: [
+          // Garbage docSize overflowing int4 must NOT reject the whole batch:
+          // the field is dropped to null and the event is kept.
+          { name: 'editor_tx_ms', value: 10, docSize: 9_999_999_999 },
+          { name: 'editor_tx_ms', value: 20, docSize: -5 },
+          { name: 'editor_tx_ms', value: 30, docSize: 4096 },
+        ],
+      },
+      WS,
+    );
+    expect(rows).toHaveLength(3);
+    expect(rows[0].docSize).toBeNull();
+    expect(rows[1].docSize).toBeNull();
+    expect(rows[2].docSize).toBe(4096);
+  });
+
+  it('keeps a docSize exactly at the int4 max', () => {
+    const rows = svc.buildRows(
+      { events: [{ name: 'editor_tx_ms', value: 1, docSize: 2147483647 }] },
+      WS,
+    );
+    expect(rows[0].docSize).toBe(2147483647);
+  });
+});

apps/server/src/core/telemetry/vitals.service.ts

@@ -0,0 +1,70 @@
+import { Injectable } from '@nestjs/common';
+import { InjectKysely } from 'nestjs-kysely';
+import { KyselyDB } from '@docmost/db/types/kysely.types';
+import {
+  ClientMetricRow,
+  MAX_BODY_BYTES,
+  MAX_EVENTS_PER_BATCH,
+  sanitizeVitalEvent,
+} from './client-metrics.constants';
+
+@Injectable()
+export class VitalsService {
+  constructor(@InjectKysely() private readonly db: KyselyDB) {}
+
+  /**
+   * Turn a raw request body into the (bounded, whitelisted) rows to persist.
+   * Pure/synchronous so it is unit-testable without a DB. Returns [] for any
+   * malformed / oversized / foreign input — the caller still responds 200.
+   */
+  buildRows(body: unknown, workspaceId: string | null): ClientMetricRow[] {
+    if (!body || typeof body !== 'object') return [];
+
+    // Defence-in-depth body cap (~16KB): drop oversized batches wholesale.
+    try {
+      if (JSON.stringify(body).length > MAX_BODY_BYTES) return [];
+    } catch {
+      return [];
+    }
+
+    // Accept either a bare array or `{ events: [...] }`.
+    const events = Array.isArray(body)
+      ? body
+      : Array.isArray((body as { events?: unknown }).events)
+        ? ((body as { events: unknown[] }).events as unknown[])
+        : null;
+    if (!events) return [];
+
+    const rows: ClientMetricRow[] = [];
+    for (const event of events) {
+      if (rows.length >= MAX_EVENTS_PER_BATCH) break;
+      const row = sanitizeVitalEvent(event, workspaceId);
+      if (row) rows.push(row);
+    }
+    return rows;
+  }
+
+  /** Batch-insert the sanitised rows in a single statement. No-op on []. */
+  async insertRows(rows: ClientMetricRow[]): Promise<void> {
+    if (rows.length === 0) return;
+    await this.db
+      .insertInto('clientMetrics')
+      .values(
+        rows.map((r) => ({
+          name: r.name,
+          value: r.value,
+          rating: r.rating,
+          route: r.route,
+          attr: r.attr,
+          docSize: r.docSize,
+          workspaceId: r.workspaceId,
+        })),
+      )
+      .execute();
+  }
+
+  async ingest(body: unknown, workspaceId: string | null): Promise<void> {
+    const rows = this.buildRows(body, workspaceId);
+    await this.insertRows(rows);
+  }
+}

apps/server/src/core/workspace/dto/update-workspace.dto.ts

@@ -55,6 +55,14 @@ export class UpdateWorkspaceDto extends PartialType(CreateWorkspaceDto) {
   @IsBoolean()
   aiDictationStreaming: boolean;
 
+  // #184: detached/autonomous agent runs (settings.ai.autonomousRuns). When on, a
+  // chat turn becomes a server-side RUN that survives a browser disconnect; only
+  // an explicit /ai-chat/stop ends it. Off by default; single-instance-only in
+  // phase 1 (see AiChatRunService.warnIfMultiInstance / AGENTS.md).
+  @IsOptional()
+  @IsBoolean()
+  autonomousRuns: boolean;
+
   // Workspace master toggle that enables/disables the HTML embed block type.
   // Persisted at settings.htmlEmbed. ABSENT/false => OFF (default). The block
   // itself renders in a sandboxed iframe, so this is a feature switch, not a

apps/server/src/core/workspace/services/workspace.service.ts

@@ -526,6 +526,20 @@ export class WorkspaceService {
         );
       }
 
+      if (typeof updateWorkspaceDto.autonomousRuns !== 'undefined') {
+        const prev = settingsBefore?.ai?.autonomousRuns ?? false;
+        if (prev !== updateWorkspaceDto.autonomousRuns) {
+          before.autonomousRuns = prev;
+          after.autonomousRuns = updateWorkspaceDto.autonomousRuns;
+        }
+        await this.workspaceRepo.updateAiSettings(
+          workspaceId,
+          'autonomousRuns',
+          updateWorkspaceDto.autonomousRuns,
+          trx,
+        );
+      }
+
       if (typeof updateWorkspaceDto.htmlEmbed !== 'undefined') {
         const prev = settingsBefore?.htmlEmbed ?? false;
         if (prev !== updateWorkspaceDto.htmlEmbed) {
@@ -579,6 +593,7 @@ export class WorkspaceService {
       delete updateWorkspaceDto.aiChat;
       delete updateWorkspaceDto.aiDictation;
       delete updateWorkspaceDto.aiDictationStreaming;
+      delete updateWorkspaceDto.autonomousRuns;
       delete updateWorkspaceDto.htmlEmbed;
       delete updateWorkspaceDto.trackerHead;
       delete updateWorkspaceDto.aiPublicShareAssistant;

apps/server/src/database/database.module.ts

@@ -31,6 +31,7 @@ import { FavoriteRepo } from '@docmost/db/repos/favorite/favorite.repo';
 import { TemplateRepo } from '@docmost/db/repos/template/template.repo';
 import { AiChatRepo } from '@docmost/db/repos/ai-chat/ai-chat.repo';
 import { AiChatMessageRepo } from '@docmost/db/repos/ai-chat/ai-chat-message.repo';
+import { AiChatRunRepo } from '@docmost/db/repos/ai-chat/ai-chat-run.repo';
 import { AiChatPageSnapshotRepo } from '@docmost/db/repos/ai-chat/ai-chat-page-snapshot.repo';
 import { AiProviderCredentialsRepo } from '@docmost/db/repos/ai-chat/ai-provider-credentials.repo';
 import { AiMcpServerRepo } from '@docmost/db/repos/ai-chat/ai-mcp-server.repo';
@@ -40,6 +41,11 @@ import { PageListener } from '@docmost/db/listeners/page.listener';
 import { PostgresJSDialect } from 'kysely-postgres-js';
 import * as postgres from 'postgres';
 import { normalizePostgresUrl } from '../common/helpers';
+import {
+  observeDbQuery,
+  isMetricsEnabled,
+} from '../integrations/metrics/metrics.registry';
+import { firstSqlToken } from '../integrations/metrics/metrics.constants';
 
 @Global()
 @Module({
@@ -67,6 +73,18 @@ import { normalizePostgresUrl } from '../common/helpers';
         }),
         plugins: [new CamelCasePlugin()],
         log: (event: LogEvent) => {
+          // #355 — db_query_duration_seconds, labelled by the leading SQL token
+          // (bounded cardinality). Gated on isMetricsEnabled() so the token work
+          // (regex + Set lookup) is skipped entirely when metrics are OFF — not
+          // just observeDbQuery no-op'd — so a non-metrics deployment pays nothing
+          // per query. Runs independent of the dev-only debug logging below.
+          if (isMetricsEnabled()) {
+            observeDbQuery(
+              firstSqlToken(event.query.sql),
+              event.queryDurationMillis / 1000,
+            );
+          }
+
           if (environmentService.getNodeEnv() !== 'development') return;
           const logger = new Logger(DatabaseModule.name);
           if (process.env.DEBUG_DB?.toLowerCase() === 'true') {
@@ -105,6 +123,7 @@ import { normalizePostgresUrl } from '../common/helpers';
     TemplateRepo,
     AiChatRepo,
     AiChatMessageRepo,
+    AiChatRunRepo,
     AiChatPageSnapshotRepo,
     AiProviderCredentialsRepo,
     AiMcpServerRepo,
@@ -139,6 +158,7 @@ import { normalizePostgresUrl } from '../common/helpers';
     TemplateRepo,
     AiChatRepo,
     AiChatMessageRepo,
+    AiChatRunRepo,
     AiChatPageSnapshotRepo,
     AiProviderCredentialsRepo,
     AiMcpServerRepo,

apps/server/src/database/migrations/20260704T120000-client-metrics.ts

@@ -0,0 +1,52 @@
+import { type Kysely, sql } from 'kysely';
+
+/**
+ * #355 — `client_metrics`: raw sink for client-side perf telemetry (web-vitals
+ * + custom editor/page metrics) posted to /api/telemetry/vitals.
+ *
+ * The table/columns/indexes here are a FIXED contract shared with the deployed
+ * Grafana infra (the `grafana_ro` role reads this table; a separate maintenance
+ * container prunes rows >90d and re-GRANTs daily). No app-side retention is
+ * added on purpose. Written as raw SQL to match that contract 1:1 (identity PK,
+ * conditional GRANT).
+ */
+export async function up(db: Kysely<any>): Promise<void> {
+  await sql`
+    CREATE TABLE client_metrics (
+      id bigint GENERATED ALWAYS AS IDENTITY PRIMARY KEY,
+      created_at timestamptz NOT NULL DEFAULT now(),
+      name text NOT NULL,          -- INP|LCP|CLS|TTFB|editor_tx_ms|page_open_ms|longtask_ms
+      value double precision NOT NULL,
+      rating text,                 -- good|needs-improvement|poor (web-vitals only)
+      route text,                  -- templated: /s/:space/p/:slug — never raw slugs
+      attr text,                   -- attribution target, truncated to 120 chars
+      doc_size int,                -- editor_tx_ms only
+      workspace_id uuid
+    )
+  `.execute(db);
+
+  await sql`
+    CREATE INDEX idx_client_metrics_name_created
+      ON client_metrics (name, created_at)
+  `.execute(db);
+
+  await sql`
+    CREATE INDEX idx_client_metrics_created
+      ON client_metrics (created_at)
+  `.execute(db);
+
+  // The read-only Grafana role only exists in the deployed environment; guard so
+  // the migration still applies cleanly in dev/CI where the role is absent.
+  await sql`
+    DO $$
+    BEGIN
+      IF EXISTS (SELECT FROM pg_roles WHERE rolname = 'grafana_ro') THEN
+        GRANT SELECT ON client_metrics TO grafana_ro;
+      END IF;
+    END $$;
+  `.execute(db);
+}
+
+export async function down(db: Kysely<any>): Promise<void> {
+  await sql`DROP TABLE IF EXISTS client_metrics`.execute(db);
+}

apps/server/src/database/migrations/20260704T130000-ai-chat-runs.ts

@@ -0,0 +1,106 @@
+import { type Kysely, sql } from 'kysely';
+
+/**
+ * `ai_chat_runs` — the agent RUN as a first-class, server-side lifecycle object
+ * (#184 phase 1: autonomous agent runs detached from the browser window).
+ *
+ * Until now an agent turn lived ONLY as long as the HTTP request was open
+ * (`res.hijack()` in ai-chat.controller.ts); a browser disconnect aborted it.
+ * This table makes a turn a persistent object the server owns: it is created
+ * when a run starts (inserted directly as 'running' in phase 1 — 'pending' is
+ * only this column's default + a reserved value, never written by code yet) and
+ * advances to succeeded|failed|aborted, surviving the subscriber (browser) going
+ * away when it settles. The DB is the source of
+ * truth — a later client reconnects/sees the result by reading this row plus the
+ * assistant message it projects (`assistant_message_id`).
+ *
+ * The assistant message row (#183 step-granular durability) is the PROJECTION of
+ * a run's output; this row is the run's LIFECYCLE. They are linked by
+ * `assistant_message_id` (SET NULL if the message is later pruned).
+ *
+ * `status`  : 'pending' | 'running' | 'succeeded' | 'failed' | 'aborted'.
+ * `trigger` : 'user' | 'autostart' | 'schedule' | 'api' | 'continue' — only
+ *             'user' is produced in phase 1; the others are reserved for the
+ *             autonomy triggers deferred to phase 2 so they need no later
+ *             migration.
+ *
+ * ONE ACTIVE RUN PER CHAT is enforced by a partial unique index on `chat_id`
+ * WHERE status IN ('pending','running'): an autonomous run and a user run can
+ * never trample each other on the same chat. Settled runs (succeeded/failed/
+ * aborted) are excluded from the index so a chat can accumulate any number of
+ * historical runs.
+ */
+export async function up(db: Kysely<any>): Promise<void> {
+  await db.schema
+    .createTable('ai_chat_runs')
+    .ifNotExists()
+    .addColumn('id', 'uuid', (col) =>
+      col.primaryKey().defaultTo(sql`gen_uuid_v7()`),
+    )
+    .addColumn('chat_id', 'uuid', (col) =>
+      col.references('ai_chats.id').onDelete('cascade').notNull(),
+    )
+    .addColumn('workspace_id', 'uuid', (col) =>
+      col.references('workspaces.id').onDelete('cascade').notNull(),
+    )
+    // The human who triggered the run (audit). SET NULL on user deletion so the
+    // run history outlives its author; NULL is also the natural value for a
+    // future system/cron/api trigger with no human actor.
+    .addColumn('created_by', 'uuid', (col) =>
+      col.references('users.id').onDelete('set null'),
+    )
+    // The assistant message this run materializes (the #183 projection). SET NULL
+    // if that message row is later deleted; nullable because the run row is
+    // created a moment BEFORE the assistant row is seeded.
+    .addColumn('assistant_message_id', 'uuid', (col) =>
+      col.references('ai_chat_messages.id').onDelete('set null'),
+    )
+    .addColumn('trigger', 'varchar(20)', (col) =>
+      col.notNull().defaultTo('user'),
+    )
+    .addColumn('status', 'varchar(20)', (col) =>
+      col.notNull().defaultTo('pending'),
+    )
+    // Terminal error message for a failed run (provider/transport cause),
+    // mirroring the assistant message's metadata.error.
+    .addColumn('error', 'text', (col) => col)
+    // Number of agent steps finished so far (kept monotonic with the projection).
+    .addColumn('step_count', 'integer', (col) => col.notNull().defaultTo(0))
+    // Set when an EXPLICIT user stop is requested (distinct from a mere browser
+    // disconnect, which never stops a run). The runner aborts the turn and the
+    // run settles as 'aborted'.
+    .addColumn('stop_requested_at', 'timestamptz', (col) => col)
+    .addColumn('started_at', 'timestamptz', (col) => col)
+    .addColumn('finished_at', 'timestamptz', (col) => col)
+    .addColumn('created_at', 'timestamptz', (col) =>
+      col.notNull().defaultTo(sql`now()`),
+    )
+    .addColumn('updated_at', 'timestamptz', (col) =>
+      col.notNull().defaultTo(sql`now()`),
+    )
+    .execute();
+
+  // Reconnect / "latest run for this chat" reads hit chat_id first.
+  await db.schema
+    .createIndex('ai_chat_runs_chat_id_idx')
+    .ifNotExists()
+    .on('ai_chat_runs')
+    .column('chat_id')
+    .execute();
+
+  // One ACTIVE run per chat (advisory at the DB level): a second pending/running
+  // run on the same chat is rejected, so a user turn and an autonomous turn can
+  // never race on the same chat. Partial so settled runs do not collide.
+  await db.schema
+    .createIndex('ai_chat_runs_one_active_per_chat')
+    .ifNotExists()
+    .on('ai_chat_runs')
+    .column('chat_id')
+    .unique()
+    .where(sql.ref('status'), 'in', sql`('pending','running')`)
+    .execute();
+}
+
+export async function down(db: Kysely<any>): Promise<void> {
+  await db.schema.dropTable('ai_chat_runs').execute();
+}

apps/server/src/database/repos/ai-chat/ai-chat-message.repo.ts

@@ -121,6 +121,23 @@ export class AiChatMessageRepo {
     return rows.reverse();
   }
 
+  /** Fetch a single message by id + workspace (e.g. a run's projection row for
+   *  the #184 reconnect read). Returns undefined when nothing matches. */
+  async findById(
+    id: string,
+    workspaceId: string,
+    trx?: KyselyTransaction,
+  ): Promise<AiChatMessage | undefined> {
+    const db = dbOrTx(this.db, trx);
+    return db
+      .selectFrom('aiChatMessages')
+      .select(this.baseFields)
+      .where('id', '=', id)
+      .where('workspaceId', '=', workspaceId)
+      .where('deletedAt', 'is', null)
+      .executeTakeFirst();
+  }
+
   async insert(
     insertable: InsertableAiChatMessage,
     trx?: KyselyTransaction,

apps/server/src/database/repos/ai-chat/ai-chat-run.repo.spec.ts

@@ -0,0 +1,82 @@
+import { AiChatRunRepo, SWEEP_RUN_STALE_MS } from './ai-chat-run.repo';
+import type { KyselyDB } from '../../types/kysely.types';
+
+/**
+ * Unit coverage for AiChatRunRepo.sweepRunning over a chainable builder mock (no
+ * live DB). The F1 invariant under test (DECISION C): the BOOT sweep is
+ * UNCONDITIONAL — it adds NO `updatedAt <` predicate, so a fresh 'running' run
+ * (updatedAt = now) IS settled rather than skipped by a staleness window. The
+ * window is added ONLY when an explicit `staleMs` is supplied (the future phase-2
+ * multi-instance timer sweep). We assert the EXACT predicates the spec mandates.
+ */
+describe('AiChatRunRepo.sweepRunning', () => {
+  type Recorded = {
+    table?: string;
+    set?: Record<string, unknown>;
+    wheres: Array<[string, string, unknown]>;
+    returning?: string;
+  };
+
+  function makeDb(swept: Array<{ id: string }>): {
+    db: KyselyDB;
+    rec: Recorded;
+  } {
+    const rec: Recorded = { wheres: [] };
+    const builder: Record<string, unknown> = {};
+    builder.set = (v: Record<string, unknown>) => {
+      rec.set = v;
+      return builder;
+    };
+    builder.where = (col: string, op: string, val: unknown) => {
+      rec.wheres.push([col, op, val]);
+      return builder;
+    };
+    builder.returning = (col: string) => {
+      rec.returning = col;
+      return builder;
+    };
+    builder.execute = () => Promise.resolve(swept);
+    const db = {
+      updateTable: (table: string) => {
+        rec.table = table;
+        return builder;
+      },
+    } as unknown as KyselyDB;
+    return { db, rec };
+  }
+
+  it('F1: the boot sweep (no staleMs) is UNCONDITIONAL — only a status filter, NO updatedAt window', async () => {
+    const { db, rec } = makeDb([{ id: 'r1' }, { id: 'r2' }]);
+    const repo = new AiChatRunRepo(db);
+
+    const swept = await repo.sweepRunning();
+
+    expect(swept).toBe(2);
+    expect(rec.table).toBe('aiChatRuns');
+    // The status filter is always present...
+    expect(rec.wheres).toContainEqual([
+      'status',
+      'in',
+      expect.arrayContaining(['pending', 'running']),
+    ]);
+    // ...but a fresh 'running' run (updatedAt = now) must NOT be skipped: no
+    // updatedAt predicate at all on the boot path.
+    expect(rec.wheres.some(([col]) => col === 'updatedAt')).toBe(false);
+    // It flips to 'aborted' and stamps finishedAt.
+    expect(rec.set).toEqual(
+      expect.objectContaining({ status: 'aborted', finishedAt: expect.any(Date) }),
+    );
+  });
+
+  it('phase-2 path: an explicit staleMs reintroduces the updatedAt window', async () => {
+    const { db, rec } = makeDb([]);
+    const repo = new AiChatRunRepo(db);
+
+    await repo.sweepRunning({ staleMs: SWEEP_RUN_STALE_MS });
+
+    const updatedAtWhere = rec.wheres.find(([col]) => col === 'updatedAt');
+    expect(updatedAtWhere).toBeDefined();
+    expect(updatedAtWhere![1]).toBe('<');
+    expect(updatedAtWhere![2]).toBeInstanceOf(Date);
+  });
+});

apps/server/src/database/repos/ai-chat/ai-chat-run.repo.ts

@@ -0,0 +1,212 @@
+import { Injectable, Logger } from '@nestjs/common';
+import { InjectKysely } from 'nestjs-kysely';
+import { sql } from 'kysely';
+import { KyselyDB, KyselyTransaction } from '../../types/kysely.types';
+import { dbOrTx } from '../../utils';
+import {
+  AiChatRun,
+  InsertableAiChatRun,
+} from '@docmost/db/types/entity.types';
+
+// Statuses that count as "the run is still live" (an autonomous and a user run
+// must never both be live on one chat — enforced by the partial unique index and
+// checked here for friendly 409s before the insert races the constraint).
+export const ACTIVE_RUN_STATUSES = ['pending', 'running'] as const;
+
+// Crash-recovery sweep recency threshold (mirrors AiChatMessageRepo.sweepStreaming,
+// #183): when a staleness window is supplied, a 'running'/'pending' run is only
+// swept to 'aborted' once it has been UNTOUCHED for this long, so a sibling
+// replica's boot-sweep can never abort a run another replica is actively
+// executing. The runner bumps `updatedAt` on every step, so a live run never
+// matches. PHASE 1 is single-process and the boot sweep passes NO window (every
+// dangling run is settled unconditionally — see sweepRunning / F1). This constant
+// is the window to reintroduce for the phase-2 multi-instance timer sweep.
+export const SWEEP_RUN_STALE_MS = 10 * 60 * 1000; // 10 minutes
+
+/**
+ * Repository for `ai_chat_runs` (#184 phase 1): the agent run as a first-class,
+ * server-side lifecycle object detached from the HTTP request. The run row is the
+ * point a client subscribes/reconnects to (by `id` or by chat); the assistant
+ * message it links to (`assistantMessageId`) is the #183 projection of its output.
+ */
+@Injectable()
+export class AiChatRunRepo {
+  private readonly logger = new Logger(AiChatRunRepo.name);
+
+  private baseFields: Array<keyof AiChatRun> = [
+    'id',
+    'chatId',
+    'workspaceId',
+    'createdBy',
+    'assistantMessageId',
+    'trigger',
+    'status',
+    'error',
+    'stepCount',
+    'stopRequestedAt',
+    'startedAt',
+    'finishedAt',
+    'createdAt',
+    'updatedAt',
+  ];
+
+  constructor(@InjectKysely() private readonly db: KyselyDB) {}
+
+  async insert(
+    insertable: InsertableAiChatRun,
+    trx?: KyselyTransaction,
+  ): Promise<AiChatRun> {
+    const db = dbOrTx(this.db, trx);
+    return db
+      .insertInto('aiChatRuns')
+      .values(insertable)
+      .returning(this.baseFields)
+      .executeTakeFirst();
+  }
+
+  async findById(
+    id: string,
+    workspaceId: string,
+    trx?: KyselyTransaction,
+  ): Promise<AiChatRun | undefined> {
+    const db = dbOrTx(this.db, trx);
+    return db
+      .selectFrom('aiChatRuns')
+      .select(this.baseFields)
+      .where('id', '=', id)
+      .where('workspaceId', '=', workspaceId)
+      .executeTakeFirst();
+  }
+
+  /** The currently-active (pending|running) run for a chat, if any. At most one
+   *  exists thanks to the partial unique index. */
+  async findActiveByChat(
+    chatId: string,
+    workspaceId: string,
+    trx?: KyselyTransaction,
+  ): Promise<AiChatRun | undefined> {
+    const db = dbOrTx(this.db, trx);
+    return db
+      .selectFrom('aiChatRuns')
+      .select(this.baseFields)
+      .where('chatId', '=', chatId)
+      .where('workspaceId', '=', workspaceId)
+      .where('status', 'in', ACTIVE_RUN_STATUSES as unknown as string[])
+      .executeTakeFirst();
+  }
+
+  /** The most-recent run for a chat (active or settled) — the reconnect target. */
+  async findLatestByChat(
+    chatId: string,
+    workspaceId: string,
+    trx?: KyselyTransaction,
+  ): Promise<AiChatRun | undefined> {
+    const db = dbOrTx(this.db, trx);
+    return db
+      .selectFrom('aiChatRuns')
+      .select(this.baseFields)
+      .where('chatId', '=', chatId)
+      .where('workspaceId', '=', workspaceId)
+      .orderBy('createdAt', 'desc')
+      .orderBy('id', 'desc')
+      .limit(1)
+      .executeTakeFirst();
+  }
+
+  /**
+   * Patch a run by id + workspace; always bumps `updatedAt`. Used for every
+   * lifecycle transition (mark running, link the assistant message, bump
+   * step_count, finalize succeeded/failed/aborted). Returns the updated row or
+   * undefined when nothing matched (e.g. a foreign workspace).
+   */
+  async update(
+    id: string,
+    workspaceId: string,
+    patch: Partial<{
+      status: string;
+      error: string | null;
+      stepCount: number;
+      assistantMessageId: string | null;
+      stopRequestedAt: Date | null;
+      startedAt: Date | null;
+      finishedAt: Date | null;
+    }>,
+    trx?: KyselyTransaction,
+  ): Promise<AiChatRun | undefined> {
+    const db = dbOrTx(this.db, trx);
+    return db
+      .updateTable('aiChatRuns')
+      .set({ ...(patch as Record<string, unknown>), updatedAt: new Date() })
+      .where('id', '=', id)
+      .where('workspaceId', '=', workspaceId)
+      .returning(this.baseFields)
+      .executeTakeFirst();
+  }
+
+  /**
+   * Mark an EXPLICIT stop request on an active run (distinct from a browser
+   * disconnect, which never stops a run). Stamps `stop_requested_at` ONLY while
+   * the run is still active, so a late stop on an already-settled run is a no-op.
+   * Returns the row when a stop was recorded, else undefined (nothing active).
+   */
+  async markStopRequested(
+    id: string,
+    workspaceId: string,
+    trx?: KyselyTransaction,
+  ): Promise<AiChatRun | undefined> {
+    const db = dbOrTx(this.db, trx);
+    return db
+      .updateTable('aiChatRuns')
+      .set({ stopRequestedAt: new Date(), updatedAt: new Date() })
+      .where('id', '=', id)
+      .where('workspaceId', '=', workspaceId)
+      .where('status', 'in', ACTIVE_RUN_STATUSES as unknown as string[])
+      .returning(this.baseFields)
+      .executeTakeFirst();
+  }
+
+  /**
+   * Crash-recovery sweep (mirrors AiChatMessageRepo.sweepStreaming): flip every
+   * run still left pending/running — a run whose process died before reaching a
+   * terminal status — to 'aborted', stamping `finished_at`. Returns the number
+   * swept. Workspace-wide on purpose (a crash can dangle runs in any workspace).
+   *
+   * F1 (DECISION C): the BOOT sweep is UNCONDITIONAL — it passes no `staleMs`, so
+   * EVERY dangling run is settled regardless of how recently it was touched. On a
+   * fresh single-process boot any pending|running run is definitionally hung (no
+   * runner is alive to own it), so a fast restart (deploy/OOM within minutes of
+   * the last step) no longer leaves a run stuck 'running' forever — which would
+   * make the one-active-run gate 409 every future turn in that chat.
+   *
+   * The optional `staleMs` window is reintroduced ONLY for the future phase-2
+   * multi-instance timer sweep (see {@link SWEEP_RUN_STALE_MS}): there a booting
+   * replica must NOT abort a run another replica is actively executing, so it
+   * sweeps only runs UNTOUCHED past the window. Phase 1 is single-process, so the
+   * boot path supplies no window.
+   */
+  async sweepRunning(
+    opts: { staleMs?: number } = {},
+    trx?: KyselyTransaction,
+  ): Promise<number> {
+    const db = dbOrTx(this.db, trx);
+    const now = new Date();
+    let query = db
+      .updateTable('aiChatRuns')
+      .set({
+        status: 'aborted',
+        finishedAt: now,
+        updatedAt: now,
+        error: sql`coalesce(error, ${'Run interrupted by a server restart.'})`,
+      })
+      .where('status', 'in', ACTIVE_RUN_STATUSES as unknown as string[]);
+    // Multi-instance (phase 2) only: skip runs touched within the window so a
+    // sibling replica's live run is never aborted. Omitted on the phase-1 boot
+    // sweep -> unconditional.
+    if (typeof opts.staleMs === 'number') {
+      const staleBefore = new Date(now.getTime() - opts.staleMs);
+      query = query.where('updatedAt', '<', staleBefore);
+    }
+    const rows = await query.returning('id').execute();
+    return rows.length;
+  }
+}

apps/server/src/database/types/db.d.ts

@@ -156,6 +156,18 @@ export interface Billing {
   workspaceId: string;
 }
 
+export interface ClientMetrics {
+  id: Generated<Int8>;
+  createdAt: Generated<Timestamp>;
+  name: string;
+  value: number;
+  rating: string | null;
+  route: string | null;
+  attr: string | null;
+  docSize: number | null;
+  workspaceId: string | null;
+}
+
 export interface Comments {
   aiChatId: string | null;
   content: Json | null;
@@ -647,6 +659,35 @@ export interface AiChatMessages {
   deletedAt: Timestamp | null;
 }
 
+// The agent RUN as a first-class server-side lifecycle object (#184 phase 1).
+// Mirrors migration 20260704T130000-ai-chat-runs.ts. A run is created when an
+// agent turn starts and survives the browser disconnecting; the DB is the source
+// of truth a later client reconnects to. `assistantMessageId` links to the #183
+// projection row (the assistant message this run materializes).
+export interface AiChatRuns {
+  id: Generated<string>;
+  chatId: string;
+  workspaceId: string;
+  // SET NULL on user deletion (the run history outlives its author); also NULL
+  // for a future non-human trigger (cron/api).
+  createdBy: string | null;
+  // The assistant message this run materializes; SET NULL if it is pruned.
+  assistantMessageId: string | null;
+  // 'user' | 'autostart' | 'schedule' | 'api' | 'continue' (only 'user' is
+  // produced in phase 1; the rest are reserved for the deferred autonomy triggers).
+  trigger: Generated<string>;
+  // 'pending' | 'running' | 'succeeded' | 'failed' | 'aborted'.
+  status: Generated<string>;
+  error: string | null;
+  stepCount: Generated<number>;
+  // Set when an EXPLICIT user stop is requested (distinct from a disconnect).
+  stopRequestedAt: Timestamp | null;
+  startedAt: Timestamp | null;
+  finishedAt: Timestamp | null;
+  createdAt: Generated<Timestamp>;
+  updatedAt: Generated<Timestamp>;
+}
+
 // Per-(chat,page) snapshot of the open page's Markdown at the END of the agent's
 // previous turn (#274). Mirrors migration 20260702T120000-ai-chat-page-snapshot.ts.
 // The next turn diffs the CURRENT Markdown against `contentMd` to surface edits a
@@ -683,6 +724,7 @@ export interface DB {
   aiAgentRoles: AiAgentRoles;
   aiChats: AiChats;
   aiChatMessages: AiChatMessages;
+  aiChatRuns: AiChatRuns;
   aiChatPageSnapshots: AiChatPageSnapshots;
   apiKeys: ApiKeys;
   attachments: Attachments;
@@ -691,6 +733,7 @@ export interface DB {
   authProviders: AuthProviders;
   backlinks: Backlinks;
   billing: Billing;
+  clientMetrics: ClientMetrics;
   comments: Comments;
   favorites: Favorites;
   fileTasks: FileTasks;

apps/server/src/database/types/entity.types.ts

@@ -3,6 +3,7 @@ import {
   AiAgentRoles,
   AiChats,
   AiChatMessages,
+  AiChatRuns,
   AiChatPageSnapshots,
   Attachments,
   Comments,
@@ -56,10 +57,12 @@ export type UpdatableAiChat = Updateable<Omit<AiChats, 'id'>>;
 // full-text search. It is omitted from the public type so it never leaks
 // into HTTP responses or the chat history fed to the language model.
 export type AiChatMessage = Omit<Selectable<AiChatMessages>, 'tsv'>;
-export type InsertableAiChatMessage = Omit<
-  Insertable<AiChatMessages>,
-  'tsv'
->;
+export type InsertableAiChatMessage = Omit<Insertable<AiChatMessages>, 'tsv'>;
+
+// AI Chat Run (#184 phase 1): the agent run as a first-class lifecycle object,
+// detached from the HTTP request / browser window.
+export type AiChatRun = Selectable<AiChatRuns>;
+export type InsertableAiChatRun = Insertable<AiChatRuns>;
 
 // AI Chat Page Snapshot (#274): per-(chat,page) Markdown snapshot taken at the
 // end of the agent's previous turn, diffed against the current page next turn to
@@ -214,11 +217,14 @@ export type UpdatableFavorite = Updateable<Omit<Favorites, 'id'>>;
 // Page Transclusion
 export type PageTransclusion = Selectable<PageTransclusions>;
 export type InsertablePageTransclusion = Insertable<PageTransclusions>;
-export type UpdatablePageTransclusion = Updateable<Omit<PageTransclusions, 'id'>>;
+export type UpdatablePageTransclusion = Updateable<
+  Omit<PageTransclusions, 'id'>
+>;
 
 // Page Transclusion Reference
 export type PageTransclusionReference = Selectable<PageTransclusionReferences>;
-export type InsertablePageTransclusionReference = Insertable<PageTransclusionReferences>;
+export type InsertablePageTransclusionReference =
+  Insertable<PageTransclusionReferences>;
 export type UpdatablePageTransclusionReference = Updateable<
   Omit<PageTransclusionReferences, 'id'>
 >;
@@ -288,7 +294,9 @@ export type UpdatablePagePermission = Updateable<Omit<_PagePermissions, 'id'>>;
 // Page Verification
 export type PageVerification = Selectable<_PageVerifications>;
 export type InsertablePageVerification = Insertable<_PageVerifications>;
-export type UpdatablePageVerification = Updateable<Omit<_PageVerifications, 'id'>>;
+export type UpdatablePageVerification = Updateable<
+  Omit<_PageVerifications, 'id'>
+>;
 
 // Page Verifier
 export type PageVerifier = Selectable<_PageVerifiers>;

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

@@ -227,6 +227,22 @@ export class EnvironmentService {
     return compactTree === 'true';
   }
 
+  /**
+   * Operator toggle for the public client-telemetry sink (#355). DEFAULT OFF:
+   * the unauthenticated POST /api/telemetry/vitals endpoint + client vitals
+   * collection are only wired when this is explicitly true. Kept SEPARATE from
+   * METRICS_PORT (the server Prometheus half) because Grafana reads the
+   * `client_metrics` table directly, independent of the scrape port — and
+   * because `client_metrics` has no app-side retention, so an operator must opt
+   * in and run an external pruner.
+   */
+  isClientTelemetryEnabled(): boolean {
+    const enabled = this.configService
+      .get<string>('CLIENT_TELEMETRY_ENABLED', 'false')
+      .toLowerCase();
+    return enabled === 'true';
+  }
+
   getStripePublishableKey(): string {
     return this.configService.get<string>('STRIPE_PUBLISHABLE_KEY');
   }

apps/server/src/integrations/export/export-markdown.spec.ts

@@ -0,0 +1,145 @@
+// export.service.ts imports the ESM-only @sindresorhus/slugify (not in jest's
+// transform allowlist). It is irrelevant to the markdown-serialization path under
+// test (only used for page-mention link slugs on the DB path), so it is mocked
+// out to keep the module graph loadable under ts-jest (mirrors the import specs).
+jest.mock('@sindresorhus/slugify', () => ({
+  __esModule: true,
+  default: (input: string) => String(input),
+}));
+
+import { convertProseMirrorToMarkdown } from '@docmost/prosemirror-markdown';
+import { ExportService } from './export.service';
+import { ExportFormat } from './dto/export-dto';
+
+/**
+ * STEP 1 golden test for issue #345: server MARKDOWN export runs DIRECTLY through
+ * the canonical converter (`convertProseMirrorToMarkdown`) — no HTML intermediate
+ * and no `@docmost/editor-ext` markdown layer — so the emitted markdown is in the
+ * canonical package forms and is byte-identical to the git-sync vault body.
+ *
+ * These are the goldens the swap has to satisfy: they assert the CANONICAL
+ * surface (callout `> [!type]`, inline footnote `^[…]`, lossless image
+ * `<!--img …-->`) rather than the old editor-ext forms (`:::type`, `[^id]`,
+ * lossy `![alt](src)`).
+ *
+ * `exportPage(..., singlePage=false)` takes no DB path (no mention rewriting), so
+ * the service is constructed with null collaborators and only the pure
+ * PM -> Markdown path is exercised.
+ */
+
+function makeService(): ExportService {
+  return new ExportService(
+    null as any, // pageRepo
+    null as any, // pagePermissionRepo
+    null as any, // db
+    null as any, // storageService
+    null as any, // environmentService
+    null as any, // domainService
+  );
+}
+
+// A representative page exercising the node types whose canonical markdown form
+// changed with the move off the editor-ext layer: callout, inline footnote, and a
+// lossless image carrying width/align attrs that the old layer dropped.
+const REPRESENTATIVE_DOC = {
+  type: 'doc',
+  content: [
+    {
+      type: 'paragraph',
+      content: [
+        { type: 'text', text: 'Body ' },
+        { type: 'footnoteReference', attrs: { id: 'fn-1' } },
+        { type: 'text', text: ' end.' },
+      ],
+    },
+    {
+      type: 'callout',
+      attrs: { type: 'info', icon: null },
+      content: [
+        {
+          type: 'paragraph',
+          content: [{ type: 'text', text: 'Heads up' }],
+        },
+      ],
+    },
+    {
+      type: 'image',
+      attrs: {
+        src: '/files/pic.png',
+        alt: 'Pic',
+        width: 320,
+        align: 'left',
+      },
+    },
+    {
+      type: 'footnotesList',
+      content: [
+        {
+          type: 'footnoteDefinition',
+          attrs: { id: 'fn-1' },
+          content: [
+            {
+              type: 'paragraph',
+              content: [{ type: 'text', text: 'the note' }],
+            },
+          ],
+        },
+      ],
+    },
+  ],
+};
+
+describe('ExportService — markdown export via the canonical converter (#345)', () => {
+  it('emits canonical callout, inline footnote and lossless image forms', async () => {
+    const service = makeService();
+    const md = (await service.exportPage(ExportFormat.Markdown, {
+      title: '',
+      content: REPRESENTATIVE_DOC,
+    } as any)) as string;
+
+    // Callout: Obsidian `> [!type]`, NOT the legacy `:::type`.
+    expect(md).toContain('> [!info]');
+    expect(md).not.toContain(':::');
+
+    // Inline footnote: `^[…]`, NOT the reference `[^id]` form.
+    expect(md).toContain('^[the note]');
+    expect(md).not.toMatch(/\[\^/);
+
+    // Lossless image: trailing `<!--img …-->` carrying the dropped attrs.
+    expect(md).toContain('![Pic](/files/pic.png)');
+    expect(md).toContain('<!--img');
+    expect(md).toContain('"width":"320"');
+    expect(md).toContain('"align":"left"');
+  });
+
+  it('export body is byte-identical to the git-sync vault serializer (export == vault)', async () => {
+    const service = makeService();
+    // A title-less page: exportPage prepends NO heading, so the whole output is
+    // the page BODY — exactly what git-sync serializes (git-sync stores the title
+    // in frontmatter / the filename, never as an in-body H1).
+    const exported = (await service.exportPage(ExportFormat.Markdown, {
+      title: '',
+      content: REPRESENTATIVE_DOC,
+    } as any)) as string;
+
+    // The git-sync vault writer feeds this SAME converter (git-sync
+    // `stabilizePageBody` = convertProseMirrorToMarkdown(content) at the
+    // fixpoint). For an already-stable doc the single pass IS the fixpoint, so
+    // the two are byte-identical by construction — assert it.
+    const vaultBody = convertProseMirrorToMarkdown(REPRESENTATIVE_DOC);
+    expect(exported).toBe(vaultBody);
+  });
+
+  it('prepends the page title as an H1 heading (the one documented export/vault delta)', async () => {
+    const service = makeService();
+    const md = (await service.exportPage(ExportFormat.Markdown, {
+      title: 'My Page',
+      content: { type: 'doc', content: [] },
+    } as any)) as string;
+
+    // Export makes standalone files, so it prepends the title as an H1. This is
+    // the ONE deliberate difference from the vault body (which carries the title
+    // in frontmatter). The body below the heading still serializes canonically.
+    expect(md.startsWith('# My Page')).toBe(true);
+  });
+});

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

@@ -37,7 +37,7 @@ import {
   getAttachmentIds,
   getProsemirrorContent,
 } from '../../common/helpers/prosemirror/utils';
-import { htmlToMarkdown } from '@docmost/editor-ext';
+import { convertProseMirrorToMarkdown } from '@docmost/prosemirror-markdown';
 
 type AllowedAttachment = { id: string; fileName: string; filePath: string };
 
@@ -79,9 +79,8 @@ export class ExportService {
       prosemirrorJson.content.unshift(titleNode);
     }
 
-    const pageHtml = jsonToHtml(prosemirrorJson);
-
     if (format === ExportFormat.HTML) {
+      const pageHtml = jsonToHtml(prosemirrorJson);
       return `<!DOCTYPE html>
       <html>
         <head>
@@ -92,11 +91,14 @@ export class ExportService {
     }
 
     if (format === ExportFormat.Markdown) {
-      const newPageHtml = pageHtml.replace(
-        /<colgroup[^>]*>[\s\S]*?<\/colgroup>/gim,
-        '',
-      );
-      return htmlToMarkdown(newPageHtml);
+      // Direct ProseMirror JSON -> Markdown via the canonical converter
+      // (`@docmost/prosemirror-markdown`). This is the SAME serializer the
+      // git-sync vault writer feeds (see git-sync `stabilizePageBody`), so an
+      // exported page body is byte-identical to its vault representation — no
+      // HTML intermediate, no second markdown layer, no format drift (issue
+      // #345). The old `<colgroup>` scrub is gone with the HTML step: the
+      // converter emits GFM tables directly and never produces `<colgroup>`.
+      return convertProseMirrorToMarkdown(prosemirrorJson);
     }
 
     return;

apps/server/src/integrations/import/services/file-import-task.service.footnote-canonicalize.spec.ts

@@ -17,6 +17,22 @@ jest.mock('image-dimensions', () => ({
   __esModule: true,
   imageDimensionsFromData: () => undefined,
 }));
+// FileImportTaskService -> PageService -> collaboration.gateway ->
+// metrics.registry imports `prom-client`, which is not resolvable in this
+// workspace's node_modules (types-only stub, no runtime entry). Metrics are
+// disabled on this path, so a virtual no-op mock keeps the module graph loadable.
+jest.mock(
+  'prom-client',
+  () => ({
+    collectDefaultMetrics: () => undefined,
+    Registry: class {},
+    Histogram: class {},
+    Gauge: class {},
+    Counter: class {},
+    Summary: class {},
+  }),
+  { virtual: true },
+);
 
 import { promises as fs } from 'fs';
 import * as os from 'os';
@@ -26,14 +42,17 @@ import { ImportService } from './import.service';
 
 /**
  * Binding test for issue #228 / review #5: FileImportTaskService.processGenericImport
- * is a NON-editor write path (markdownToHtml -> processHTML -> JSON, never runs
- * footnoteSyncPlugin), so it canonicalizes footnotes before persisting. This pins
- * that binding — the same one import.service has a spec for — which previously had
- * NO spec at all.
+ * is a NON-editor write path, so a zip-imported `.md` page ends up with canonical
+ * footnotes before persisting: ordered by first reference, reused refs deduped,
+ * orphan definitions dropped.
  *
- * The markdown -> HTML -> ProseMirror conversion is REAL (a real ImportService,
- * its createYdoc stubbed); the filesystem is a real temp dir with one .md file;
- * the DB transaction is stubbed to capture the persisted page content.
+ * Since #345 the `.md` parse runs `normalizeForeignMarkdown` ->
+ * `markdownToProseMirror` -> `jsonToHtml` (feeding the shared HTML attachment /
+ * link pipeline) -> `processHTML` -> `canonicalizeFootnotes`. The parser assigns
+ * fresh `fn-*` ids, so we assert by definition BODY order rather than the source
+ * labels. The conversion is REAL (a real ImportService, its createYdoc stubbed);
+ * the filesystem is a real temp dir with one .md file; the DB transaction is
+ * stubbed to capture the persisted page content.
  */
 
 // Out-of-order references (c, a, b), a REUSED reference ([^a] twice), and an
@@ -49,13 +68,14 @@ const MARKDOWN = [
   '[^z]: orphan note',
 ].join('\n');
 
-function footnoteListIds(content: any): string[] {
+/** Definition body texts of the (single) footnotesList, in list order. */
+function footnoteListBodies(content: any): string[] {
   const list = (content?.content ?? []).find(
     (n: any) => n.type === 'footnotesList',
   );
   return (list?.content ?? [])
     .filter((n: any) => n.type === 'footnoteDefinition')
-    .map((n: any) => n.attrs?.id);
+    .map((n: any) => n.content?.[0]?.content?.[0]?.text);
 }
 
 // A permissive chainable stub for the spaces lookup (selectFrom(...).select(...)
@@ -71,80 +91,127 @@ function chainable(result: any): any {
   return proxy;
 }
 
+/**
+ * Run one markdown file through the REAL zip-import pipeline
+ * (`processGenericImport` -> `markdownToProseMirror` -> `jsonToHtml` ->
+ * `processHTML`/`htmlToJson`) and return the persisted page `content`. This is
+ * the server-specific PM->HTML->PM hop that the package's own PM<->MD tests do
+ * NOT cover.
+ */
+async function runZipImport(markdown: string): Promise<any> {
+  const extractDir = await fs.mkdtemp(path.join(os.tmpdir(), 'fit-canon-'));
+  await fs.writeFile(path.join(extractDir, 'note.md'), markdown, 'utf-8');
+
+  const importService = new ImportService(
+    {} as any,
+    {} as any,
+    {} as any,
+    {} as any,
+  );
+  jest
+    .spyOn(importService as any, 'createYdoc')
+    .mockResolvedValue(Buffer.from([]) as any);
+
+  let captured: any = null;
+  const trx = {
+    insertInto: (table: string) => ({
+      values: (v: any) => {
+        if (table === 'pages') captured = v;
+        return { execute: async () => {} };
+      },
+    }),
+  };
+  const db: any = {
+    selectFrom: () => chainable({ slug: 'space-slug' }),
+    transaction: () => ({ execute: (fn: any) => fn(trx) }),
+  };
+
+  const importAttachmentService = {
+    processAttachments: async ({ html }: any) => html,
+  };
+  const service = new FileImportTaskService(
+    {} as any, // storageService
+    importService as any,
+    { nextPagePosition: async () => 'a0' } as any,
+    { insertBacklink: jest.fn() } as any,
+    db,
+    importAttachmentService as any,
+    { emit: jest.fn() } as any,
+    { logBatchWithContext: jest.fn() } as any,
+  );
+
+  const fileTask: any = {
+    id: 'task-1',
+    source: 'generic',
+    spaceId: 'space-1',
+    workspaceId: 'ws-1',
+    creatorId: 'user-1',
+  };
+
+  try {
+    await service.processGenericImport({ extractDir, fileTask });
+    expect(captured).toBeTruthy();
+    return captured.content;
+  } finally {
+    await fs.rm(extractDir, { recursive: true, force: true });
+  }
+}
+
+/** Find the first node of a given type anywhere in a PM content tree. */
+function findFirst(node: any, type: string): any {
+  if (!node || typeof node !== 'object') return null;
+  if (node.type === type) return node;
+  for (const child of node.content ?? []) {
+    const hit = findFirst(child, type);
+    if (hit) return hit;
+  }
+  return null;
+}
+
 describe('FileImportTaskService.processGenericImport — footnote canonicalization (#228)', () => {
   it('orders footnotes by first reference, dedupes reuse, and drops orphans on zip import', async () => {
-    const extractDir = await fs.mkdtemp(path.join(os.tmpdir(), 'fit-canon-'));
-    await fs.writeFile(path.join(extractDir, 'note.md'), MARKDOWN, 'utf-8');
-
-    // Real ImportService for the html -> JSON conversion; stub the yjs encode.
-    const importService = new ImportService(
-      {} as any,
-      {} as any,
-      {} as any,
-      {} as any,
+    const content = await runZipImport(MARKDOWN);
+    // Definitions ordered by FIRST REFERENCE (C, A, B), NOT the markdown
+    // definition order (A, B, C). Ids are the parser's fresh `fn-*`, so pin
+    // the BODIES.
+    expect(footnoteListBodies(content)).toEqual(['note C', 'note A', 'note B']);
+    // Orphan [^z] dropped; reused [^a] collapses to one definition; one list.
+    expect(footnoteListBodies(content)).not.toContain('orphan note');
+    const lists = (content.content ?? []).filter(
+      (n: any) => n.type === 'footnotesList',
     );
-    jest
-      .spyOn(importService as any, 'createYdoc')
-      .mockResolvedValue(Buffer.from([]) as any);
+    expect(lists).toHaveLength(1);
+    expect(
+      footnoteListBodies(content).filter((b) => b === 'note A'),
+    ).toHaveLength(1);
+  });
 
-    let captured: any = null;
-    const trx = {
-      insertInto: (table: string) => ({
-        values: (v: any) => {
-          if (table === 'pages') captured = v;
-          return { execute: async () => {} };
-        },
-      }),
-    };
-    const db: any = {
-      selectFrom: () => chainable({ slug: 'space-slug' }),
-      transaction: () => ({ execute: (fn: any) => fn(trx) }),
-    };
+  // #345 F4: the zip path routes markdown through jsonToHtml -> processHTML ->
+  // htmlToJson (the shared HTML attachment pipeline). #345's headline is LOSSLESS
+  // image width/align via the `<!--img {...}-->` comment; a callout carries its
+  // `type`. This asserts those survive the PM->HTML->PM hop — the one hop the
+  // package's PM<->MD suite does not exercise.
+  it('preserves image width/align and callout type through the PM->HTML->PM hop', async () => {
+    const md = [
+      '# Doc',
+      '',
+      '![a picture](https://example.com/i.png) <!--img {"width":"320","align":"left"}-->',
+      '',
+      ':::warning',
+      'Careful now.',
+      ':::',
+    ].join('\n');
 
-    const importAttachmentService = {
-      processAttachments: async ({ html }: any) => html,
-    };
-    const backlinkRepo = { insertBacklink: jest.fn() };
-    const eventEmitter = { emit: jest.fn() };
-    const auditService = { logBatchWithContext: jest.fn() };
+    const content = await runZipImport(md);
 
-    const pageService = { nextPagePosition: async () => 'a0' };
+    const image = findFirst(content, 'image');
+    expect(image).toBeTruthy();
+    // The lossless sizing/alignment must survive the HTML hop.
+    expect(String(image.attrs?.width)).toBe('320');
+    expect(image.attrs?.align).toBe('left');
 
-    const service = new FileImportTaskService(
-      {} as any, // storageService
-      importService as any,
-      pageService as any,
-      backlinkRepo as any,
-      db,
-      importAttachmentService as any,
-      eventEmitter as any,
-      auditService as any,
-    );
-
-    const fileTask: any = {
-      id: 'task-1',
-      source: 'generic',
-      spaceId: 'space-1',
-      workspaceId: 'ws-1',
-      creatorId: 'user-1',
-    };
-
-    try {
-      await service.processGenericImport({ extractDir, fileTask });
-
-      expect(captured).toBeTruthy();
-      const content = captured.content;
-      // Reference order is c, a, b (NOT the markdown definition order a, b, c).
-      expect(footnoteListIds(content)).toEqual(['c', 'a', 'b']);
-      // Orphan [^z] dropped; reused [^a] collapses to one definition; one list.
-      expect(footnoteListIds(content)).not.toContain('z');
-      const lists = (content.content ?? []).filter(
-        (n: any) => n.type === 'footnotesList',
-      );
-      expect(lists).toHaveLength(1);
-      expect(footnoteListIds(content).filter((id) => id === 'a')).toHaveLength(1);
-    } finally {
-      await fs.rm(extractDir, { recursive: true, force: true });
-    }
+    const callout = findFirst(content, 'callout');
+    expect(callout).toBeTruthy();
+    expect(callout.attrs?.type).toBe('warning');
   });
 });

apps/server/src/integrations/import/services/file-import-task.service.ts

@@ -1,6 +1,9 @@
 import { Inject, Injectable, Logger } from '@nestjs/common';
 import * as path from 'path';
-import { jsonToText } from '../../../collaboration/collaboration.util';
+import {
+  jsonToHtml,
+  jsonToText,
+} from '../../../collaboration/collaboration.util';
 import { InjectKysely } from 'nestjs-kysely';
 import { KyselyDB } from '@docmost/db/types/kysely.types';
 import {
@@ -18,9 +21,11 @@ import { generateSlugId } from '../../../common/helpers';
 import { v7 } from 'uuid';
 import { generateJitteredKeyBetween } from 'fractional-indexing-jittered';
 import { FileTask, InsertablePage } from '@docmost/db/types/entity.types';
-import { markdownToHtml, canonicalizeFootnotes } from '@docmost/editor-ext';
+import { canonicalizeFootnotes } from '@docmost/editor-ext';
+import { markdownToProseMirror } from '@docmost/prosemirror-markdown';
 import { getProsemirrorContent } from '../../../common/helpers/prosemirror/utils';
 import { formatImportHtml } from '../utils/import-formatter';
+import { normalizeForeignMarkdown } from '../utils/foreign-markdown';
 import {
   buildAttachmentCandidates,
   collectMarkdownAndHtmlFiles,
@@ -461,7 +466,18 @@ export class FileImportTaskService {
               content = await fs.readFile(absPath, 'utf-8');
 
               if (page.fileExtension.toLowerCase() === '.md') {
-                content = await markdownToHtml(content);
+                // Parse markdown with the single canonical converter
+                // (`@docmost/prosemirror-markdown`), after normalizing foreign
+                // reference footnotes, then serialize to HTML so the shared HTML
+                // pipeline below (processAttachments + formatImportHtml +
+                // processHTML) keeps handling `.md` and `.html` imports
+                // uniformly. The markdown PARSE no longer goes through the
+                // editor-ext markdown layer (issue #345) — the drift source is
+                // gone. The PM -> HTML -> PM hop that follows is lossless
+                // plumbing for attachment/link resolution, NOT a second parse.
+                content = jsonToHtml(
+                  await markdownToProseMirror(normalizeForeignMarkdown(content)),
+                );
               }
             } catch (err: any) {
               if (err?.code === 'ENOENT') {
@@ -500,10 +516,12 @@ export class FileImportTaskService {
               this.importService.extractTitleAndRemoveHeading(pmState);
 
             // Canonicalize footnote topology on this non-editor write path
-            // (markdownToHtml/processHTML never runs footnoteSyncPlugin), so a
-            // zip-imported page's footnotes are reference-ordered, deduped, and
+            // (the HTML pipeline's processHTML never runs footnoteSyncPlugin), so
+            // a zip-imported page's footnotes are reference-ordered, deduped, and
             // orphan-free like the editor's invariant (issue #228). Pure +
-            // idempotent + shape-safe; a footnote-free doc is unchanged.
+            // idempotent + shape-safe; a footnote-free doc is unchanged. (For a
+            // `.md` file the package parser already yields canonical footnotes,
+            // so this is a no-op there.)
             // (Future consolidation, architecture B: like import.service, this
             // path persists directly rather than via PageService — a shared
             // "prepare JSON for persist" helper would centralize this call.)

apps/server/src/integrations/import/services/import.service.footnote-canonicalize.spec.ts

@@ -12,13 +12,19 @@ import { canonicalizeFootnotes } from '@docmost/editor-ext';
 
 /**
  * Integration-ish test for the USER-FACING markdown import path
- * (`ImportService.importPage`). It exercises the REAL markdown -> HTML -> JSON
- * conversion and asserts that the stored page content has its footnotes
- * canonicalized — the gap that issue #228 fixes: the import path builds
- * ProseMirror JSON directly (never running the editor's footnoteSyncPlugin), so
- * before this wiring the stored footnotes kept the markdown's physical
- * definition order (out of order vs. references), retained orphan definitions,
- * and did not collapse reused references.
+ * (`ImportService.importPage`). It exercises the REAL markdown -> ProseMirror
+ * conversion and asserts the stored page's footnotes are canonical: ordered by
+ * FIRST REFERENCE (not markdown definition order), reused references deduped to a
+ * single definition, and orphan definitions dropped.
+ *
+ * Since #345 the markdown parse runs through the canonical package
+ * (`normalizeForeignMarkdown` -> `markdownToProseMirror`), which owns this
+ * canonicalization: the input's GFM `[^id]` reference footnotes are normalized to
+ * inline `^[…]`, and the parser assigns fresh sequential ids (`fn-*`) in
+ * reference order while merging identical bodies — so we assert by definition
+ * BODY order, not by the source labels. `canonicalizeFootnotes` remains wired as
+ * an idempotent safety net (issue #228) and is a no-op on this already-canonical
+ * output.
  *
  * The DB/ydoc side-effects are stubbed: `getNewPagePosition` (DB query) and
  * `createYdoc` (Yjs encode) are spied, and `pageRepo.insertPage` captures the
@@ -67,24 +73,14 @@ function makeService() {
 }
 
 /** List the footnote-definition ids of the (single) footnotesList, in order. */
-function footnoteListIds(content: any): string[] {
+/** Definition body texts of the (single) footnotesList, in list order. */
+function footnoteListBodies(content: any): string[] {
   const list = (content.content ?? []).find(
     (n: any) => n.type === 'footnotesList',
   );
-  if (!list) return [];
-  return (list.content ?? [])
+  return (list?.content ?? [])
     .filter((n: any) => n.type === 'footnoteDefinition')
-    .map((n: any) => n.attrs?.id);
-}
-
-function definitionText(content: any, id: string): string | undefined {
-  const list = (content.content ?? []).find(
-    (n: any) => n.type === 'footnotesList',
-  );
-  const def = (list?.content ?? []).find(
-    (n: any) => n.type === 'footnoteDefinition' && n.attrs?.id === id,
-  );
-  return def?.content?.[0]?.content?.[0]?.text;
+    .map((n: any) => n.content?.[0]?.content?.[0]?.text);
 }
 
 describe('ImportService.importPage — footnote canonicalization (#228)', () => {
@@ -101,23 +97,23 @@ describe('ImportService.importPage — footnote canonicalization (#228)', () =>
     const content = getCaptured().content;
     expect(content).toBeTruthy();
 
-    // Reference order is c, a, b (NOT the markdown definition order a, b, c).
-    expect(footnoteListIds(content)).toEqual(['c', 'a', 'b']);
-
-    // Definitions preserved and attached to the right ids.
-    expect(definitionText(content, 'c')).toBe('note C');
-    expect(definitionText(content, 'a')).toBe('note A');
-    expect(definitionText(content, 'b')).toBe('note B');
+    // Definitions ordered by FIRST REFERENCE (C, A, B) — NOT the markdown
+    // definition order (A, B, C) — with the orphan [^z] dropped and the reused
+    // [^a] collapsed to a single definition. (Ids are the parser's fresh `fn-*`,
+    // so we pin the BODIES.)
+    expect(footnoteListBodies(content)).toEqual(['note C', 'note A', 'note B']);
 
     // Orphan definition [^z] is dropped.
-    expect(footnoteListIds(content)).not.toContain('z');
+    expect(footnoteListBodies(content)).not.toContain('orphan note');
 
     // Reused [^a] yields exactly ONE definition, and exactly one list.
     const lists = (content.content ?? []).filter(
       (n: any) => n.type === 'footnotesList',
     );
     expect(lists).toHaveLength(1);
-    expect(footnoteListIds(content).filter((id) => id === 'a')).toHaveLength(1);
+    expect(
+      footnoteListBodies(content).filter((b) => b === 'note A'),
+    ).toHaveLength(1);
   });
 
   it('is idempotent: canonicalizing the stored output again is a no-op', async () => {
@@ -134,6 +130,6 @@ describe('ImportService.importPage — footnote canonicalization (#228)', () =>
     // time must not change it (safe to wire into every write path).
     const second = canonicalizeFootnotes(stored);
     expect(second).toEqual(stored);
-    expect(footnoteListIds(second)).toEqual(['c', 'a', 'b']);
+    expect(footnoteListBodies(second)).toEqual(['note C', 'note A', 'note B']);
   });
 });

apps/server/src/integrations/import/services/import.service.ts

@@ -17,7 +17,9 @@ import {
 import { generateJitteredKeyBetween } from 'fractional-indexing-jittered';
 import { TiptapTransformer } from '@hocuspocus/transformer';
 import * as Y from 'yjs';
-import { markdownToHtml, canonicalizeFootnotes } from '@docmost/editor-ext';
+import { canonicalizeFootnotes } from '@docmost/editor-ext';
+import { markdownToProseMirror } from '@docmost/prosemirror-markdown';
+import { normalizeForeignMarkdown } from '../utils/foreign-markdown';
 import {
   FileTaskStatus,
   FileTaskType,
@@ -85,11 +87,13 @@ export class ImportService {
 
     const extracted = this.extractTitleAndRemoveHeading(prosemirrorState);
     const title = extracted.title;
-    // Imported markdown/HTML is built via markdownToHtml -> htmlToJson, which
-    // never runs the editor's footnoteSyncPlugin, so the footnote topology keeps
-    // the source's PHYSICAL definition order (out of order vs. references),
-    // retains orphan definitions, and is not deduped. Canonicalize before
-    // persisting so the stored page matches the editor's invariant (issue #228).
+    // The markdown path now canonicalizes footnotes itself (the package parser),
+    // but the HTML path (processHTML -> htmlToJson) does NOT run the editor's
+    // footnoteSyncPlugin, so an imported HTML doc can keep its source's PHYSICAL
+    // definition order (out of order vs. references), retain orphan definitions,
+    // and not be deduped. Canonicalize before persisting so the stored page
+    // matches the editor's invariant (issue #228); it is an idempotent no-op on
+    // the already-canonical markdown output.
     // Pure + idempotent + shape-safe: a doc with no footnotes is unchanged.
     // (Future consolidation, architecture B: this import path persists directly
     // via pageRepo.insertPage rather than through PageService.createPage, so the
@@ -133,12 +137,15 @@ export class ImportService {
   }
 
   async processMarkdown(markdownInput: string): Promise<any> {
-    try {
-      const html = await markdownToHtml(markdownInput);
-      return this.processHTML(html);
-    } catch (err) {
-      throw err;
-    }
+    // Canonical markdown -> ProseMirror JSON directly via
+    // `@docmost/prosemirror-markdown` (issue #345) — no HTML intermediate and no
+    // second editor-ext markdown layer. Foreign markdown surfaces the strict
+    // canonical parser does not accept (GFM `[^id]` reference footnotes) are
+    // rewritten to the canonical inline form by `normalizeForeignMarkdown` first.
+    // The HTML-cleanup pass (`normalizeImportHtml`) is intentionally skipped here:
+    // it targets foreign *HTML* (Notion/XWiki), which only ever arrives on the
+    // `.html` path (`processHTML`), never as canonical markdown.
+    return markdownToProseMirror(normalizeForeignMarkdown(markdownInput));
   }
 
   async processHTML(htmlInput: string): Promise<any> {

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

@@ -0,0 +1,218 @@
+import {
+  convertProseMirrorToMarkdown,
+  markdownToProseMirror,
+} from '@docmost/prosemirror-markdown';
+import { normalizeForeignMarkdown } from './foreign-markdown';
+
+/**
+ * STEP 2 goldens for issue #345: the foreign-markdown normalizer that runs at the
+ * import boundary BEFORE the strict canonical parser (`markdownToProseMirror`).
+ *
+ * Two layers:
+ *  1. PURE string→string cases pinning the normalizer's own behavior (GFM
+ *     reference footnotes → inline `^[…]`).
+ *  2. END-TO-END acceptance: for a foreign corpus, `normalizeForeignMarkdown`
+ *     then `markdownToProseMirror` then `convertProseMirrorToMarkdown` must leave
+ *     NO literal `[^id]` / `:::` garbage in the document and must re-export in the
+ *     canonical forms.
+ */
+
+describe('normalizeForeignMarkdown — GFM reference footnotes', () => {
+  it('inlines a single-line reference footnote and drops its definition', () => {
+    const out = normalizeForeignMarkdown(
+      'A note[^1] here.\n\n[^1]: The definition.',
+    );
+    expect(out).toBe('A note^[The definition.] here.\n');
+  });
+
+  it('inlines every reference to a reused id (downstream dedups)', () => {
+    const out = normalizeForeignMarkdown(
+      'X[^a] and Y[^a].\n\n[^a]: shared.',
+    );
+    expect(out).toBe('X^[shared.] and Y^[shared.].\n');
+  });
+
+  it('joins indented continuation lines of a definition with a space', () => {
+    const out = normalizeForeignMarkdown(
+      'See[^n].\n\n[^n]: line one\n    line two',
+    );
+    expect(out).toBe('See^[line one line two].\n');
+  });
+
+  it('never rewrites a reference inside a fenced code block', () => {
+    const out = normalizeForeignMarkdown(
+      '```\ncode[^1] here\n```\n\n[^1]: def.',
+    );
+    expect(out).toContain('code[^1] here');
+    // The (now orphaned) definition line is still removed.
+    expect(out).not.toContain('[^1]: def.');
+  });
+
+  it('never rewrites a reference inside an INLINE-code span (backticks)', () => {
+    // The `[^1]` inside backticks is literal code and must survive verbatim;
+    // the one outside is rewritten. (Bug #1: only fenced blocks were protected.)
+    const out = normalizeForeignMarkdown(
+      'Use `arr[^1]` in code but note[^1] in prose.\n\n[^1]: def.',
+    );
+    expect(out).toBe('Use `arr[^1]` in code but note^[def.] in prose.\n');
+  });
+
+  it('escapes brackets in a body so an unbalanced ] cannot truncate the footnote', () => {
+    // A foreign definition body with a stray `]` would, unescaped, close the
+    // canonical `^[...]` early and leak the tail as text (bug #2). The body's
+    // brackets are backslash-escaped so the footnote stays whole.
+    const out = normalizeForeignMarkdown(
+      'Ref[^1] here.\n\n[^1]: see item ] and [more] later',
+    );
+    expect(out).toBe('Ref^[see item \\] and \\[more\\] later] here.\n');
+    // The tokenizer must see exactly one unescaped closing bracket (our own).
+    expect(out.match(/(?<!\\)\]/g)).toHaveLength(1);
+  });
+
+  it('leaves a reference with no matching definition literal (no body to inline)', () => {
+    const out = normalizeForeignMarkdown('Dangling[^x] ref.');
+    expect(out).toBe('Dangling[^x] ref.');
+  });
+
+  it('returns the input unchanged when there are no reference footnotes', () => {
+    const md = '# Title\n\nJust text with `inline code` and a [link](/x).';
+    expect(normalizeForeignMarkdown(md)).toBe(md);
+  });
+
+  it('does NOT touch callout surfaces — the canonical parser handles them', () => {
+    const callouts = ':::info\nHi\n:::\n\n> [!warning]\n> Careful';
+    expect(normalizeForeignMarkdown(callouts)).toBe(callouts);
+  });
+
+  it('strips a leading YAML front-matter block (Obsidian/Hugo/git-sync files)', () => {
+    const out = normalizeForeignMarkdown(
+      '---\ntitle: My Page\ntags: [a, b]\n---\n\n# Heading\n\nBody.',
+    );
+    expect(out).toBe('# Heading\n\nBody.');
+    // The front-matter must not leak into the body as a setext heading.
+    expect(out).not.toContain('title: My Page');
+    expect(out).not.toContain('---');
+  });
+
+  it('does not strip a horizontal rule that is not leading front-matter', () => {
+    const md = 'Intro paragraph.\n\n---\n\nAfter the rule.';
+    expect(normalizeForeignMarkdown(md)).toBe(md);
+  });
+
+  it('is linear on a document with thousands of definitions (no quadratic blowup)', () => {
+    // F2(a): the pass-2 rewrite must be O(text), not O(text × defs). Build a
+    // pathological doc (many defs + many plain text lines) and assert it
+    // completes well under a second — a quadratic implementation took ~14s.
+    const N = 4000;
+    const refs = Array.from({ length: N }, (_, i) => `line ${i} plain text`).join('\n');
+    const defs = Array.from({ length: N }, (_, i) => `[^n${i}]: def ${i}`).join('\n');
+    const doc = `start[^n0] and[^n${N - 1}] end\n\n${refs}\n\n${defs}`;
+    const t0 = Date.now();
+    const out = normalizeForeignMarkdown(doc);
+    const elapsed = Date.now() - t0;
+    expect(elapsed).toBeLessThan(2000);
+    // Sanity: the two real references were still inlined.
+    expect(out).toContain('^[def 0]');
+    expect(out).toContain(`^[def ${N - 1}]`);
+  });
+
+  it('is bounded on a long unclosed backtick run (no inline-split ReDoS)', () => {
+    // F2(b): a huge unterminated backtick run must not cause quadratic
+    // backtracking in the inline-code split. Oversized lines skip the split
+    // entirely (left untouched), so this returns promptly.
+    const line = 'x' + '`'.repeat(200000);
+    const doc = `${line}\n\n[^1]: def`;
+    const t0 = Date.now();
+    normalizeForeignMarkdown(doc);
+    expect(Date.now() - t0).toBeLessThan(2000);
+  });
+
+  it('does not crash or slow down on thousands of prefix-chain definition ids', () => {
+    // F7: the rewrite must use a FIXED generic scanner, not an alternation built
+    // from the ids. A `(a|aa|aaa|…)` alternation over prefix-chain ids blows the
+    // V8 regex compiler (FATAL RegExpCompiler Allocation failed — uncatchable,
+    // kills the process). A fixed scanner has no id-dependent compilation cost.
+    const N = 4000;
+    const ids = Array.from({ length: N }, (_, i) => 'a'.repeat(i + 1));
+    const defs = ids.map((id) => `[^${id}]: body ${id.length}`).join('\n');
+    const doc = `ref[^${ids[0]}] and[^${ids[N - 1]}] end\n\n${defs}`;
+    const t0 = Date.now();
+    const out = normalizeForeignMarkdown(doc);
+    expect(Date.now() - t0).toBeLessThan(2000);
+    // Prefix disambiguation is correct: [^a] and [^aaaa...] inline their OWN body.
+    expect(out).toContain('^[body 1]');
+    expect(out).toContain(`^[body ${N}]`);
+  });
+
+  it('strips a CRLF (Windows) front-matter block, not just LF', () => {
+    // F9: the line-anchored regex needs LF after the opening `---`, so a Windows
+    // file (`---\r\n…`) would slip past the strip and leak the front-matter into
+    // the body. normalizeForeignMarkdown normalizes CRLF -> LF first.
+    const out = normalizeForeignMarkdown(
+      '---\r\ntitle: Foo\r\ntags: [a]\r\n---\r\n\r\n# Heading\r\n\r\nBody.',
+    );
+    expect(out).toBe('# Heading\n\nBody.');
+    expect(out).not.toContain('title: Foo');
+    expect(out).not.toContain('---');
+  });
+
+  it('strips front-matter whose value contains a triple-dash (line-anchored)', () => {
+    // F8: the block must close only on a `\n---` LINE, not the first inline
+    // `---`. A value like `title: Q1 --- Q2` must not truncate the front-matter
+    // and leak the rest (author/closing ---) into the body.
+    const out = normalizeForeignMarkdown(
+      '---\ntitle: Q1 --- Q2 results\nauthor: bob\n---\n\nReal body.',
+    );
+    expect(out).toBe('Real body.');
+    expect(out).not.toContain('author: bob');
+    expect(out).not.toContain('Q2 results');
+  });
+});
+
+describe('foreign markdown import acceptance (normalizer + canonical parser)', () => {
+  const FOREIGN = [
+    '# Doc',
+    '',
+    'Body refs [^c] and [^a] and [^b] and again [^a].',
+    '',
+    ':::info',
+    'A legacy callout.',
+    ':::',
+    '',
+    '| h1 | h2 |',
+    '| --- | --- |',
+    '| 1 | 2 |',
+    '',
+    '[^a]: note A',
+    '[^b]: note B',
+    '[^c]: note C',
+    '[^z]: orphan note',
+  ].join('\n');
+
+  it('leaves no literal [^id] or ::: in the imported doc and re-exports canonically', async () => {
+    const normalized = normalizeForeignMarkdown(FOREIGN);
+    const doc = await markdownToProseMirror(normalized);
+    const reexport = convertProseMirrorToMarkdown(doc);
+
+    // No foreign garbage leaks into the document.
+    expect(reexport).not.toMatch(/\[\^/); // no reference footnote refs/defs
+    expect(reexport).not.toContain(':::'); // no legacy callout fences
+
+    // Canonical forms are present.
+    expect(reexport).toContain('^[note C]');
+    expect(reexport).toContain('> [!info]');
+    expect(reexport).toContain('| h1 | h2 |');
+
+    // Footnotes: ordered by first reference (C, A, B), reused [^a] deduped to one,
+    // orphan [^z] dropped (it had no reference after normalization).
+    const list = doc.content.find((n: any) => n.type === 'footnotesList');
+    const bodies = list.content.map(
+      (d: any) => d.content[0].content[0].text,
+    );
+    expect(bodies).toEqual(['note C', 'note A', 'note B']);
+    expect(bodies).not.toContain('orphan note');
+    expect(
+      doc.content.filter((n: any) => n.type === 'footnotesList'),
+    ).toHaveLength(1);
+  });
+});

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

@@ -0,0 +1,265 @@
+/**
+ * Foreign-markdown normalizer — an input-liberal / output-canonical adapter that
+ * runs at the IMPORT boundary, BEFORE the canonical parser
+ * (`markdownToProseMirror` from `@docmost/prosemirror-markdown`).
+ *
+ * The canonical parser is deliberately STRICT: it only understands Docmost's
+ * canonical markdown surface (Obsidian-style `> [!type]` callouts, Pandoc/Obsidian
+ * inline footnotes `^[body]`, lossless `![alt](src) <!--img {...}-->` images, …).
+ * Import, however, ingests FOREIGN files (GitHub/GFM, Notion, old Docmost
+ * exports). Those use surfaces the canonical parser does not accept, most notably
+ * GitHub-flavoured *reference* footnotes:
+ *
+ *     Text with a note[^1] and another[^long].
+ *
+ *     [^1]: The first definition.
+ *     [^long]: A second one.
+ *
+ * Left untouched, the parser does NOT recognise `[^id]` (it only parses `^[body]`),
+ * so the reference leaks as literal text — and worse, the trailing `[^id]: def`
+ * line is a valid CommonMark *link-reference definition*, so `[^id]` is silently
+ * rendered as a bogus link. This normalizer rewrites reference footnotes into the
+ * canonical inline form so the parser materialises real footnote nodes.
+ *
+ * This is a TEXT pre-pass, NOT a second parser fork: it does not re-implement any
+ * converter logic. Callout surfaces (`:::type` and `> [!type]`) are intentionally
+ * NOT touched here — the canonical parser already accepts BOTH natively (its
+ * `preprocessCallouts` pass), so normalizing them would be redundant and would
+ * only risk degrading the parser's nesting/code-fence-aware handling.
+ */
+
+/** Matches a fenced code block delimiter (``` or ~~~), capturing the marker run. */
+const CODE_FENCE_RE = /^(\s*)(`{3,}|~{3,})/;
+
+/**
+ * Matches a GFM footnote DEFINITION line: `[^id]: body`. The id is any run of
+ * non-`]` characters; the body is the remainder of the line (possibly empty).
+ */
+const FOOTNOTE_DEF_RE = /^\[\^([^\]]+)\]:[ \t]?(.*)$/;
+
+/** True when a line is a code-fence delimiter that toggles fenced-code state. */
+function fenceMarker(line: string): string | null {
+  const m = line.match(CODE_FENCE_RE);
+  return m ? m[2] : null;
+}
+
+/** True when a line is indented (leading space/tab) and not blank — a continuation. */
+function isIndentedContinuation(line: string): boolean {
+  return /^[ \t]+\S/.test(line);
+}
+
+function escapeRegExp(value: string): string {
+  return value.replace(/[.*+?^${}()|[\]\\]/g, '\\$&');
+}
+
+/**
+ * Backslash-escape any square bracket in a footnote body before it is wrapped in
+ * `^[...]`. The canonical inline-footnote tokenizer scans the body with bracket
+ * balancing and closes on the first UNMATCHED `]`, so an unbalanced bracket in a
+ * foreign definition (e.g. `[^1]: see item ] later`) would otherwise truncate the
+ * footnote and leak the tail as literal text. Escaping every `[`/`]` makes the
+ * body an inert run of characters — the tokenizer then closes only on our own
+ * closing `]`. (A balanced `[link](url)` inside a body still round-trips because
+ * the escaped form renders the literal brackets, which is the safe reading for a
+ * footnote body; the alternative — brittle balance tracking — risks worse.)
+ */
+function escapeFootnoteBody(body: string): string {
+  return body.replace(/[[\]]/g, '\\$&');
+}
+
+/**
+ * Rewrite every `[^id]` reference on a line to its `^[body]` form, but ONLY in the
+ * text OUTSIDE inline-code spans. A `[^id]` inside backticks is literal code
+ * content and must be preserved verbatim (a footnote ref never lives inside code).
+ * We split the line on inline-code spans (paired backtick runs) and rewrite only
+ * the non-code segments.
+ */
+// Above this length a single line is not split into inline-code spans (see
+// below). A genuine markdown line carrying a footnote reference is never tens of
+// KB; the cap only bypasses the inline-code protection for pathological lines.
+const INLINE_SPLIT_MAX_LINE = 8192;
+
+function rewriteRefsOutsideInlineCode(
+  line: string,
+  replace: (text: string) => string,
+): string {
+  // The inline-code split alternation `(`+)(?:(?!\1)[\s\S])*\1` backtracks
+  // quadratically on a long UNCLOSED backtick run (its middle can consume the
+  // rest of the line, then fail to find a closing run and retry from each
+  // position). On an untrusted import this is a request-thread ReDoS. A real
+  // footnote line is short, so for an oversized line we skip the inline-code
+  // protection entirely and leave the line UNTOUCHED (rewriting it wholesale
+  // could corrupt a `[^id]` that legitimately lives inside inline code). This is
+  // a conservative bypass: an over-8KB line simply does not get its reference
+  // footnotes inlined — acceptable for a pathological input.
+  if (line.length > INLINE_SPLIT_MAX_LINE) return line;
+
+  // Alternation: an inline-code span (one or more backticks, then anything up to
+  // the SAME run of backticks) OR a run of non-backtick text. Unterminated
+  // backticks fall through as ordinary text (matched by the second branch on the
+  // leftover), so a stray backtick never swallows the rest of the line.
+  const parts = line.match(/(`+)(?:(?!\1)[\s\S])*\1|[^`]+|`+/g);
+  if (!parts) return line;
+  return parts
+    .map((seg) => (seg.startsWith('`') ? seg : replace(seg)))
+    .join('');
+}
+
+/**
+ * Convert GFM reference footnotes (`[^id]` + `[^id]: def`) into canonical inline
+ * footnotes (`^[def]`).
+ *
+ * - Definitions are collected first (a leading `[^id]: text` line plus any
+ *   immediately-following indented continuation lines, joined with a space) and
+ *   removed from the output.
+ * - Each in-text reference `[^id]` for which a definition was found is replaced by
+ *   `^[def]`. References with no matching definition are left literal (there is no
+ *   body to inline; the parser fails them open the same way).
+ * - Code is respected on both passes: `[^id]` inside a fenced ``` / ~~~ block is
+ *   never rewritten and a `[^id]:` line inside a fence is never a definition; and
+ *   on the rewrite pass a `[^id]` inside an INLINE-code span (backticks) is left
+ *   literal too.
+ * - The inlined body is bracket-escaped so an unbalanced `[`/`]` in a foreign
+ *   definition cannot truncate the resulting `^[...]` footnote.
+ *
+ * Deduplication / reference-ordering / orphan-dropping of the resulting footnotes
+ * is handled downstream by the canonical parser (`assembleFootnotes`); this pass
+ * only changes the surface syntax.
+ */
+function convertReferenceFootnotes(markdown: string): string {
+  const lines = markdown.split('\n');
+
+  // Pass 1: collect definitions and mark their lines for removal.
+  const defs = new Map<string, string>();
+  const dropped = new Array<boolean>(lines.length).fill(false);
+  let inFence = false;
+  let fence = '';
+
+  for (let i = 0; i < lines.length; i++) {
+    const line = lines[i];
+    const marker = fenceMarker(line);
+    if (inFence) {
+      if (marker && marker[0] === fence[0] && marker.length >= fence.length) {
+        inFence = false;
+        fence = '';
+      }
+      continue;
+    }
+    if (marker) {
+      inFence = true;
+      fence = marker;
+      continue;
+    }
+
+    const def = line.match(FOOTNOTE_DEF_RE);
+    if (!def) continue;
+
+    const id = def[1];
+    const body: string[] = [def[2].trim()];
+    dropped[i] = true;
+
+    // Consume immediately-following indented continuation lines (GFM lazy
+    // continuation is not supported by design — keep it simple and predictable).
+    let j = i + 1;
+    while (j < lines.length && isIndentedContinuation(lines[j])) {
+      body.push(lines[j].trim());
+      dropped[j] = true;
+      j++;
+    }
+    i = j - 1;
+
+    // Last definition wins for a duplicated id (matches CommonMark link-ref
+    // semantics closely enough for a foreign-input adapter).
+    defs.set(id, body.filter((s) => s.length > 0).join(' '));
+  }
+
+  if (defs.size === 0) {
+    return markdown;
+  }
+
+  // ONE fixed, generic scanner regex — NOT one built from the definition ids.
+  // It matches ANY `[^id]` shape, and the replacer decides per match via a map
+  // lookup whether that id is a real definition (replace) or not (leave as-is).
+  // This is genuinely O(total text) with no per-document regex compilation.
+  //
+  // Do NOT rebuild this as an alternation over `[...defs.keys()]`: a giant
+  // `(id1|id2|...)` alternation over thousands of ids can blow the V8 regex
+  // compiler's stack — a fatal, UNCATCHABLE "RegExpCompiler Allocation failed"
+  // on prefix-chain ids (`a`, `aa`, `aaa`, ...) that kills the whole process
+  // (worse than the earlier per-def thread-hang). A fixed scanner has no
+  // id-dependent compilation cost and cannot blow up.
+  const refRe = /\[\^([^\]]+)\]/g;
+  const rewriteSegment = (segment: string): string =>
+    segment.replace(refRe, (whole, id: string) => {
+      const body = defs.get(id);
+      // Only real definitions are inlined; an unknown id is left literal (same as
+      // the old per-def loop, which simply never matched it).
+      return body === undefined ? whole : `^[${escapeFootnoteBody(body)}]`;
+    });
+
+  // Pass 2: rewrite in-text references, skipping fenced code and dropped lines.
+  const out: string[] = [];
+  inFence = false;
+  fence = '';
+  for (let i = 0; i < lines.length; i++) {
+    if (dropped[i]) continue;
+    let line = lines[i];
+
+    const marker = fenceMarker(line);
+    if (inFence) {
+      out.push(line);
+      if (marker && marker[0] === fence[0] && marker.length >= fence.length) {
+        inFence = false;
+        fence = '';
+      }
+      continue;
+    }
+    if (marker) {
+      inFence = true;
+      fence = marker;
+      out.push(line);
+      continue;
+    }
+
+    line = rewriteRefsOutsideInlineCode(line, rewriteSegment);
+    out.push(line);
+  }
+
+  return out.join('\n');
+}
+
+/**
+ * Strip a single leading YAML front-matter block (`---\n…\n---`). Foreign files
+ * from Obsidian / Hugo / Jekyll / Notion — and Docmost's OWN git-sync page files
+ * — open with front-matter that the canonical parser does not consume, so
+ * without this it leaks into the body (and `title: Foo` above the closing `---`
+ * renders as a setext `<h2>` that `extractTitleAndRemoveHeading` can hijack as
+ * the page title). It is a no-op for front-matter-free input.
+ *
+ * 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
+ * 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.
+ */
+const YAML_FRONT_MATTER_RE = /^\uFEFF?---\n[\s\S]*?\n---\n?/;
+
+/**
+ * Normalize a foreign markdown string into Docmost's canonical markdown surface
+ * so the strict canonical parser accepts it losslessly: normalize line endings,
+ * strip a leading YAML front-matter block, then rewrite GFM reference footnotes
+ * into inline footnotes. Add further fixture-driven foreign-surface cases here as
+ * they are found.
+ */
+export function normalizeForeignMarkdown(markdown: string): string {
+  if (!markdown) return markdown;
+  // Normalize CRLF -> LF FIRST. The line-anchored front-matter regex requires a
+  // bare `\n` after the opening `---`, and convertReferenceFootnotes splits on
+  // `\n`; a Windows/CRLF foreign file (`---\r\n…`) would otherwise slip past the
+  // front-matter strip and leak into the body. The canonical parser
+  // (page-file.ts parsePageFile) normalizes the same way before its FRONTMATTER_RE.
+  const src = markdown.replace(/\r\n/g, '\n');
+  const withoutFrontMatter = src.replace(YAML_FRONT_MATTER_RE, '').trimStart();
+  return convertReferenceFootnotes(withoutFrontMatter);
+}

apps/server/src/integrations/metrics/http-metrics.hook.ts

@@ -0,0 +1,46 @@
+import { FastifyReply, FastifyRequest } from 'fastify';
+import { isStreamingResponse } from './metrics.constants';
+import { observeHttp } from './metrics.registry';
+
+/**
+ * Resolve the BOUNDED route label for an HTTP response.
+ *
+ * HARD REQUIREMENT (#355): use the ROUTE TEMPLATE (`/pages/:id`), NEVER the raw
+ * URL (`/pages/abc-123`), so label cardinality stays finite. Fastify exposes the
+ * matched template on `req.routeOptions.url`. On 404s (no route matched) that is
+ * missing → collapse to the literal `unknown`.
+ */
+export function resolveRouteLabel(req: FastifyRequest): string {
+  const url = req.routeOptions?.url;
+  return typeof url === 'string' && url.length > 0 ? url : 'unknown';
+}
+
+/**
+ * Fastify onResponse handler that records http_request_duration_seconds.
+ * No-op when metrics are disabled (the hook is only registered when enabled,
+ * but the observe helpers are also guarded). Never throws into the response
+ * pipeline — telemetry must not break request handling.
+ */
+export function recordHttpResponse(
+  req: FastifyRequest,
+  reply: FastifyReply,
+): void {
+  try {
+    const route = resolveRouteLabel(req);
+
+    // Exclude SSE/streaming responses: onResponse fires at connection close for
+    // those, so it would record the stream lifetime and poison p95/p99.
+    const contentType = reply.getHeader('content-type');
+    if (isStreamingResponse(contentType, route)) return;
+
+    observeHttp(
+      req.method,
+      route,
+      reply.statusCode,
+      // Fastify measures elapsed time in ms; the metric is in seconds.
+      reply.elapsedTime / 1000,
+    );
+  } catch {
+    // Swallow: a telemetry failure must never affect the served response.
+  }
+}

apps/server/src/integrations/metrics/metrics-bull.service.ts

@@ -0,0 +1,146 @@
+import {
+  Injectable,
+  Logger,
+  OnModuleDestroy,
+  OnModuleInit,
+} from '@nestjs/common';
+import { InjectQueue } from '@nestjs/bullmq';
+import { Queue, QueueEvents } from 'bullmq';
+import { QueueName } from '../queue/constants';
+import { EnvironmentService } from '../environment/environment.service';
+import { parseRedisUrl } from '../../common/helpers';
+import {
+  isMetricsEnabled,
+  observeJobDuration,
+  setQueueDepth,
+} from './metrics.registry';
+
+const POLL_INTERVAL_MS = 15_000;
+// Cap the in-flight start-time map so a job that never emits completed/failed
+// (worker crash) cannot leak memory unbounded. Well above realistic concurrency.
+const MAX_INFLIGHT = 10_000;
+
+/**
+ * BullMQ instrumentation for #355:
+ *  - `bullmq_queue_depth{queue}`: polled from getJobCounts() every 15s.
+ *  - `bullmq_job_duration_seconds{queue}`: wall-clock time between a job going
+ *    `active` and `completed`/`failed`, observed via per-queue QueueEvents.
+ *
+ * Queue names are a FINITE list (the QueueName enum), so labels are bounded — no
+ * job ids ever enter a label. Everything is gated on METRICS_PORT: when metrics
+ * are off, onModuleInit does nothing (no interval, no QueueEvents connections).
+ */
+@Injectable()
+export class MetricsBullService implements OnModuleInit, OnModuleDestroy {
+  private readonly logger = new Logger(MetricsBullService.name);
+  private readonly queues: { label: string; queue: Queue }[];
+  private timer: NodeJS.Timeout | null = null;
+  private queueEvents: QueueEvents[] = [];
+  // jobId -> start timestamp (ms). Bounded by MAX_INFLIGHT.
+  private readonly inflight = new Map<string, number>();
+
+  constructor(
+    private readonly environmentService: EnvironmentService,
+    @InjectQueue(QueueName.EMAIL_QUEUE) emailQueue: Queue,
+    @InjectQueue(QueueName.ATTACHMENT_QUEUE) attachmentQueue: Queue,
+    @InjectQueue(QueueName.GENERAL_QUEUE) generalQueue: Queue,
+    @InjectQueue(QueueName.BILLING_QUEUE) billingQueue: Queue,
+    @InjectQueue(QueueName.FILE_TASK_QUEUE) fileTaskQueue: Queue,
+    @InjectQueue(QueueName.SEARCH_QUEUE) searchQueue: Queue,
+    @InjectQueue(QueueName.AI_QUEUE) aiQueue: Queue,
+    @InjectQueue(QueueName.HISTORY_QUEUE) historyQueue: Queue,
+    @InjectQueue(QueueName.NOTIFICATION_QUEUE) notificationQueue: Queue,
+    @InjectQueue(QueueName.AUDIT_QUEUE) auditQueue: Queue,
+  ) {
+    this.queues = [
+      { label: 'email', queue: emailQueue },
+      { label: 'attachment', queue: attachmentQueue },
+      { label: 'general', queue: generalQueue },
+      { label: 'billing', queue: billingQueue },
+      { label: 'file-task', queue: fileTaskQueue },
+      { label: 'search', queue: searchQueue },
+      { label: 'ai', queue: aiQueue },
+      { label: 'history', queue: historyQueue },
+      { label: 'notification', queue: notificationQueue },
+      { label: 'audit', queue: auditQueue },
+    ];
+  }
+
+  onModuleInit(): void {
+    if (!isMetricsEnabled()) return;
+
+    // Poll queue depth.
+    this.timer = setInterval(() => {
+      void this.pollDepths();
+    }, POLL_INTERVAL_MS);
+    // Do not keep the event loop alive solely for polling.
+    this.timer.unref?.();
+    void this.pollDepths();
+
+    // Wire per-queue job-duration events.
+    const redisConfig = parseRedisUrl(this.environmentService.getRedisUrl());
+    const connection = {
+      host: redisConfig.host,
+      port: redisConfig.port,
+      password: redisConfig.password,
+      db: redisConfig.db,
+      family: redisConfig.family,
+    };
+
+    for (const { label, queue } of this.queues) {
+      const events = new QueueEvents(queue.name, { connection });
+      events.on('active', ({ jobId }) => {
+        if (this.inflight.size >= MAX_INFLIGHT) {
+          // Drop the oldest tracked start to keep the map bounded.
+          const oldest = this.inflight.keys().next().value;
+          if (oldest !== undefined) this.inflight.delete(oldest);
+        }
+        this.inflight.set(jobId, Date.now());
+      });
+      const finalize = ({ jobId }: { jobId: string }) => {
+        const start = this.inflight.get(jobId);
+        if (start === undefined) return;
+        this.inflight.delete(jobId);
+        observeJobDuration(label, (Date.now() - start) / 1000);
+      };
+      events.on('completed', finalize);
+      events.on('failed', finalize);
+      events.on('error', (err) => {
+        this.logger.debug(`QueueEvents error (${label}): ${err?.message}`);
+      });
+      this.queueEvents.push(events);
+    }
+  }
+
+  private async pollDepths(): Promise<void> {
+    for (const { label, queue } of this.queues) {
+      try {
+        const counts = await queue.getJobCounts();
+        // "Depth" = jobs not yet finished (backlog + in-flight).
+        const depth =
+          (counts.waiting ?? 0) +
+          (counts.active ?? 0) +
+          (counts.delayed ?? 0) +
+          (counts.prioritized ?? 0) +
+          (counts.paused ?? 0);
+        setQueueDepth(label, depth);
+      } catch (err) {
+        this.logger.debug(
+          `Failed to read job counts for ${label}: ${(err as Error)?.message}`,
+        );
+      }
+    }
+  }
+
+  async onModuleDestroy(): Promise<void> {
+    if (this.timer) {
+      clearInterval(this.timer);
+      this.timer = null;
+    }
+    await Promise.all(
+      this.queueEvents.map((e) => e.close().catch(() => undefined)),
+    );
+    this.queueEvents = [];
+    this.inflight.clear();
+  }
+}

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

@@ -0,0 +1,16 @@
+import { Injectable, OnModuleDestroy } from '@nestjs/common';
+import { closeMetricsServer } from './metrics.server';
+
+/**
+ * Ties the bare node:http metrics scrape server (started in main.ts after the
+ * Fastify app is up, outside the DI container) into Nest's shutdown lifecycle.
+ * With `app.enableShutdownHooks()`, onModuleDestroy fires on SIGTERM/SIGINT and
+ * closes the listener so it is not left dangling (jest/e2e never exits, and a
+ * prod restart doesn't leak the port). No-op when metrics are disabled.
+ */
+@Injectable()
+export class MetricsServerLifecycle implements OnModuleDestroy {
+  async onModuleDestroy(): Promise<void> {
+    await closeMetricsServer();
+  }
+}

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

@@ -0,0 +1,84 @@
+/**
+ * Perf-metrics contract (#355). These names/labels are FIXED by the already
+ * deployed scrape+dashboard infra (VictoriaMetrics scraping docmost:9464,
+ * Grafana dashboards, alerts). Do NOT rename them.
+ */
+export const METRIC_HTTP_REQUEST_DURATION = 'http_request_duration_seconds';
+export const METRIC_DB_QUERY_DURATION = 'db_query_duration_seconds';
+export const METRIC_BULLMQ_QUEUE_DEPTH = 'bullmq_queue_depth';
+export const METRIC_BULLMQ_JOB_DURATION = 'bullmq_job_duration_seconds';
+export const METRIC_COLLAB_STORE_DURATION = 'collab_store_duration_seconds';
+
+// Histogram buckets (seconds). Chosen to give useful p50/p95/p99 resolution
+// for typical web/DB latencies without exploding series cardinality.
+export const HTTP_BUCKETS = [
+  0.005, 0.01, 0.025, 0.05, 0.1, 0.25, 0.5, 1, 2.5, 5, 10,
+];
+export const DB_BUCKETS = [
+  0.001, 0.005, 0.01, 0.025, 0.05, 0.1, 0.25, 0.5, 1, 2.5,
+];
+export const COLLAB_BUCKETS = [
+  0.005, 0.01, 0.025, 0.05, 0.1, 0.25, 0.5, 1, 2.5, 5,
+];
+export const JOB_BUCKETS = [
+  0.01, 0.05, 0.1, 0.25, 0.5, 1, 2.5, 5, 10, 30, 60, 120,
+];
+
+/**
+ * Extract the first SQL token (select/insert/update/delete/...) from a query,
+ * lower-cased, to use as a BOUNDED label for db_query_duration_seconds. Using
+ * the full query text would blow up label cardinality; the leading keyword is a
+ * finite set. Unknown/empty queries collapse to `other`.
+ */
+// The bounded set of SQL leading keywords used as db_query_duration_seconds
+// labels. Module-const so it is built ONCE, not per query (this runs on every DB
+// query when metrics are enabled).
+const KNOWN_SQL_TOKENS = new Set([
+  'select',
+  'insert',
+  'update',
+  'delete',
+  'with',
+  'begin',
+  'commit',
+  'rollback',
+  'alter',
+  'create',
+  'drop',
+  'truncate',
+  'explain',
+]);
+
+export function firstSqlToken(sql: string | undefined): string {
+  if (!sql) return 'other';
+  // Skip leading whitespace / comments and grab the first word.
+  const match = /^[\s(]*([a-zA-Z]+)/.exec(sql);
+  if (!match) return 'other';
+  const token = match[1].toLowerCase();
+  return KNOWN_SQL_TOKENS.has(token) ? token : 'other';
+}
+
+/**
+ * Whether an HTTP response must be EXCLUDED from http_request_duration_seconds.
+ *
+ * SSE/streaming responses (the AI-chat `text/event-stream`) keep the connection
+ * open for the whole conversation, so Fastify's onResponse fires only when the
+ * client disconnects — recording the connection lifetime, not a response time,
+ * which would poison p95/p99. We skip by content-type (authoritative) with a
+ * route-suffix fallback for the two known stream endpoints.
+ */
+export function isStreamingResponse(
+  contentType: unknown,
+  route: string | undefined,
+): boolean {
+  if (
+    typeof contentType === 'string' &&
+    contentType.toLowerCase().includes('text/event-stream')
+  ) {
+    return true;
+  }
+  // Fallback: the AI-chat stream routes (/api/ai-chat/stream,
+  // /api/shares/ai/stream) both end in `/stream`.
+  if (route && route.endsWith('/stream')) return true;
+  return false;
+}

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

@@ -0,0 +1,15 @@
+import { Module } from '@nestjs/common';
+import { MetricsBullService } from './metrics-bull.service';
+import { MetricsServerLifecycle } from './metrics-server.lifecycle';
+
+/**
+ * Wires the BullMQ collectors (#355). The queues are provided by the @Global
+ * QueueModule (which exports BullModule), so no re-registration is needed here.
+ * The HTTP histogram, DB-query and collab-store collectors live in module-level
+ * singletons (metrics.registry) and are wired directly at their call sites.
+ * MetricsServerLifecycle closes the scrape server on shutdown.
+ */
+@Module({
+  providers: [MetricsBullService, MetricsServerLifecycle],
+})
+export class MetricsModule {}

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

@@ -0,0 +1,126 @@
+import {
+  collectDefaultMetrics,
+  Histogram,
+  Gauge,
+  Registry,
+} from 'prom-client';
+import {
+  COLLAB_BUCKETS,
+  DB_BUCKETS,
+  HTTP_BUCKETS,
+  JOB_BUCKETS,
+  METRIC_BULLMQ_JOB_DURATION,
+  METRIC_BULLMQ_QUEUE_DEPTH,
+  METRIC_COLLAB_STORE_DURATION,
+  METRIC_DB_QUERY_DURATION,
+  METRIC_HTTP_REQUEST_DURATION,
+} from './metrics.constants';
+
+/**
+ * Process-wide perf-metrics registry (#355).
+ *
+ * This is a plain module singleton (NOT a Nest provider) because the collectors
+ * are cross-cutting: the Kysely `log` callback (built in a DI factory), the
+ * Fastify onResponse hook (main.ts, before the Nest container hands out
+ * providers) and the collab persistence extension all need the SAME instruments
+ * without threading DI through them.
+ *
+ * HARD CONTRACT: when `METRICS_PORT` is unset the whole subsystem is OFF — the
+ * registry is never created, `collectDefaultMetrics` never runs, and every
+ * observe/set helper is a cheap no-op. Nothing is exposed on :3000.
+ */
+
+// Decided once at process start. Deliberately read here (not via
+// EnvironmentService) so the toggle is identical for the DI and non-DI callers.
+const enabled = Boolean(process.env.METRICS_PORT);
+
+let registry: Registry | null = null;
+let httpHist: Histogram<'method' | 'route' | 'status'> | null = null;
+let dbHist: Histogram<'op'> | null = null;
+let queueDepthGauge: Gauge<'queue'> | null = null;
+let jobHist: Histogram<'queue'> | null = null;
+let collabHist: Histogram | null = null;
+
+function init(): void {
+  if (registry || !enabled) return;
+
+  registry = new Registry();
+
+  // Node/runtime metrics: gives nodejs_eventloop_lag_p99_seconds, GC, heap, etc.
+  collectDefaultMetrics({ register: registry });
+
+  httpHist = new Histogram({
+    name: METRIC_HTTP_REQUEST_DURATION,
+    help: 'HTTP request duration in seconds, by method, route template and status',
+    labelNames: ['method', 'route', 'status'],
+    buckets: HTTP_BUCKETS,
+    registers: [registry],
+  });
+
+  dbHist = new Histogram({
+    name: METRIC_DB_QUERY_DURATION,
+    help: 'Database query duration in seconds, by leading SQL keyword',
+    labelNames: ['op'],
+    buckets: DB_BUCKETS,
+    registers: [registry],
+  });
+
+  queueDepthGauge = new Gauge({
+    name: METRIC_BULLMQ_QUEUE_DEPTH,
+    help: 'Number of not-yet-finished BullMQ jobs per queue',
+    labelNames: ['queue'],
+    registers: [registry],
+  });
+
+  jobHist = new Histogram({
+    name: METRIC_BULLMQ_JOB_DURATION,
+    help: 'BullMQ job processing duration in seconds, per queue',
+    labelNames: ['queue'],
+    buckets: JOB_BUCKETS,
+    registers: [registry],
+  });
+
+  collabHist = new Histogram({
+    name: METRIC_COLLAB_STORE_DURATION,
+    help: 'Collaboration onStoreDocument duration in seconds',
+    buckets: COLLAB_BUCKETS,
+    registers: [registry],
+  });
+}
+
+// Runs once when this module is first imported. Safe to call again (idempotent).
+init();
+
+export function isMetricsEnabled(): boolean {
+  return enabled;
+}
+
+/** The prom-client registry, or null when metrics are disabled. */
+export function getMetricsRegistry(): Registry | null {
+  return registry;
+}
+
+export function observeHttp(
+  method: string,
+  route: string,
+  status: number,
+  seconds: number,
+): void {
+  httpHist?.observe({ method, route, status }, seconds);
+}
+
+export function observeDbQuery(op: string, seconds: number): void {
+  dbHist?.observe({ op }, seconds);
+}
+
+export function setQueueDepth(queue: string, depth: number): void {
+  queueDepthGauge?.set({ queue }, depth);
+}
+
+export function observeJobDuration(queue: string, seconds: number): void {
+  jobHist?.observe({ queue }, seconds);
+}
+
+export function observeCollabStore(seconds: number): void {
+  collabHist?.observe(seconds);
+}

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

@@ -0,0 +1,86 @@
+import { createServer, Server } from 'node:http';
+import { Logger } from '@nestjs/common';
+import { getMetricsRegistry, isMetricsEnabled } from './metrics.registry';
+
+/**
+ * Start the Prometheus scrape endpoint on a SEPARATE port, taken from
+ * `METRICS_PORT`. There is NO default port: when `METRICS_PORT` is unset the
+ * whole metrics subsystem is OFF and this returns null. This is a bare node:http
+ * server, NOT part of the Fastify app, so `/metrics` never exists on the public
+ * :3000 listener.
+ *
+ * Returns the http.Server (so callers can close it on shutdown) or null when
+ * metrics are disabled. The reference is also kept module-side so the Nest
+ * lifecycle (see MetricsModule) can close it on application shutdown without
+ * threading the handle back through the non-DI bootstrap.
+ */
+let metricsServer: Server | null = null;
+
+export function startMetricsServer(): Server | null {
+  if (!isMetricsEnabled()) return null;
+
+  const logger = new Logger('MetricsServer');
+  const register = getMetricsRegistry();
+  if (!register) return null;
+
+  const port = Number(process.env.METRICS_PORT);
+  if (!Number.isInteger(port) || port <= 0) {
+    logger.warn(
+      `Invalid METRICS_PORT="${process.env.METRICS_PORT}", metrics endpoint not started`,
+    );
+    return null;
+  }
+
+  const server = createServer(async (req, res) => {
+    if (req.method === 'GET' && req.url === '/metrics') {
+      try {
+        const body = await register.metrics();
+        res.setHeader('Content-Type', register.contentType);
+        res.statusCode = 200;
+        res.end(body);
+      } catch (err) {
+        res.statusCode = 500;
+        res.end(String((err as Error)?.message ?? 'error'));
+      }
+      return;
+    }
+    res.statusCode = 404;
+    res.end();
+  });
+
+  // Bind on all interfaces: the scraper (VictoriaMetrics) reaches this from
+  // another container as docmost:9464. The port is not published to the host.
+  server.listen(port, '0.0.0.0', () => {
+    logger.log(`Metrics endpoint listening on :${port}/metrics`);
+  });
+
+  server.on('error', (err) => {
+    logger.error(`Metrics server error: ${err?.message}`);
+  });
+
+  metricsServer = server;
+  return server;
+}
+
+/**
+ * Close the metrics scrape server if one is running. Idempotent and safe to call
+ * when metrics are disabled (no server was ever started). Wired into Nest's
+ * shutdown lifecycle so the listener is not left dangling on shutdown.
+ */
+export function closeMetricsServer(): Promise<void> {
+  const server = metricsServer;
+  metricsServer = null;
+  if (!server) return Promise.resolve();
+  return new Promise((resolve) => {
+    server.close(() => resolve());
+    // server.close() stops accepting NEW connections but its callback does not
+    // fire until existing keep-alive sockets drain. The scraper (VictoriaMetrics/
+    // vmagent) holds an idle HTTP keep-alive socket, so without this the callback
+    // — and thus shutdown — would hang until the scraper disconnects or the
+    // orchestrator escalates to SIGKILL on the kill-grace window. Force-close idle
+    // keep-alive sockets so close() completes immediately, and unref so this
+    // server never keeps the event loop alive on its own.
+    server.closeIdleConnections();
+    server.unref();
+  });
+}

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

@@ -0,0 +1,70 @@
+import { FastifyRequest } from 'fastify';
+import { resolveRouteLabel } from './http-metrics.hook';
+import { firstSqlToken, isStreamingResponse } from './metrics.constants';
+
+describe('resolveRouteLabel (histogram route label)', () => {
+  it('uses the ROUTE TEMPLATE, never the raw URL', () => {
+    // routeOptions.url is the matched template; url is the raw path with the id.
+    const req = {
+      url: '/api/pages/abc-123-def',
+      routeOptions: { url: '/api/pages/:id' },
+    } as unknown as FastifyRequest;
+    expect(resolveRouteLabel(req)).toBe('/api/pages/:id');
+    expect(resolveRouteLabel(req)).not.toContain('abc-123-def');
+  });
+
+  it('falls back to "unknown" on a 404 (no matched route template)', () => {
+    const req = {
+      url: '/totally/unmatched/path',
+      routeOptions: {},
+    } as unknown as FastifyRequest;
+    expect(resolveRouteLabel(req)).toBe('unknown');
+  });
+
+  it('falls back to "unknown" when routeOptions is missing', () => {
+    const req = { url: '/x' } as unknown as FastifyRequest;
+    expect(resolveRouteLabel(req)).toBe('unknown');
+  });
+});
+
+describe('isStreamingResponse (SSE exclusion)', () => {
+  it('excludes text/event-stream responses by content-type', () => {
+    expect(isStreamingResponse('text/event-stream', '/api/ai-chat/stream')).toBe(
+      true,
+    );
+    expect(isStreamingResponse('text/event-stream; charset=utf-8', '/x')).toBe(
+      true,
+    );
+  });
+
+  it('excludes known /stream routes by suffix as a fallback', () => {
+    expect(isStreamingResponse('application/json', '/api/ai-chat/stream')).toBe(
+      true,
+    );
+    expect(isStreamingResponse(undefined, '/api/shares/ai/stream')).toBe(true);
+  });
+
+  it('does not exclude ordinary JSON responses', () => {
+    expect(isStreamingResponse('application/json', '/api/pages/:id')).toBe(
+      false,
+    );
+    expect(isStreamingResponse(undefined, '/api/pages/:id')).toBe(false);
+  });
+});
+
+describe('firstSqlToken (bounded db label)', () => {
+  it('returns the lower-cased leading keyword', () => {
+    expect(firstSqlToken('SELECT * FROM pages')).toBe('select');
+    expect(firstSqlToken('  insert into x values (1)')).toBe('insert');
+    expect(firstSqlToken('UPDATE pages SET a=1')).toBe('update');
+    expect(firstSqlToken('delete from pages')).toBe('delete');
+    expect(firstSqlToken('(SELECT 1)')).toBe('select');
+  });
+
+  it('collapses unknown/empty queries to "other"', () => {
+    expect(firstSqlToken('')).toBe('other');
+    expect(firstSqlToken(undefined)).toBe('other');
+    expect(firstSqlToken('123 not sql')).toBe('other');
+    expect(firstSqlToken('vacuum analyze')).toBe('other');
+  });
+});

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

@@ -1,35 +0,0 @@
-import { resolveStaticAssetHeaders } from './static.module';
-
-// Unit tests for the static-asset cache classifier extracted from the
-// @fastify/static setHeaders callback (precedent: sandbox.controller.spec.ts).
-describe('resolveStaticAssetHeaders', () => {
-  it('marks a content-hashed /assets/ file immutable and sets Vary', () => {
-    const headers = resolveStaticAssetHeaders(
-      '/app/apps/client/dist/assets/index-a1b2c3.js',
-    );
-    expect(headers['cache-control']).toBe(
-      'public, max-age=31536000, immutable',
-    );
-    expect(headers['vary']).toBe('Accept-Encoding');
-  });
-
-  it('makes index.html always revalidate (never immutable)', () => {
-    const headers = resolveStaticAssetHeaders(
-      '/app/apps/client/dist/index.html',
-    );
-    expect(headers['cache-control']).toBe(
-      'no-cache, no-store, must-revalidate',
-    );
-    expect(headers['vary']).toBe('Accept-Encoding');
-  });
-
-  it('does NOT mark a non-hashed asset immutable but still sets Vary', () => {
-    const headers = resolveStaticAssetHeaders(
-      '/app/apps/client/dist/locales/en.json',
-    );
-    // No immutable cache-control — this path keeps @fastify/static's default
-    // etag/last-modified revalidation.
-    expect(headers['cache-control']).toBeUndefined();
-    expect(headers['vary']).toBe('Accept-Encoding');
-  });
-});

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

@@ -5,46 +5,6 @@ import * as fs from 'node:fs';
 import fastifyStatic from '@fastify/static';
 import { EnvironmentService } from '../environment/environment.service';
 
-/**
- * Resolve the response headers for a statically served client asset.
- *
- * Extracted from the @fastify/static `setHeaders` callback so the cache
- * classification stays a pure, unit-testable function (see
- * static.module.spec.ts).
- *
- * `Vary: Accept-Encoding` is emitted for every static response because
- * @fastify/static negotiates a precompressed .br/.gz neighbour by the client's
- * Accept-Encoding but does NOT set Vary itself. Without it a shared/proxy cache
- * keyed on the URL alone could store the brotli variant and later serve it to a
- * client that only sent `Accept-Encoding: identity`/gzip → an undecodable body.
- * This matters most for the immutable /assets/ files, which proxies may keep
- * for a year.
- */
-export function resolveStaticAssetHeaders(
-  filePath: string,
-): Record<string, string> {
-  const headers: Record<string, string> = { vary: 'Accept-Encoding' };
-
-  // Content-hashed files under /assets/ never change for a given URL, so they
-  // can be cached forever and skip revalidation entirely.
-  if (filePath.includes('/assets/')) {
-    headers['cache-control'] = 'public, max-age=31536000, immutable';
-    return headers;
-  }
-
-  // index.html is rewritten at boot (window.CONFIG injection) and on every
-  // deploy — it must be revalidated on every load.
-  if (filePath.endsWith('index.html')) {
-    headers['cache-control'] = 'no-cache, no-store, must-revalidate';
-    return headers;
-  }
-
-  // Everything else (locales, vad, icons, manifest) is NOT content-hashed and
-  // changes between deploys, so it keeps @fastify/static's default
-  // etag/last-modified revalidation — do NOT mark it immutable.
-  return headers;
-}
-
 @Module({})
 export class StaticModule implements OnModuleInit {
   constructor(
@@ -90,6 +50,10 @@ export class StaticModule implements OnModuleInit {
           : undefined,
         POSTHOG_HOST: this.environmentService.getPostHogHost(),
         POSTHOG_KEY: this.environmentService.getPostHogKey(),
+        // #355 — mirrors the server-side CLIENT_TELEMETRY_ENABLED gate so the
+        // client only collects/sends vitals when the operator opts in.
+        CLIENT_TELEMETRY_ENABLED:
+          this.environmentService.isClientTelemetryEnabled(),
       };
 
       const windowScriptContent = `<script>window.CONFIG=${JSON.stringify(configString)};</script>`;
@@ -108,16 +72,6 @@ export class StaticModule implements OnModuleInit {
       await app.register(fastifyStatic, {
         root: clientDistPath,
         wildcard: false,
-        // Serve the build-time .br/.gz neighbour when the client accepts it
-        // (see vite-plugin-compression2 in apps/client/vite.config.ts).
-        preCompressed: true,
-        setHeaders: (res, filePath) => {
-          for (const [name, value] of Object.entries(
-            resolveStaticAssetHeaders(filePath),
-          )) {
-            res.setHeader(name, value);
-          }
-        },
       });
 
       app.get(RENDER_PATH, (req: any, res: any) => {

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

@@ -9,6 +9,7 @@ import {
   AI_CHAT_THROTTLER,
   PAGE_TEMPLATE_THROTTLER,
   PUBLIC_SHARE_AI_THROTTLER,
+  VITALS_THROTTLER,
 } from './throttler-names';
 
 @Module({
@@ -29,6 +30,8 @@ import {
             { name: PAGE_TEMPLATE_THROTTLER, ttl: 60_000, limit: 30 },
             // Anonymous public-share assistant: ~5 req/min per IP.
             { name: PUBLIC_SHARE_AI_THROTTLER, ttl: 60_000, limit: 5 },
+            // Anonymous client perf-telemetry sink: 120 batched posts/min per IP.
+            { name: VITALS_THROTTLER, ttl: 60_000, limit: 120 },
           ],
           errorMessage: 'Too many requests',
           // Pass ioredis options (not a pre-built Redis instance) so

apps/server/src/integrations/throttle/throttler-names.ts

@@ -6,3 +6,7 @@ export const PAGE_TEMPLATE_THROTTLER = 'page-template';
 // ThrottlerGuard tracker) to bound anonymous abuse — the workspace owner pays
 // for the tokens.
 export const PUBLIC_SHARE_AI_THROTTLER = 'public-share-ai';
+// IP-keyed throttler for the anonymous client perf-telemetry sink
+// (POST /api/telemetry/vitals). Browsers batch metrics, so the limit is
+// generous; it only exists to bound abuse of the public, unauthenticated route.
+export const VITALS_THROTTLER = 'vitals';

apps/server/src/main.ts

@@ -10,13 +10,15 @@ import { TransformHttpResponseInterceptor } from './common/interceptors/http-res
 import { WsRedisIoAdapter } from './ws/adapter/ws-redis.adapter';
 import fastifyMultipart from '@fastify/multipart';
 import fastifyCookie from '@fastify/cookie';
-import fastifyCompress from '@fastify/compress';
 import fastifyIp from 'fastify-ip';
 import { InternalLogFilter } from './common/logger/internal-log-filter';
 import { EnvironmentService } from './integrations/environment/environment.service';
 import { SANDBOX_API_PATH } from './integrations/sandbox/sandbox.constants';
 import { resolveFrameHeader } from './common/helpers';
 import { resolveTrustProxy } from './integrations/environment/trust-proxy.util';
+import { isMetricsEnabled } from './integrations/metrics/metrics.registry';
+import { recordHttpResponse } from './integrations/metrics/http-metrics.hook';
+import { startMetricsServer } from './integrations/metrics/metrics.server';
 
 async function bootstrap() {
   const app = await NestFactory.create<NestFastifyApplication>(
@@ -61,17 +63,6 @@ async function bootstrap() {
   await app.register(fastifyIp);
   await app.register(fastifyMultipart);
   await app.register(fastifyCookie);
-  // Compress dynamic responses (API JSON, the rewritten share-SEO HTML) when the
-  // client accepts br/gzip. @fastify/compress only compresses content-types that
-  // mime-db flags `compressible` (application/json, text/html, …); `text/event-stream`
-  // is not in mime-db, so SSE is never compressed by the allowlist. The AI-chat
-  // stream additionally hijacks the raw socket (pipeUIMessageStreamToResponse ->
-  // res.raw in ai-chat.service.ts), bypassing Fastify's reply/onSend lifecycle
-  // entirely, so this hook can never buffer that stream.
-  await app.register(fastifyCompress, {
-    // Skip tiny payloads where compression overhead outweighs the savings.
-    threshold: 1024,
-  });
 
   const environmentService = app.get(EnvironmentService);
   const frameHeader = resolveFrameHeader(
@@ -103,6 +94,19 @@ async function bootstrap() {
       done();
     });
 
+  // #355 — HTTP request-duration histogram. Registered ONLY when METRICS_PORT is
+  // set (otherwise no collector runs at all). Uses the bounded route template
+  // label and excludes SSE/streaming responses (see recordHttpResponse).
+  if (isMetricsEnabled()) {
+    app
+      .getHttpAdapter()
+      .getInstance()
+      .addHook('onResponse', (req, reply, done) => {
+        recordHttpResponse(req, reply);
+        done();
+      });
+  }
+
   app
     .getHttpAdapter()
     .getInstance()
@@ -139,6 +143,9 @@ async function bootstrap() {
         '/api/workspace/create',
         '/api/workspace/joined',
         '/api/workspace/find-by-email',
+        // Public client perf-telemetry sink: browsers post it without a
+        // resolved workspace host, so the workspace-resolution gate must not 404 it.
+        '/api/telemetry/vitals',
         // Anonymous in-RAM blob sandbox: a remote consumer fetches blobs by an
         // unguessable UUID without any workspace host context, so the
         // workspace-resolution gate must not apply.
@@ -187,6 +194,11 @@ async function bootstrap() {
       `Listening on http://127.0.0.1:${port} / ${process.env.APP_URL}`,
     );
   });
+
+  // #355 — Prometheus scrape endpoint on a SEPARATE port (METRICS_PORT),
+  // started after the app is up. No default port: a no-op when METRICS_PORT is
+  // unset. Closed on shutdown by MetricsServerLifecycle (MetricsModule).
+  startMetricsServer();
 }
 
 bootstrap();

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

@@ -0,0 +1,304 @@
+import { Kysely } from 'kysely';
+import {
+  AiChatRunRepo,
+  SWEEP_RUN_STALE_MS,
+} from '@docmost/db/repos/ai-chat/ai-chat-run.repo';
+import { AiChatMessageRepo } from '@docmost/db/repos/ai-chat/ai-chat-message.repo';
+import { AiChatRunService } from '../../src/core/ai-chat/ai-chat-run.service';
+import {
+  getTestDb,
+  destroyTestDb,
+  createWorkspace,
+  createUser,
+  createChat,
+} from './db';
+
+/**
+ * Integration coverage for the #184 phase-1 durable agent run: real SQL against
+ * docmost_test. Proves the core invariant primitives — a run is a first-class
+ * lifecycle row, at most one is active per chat, a detached run's progress
+ * survives with NO subscriber, an explicit stop settles it as aborted, a
+ * reconnect read returns the persisted state, and a crash sweep recovers
+ * dangling runs.
+ */
+describe('AiChatRun durable lifecycle [integration]', () => {
+  let db: Kysely<any>;
+  let runRepo: AiChatRunRepo;
+  let messageRepo: AiChatMessageRepo;
+  let service: AiChatRunService;
+  let workspaceId: string;
+  let otherWorkspaceId: string;
+  let userId: string;
+  let chatId: string;
+
+  beforeAll(async () => {
+    db = getTestDb();
+    runRepo = new AiChatRunRepo(db as any);
+    messageRepo = new AiChatMessageRepo(db as any);
+    // Boot-sweep isn't triggered here; the isCloud stub is all the service needs
+    // for these direct-call integration cases (F7).
+    service = new AiChatRunService(runRepo, { isCloud: () => false } as never);
+    workspaceId = (await createWorkspace(db)).id;
+    otherWorkspaceId = (await createWorkspace(db)).id;
+    userId = (await createUser(db, workspaceId)).id;
+    chatId = (await createChat(db, { workspaceId, creatorId: userId })).id;
+  });
+
+  afterAll(async () => {
+    await destroyTestDb();
+  });
+
+  // Each test that creates an active run settles it (or uses its own chat) so the
+  // partial unique index does not bleed across tests.
+
+  it('insert + findById round-trips a run row, defaulting status/trigger', async () => {
+    const run = await runRepo.insert({
+      chatId,
+      workspaceId,
+      createdBy: userId,
+    });
+    expect(run.status).toBe('pending');
+    expect(run.trigger).toBe('user');
+    expect(run.stepCount).toBe(0);
+
+    const found = await runRepo.findById(run.id, workspaceId);
+    expect(found!.id).toBe(run.id);
+    // Workspace-scoped: a foreign workspace sees nothing.
+    expect(await runRepo.findById(run.id, otherWorkspaceId)).toBeUndefined();
+
+    // settle so it does not occupy the active slot
+    await runRepo.update(run.id, workspaceId, {
+      status: 'succeeded',
+      finishedAt: new Date(),
+    });
+  });
+
+  it('enforces ONE ACTIVE run per chat (partial unique index rejects a second)', async () => {
+    const activeChat = (
+      await createChat(db, { workspaceId, creatorId: userId })
+    ).id;
+    const first = await runRepo.insert({
+      chatId: activeChat,
+      workspaceId,
+      createdBy: userId,
+      status: 'running',
+    });
+    // A second pending/running run on the SAME chat must be rejected by the DB.
+    await expect(
+      runRepo.insert({
+        chatId: activeChat,
+        workspaceId,
+        createdBy: userId,
+        status: 'running',
+      }),
+    ).rejects.toThrow();
+
+    // findActiveByChat returns exactly the one active run.
+    const active = await runRepo.findActiveByChat(activeChat, workspaceId);
+    expect(active!.id).toBe(first.id);
+
+    // Once it settles, the slot frees and a new run may start.
+    await runRepo.update(first.id, workspaceId, {
+      status: 'succeeded',
+      finishedAt: new Date(),
+    });
+    expect(
+      await runRepo.findActiveByChat(activeChat, workspaceId),
+    ).toBeUndefined();
+    const second = await runRepo.insert({
+      chatId: activeChat,
+      workspaceId,
+      createdBy: userId,
+      status: 'running',
+    });
+    expect(second.id).not.toBe(first.id);
+    await runRepo.update(second.id, workspaceId, {
+      status: 'aborted',
+      finishedAt: new Date(),
+    });
+  });
+
+  it('DETACHED run: persists + finalizes succeeded with NO subscriber, reconnect returns state', async () => {
+    // A dedicated chat so the active-run slot is clean.
+    const runChat = (
+      await createChat(db, { workspaceId, creatorId: userId })
+    ).id;
+
+    // beginRun = the runner starts the turn (registers an in-memory controller).
+    const handle = await service.beginRun({
+      chatId: runChat,
+      workspaceId,
+      userId,
+    });
+    expect(handle.signal.aborted).toBe(false);
+    expect(service.isLocallyActive(handle.runId)).toBe(true);
+
+    // The assistant projection row (#183) is seeded + linked.
+    const seeded = await messageRepo.insert({
+      chatId: runChat,
+      workspaceId,
+      userId,
+      role: 'assistant',
+      content: '',
+      status: 'streaming',
+      metadata: { parts: [] } as never,
+    });
+    await service.linkAssistantMessage(handle.runId, workspaceId, seeded.id);
+
+    // Progress is persisted as steps finish — NO HTTP socket involved here at all.
+    await service.recordStep(handle.runId, workspaceId, 1);
+    await messageRepo.update(seeded.id, workspaceId, {
+      content: 'partial work',
+      metadata: { parts: [{ type: 'text', text: 'partial work' }] },
+    });
+
+    // The turn completes; finalize the projection then the run.
+    await messageRepo.update(seeded.id, workspaceId, {
+      content: 'final answer',
+      status: 'completed',
+    });
+    await service.finalizeRun(handle.runId, workspaceId, 'completed');
+
+    expect(service.isLocallyActive(handle.runId)).toBe(false);
+
+    // Reconnect: the latest run for the chat + its projected message, from the DB.
+    const run = await service.getLatestForChat(runChat, workspaceId);
+    expect(run!.status).toBe('succeeded');
+    expect(run!.stepCount).toBe(1);
+    expect(run!.assistantMessageId).toBe(seeded.id);
+    expect(run!.finishedAt).toBeTruthy();
+    const message = await messageRepo.findById(seeded.id, workspaceId);
+    expect(message!.status).toBe('completed');
+    expect(message!.content).toBe('final answer');
+  });
+
+  it('EXPLICIT stop aborts the run signal, marks the row, and settles as aborted', async () => {
+    const runChat = (
+      await createChat(db, { workspaceId, creatorId: userId })
+    ).id;
+    const handle = await service.beginRun({
+      chatId: runChat,
+      workspaceId,
+      userId,
+    });
+
+    // User presses Stop.
+    const stopped = await service.requestStop(handle.runId, workspaceId);
+    expect(stopped).toBe(true);
+    expect(handle.signal.aborted).toBe(true);
+
+    // The row carries the stop request (distinct from a disconnect, which would
+    // leave stop_requested_at NULL).
+    const afterStop = await runRepo.findById(handle.runId, workspaceId);
+    expect(afterStop!.stopRequestedAt).toBeTruthy();
+
+    // The terminal callback (onAbort) settles the run.
+    await service.finalizeRun(handle.runId, workspaceId, 'aborted');
+    const run = await service.getLatestForChat(runChat, workspaceId);
+    expect(run!.status).toBe('aborted');
+  });
+
+  it('markStopRequested is a no-op on an already-settled run (returns undefined)', async () => {
+    const runChat = (
+      await createChat(db, { workspaceId, creatorId: userId })
+    ).id;
+    const run = await runRepo.insert({
+      chatId: runChat,
+      workspaceId,
+      createdBy: userId,
+      status: 'running',
+    });
+    await runRepo.update(run.id, workspaceId, {
+      status: 'succeeded',
+      finishedAt: new Date(),
+    });
+    const marked = await runRepo.markStopRequested(run.id, workspaceId);
+    expect(marked).toBeUndefined();
+  });
+
+  it('sweepRunning aborts STALE dangling runs but not fresh or settled ones', async () => {
+    const sweepChat1 = (
+      await createChat(db, { workspaceId, creatorId: userId })
+    ).id;
+    const sweepChat2 = (
+      await createChat(db, { workspaceId, creatorId: userId })
+    ).id;
+    const sweepChat3 = (
+      await createChat(db, { workspaceId, creatorId: userId })
+    ).id;
+
+    const stale = await runRepo.insert({
+      chatId: sweepChat1,
+      workspaceId,
+      createdBy: userId,
+      status: 'running',
+    });
+    const fresh = await runRepo.insert({
+      chatId: sweepChat2,
+      workspaceId,
+      createdBy: userId,
+      status: 'running',
+    });
+    const settled = await runRepo.insert({
+      chatId: sweepChat3,
+      workspaceId,
+      createdBy: userId,
+      status: 'running',
+    });
+    await runRepo.update(settled.id, workspaceId, {
+      status: 'succeeded',
+      finishedAt: new Date(),
+    });
+    // Backdate the stale run's updatedAt past the 10-minute staleness window.
+    await db
+      .updateTable('aiChatRuns')
+      .set({ updatedAt: new Date(Date.now() - 20 * 60 * 1000) })
+      .where('id', '=', stale.id)
+      .execute();
+
+    // WINDOWED sweep (phase-2 multi-instance timer path): only runs older than the
+    // staleness window are aborted, so a sibling replica's fresh run survives. The
+    // no-arg boot sweep (variant C) is unconditional — covered separately below.
+    const swept = await runRepo.sweepRunning({ staleMs: SWEEP_RUN_STALE_MS });
+    expect(swept).toBeGreaterThanOrEqual(1);
+
+    expect((await runRepo.findById(stale.id, workspaceId))!.status).toBe(
+      'aborted',
+    );
+    // Fresh (recently-updated) running run survives the WINDOWED sweep — a sibling
+    // replica may still be executing it.
+    expect((await runRepo.findById(fresh.id, workspaceId))!.status).toBe(
+      'running',
+    );
+    expect((await runRepo.findById(settled.id, workspaceId))!.status).toBe(
+      'succeeded',
+    );
+
+    // cleanup active fresh run
+    await runRepo.update(fresh.id, workspaceId, {
+      status: 'aborted',
+      finishedAt: new Date(),
+    });
+  });
+
+  it('sweepRunning() with NO args (boot sweep / variant C) aborts even a FRESH running run', async () => {
+    // F1/DECISION C at the SQL level: the unconditional boot sweep has NO
+    // staleness window, so a run updated just now (a fast restart) is settled too
+    // — otherwise it would stay 'running' forever and 409 every future turn.
+    const bootChat = (
+      await createChat(db, { workspaceId, creatorId: userId })
+    ).id;
+    const fresh = await runRepo.insert({
+      chatId: bootChat,
+      workspaceId,
+      createdBy: userId,
+      status: 'running',
+    });
+    // updatedAt = now (fresh, untouched). The no-arg sweep settles it anyway.
+    const swept = await runRepo.sweepRunning();
+    expect(swept).toBeGreaterThanOrEqual(1);
+    expect((await runRepo.findById(fresh.id, workspaceId))!.status).toBe(
+      'aborted',
+    );
+  });
+});

apps/server/test/stubs/tiptap-react.js

@@ -0,0 +1,23 @@
+// Jest stub for @tiptap/react.
+//
+// The server export/import code paths transitively import editor-ext, whose node
+// extensions import from `@tiptap/react`. The real module re-exports all of
+// `@tiptap/core` (headless, safe under node) AND adds React view helpers
+// (`ReactNodeViewRenderer`, …) that eagerly pull in react-dom — which throws
+// `navigator is not defined` under jest's node environment.
+//
+// So this stub DELEGATES to the real `@tiptap/core` (keeping `mergeAttributes`,
+// `Node`, `Mark`, `nodeInputRule`, … working — they are used by
+// `jsonToHtml`/`htmlToJson` on the server) and overrides ONLY the React view
+// helpers with no-ops. Those helpers are referenced solely inside `addNodeView()`
+// — code that runs only in a live browser editor, never on the server; if any
+// were actually invoked here it would (correctly) surface as a test failure.
+const core = require('@tiptap/core');
+
+module.exports = {
+  ...core,
+  ReactNodeViewRenderer: () => () => ({}),
+  NodeViewWrapper: () => null,
+  NodeViewContent: () => null,
+  ReactRenderer: class {},
+};

docker-compose.yml

@@ -12,11 +12,6 @@ services:
     ports:
       - "3000:3000"
     restart: unless-stopped
-    # The app already serves precompressed (brotli/gzip) static assets with
-    # long-lived cache headers and gzips dynamic API responses. For the best
-    # cold-load latency you can OPTIONALLY put a reverse proxy (caddy / nginx /
-    # traefik) in front with HTTP/2 (or HTTP/3) and brotli enabled — none is
-    # required for compression to work.
     volumes:
       - docmost:/app/data/storage
 

packages/mcp/test-e2e.mjs

@@ -450,7 +450,7 @@ async function main() {
     // 8. get_page markdown round-trip sanity (table separator present)
     const md = await client.getPage(pageId);
     check("get_page md: table separator emitted", md.data.content.includes("| --- |"), "");
-    check("get_page md: callout exported as :::", md.data.content.includes(":::info"));
+    check("get_page md: callout exported as Obsidian '> [!info]'", md.data.content.includes("> [!info]"));
 
     // 9. comments: create / list / reply / update / check_new / delete
     const beforeComments = new Date(Date.now() - 1000).toISOString();

packages/prosemirror-markdown/src/lib/docmost-schema.ts

@@ -635,13 +635,17 @@ const Attachment = Node.create({
       },
       name: {
         default: null,
-        parseHTML: (el: HTMLElement) => el.getAttribute("data-attachment-name"),
+        // Empty-string-vs-absent idempotency (GS-EDIT-REVERT class): "" -> default.
+        parseHTML: (el: HTMLElement) =>
+          el.getAttribute("data-attachment-name") || null,
         renderHTML: (attrs: Record<string, any>) =>
           attrs.name ? { "data-attachment-name": attrs.name } : {},
       },
       mime: {
         default: null,
-        parseHTML: (el: HTMLElement) => el.getAttribute("data-attachment-mime"),
+        // Empty-string-vs-absent idempotency (GS-EDIT-REVERT class): "" -> default.
+        parseHTML: (el: HTMLElement) =>
+          el.getAttribute("data-attachment-mime") || null,
         renderHTML: (attrs: Record<string, any>) =>
           attrs.mime ? { "data-attachment-mime": attrs.mime } : {},
       },
@@ -689,7 +693,10 @@ const Video = Node.create({
       },
       alt: {
         default: null,
-        parseHTML: (el: HTMLElement) => el.getAttribute("aria-label"),
+        // Empty-string-vs-absent idempotency: coerce "" back to the default so a
+        // stray empty `aria-label` never materializes `alt: ""` on a video stored
+        // with no alt (same GS-EDIT-REVERT class as the image `alt` fix).
+        parseHTML: (el: HTMLElement) => el.getAttribute("aria-label") || null,
         renderHTML: (attrs: Record<string, any>) =>
           attrs.alt ? { "aria-label": attrs.alt } : {},
       },
@@ -864,13 +871,15 @@ const diagramAttributes = () => ({
   },
   title: {
     default: null,
-    parseHTML: (el: HTMLElement) => el.getAttribute("data-title"),
+    // Empty-string-vs-absent idempotency (GS-EDIT-REVERT class): "" -> default.
+    parseHTML: (el: HTMLElement) => el.getAttribute("data-title") || null,
     renderHTML: (attrs: Record<string, any>) =>
       attrs.title ? { "data-title": attrs.title } : {},
   },
   alt: {
     default: null,
-    parseHTML: (el: HTMLElement) => el.getAttribute("data-alt"),
+    // Empty-string-vs-absent idempotency (GS-EDIT-REVERT class): "" -> default.
+    parseHTML: (el: HTMLElement) => el.getAttribute("data-alt") || null,
     renderHTML: (attrs: Record<string, any>) =>
       attrs.alt ? { "data-alt": attrs.alt } : {},
   },
@@ -1106,7 +1115,8 @@ const Pdf = Node.create({
       },
       name: {
         default: null,
-        parseHTML: (el: HTMLElement) => el.getAttribute("data-name"),
+        // Empty-string-vs-absent idempotency (GS-EDIT-REVERT class): "" -> default.
+        parseHTML: (el: HTMLElement) => el.getAttribute("data-name") || null,
         renderHTML: (attrs: Record<string, any>) =>
           attrs.name ? { "data-name": attrs.name } : {},
       },
@@ -1491,6 +1501,29 @@ export const docmostExtensions = [
           ...parent.height,
           parseHTML: (el: HTMLElement) => el.getAttribute("height"),
         },
+        // Empty-string-vs-absent idempotency (GS-EDIT-REVERT class). `marked`
+        // renders `![](src)` as `<img alt="">`, so the stock Image `alt`
+        // parseHTML (`getAttribute("alt")`) materializes `alt: ""` on an image
+        // that was stored with NO alt (attr absent). That is a false diff against
+        // the editor-stored form (a no-alt image has alt ABSENT, not ""), so a
+        // git-sync / ai-chat touch of a page with a plain image produced phantom
+        // churn. Coerce an empty string back to the attr's default (null) so the
+        // import is idempotent. A real alt survives verbatim (`|| undefined` keeps
+        // the truthy value; the default fills the empty case). `title` is coerced
+        // the same way for the whole class, even though `marked` does not
+        // currently emit `title=""` — defence in depth against any path that does.
+        // NOTE: this DIVERGES from editor-ext's literal image `alt` parseHTML
+        // (`getAttribute("alt")`, which returns "" verbatim), but CONVERGES on
+        // editor-ext's real STORED shape: an editor image inserted without alt
+        // renders with no `alt` attribute and re-parses as absent, never "".
+        alt: {
+          ...parent.alt,
+          parseHTML: (el: HTMLElement) => el.getAttribute("alt") || null,
+        },
+        title: {
+          ...parent.title,
+          parseHTML: (el: HTMLElement) => el.getAttribute("title") || null,
+        },
       };
     },
   }).configure({ inline: false }),

packages/prosemirror-markdown/test/roundtrip-stability.helper.ts

@@ -0,0 +1,443 @@
+/**
+ * Reusable round-trip-STABILITY matrix helper (fixtures-first).
+ *
+ * A single stored node authored WITHOUT a given string attribute (attr
+ * absent / undefined) must not gain a phantom EMPTY-STRING value after a
+ * markdown round-trip — the "empty-string-vs-absent" churn class. This helper,
+ * given a node spec, drives a matrix of attribute combinations through the REAL
+ * converter (`convertProseMirrorToMarkdown` -> `markdownToProseMirror`) and
+ * asserts byte-stability on two contours:
+ *
+ *   1. RAW round-trip: for the node under test, every attribute the round-trip
+ *      materializes must equal what the INPUT authored — an authored attr keeps
+ *      its value, an ABSENT attr may only reappear at its SCHEMA DEFAULT. If an
+ *      absent attr comes back as a NON-default value (e.g. `alt: ""` where the
+ *      default is `null`), that is an instability and is reported precisely as
+ *      `type.attr: absent -> "<got>"`. This is the contour git-sync / stored
+ *      JSON diffs on, so masking it only in `canonicalize` would leave the noise.
+ *
+ *   2. CANONICAL round-trip: `canonicalizeContent(original)` must deep-equal
+ *      `canonicalizeContent(roundtrip)` (a second, semantic contour).
+ *
+ * The ONLY normalization the helper treats as allowed (not an instability) is
+ * the DOCUMENTED numeric width/height/size/aspectRatio -> string coercion the
+ * converter performs on purpose (a stored numeric `640` re-parses via
+ * `getAttribute` as the string `"640"`). It is encoded here as an explicit
+ * per-spec `numericStringAttrs` set applied to BOTH contours, NOT a silent skip.
+ *
+ * The helper is node-type agnostic: image and the whole media family share the
+ * `align !== "center"` predicate + `<!--name {…}-->` comment machinery, so one
+ * matrix guards the shared class.
+ */
+import { getSchema } from "@tiptap/core";
+import {
+  convertProseMirrorToMarkdown,
+  markdownToProseMirror,
+  canonicalizeContent,
+  docmostExtensions,
+} from "../src/lib/index.js";
+import { firstDivergence } from "./roundtrip-helpers.js";
+
+/** One attribute's two probe values. */
+export interface AttrMatrixEntry {
+  /** Attribute name on the node. */
+  attr: string;
+  /**
+   * The "default" pick. `undefined` means the attribute is OMITTED entirely
+   * (the absent case — the one that can materialize an empty string on import).
+   * A concrete value is authored verbatim.
+   */
+  default: unknown;
+  /** A representative NON-default value to exercise (must survive verbatim). */
+  nonDefault: unknown;
+  /**
+   * Marks the attr as a member of the EMPTY-STRING class the fix targets: a
+   * string attr whose schema default is `null`/absent and whose parseHTML
+   * coerces `"" -> default` (image/drawio `alt`+`title`, video `alt` via
+   * aria-label, pdf/attachment `name`, attachment `mime`). Set true to also
+   * drive the THIRD-STATE convergence case (see runConvergenceCase) for this
+   * attr. Attrs whose default is NOT null (e.g. embed `provider`, default "")
+   * or that are not `""`-coerced (control attrs) are left unset.
+   */
+  emptyStringClass?: boolean;
+}
+
+/** A node type + the attribute matrix to sweep for it. */
+export interface NodeStabilitySpec {
+  /** Node type (e.g. "image", "video"). */
+  type: string;
+  /** Attributes always present on the node (e.g. `{ src: "/i.png" }`). */
+  baseAttrs?: Record<string, unknown>;
+  /** Attributes to sweep at default and non-default. */
+  attrMatrix: AttrMatrixEntry[];
+  /**
+   * Attributes whose numeric -> string coercion on round-trip is DOCUMENTED and
+   * intentional; compared modulo `String(x)` on both sides. Defaults to the
+   * converter's known sizing set.
+   */
+  numericStringAttrs?: string[];
+}
+
+/** A single unstable finding, legible enough to tie a gate-lock to. */
+export interface Instability {
+  type: string;
+  attr: string;
+  /** What the input authored: the literal value, or the ABSENT sentinel. */
+  authored: unknown | typeof ABSENT;
+  /** What the round-trip produced. */
+  got: unknown;
+  /** What a stable round-trip should have produced (authored value or default). */
+  expected: unknown;
+}
+
+/** One matrix cell's result. */
+export interface ComboResult {
+  label: string;
+  authored: Record<string, unknown>;
+  /** RAW-contour instabilities on the node under test. */
+  raw: Instability[];
+  /** CANONICAL-contour divergence (path + values) or null when equal. */
+  canonical: { path: string; a: unknown; b: unknown } | null;
+  /** True when the node type failed to round-trip at all (structural loss). */
+  missing: boolean;
+  md: string;
+}
+
+/** Whole-matrix report for one node spec. */
+export interface MatrixReport {
+  type: string;
+  combos: ComboResult[];
+}
+
+/** Sentinel marking an attribute the input did NOT author. */
+export const ABSENT = Symbol("ABSENT");
+
+const DEFAULT_NUMERIC_STRING_ATTRS = [
+  "width",
+  "height",
+  "size",
+  "aspectRatio",
+];
+
+// The ProseMirror schema the converter targets — its attribute `default`s are
+// the authoritative "what an absent attr should re-materialize as" oracle.
+const schema = getSchema(docmostExtensions);
+
+/** Read the schema default for every attribute of a node type. */
+function schemaDefaults(type: string): Record<string, unknown> {
+  const specAttrs = (schema.nodes[type]?.spec?.attrs ?? {}) as Record<
+    string,
+    { default: unknown }
+  >;
+  const out: Record<string, unknown> = {};
+  for (const [k, v] of Object.entries(specAttrs)) out[k] = v.default;
+  return out;
+}
+
+/** Find the first node of a given type anywhere in a PM doc tree. */
+function findFirst(node: any, type: string): any {
+  if (node && node.type === type) return node;
+  for (const child of node?.content ?? []) {
+    const hit = findFirst(child, type);
+    if (hit) return hit;
+  }
+  return null;
+}
+
+/** Coerce a scalar for the documented numeric->string comparison. */
+const numStr = (x: unknown): unknown => (x == null ? x : String(x));
+
+/**
+ * Enumerate the cartesian product of the matrix: every attribute independently
+ * at its default (index 0) or non-default (index 1) pick. The all-default
+ * corner is included (the baseline). Small by construction (2^N over a handful
+ * of at-risk string attrs).
+ */
+function enumerateCombos(matrix: AttrMatrixEntry[]): number[][] {
+  let combos: number[][] = [[]];
+  for (let i = 0; i < matrix.length; i++) {
+    const next: number[][] = [];
+    for (const c of combos) {
+      next.push([...c, 0]);
+      next.push([...c, 1]);
+    }
+    combos = next;
+  }
+  return combos;
+}
+
+/** Build the authored attrs for one combo pick vector. */
+function authoredAttrs(
+  spec: NodeStabilitySpec,
+  picks: number[],
+): Record<string, unknown> {
+  const attrs: Record<string, unknown> = { ...(spec.baseAttrs ?? {}) };
+  spec.attrMatrix.forEach((entry, i) => {
+    if (picks[i] === 1) {
+      attrs[entry.attr] = entry.nonDefault;
+    } else if (entry.default !== undefined) {
+      attrs[entry.attr] = entry.default;
+    }
+    // default === undefined -> OMIT the attr entirely (the absent case).
+  });
+  return attrs;
+}
+
+/** Human-readable label for a combo (which attrs are at non-default). */
+function comboLabel(spec: NodeStabilitySpec, picks: number[]): string {
+  const on = spec.attrMatrix
+    .filter((_, i) => picks[i] === 1)
+    .map((e) => e.attr);
+  return on.length === 0 ? "<all-default>" : on.join("+");
+}
+
+/**
+ * Run the full stability matrix for one node spec and return a structured
+ * report (does NOT throw — the caller asserts, so a failure can print the whole
+ * report). Every combo runs the real export->import pipeline once.
+ */
+export async function runStabilityMatrix(
+  spec: NodeStabilitySpec,
+): Promise<MatrixReport> {
+  const numericStringAttrs = new Set(
+    spec.numericStringAttrs ?? DEFAULT_NUMERIC_STRING_ATTRS,
+  );
+  const defaults = schemaDefaults(spec.type);
+  const combos: ComboResult[] = [];
+
+  for (const picks of enumerateCombos(spec.attrMatrix)) {
+    const authored = authoredAttrs(spec, picks);
+    const doc = { type: "doc", content: [{ type: spec.type, attrs: authored }] };
+    const md = convertProseMirrorToMarkdown(doc);
+    const rt = await markdownToProseMirror(md);
+    const node = findFirst(rt, spec.type);
+
+    const result: ComboResult = {
+      label: comboLabel(spec, picks),
+      authored,
+      raw: [],
+      canonical: null,
+      missing: node == null,
+      md,
+    };
+
+    if (node != null) {
+      // RAW contour: every materialized attr must equal the authored value, or
+      // (for an absent attr) the schema default — modulo the documented numeric
+      // string coercion.
+      const rtAttrs = (node.attrs ?? {}) as Record<string, unknown>;
+      for (const key of Object.keys(rtAttrs)) {
+        const authoredHas = Object.prototype.hasOwnProperty.call(authored, key);
+        const expected = authoredHas ? authored[key] : defaults[key];
+        let got = rtAttrs[key];
+        let exp = expected;
+        if (numericStringAttrs.has(key)) {
+          got = numStr(got);
+          exp = numStr(exp);
+        }
+        if (firstDivergence(got, exp) !== null) {
+          result.raw.push({
+            type: spec.type,
+            attr: key,
+            authored: authoredHas ? authored[key] : ABSENT,
+            got: rtAttrs[key],
+            expected,
+          });
+        }
+      }
+
+      // CANONICAL contour: canonical forms deep-equal, modulo the same numeric
+      // string coercion (applied to both trees so a documented coercion is not
+      // counted as a divergence).
+      const ca = normalizeNumeric(canonicalizeContent(doc), numericStringAttrs);
+      const cb = normalizeNumeric(canonicalizeContent(rt), numericStringAttrs);
+      result.canonical = firstDivergence(ca, cb);
+    }
+
+    combos.push(result);
+  }
+
+  return { type: spec.type, combos };
+}
+
+/**
+ * Deep-copy a canonical tree, coercing the documented numeric->string attrs to
+ * their string form so an intentional `640 -> "640"` coercion is not reported
+ * as a canonical divergence. Only touches the listed attribute keys.
+ */
+function normalizeNumeric(node: any, attrs: Set<string>): any {
+  if (Array.isArray(node)) return node.map((n) => normalizeNumeric(n, attrs));
+  if (node === null || typeof node !== "object") return node;
+  const out: Record<string, unknown> = {};
+  for (const key of Object.keys(node)) {
+    if (key === "attrs" && node.attrs && typeof node.attrs === "object") {
+      const a: Record<string, unknown> = {};
+      for (const [k, v] of Object.entries(node.attrs)) {
+        a[k] = attrs.has(k) ? numStr(v) : v;
+      }
+      out.attrs = a;
+    } else {
+      out[key] = normalizeNumeric(node[key], attrs);
+    }
+  }
+  return out;
+}
+
+/** Flatten a report to just its unstable combos (for a terse assertion). */
+export function unstableCombos(report: MatrixReport): ComboResult[] {
+  return report.combos.filter(
+    (c) => c.missing || c.raw.length > 0 || c.canonical !== null,
+  );
+}
+
+// ---------------------------------------------------------------------------
+// THIRD STATE: an EXPLICITLY-STORED empty string on a string attr.
+//
+// The matrix above sweeps TWO states per string attr: absent/default and a
+// non-default value — and asserts FIRST-pass byte-stability for both. There is
+// a third, degenerate state the matrix does NOT cover: the attr stored as a
+// LITERAL `""`. This is DISTINCT from "the node never had the attr": a user
+// types an alt in the editor, then deletes it, and Tiptap's
+// `updateAttributes({ alt: "" })` persists a literal `alt: ""` in the stored
+// JSON. There is no absent-vs-"" distinction in the DOM once serialized, so the
+// fix's `getAttribute("alt") || null` coercion canonicalizes BOTH to the
+// default (`null`).
+//
+// Consequence — and this is CORRECT, not a bug: a doc carrying an explicit `""`
+// converges to the default on the FIRST round-trip (a ONE-TIME diff: `"" ->
+// null`), then is byte-stable from the SECOND round-trip on (idempotent). So
+// this state must be pinned with a DIFFERENT contract than the matrix's:
+//   - do NOT assert first-pass byte-stability (the first pass legitimately
+//     changes `""` -> default), and
+//   - DO assert the first pass converges to the default AND the second pass is
+//     idempotent (rt2 deep-equals rt1).
+//
+// A future sync/QA pass diffing stored pages will see this one-time `"" -> null`
+// normalization exactly once per affected node; it is the converter canon, not
+// corruption, and must not be flagged as data loss.
+// ---------------------------------------------------------------------------
+
+/** Result of the third-state ("explicit empty string") convergence probe. */
+export interface ConvergenceResult {
+  type: string;
+  attr: string;
+  /** The schema default the attr must converge to on pass 1 (null / absent). */
+  expectedDefault: unknown;
+  /** rt1's materialized value for the attr — must equal `expectedDefault`. */
+  firstPassValue: unknown;
+  /** True when the node round-tripped AND rt1 converged the attr to default. */
+  convergedToDefault: boolean;
+  /** rt1-vs-rt2 divergence; MUST be null (idempotent from pass 2 on). */
+  secondPassDivergence: { path: string; a: unknown; b: unknown } | null;
+  /** True when the node type failed to round-trip at all (structural loss). */
+  missing: boolean;
+}
+
+/** Round-trip a full PM doc through the real converter once. */
+async function roundtripDoc(doc: any): Promise<any> {
+  return markdownToProseMirror(convertProseMirrorToMarkdown(doc));
+}
+
+/**
+ * Third-state convergence probe for one string attr of the empty-string class.
+ *
+ * (a) builds a doc with the attr EXPLICITLY set to `""` (baseAttrs + `""`),
+ * (b) rt1 = roundtrip(doc); asserts rt1's attr equals the schema default — the
+ *     documented ONE-TIME `"" -> default` normalization (NOT byte-stable vs the
+ *     `""` input, so first-pass stability is deliberately NOT asserted here),
+ * (c) rt2 = roundtrip(rt1); asserts rt2 deep-equals rt1 — idempotent from the
+ *     second round-trip on.
+ *
+ * Returns a structured result (does NOT throw) so the caller can assert and
+ * print. Reusable across the whole node family: drive it for every attr flagged
+ * `emptyStringClass` on every spec (see convergenceCasesFor / the test driver).
+ */
+export async function runConvergenceCase(
+  spec: NodeStabilitySpec,
+  attr: string,
+): Promise<ConvergenceResult> {
+  const expectedDefault = schemaDefaults(spec.type)[attr];
+
+  // (a) The degenerate third state: attr persisted as a LITERAL "".
+  const authored = { ...(spec.baseAttrs ?? {}), [attr]: "" };
+  const doc = { type: "doc", content: [{ type: spec.type, attrs: authored }] };
+
+  // (b) First round-trip: "" must normalize to the default (a one-time diff).
+  const rt1 = await roundtripDoc(doc);
+  const node1 = findFirst(rt1, spec.type);
+  const firstPassValue = node1?.attrs?.[attr];
+  const convergedToDefault =
+    node1 != null && firstDivergence(firstPassValue, expectedDefault) === null;
+
+  // (c) Second round-trip: must be byte-stable (rt2 deep-equals rt1). We compare
+  // the WHOLE docs — both are converter OUTPUTS already in the same materialized
+  // form (numeric attrs are strings on both sides), so no numeric normalization
+  // is needed here, unlike the raw/canonical contours above.
+  const rt2 = node1 != null ? await roundtripDoc(rt1) : rt1;
+  const secondPassDivergence =
+    node1 != null ? firstDivergence(rt1, rt2) : null;
+
+  return {
+    type: spec.type,
+    attr,
+    expectedDefault,
+    firstPassValue,
+    convergedToDefault,
+    secondPassDivergence,
+    missing: node1 == null,
+  };
+}
+
+/** The attrs of a spec flagged as members of the empty-string class. */
+export function convergenceCasesFor(spec: NodeStabilitySpec): string[] {
+  return spec.attrMatrix
+    .filter((e) => e.emptyStringClass)
+    .map((e) => e.attr);
+}
+
+/** True when a convergence result honours the "converges once, then stable" contract. */
+export function convergenceOk(r: ConvergenceResult): boolean {
+  return !r.missing && r.convergedToDefault && r.secondPassDivergence === null;
+}
+
+/** Render a convergence result as a legible one-liner for a failed assertion. */
+export function formatConvergence(r: ConvergenceResult): string {
+  if (r.missing) return `${r.type}.${r.attr}: DID-NOT-ROUND-TRIP`;
+  const parts: string[] = [];
+  if (!r.convergedToDefault) {
+    parts.push(
+      `pass1 did NOT converge: got ${JSON.stringify(r.firstPassValue)} (expected default ${JSON.stringify(r.expectedDefault)})`,
+    );
+  }
+  if (r.secondPassDivergence) {
+    parts.push(
+      `pass2 NOT idempotent @ ${r.secondPassDivergence.path}: ${JSON.stringify(r.secondPassDivergence.a)} vs ${JSON.stringify(r.secondPassDivergence.b)}`,
+    );
+  }
+  const status = parts.length === 0 ? "converges-once-then-stable" : parts.join("; ");
+  return `${r.type}.${r.attr}: ${status}`;
+}
+
+/** Render a report as a legible multi-line string for a failed assertion. */
+export function formatReport(report: MatrixReport): string {
+  const lines: string[] = [`node "${report.type}":`];
+  for (const c of report.combos) {
+    const flags: string[] = [];
+    if (c.missing) flags.push("DID-NOT-ROUND-TRIP");
+    for (const i of c.raw) {
+      const authored =
+        i.authored === ABSENT ? "absent" : JSON.stringify(i.authored);
+      flags.push(
+        `RAW ${i.type}.${i.attr}: ${authored} -> ${JSON.stringify(i.got)} (expected ${JSON.stringify(i.expected)})`,
+      );
+    }
+    if (c.canonical) {
+      flags.push(
+        `CANON @ ${c.canonical.path}: ${JSON.stringify(c.canonical.a)} vs ${JSON.stringify(c.canonical.b)}`,
+      );
+    }
+    const status = flags.length === 0 ? "stable" : flags.join("; ");
+    lines.push(`  [${c.label}] ${status}`);
+  }
+  return lines.join("\n");
+}

packages/prosemirror-markdown/test/roundtrip-stability.test.ts

@@ -0,0 +1,164 @@
+import { describe, expect, it } from "vitest";
+import {
+  runStabilityMatrix,
+  unstableCombos,
+  formatReport,
+  runConvergenceCase,
+  convergenceCasesFor,
+  convergenceOk,
+  formatConvergence,
+  type NodeStabilitySpec,
+} from "./roundtrip-stability.helper.js";
+
+// ---------------------------------------------------------------------------
+// Round-trip STABILITY matrix for image + the media family.
+//
+// Guards the "empty-string-vs-absent" churn class (GS-EDIT-REVERT family): a
+// stored node authored WITHOUT a string attr (alt/title/caption/aria-label/...)
+// must not gain a phantom `attr: ""` after `markdownToProseMirror(convert…)`.
+// Each spec sweeps the at-risk string attrs at DEFAULT (absent) and at a real
+// NON-default value; the helper asserts both the RAW round-trip (attrs equal the
+// input's, modulo the documented numeric width/height/size/aspectRatio -> string
+// coercion) and the CANONICAL round-trip (canonical forms deep-equal).
+//
+// The image + media family share the `align !== "center"` predicate and the
+// `<!--name {…}-->` comment machinery, so one matrix guards the shared class.
+// align is NOT part of this class (it round-trips correctly) and is not swept.
+// ---------------------------------------------------------------------------
+
+const SPECS: NodeStabilitySpec[] = [
+  {
+    // Image carries the most at-risk string attrs. `alt` is the one marked
+    // materializes as `<img alt="">` on `![](src)` import (the real bug); title
+    // and caption are covered as the same class. attachmentId is a string attr
+    // that must stay absent when unset (control).
+    type: "image",
+    baseAttrs: { src: "/i.png" },
+    attrMatrix: [
+      { attr: "alt", default: undefined, nonDefault: "a real alt text", emptyStringClass: true },
+      { attr: "title", default: undefined, nonDefault: "a real title", emptyStringClass: true },
+      { attr: "caption", default: undefined, nonDefault: "a real caption" },
+      { attr: "attachmentId", default: undefined, nonDefault: "att-42" },
+    ],
+  },
+  {
+    // Video's `alt` rides the `aria-label` attribute (media aria-label at risk).
+    type: "video",
+    baseAttrs: { src: "/v.mp4" },
+    attrMatrix: [
+      { attr: "alt", default: undefined, nonDefault: "a clip", emptyStringClass: true },
+      { attr: "attachmentId", default: undefined, nonDefault: "att-1" },
+    ],
+  },
+  {
+    // Audio carries no alt/title; attachmentId is its only optional string attr.
+    type: "audio",
+    baseAttrs: { src: "/a.mp3" },
+    attrMatrix: [
+      { attr: "attachmentId", default: undefined, nonDefault: "att-2" },
+    ],
+  },
+  {
+    // pdf: link-form media. `name` (filename) is its at-risk string attr.
+    type: "pdf",
+    baseAttrs: { src: "/d.pdf" },
+    attrMatrix: [
+      { attr: "name", default: undefined, nonDefault: "report.pdf", emptyStringClass: true },
+      { attr: "attachmentId", default: undefined, nonDefault: "att-3" },
+    ],
+  },
+  {
+    // attachment: link-form media (file card). `name` + `mime` string attrs.
+    type: "attachment",
+    baseAttrs: { url: "/f.zip" },
+    attrMatrix: [
+      { attr: "name", default: undefined, nonDefault: "bundle.zip", emptyStringClass: true },
+      { attr: "mime", default: undefined, nonDefault: "application/zip", emptyStringClass: true },
+      { attr: "attachmentId", default: undefined, nonDefault: "att-4" },
+    ],
+  },
+  {
+    // embed: link-form media. `provider` is its at-risk string attr (schema
+    // default ""). embed's numeric width/height defaults (800/600) are a SEPARATE,
+    // documented limitation OUTSIDE the empty-string class: they are not in
+    // canonicalize's KNOWN_DEFAULTS, so an ABSENT width/height re-imports as the
+    // 800/600 default and diverges canonically (see the note in canonicalize.ts).
+    // That is canonicalize-owned and out of scope here, so we author the
+    // dimensions at their defaults (as real editor embeds carry them) to keep this
+    // guard focused on the empty-string/provider class.
+    // provider's schema default is "" (NOT null), so a re-imported "" is the
+    // correct value, not a phantom — it is outside the null-default empty-string
+    // class. We author it at its "" default (the default pick) so the sweep still
+    // asserts a non-default provider ("youtube") round-trips, without tripping the
+    // canonicalize KNOWN_DEFAULTS gap for embed's non-null defaults.
+    type: "embed",
+    baseAttrs: { src: "https://example.com/x", width: 800, height: 600 },
+    attrMatrix: [
+      { attr: "provider", default: "", nonDefault: "youtube" },
+    ],
+  },
+  {
+    // drawio: image-form diagram. `title` + `alt` string attrs (data-title/-alt).
+    type: "drawio",
+    baseAttrs: { src: "blob:drawio" },
+    attrMatrix: [
+      { attr: "title", default: undefined, nonDefault: "flow chart", emptyStringClass: true },
+      { attr: "alt", default: undefined, nonDefault: "an alt", emptyStringClass: true },
+      { attr: "attachmentId", default: undefined, nonDefault: "att-5" },
+    ],
+  },
+  {
+    // excalidraw: image-form diagram, same shared diagramAttributes set.
+    type: "excalidraw",
+    baseAttrs: { src: "blob:excalidraw" },
+    attrMatrix: [
+      { attr: "title", default: undefined, nonDefault: "sketch", emptyStringClass: true },
+      { attr: "alt", default: undefined, nonDefault: "an alt", emptyStringClass: true },
+      { attr: "attachmentId", default: undefined, nonDefault: "att-6" },
+    ],
+  },
+];
+
+describe("round-trip stability matrix (image + media family)", () => {
+  for (const spec of SPECS) {
+    it(`${spec.type}: no attr materializes an empty-string / phantom value`, async () => {
+      const report = await runStabilityMatrix(spec);
+      const unstable = unstableCombos(report);
+      // On failure, print the WHOLE matrix so which (attr, value) combos are
+      // unstable is legible.
+      expect(unstable, `\n${formatReport(report)}\n`).toEqual([]);
+    });
+  }
+});
+
+// ---------------------------------------------------------------------------
+// THIRD STATE: an attr EXPLICITLY stored as a literal "" (GS-EDIT-REVERT: a user
+// typed alt/title/name/... then deleted it, so Tiptap persisted `attr: ""` — a
+// value DISTINCT from "attr was never set"). Unlike the absent case above, this
+// state is NOT first-pass byte-stable: the fix's `"" -> default` coercion is a
+// deliberate ONE-TIME normalization on the FIRST sync round-trip, stable
+// thereafter. We therefore assert a DIFFERENT contract — "converges to default
+// on pass 1, then idempotent from pass 2 on" — for every empty-string-class attr
+// across the whole node family (image/video/pdf/attachment/drawio/excalidraw).
+//
+// IMPORTANT for a future sync/QA pass: the pass-1 `"" -> null` diff is the
+// converter canon, not corruption. It appears at most once per affected node and
+// must NOT be flagged as "the converter is losing/corrupting page data".
+// ---------------------------------------------------------------------------
+describe("round-trip third state: explicit empty string converges once, then idempotent", () => {
+  for (const spec of SPECS) {
+    for (const attr of convergenceCasesFor(spec)) {
+      it(`${spec.type}.${attr}: "" normalizes to default on pass 1, byte-stable from pass 2`, async () => {
+        const r = await runConvergenceCase(spec, attr);
+        // Pass 1 must converge "" -> the schema default (the one-time diff) and
+        // pass 2 (roundtrip of pass-1 output) must be byte-stable. formatConvergence
+        // prints exactly which half failed.
+        expect(convergenceOk(r), `\n${formatConvergence(r)}\n`).toBe(true);
+        // Spell the contract out explicitly so the intent is legible in the test:
+        expect(r.convergedToDefault, `\n${formatConvergence(r)}\n`).toBe(true);
+        expect(r.firstPassValue).toEqual(r.expectedDefault);
+        expect(r.secondPassDivergence, `\n${formatConvergence(r)}\n`).toBeNull();
+      });
+    }
+  }
+});

pnpm-lock.yaml

@@ -416,6 +416,9 @@ importers:
       socket.io-client:
         specifier: 4.8.3
         version: 4.8.3
+      web-vitals:
+        specifier: ^5.1.0
+        version: 5.1.0
       zod:
         specifier: 4.3.6
         version: 4.3.6
@@ -501,9 +504,6 @@ importers:
       vite:
         specifier: 8.0.5
         version: 8.0.5(@types/node@22.19.1)(esbuild@0.28.0)(jiti@2.4.2)(less@4.2.0)(sugarss@5.0.1(postcss@8.5.14))(terser@5.39.0)(tsx@4.21.0)(yaml@2.8.3)
-      vite-plugin-compression2:
-        specifier: 2.5.3
-        version: 2.5.3
       vitest:
         specifier: 4.1.6
         version: 4.1.6(@opentelemetry/api@1.9.0)(@types/node@22.19.1)(@vitest/coverage-v8@4.1.6)(happy-dom@20.8.9)(jsdom@25.0.0)(vite@8.0.5(@types/node@22.19.1)(esbuild@0.28.0)(jiti@2.4.2)(less@4.2.0)(sugarss@5.0.1(postcss@8.5.14))(terser@5.39.0)(tsx@4.21.0)(yaml@2.8.3))
@@ -543,9 +543,9 @@ importers:
       '@docmost/pdf-inspector':
         specifier: 1.9.6
         version: 1.9.6
-      '@fastify/compress':
-        specifier: ^9.0.0
-        version: 9.0.0
+      '@docmost/prosemirror-markdown':
+        specifier: workspace:*
+        version: link:../../packages/prosemirror-markdown
       '@fastify/cookie':
         specifier: ^11.0.2
         version: 11.0.2
@@ -750,6 +750,9 @@ importers:
       postmark:
         specifier: ^4.0.7
         version: 4.0.7
+      prom-client:
+        specifier: ^15.1.3
+        version: 15.1.3
       react:
         specifier: ^18.3.1
         version: 18.3.1
@@ -2700,9 +2703,6 @@ packages:
   '@fastify/busboy@3.1.1':
     resolution: {integrity: sha512-5DGmA8FTdB2XbDeEwc/5ZXBl6UbBAyBOOLlPuBnZ/N1SwdH9Ii+cOX3tBROlDgcTXxjOYnLMVoKk9+FXAw0CJw==}
 
-  '@fastify/compress@9.0.0':
-    resolution: {integrity: sha512-PZRg+ut5xd/ubsGPWfoPNryoCOtEdHboIWpDieTUHov1gKdLitF8mRmT3JbqNnRbelQXSNXUsIpakAEKR6AcTQ==}
-
   '@fastify/cookie@11.0.2':
     resolution: {integrity: sha512-GWdwdGlgJxyvNv+QcKiGNevSspMQXncjMZ1J8IvuDQk0jvkzgWWZFNC2En3s+nHndZBGV8IbLwOI/sxCZw/mzA==}
 
@@ -4496,15 +4496,6 @@ packages:
   '@rolldown/pluginutils@1.0.0-rc.7':
     resolution: {integrity: sha512-qujRfC8sFVInYSPPMLQByRh7zhwkGFS4+tyMQ83srV1qrxL4g8E2tyxVVyxd0+8QeBM1mIk9KbWxkegRr76XzA==}
 
-  '@rollup/pluginutils@5.4.0':
-    resolution: {integrity: sha512-MfPp06CjRLfXQ3wY0R8vJDYBy/MvVcc9OulEfR0B8Iv9ko+GCNaRZ+EpJYFl27LhKsZK0o420sYCRHCjfCgeUg==}
-    engines: {node: '>=14.0.0'}
-    peerDependencies:
-      rollup: ^1.20.0||^2.0.0||^3.0.0||^4.0.0
-    peerDependenciesMeta:
-      rollup:
-        optional: true
-
   '@selderee/plugin-htmlparser2@0.11.0':
     resolution: {integrity: sha512-P33hHGdldxGabLFjPPpaTxVolMrzrcegejx+0GxjrIb9Zv48D8yAIA/QTDR2dFl7Uz7urX8aX6+5bCZslr+gWQ==}
 
@@ -5694,10 +5685,6 @@ packages:
     resolution: {integrity: sha512-/XrFJgzQQQHpti1raDJC6m4ws6aNktmjBlhk8Fdlk7LwCEuDoieEJJY9OFHjfiFJFFRM2tK+Ky/IsfbbmlMu1w==}
     engines: {node: ^22.22.2 || ^24.15.0 || >=26.0.0}
 
-  abort-controller@3.0.0:
-    resolution: {integrity: sha512-h8lQ8tacZYnR3vNQTgibj+tODHI5/+l06Au2Pcriv/Gmet0eaj4TwWH41sO9wnHDiQsEj19q0drzdWdeAHtweg==}
-    engines: {node: '>=6.5'}
-
   abstract-logging@2.0.1:
     resolution: {integrity: sha512-2BjRTZxTPvheOvGbBslFSYOUkr+SjPtOnrLP33f+VIWLzezQpZcqVg7ja3L4dBXmzzgwT+a029jRx5PCi3JuiA==}
 
@@ -6010,6 +5997,9 @@ packages:
   bind-event-listener@3.0.0:
     resolution: {integrity: sha512-PJvH288AWQhKs2v9zyfYdPzlPqf5bXbGMmhmUIY9x4dAUGIWgomO771oBQNwJnMQSnUIXhKu6sgzpBRXTlvb8Q==}
 
+  bintrees@1.0.2:
+    resolution: {integrity: sha512-VOMgTMwjAaUG580SXn3LacVgjurrbMme7ZZNYGSSV7mmtY6QQRh0Eg3pwIcntQ77DErK1L0NxkbetjcoXzVwKw==}
+
   bl@4.1.0:
     resolution: {integrity: sha512-1W07cM9gS6DcLperZfFSj+bWLtaPGSOHWhPiGzXmvVJbRLdG82sH/Kn8EtW1VqWVA54AKf2h5k5BbnIbwF3h6w==}
 
@@ -6077,9 +6067,6 @@ packages:
   buffer@5.7.1:
     resolution: {integrity: sha512-EHcyIPBQ4BSGlvjB16k5KgAJ27CIsHY/2JBmCRReo48y9rQ3MaUzWX3KVlBa4U7MyX02HdVj0K7C3WaB3ju7FQ==}
 
-  buffer@6.0.3:
-    resolution: {integrity: sha512-FTiCpNxtwiZZHEZbcbTIcZjERVICn9yq/pDFkTl95/AxzD1naBctN7YO68riM/gLSDY7sdrMby8hofADYuuqOA==}
-
   bullmq@5.76.10:
     resolution: {integrity: sha512-LWve7SpQjYSpCP2GEsWmoyzTz2H37L8HRmSTu3YihYsTOr5kJxrfEX6aEV7m6eskEMWXSHZYTMZepX6qNaH6CQ==}
     engines: {node: '>=12.22.0'}
@@ -6835,9 +6822,6 @@ packages:
     resolution: {integrity: sha512-KIN/nDJBQRcXw0MLVhZE9iQHmG68qAVIBg9CqmUYjmQIhgij9U5MFvrqkUL5FbtyyzZuOeOt0zdeRe4UY7ct+A==}
     engines: {node: '>= 0.4'}
 
-  duplexify@3.7.1:
-    resolution: {integrity: sha512-07z8uv2wMyS51kKhD1KsdXJg5WQ6t93RneqRxUHnskXVtlYYkLqM0gqStQZ3pj073g687jPCHrqNfCzawLYh5g==}
-
   ecdsa-sig-formatter@1.0.11:
     resolution: {integrity: sha512-nagl3RYrbNv6kQkeJIpt6NJZy8twLB/2vtz6yN9Z4vRKHN4/QZJIEbqohALSgwKdnksuY3k5Addp5lg8sVoVcQ==}
 
@@ -7081,9 +7065,6 @@ packages:
     resolution: {integrity: sha512-MMdARuVEQziNTeJD8DgMqmhwR11BRQ/cBP+pLtYdSTnf3MIO8fFeiINEbX36ZdNlfU/7A9f3gUw49B3oQsvwBA==}
     engines: {node: '>=4.0'}
 
-  estree-walker@2.0.2:
-    resolution: {integrity: sha512-Rfkk/Mp/DL7JVje3u18FxFujQlTNR2q6QfMSMB7AvCBx91NGj/ba3kCfza0f6dVDbw7YlRf/nDrn7pQrCCyQ/w==}
-
   estree-walker@3.0.3:
     resolution: {integrity: sha512-7RUKfXgSMMkzt6ZuXmqapOurLGPPfgj6l9uRZ7lRGolvk0y2yocc35LdcxKC5PQZdn2DMqioAQ2NoWcrTKmm6g==}
 
@@ -7095,10 +7076,6 @@ packages:
     resolution: {integrity: sha512-aIL5Fx7mawVa300al2BnEE4iNvo1qETxLrPI/o05L7z6go7fCw1J6EQmbK4FmJ2AS7kgVF/KEZWufBfdClMcPg==}
     engines: {node: '>= 0.6'}
 
-  event-target-shim@5.0.1:
-    resolution: {integrity: sha512-i/2XbnSz/uxRCU6+NdVJgKWDTM427+MqYbkQzD321DuCQJUqOuJKIA0IM2+W2xtYHdKOmZ4dR6fExsd4SXL+WQ==}
-    engines: {node: '>=6'}
-
   eventemitter2@6.4.9:
     resolution: {integrity: sha512-JEPTiaOt9f04oa6NOkc4aH+nVp5I3wEjpHbIPqfgCdD5v5bUzy7xQqwcVO2aDQgOWhI28da57HksMrzK9HlRxg==}
 
@@ -9108,9 +9085,6 @@ packages:
   peberminta@0.9.0:
     resolution: {integrity: sha512-XIxfHpEuSJbITd1H3EeQwpcZbTLHc+VVr8ANI9t5sit565tsI4/xK3KWTUFE2e6QiangUkh3B0jihzmGnNrRsQ==}
 
-  peek-stream@1.1.3:
-    resolution: {integrity: sha512-FhJ+YbOSBb9/rIl2ZeE/QHEsWn7PqNYt8ARAY3kIgNGOk13g9FGyIY6JIl/xB/3TFRVoTv5as0l11weORrTekA==}
-
   pend@1.2.0:
     resolution: {integrity: sha512-F3asv42UuXchdzt+xXqfW1OGlVBe+mxa2mqI0pg5yAHZPvFmY3Y6drSf/GQ1A86WgWEN9Kzh/WrgKa6iGcHXLg==}
 
@@ -9356,9 +9330,9 @@ packages:
   process-warning@5.0.0:
     resolution: {integrity: sha512-a39t9ApHNx2L4+HBnQKqxxHNs1r7KF+Intd8Q/g1bUh6q0WIp9voPXJ/x0j+ZL45KF1pJd9+q2jLIRMfvEshkA==}
 
-  process@0.11.10:
-    resolution: {integrity: sha512-cdGef/drWFoydD1JsMzuFf8100nZl+GT+yacc2bEced5f9Rjk4z+WtFUTBu9PhOi9j/jfmBPu0mMEY4wIdAF8A==}
-    engines: {node: '>= 0.6.0'}
+  prom-client@15.1.3:
+    resolution: {integrity: sha512-6ZiOBfCywsD4k1BN9IX0uZhF+tJkV8q8llP64G5Hajs4JOeVLPCwpPVcpXy3BwYiUGgyJzsJJQeOIv7+hDSq8g==}
+    engines: {node: ^16 || ^18 || >=20}
 
   prompts@2.4.2:
     resolution: {integrity: sha512-NxNv/kLguCA7p3jE8oL2aEBsrJWgAakBpgmgK6lpPWV+WuOmY6r2/zbAVnP+T8bQlA0nzHXSJSJW0Hq7ylaD2Q==}
@@ -9651,10 +9625,6 @@ packages:
     resolution: {integrity: sha512-9u/sniCrY3D5WdsERHzHE4G2YCXqoG5FTHUiCC4SIbr6XcLZBY05ya9EKjYek9O5xOAwjGq+1JdGBAS7Q9ScoA==}
     engines: {node: '>= 6'}
 
-  readable-stream@4.7.0:
-    resolution: {integrity: sha512-oIGGmcpTLwPga8Bn6/Z75SVaH1z5dUut2ibSyAMVhmUggWpmDn2dapB0n7f8nwaSiRtepAsfJyfXIO5DCVAODg==}
-    engines: {node: ^12.22.0 || ^14.17.0 || >=16.0.0}
-
   readdirp@3.6.0:
     resolution: {integrity: sha512-hOS089on8RduqdbhvQ5Z37A0ESjsqz6qnRcffsMU3495FuTdqSm+7bhJ29JvIOsBDEEnan5DPu9t3To9VRlMzA==}
     engines: {node: '>=8.10.0'}
@@ -10043,9 +10013,6 @@ packages:
   stream-browserify@3.0.0:
     resolution: {integrity: sha512-H73RAHsVBapbim0tU2JwwOiXUj+fikfiaoYAKHF3VJfA0pe2BCzkhAHBlLG6REzE+2WNZcxOXjK7lkso+9euLA==}
 
-  stream-shift@1.0.3:
-    resolution: {integrity: sha512-76ORR0DO1o1hlKwTbi/DM3EXWGf3ZJYO8cXX5RJwnul2DEg2oyoZyjLNoQM8WsvZiFKCRfC1O0J7iCvie3RZmQ==}
-
   strict-event-emitter-types@2.0.0:
     resolution: {integrity: sha512-Nk/brWYpD85WlOgzw5h173aci0Teyv8YdIAEtV+N88nDB0dLlazZyJMIsN6eo1/AR61l+p6CJTG1JIyFaoNEEA==}
 
@@ -10186,9 +10153,6 @@ packages:
     resolution: {integrity: sha512-g9ljZiwki/LfxmQADO3dEY1CbpmXT5Hm2fJ+QaGKwSXUylMybePR7/67YW7jOrrvjEgL1Fmz5kzyAjWVWLlucg==}
     engines: {node: '>=6'}
 
-  tar-mini@0.2.0:
-    resolution: {integrity: sha512-+qfUHz700DWnRutdUsxRRVZ38G1Qr27OetwaMYTdg8hcPxf46U0S1Zf76dQMWRBmusOt2ZCK5kbIaiLkoGO7WQ==}
-
   tar-stream@2.2.0:
     resolution: {integrity: sha512-ujeqbceABgwMZxEJnk2HDY2DlnUZ+9oEcb1KzTVfYHio0UE6dG71n60d8D2I4qNvleWrrXpmjpt7vZeF1LnMZQ==}
     engines: {node: '>=6'}
@@ -10197,6 +10161,9 @@ packages:
     resolution: {integrity: sha512-4LeEWl96twnS2Q7Bz4MGqgazLqO+hJN63GZxXoIqh1T3VweYD997gbU1ItNsQafqqXTXd5WFyFdReLtwvRBNiw==}
     engines: {node: '>=18'}
 
+  tdigest@0.1.2:
+    resolution: {integrity: sha512-+G0LLgjjo9BZX2MfdvPfH+MKLCrxlXSYec5DaPYP1fe6Iyhf0/fSmJ0bFiZ1F8BT6cGXl2LpltQptzjXKWEkKA==}
+
   terser-webpack-plugin@5.4.0:
     resolution: {integrity: sha512-Bn5vxm48flOIfkdl5CaD2+1CiUVbonWQ3KQPyP7/EuIl9Gbzq/gQFOzaMFUEgVjB1396tcK0SG8XcNJ/2kDH8g==}
     engines: {node: '>= 10.13.0'}
@@ -10229,9 +10196,6 @@ packages:
     resolution: {integrity: sha512-nt6AMGKW1p/70DF/hGBdJB57B8Tspmbp5gfJ8ilhLnt7kkr2ye7hzD6NVG8GGErk2HWF34igrL2CXmNIkzKqKw==}
     engines: {node: '>=18'}
 
-  through2@2.0.5:
-    resolution: {integrity: sha512-/mrRod8xqpA+IHSLyGCQ2s8SPHiCDEeQJSep1jqLYeEUClOFG2Qsh+4FU6G9VeqpZnGW/Su8LQGc4YKni5rYSQ==}
-
   tiny-invariant@1.3.3:
     resolution: {integrity: sha512-+FbBPE1o9QAYvviau/qC5SE3caw21q3xkvWKBtja5vgqOWIHHJ3ioaq1VPfn/Szqctz2bU/oYeKd9/z5BL+PVg==}
 
@@ -10637,9 +10601,6 @@ packages:
     resolution: {integrity: sha512-BNGbWLfd0eUPabhkXUVm0j8uuvREyTh5ovRa/dyow/BqAbZJyC+5fU+IzQOzmAKzYqYRAISoRhdQr3eIZ/PXqg==}
     engines: {node: '>= 0.8'}
 
-  vite-plugin-compression2@2.5.3:
-    resolution: {integrity: sha512-ItPgqQWkcnBbVw7is9OKwiZ8v6+ju9rYROl5Lp6QfQDEx/d55AwJQb/KLpsQqsU9HoigYBsZ8tK6I02UwJNvEw==}
-
   vite@8.0.5:
     resolution: {integrity: sha512-nmu43Qvq9UopTRfMx2jOYW5l16pb3iDC1JH6yMuPkpVbzK0k+L7dfsEDH4jRgYFmsg0sTAqkojoZgzLMlwHsCQ==}
     engines: {node: ^20.19.0 || >=22.12.0}
@@ -12979,15 +12940,6 @@ snapshots:
 
   '@fastify/busboy@3.1.1': {}
 
-  '@fastify/compress@9.0.0':
-    dependencies:
-      '@fastify/accept-negotiator': 2.0.1
-      fastify-plugin: 5.1.0
-      mime-db: 1.54.0
-      minipass: 7.1.3
-      peek-stream: 1.1.3
-      readable-stream: 4.7.0
-
   '@fastify/cookie@11.0.2':
     dependencies:
       cookie: 1.1.1
@@ -15003,12 +14955,6 @@ snapshots:
 
   '@rolldown/pluginutils@1.0.0-rc.7': {}
 
-  '@rollup/pluginutils@5.4.0':
-    dependencies:
-      '@types/estree': 1.0.9
-      estree-walker: 2.0.2
-      picomatch: 4.0.4
-
   '@selderee/plugin-htmlparser2@0.11.0':
     dependencies:
       domhandler: 5.0.3
@@ -16382,10 +16328,6 @@ snapshots:
 
   abbrev@5.0.0: {}
 
-  abort-controller@3.0.0:
-    dependencies:
-      event-target-shim: 5.0.1
-
   abstract-logging@2.0.1: {}
 
   accepts@1.3.8:
@@ -16742,6 +16684,8 @@ snapshots:
 
   bind-event-listener@3.0.0: {}
 
+  bintrees@1.0.2: {}
+
   bl@4.1.0:
     dependencies:
       buffer: 5.7.1
@@ -16832,11 +16776,6 @@ snapshots:
       base64-js: 1.5.1
       ieee754: 1.2.1
 
-  buffer@6.0.3:
-    dependencies:
-      base64-js: 1.5.1
-      ieee754: 1.2.1
-
   bullmq@5.76.10:
     dependencies:
       cron-parser: 4.9.0
@@ -17590,13 +17529,6 @@ snapshots:
       es-errors: 1.3.0
       gopd: 1.2.0
 
-  duplexify@3.7.1:
-    dependencies:
-      end-of-stream: 1.4.4
-      inherits: 2.0.4
-      readable-stream: 2.3.8
-      stream-shift: 1.0.3
-
   ecdsa-sig-formatter@1.0.11:
     dependencies:
       safe-buffer: 5.2.1
@@ -18023,8 +17955,6 @@ snapshots:
 
   estraverse@5.3.0: {}
 
-  estree-walker@2.0.2: {}
-
   estree-walker@3.0.3:
     dependencies:
       '@types/estree': 1.0.9
@@ -18033,8 +17963,6 @@ snapshots:
 
   etag@1.8.1: {}
 
-  event-target-shim@5.0.1: {}
-
   eventemitter2@6.4.9: {}
 
   eventemitter3@4.0.7: {}
@@ -20298,12 +20226,6 @@ snapshots:
 
   peberminta@0.9.0: {}
 
-  peek-stream@1.1.3:
-    dependencies:
-      buffer-from: 1.1.2
-      duplexify: 3.7.1
-      through2: 2.0.5
-
   pend@1.2.0: {}
 
   perfect-freehand@1.2.0: {}
@@ -20575,7 +20497,10 @@ snapshots:
 
   process-warning@5.0.0: {}
 
-  process@0.11.10: {}
+  prom-client@15.1.3:
+    dependencies:
+      '@opentelemetry/api': 1.9.0
+      tdigest: 0.1.2
 
   prompts@2.4.2:
     dependencies:
@@ -20993,14 +20918,6 @@ snapshots:
       string_decoder: 1.3.0
       util-deprecate: 1.0.2
 
-  readable-stream@4.7.0:
-    dependencies:
-      abort-controller: 3.0.0
-      buffer: 6.0.3
-      events: 3.3.0
-      process: 0.11.10
-      string_decoder: 1.3.0
-
   readdirp@3.6.0:
     dependencies:
       picomatch: 2.3.2
@@ -21454,8 +21371,6 @@ snapshots:
       inherits: 2.0.4
       readable-stream: 3.6.2
 
-  stream-shift@1.0.3: {}
-
   strict-event-emitter-types@2.0.0: {}
 
   string-length@4.0.2:
@@ -21616,8 +21531,6 @@ snapshots:
 
   tapable@2.3.0: {}
 
-  tar-mini@0.2.0: {}
-
   tar-stream@2.2.0:
     dependencies:
       bl: 4.1.0
@@ -21634,6 +21547,10 @@ snapshots:
       minizlib: 3.1.0
       yallist: 5.0.0
 
+  tdigest@0.1.2:
+    dependencies:
+      bintrees: 1.0.2
+
   terser-webpack-plugin@5.4.0(@swc/core@1.5.25(@swc/helpers@0.5.5))(webpack@5.106.0(@swc/core@1.5.25(@swc/helpers@0.5.5))):
     dependencies:
       '@jridgewell/trace-mapping': 0.3.31
@@ -21663,11 +21580,6 @@ snapshots:
 
   throttleit@2.1.0: {}
 
-  through2@2.0.5:
-    dependencies:
-      readable-stream: 2.3.8
-      xtend: 4.0.2
-
   tiny-invariant@1.3.3: {}
 
   tinybench@2.9.0: {}
@@ -22072,13 +21984,6 @@ snapshots:
 
   vary@1.1.2: {}
 
-  vite-plugin-compression2@2.5.3:
-    dependencies:
-      '@rollup/pluginutils': 5.4.0
-      tar-mini: 0.2.0
-    transitivePeerDependencies:
-      - rollup
-
   vite@8.0.5(@types/node@20.19.43)(esbuild@0.28.0)(jiti@2.4.2)(less@4.2.0)(sugarss@5.0.1(postcss@8.5.14))(terser@5.39.0)(tsx@4.21.0)(yaml@2.8.3):
     dependencies:
       lightningcss: 1.32.0
@@ -22459,7 +22364,8 @@ snapshots:
 
   xpath@0.0.34: {}
 
-  xtend@4.0.2: {}
+  xtend@4.0.2:
+    optional: true
 
   y-indexeddb@9.0.12(yjs@13.6.30(patch_hash=1ceeb66dba1f86545c98a3ff7f5152aff9b35caf409091cef9caedb5e65c8810)):
     dependencies: