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

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

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/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/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",
@@ -43,6 +43,7 @@
     "@clickhouse/client": "^1.18.2",
     "@docmost/mcp": "workspace:*",
     "@docmost/pdf-inspector": "1.9.6",
+    "@docmost/prosemirror-markdown": "workspace:*",
     "@fastify/cookie": "^11.0.2",
     "@fastify/multipart": "^10.0.0",
     "@fastify/static": "^9.1.3",
@@ -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/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/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/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/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';
@@ -122,6 +123,7 @@ import { firstSqlToken } from '../integrations/metrics/metrics.constants';
     TemplateRepo,
     AiChatRepo,
     AiChatMessageRepo,
+    AiChatRunRepo,
     AiChatPageSnapshotRepo,
     AiProviderCredentialsRepo,
     AiMcpServerRepo,
@@ -156,6 +158,7 @@ import { firstSqlToken } from '../integrations/metrics/metrics.constants';
     TemplateRepo,
     AiChatRepo,
     AiChatMessageRepo,
+    AiChatRunRepo,
     AiChatPageSnapshotRepo,
     AiProviderCredentialsRepo,
     AiMcpServerRepo,

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

@@ -659,6 +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
@@ -695,6 +724,7 @@ export interface DB {
   aiAgentRoles: AiAgentRoles;
   aiChats: AiChats;
   aiChatMessages: AiChatMessages;
+  aiChatRuns: AiChatRuns;
   aiChatPageSnapshots: AiChatPageSnapshots;
   apiKeys: ApiKeys;
   attachments: Attachments;

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/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/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 {},
+};

pnpm-lock.yaml

@@ -543,6 +543,9 @@ importers:
       '@docmost/pdf-inspector':
         specifier: 1.9.6
         version: 1.9.6
+      '@docmost/prosemirror-markdown':
+        specifier: workspace:*
+        version: link:../../packages/prosemirror-markdown
       '@fastify/cookie':
         specifier: ^11.0.2
         version: 11.0.2