docs(mcp): sync write-tool specs with #502 literal-markdown behavior (#502 review)

The four MCP markdown-write tools (updatePageMarkdown/createPage/patchNode/
insertNode) still described the old parse-everything behavior after #502 turned
TeX math and fuzzy autolink OFF on the write paths. Add a concise contract hint
to each: $...$ / $$...$$ stay literal (not a math formula) and schemeless
www.host / bare emails are not auto-linked (explicit https:// still links); for
a real formula use updatePageJson (or a mathInline/mathBlock node via `node` on
patch/insert). Also note getPage format:"text" in README.md/README.ru.md.

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

.env.example

@@ -251,6 +251,16 @@ MCP_DOCMOST_PASSWORD=
 # Default 120000 (2 min).
 # AI_MCP_CALL_TIMEOUT_MS=120000
 
+# Kill-switch for the agent API-key feature (#501). Default ON when unset — a
+# deploy that never sets it must NOT silently kill every agent. STRICT parse:
+# only the literals `true` / `false` are accepted; a typo like `=0`/`=off`/`=False`
+# FAILS AT BOOT by design (never silently read as "enabled"), so the switch is
+# guaranteed to actually flip when an operator flips it during an incident. When
+# set to `false`: all api-key auth is DENIED (every api-key token is rejected) and
+# the api-key management endpoints return 404. The resolved state is logged at boot
+# (`API keys: ENABLED/DISABLED (API_KEYS_ENABLED=...)`) so it is verifiable per deploy.
+# API_KEYS_ENABLED=true
+
 # Max JSON/urlencoded request body size (bytes). Fastify's 1 MiB default is too
 # small for a long AI-chat research turn: the client resends the FULL message
 # history (every tool call + search result) on each turn, so a deep conversation's

.github/workflows/develop.yml

@@ -226,6 +226,13 @@ jobs:
       - name: Build mcp
         run: pnpm --filter @docmost/mcp build
 
+      # apps/server imports @docmost/token-estimate at runtime (history-budget.ts,
+      # #490); its dist/ is gitignored and `test:e2e` type-checks + runs the code,
+      # so build it here or tsc fails with TS2307 Cannot find module
+      # '@docmost/token-estimate' (mirrors the editor-ext / mcp build steps above).
+      - name: Build token-estimate
+        run: pnpm --filter @docmost/token-estimate build
+
       - name: Run migrations
         run: pnpm --filter ./apps/server migration:latest
 

.github/workflows/test.yml

@@ -159,6 +159,14 @@ jobs:
       - name: Build prosemirror-markdown
         run: pnpm --filter @docmost/prosemirror-markdown build
 
+      # @docmost/token-estimate is a shared workspace package the client vitest
+      # suite resolves via its dist build (main: ./dist/index.js); dist/ is
+      # gitignored and `pnpm -r test` does NOT honour nx `dependsOn: ^build`, so
+      # build it before the recursive test run or the client suite fails with
+      # "Failed to resolve import '@docmost/token-estimate'" (#490).
+      - name: Build token-estimate
+        run: pnpm --filter @docmost/token-estimate build
+
       - name: Run unit tests
         run: pnpm -r test
 

CHANGELOG.md

@@ -392,6 +392,25 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   `@docmost/token-estimate` package) so they can never diverge. Deferred-tool
   activation is also cached in the chat metadata to avoid re-resolving it each
   turn. (#490)
+- **Cyrillic (and any non-ASCII) draw.io labels no longer turn into mojibake
+  when a diagram is opened in the draw.io editor.** Agent-created diagrams
+  (`drawioCreate`) and Confluence-imported diagrams stored their model in the
+  SVG's `content=` attribute as base64; the draw.io editor decodes that via
+  Latin-1 `atob` (no UTF-8 step), so every non-ASCII char (e.g. `Старт-бит`,
+  `ё`, `—`) split into garbage and the editor's autosave then persisted the
+  corrupted model, breaking the page preview too. Both write paths
+  (`buildDrawioSvg`, the import service's `createDrawioSvg`) now write `content=`
+  as XML-entity-escaped mxfile XML — draw.io's own native form, decoded by the
+  DOM as UTF-8 — so labels open intact. The decoder reads both the new
+  entity-encoded form and the old base64 form, so existing diagrams still open.
+  *Healing pre-fix diagrams:* only a diagram that still holds its original
+  (correct-UTF-8) base64 — i.e. one not yet opened/autosaved in the draw.io
+  editor — can be repaired in place by `drawioGet` → `drawioUpdate` with the
+  same XML (rewrites the attachment in the new form); no migration script is
+  needed. A diagram that was already opened in the editor persisted the
+  mojibake at rest, so `drawioGet` reads the already-corrupted text and
+  `drawioUpdate` faithfully rewrites it — that text is lost and is not
+  recoverable by a rewrite. (#507)
 - **A chat with one malformed message part no longer 500s on every turn, and a
   failed send no longer duplicates the user's message.** Incoming client parts
   are now whitelisted to `text` (a forged tool-result part can no longer reach

Dockerfile

@@ -59,6 +59,14 @@ COPY --from=builder /app/packages/mcp/data /app/packages/mcp/data
 COPY --from=builder /app/packages/prosemirror-markdown/build /app/packages/prosemirror-markdown/build
 COPY --from=builder /app/packages/prosemirror-markdown/package.json /app/packages/prosemirror-markdown/package.json
 
+# apps/server imports @docmost/token-estimate (workspace:*) at runtime
+# (history-budget.ts, #490). tsc emits only dist/ and dist/ is gitignored, so the
+# prod install would resolve a broken workspace symlink and the server would die
+# with ERR_MODULE_NOT_FOUND on the first history-budget call. Ship the built
+# package + its manifest, mirroring prosemirror-markdown above.
+COPY --from=builder /app/packages/token-estimate/dist /app/packages/token-estimate/dist
+COPY --from=builder /app/packages/token-estimate/package.json /app/packages/token-estimate/package.json
+
 # Copy root package files
 COPY --from=builder /app/package.json /app/package.json
 COPY --from=builder /app/pnpm*.yaml /app/

apps/client/src/features/page/tree/components/space-tree.tsx

@@ -281,10 +281,12 @@ const SpaceTree = forwardRef<SpaceTreeApi, SpaceTreeProps>(function SpaceTree(
       setOpenTreeNodes((prev) => ({ ...prev, [id]: isOpen }));
       if (isOpen) {
         const node = treeModel.find(data, id) as SpaceTreeNode | null;
-        if (
-          node?.hasChildren &&
-          (!node.children || node.children.length === 0)
-        ) {
+        // Same "unloaded branch" predicate the realtime insert paths use
+        // (`isUnloadedBranch`) so the lazy-load gate and the realtime inserts
+        // (`insertByPosition` / `placeByPosition`) can never disagree about what
+        // counts as unloaded (#525). Note: local raw `insert` (DnD/create-page)
+        // does not yet route through it — see #525 follow-up.
+        if (treeModel.isUnloadedBranch(node)) {
           const fetched = await fetchAllAncestorChildren({
             pageId: id,
             spaceId: node.spaceId,

apps/client/src/features/page/tree/model/tree-model.test.ts

@@ -74,6 +74,48 @@ describe("treeModel.isDescendant", () => {
   });
 });
 
+// #525: the single "is this branch unloaded?" predicate shared by the lazy-load
+// gate and the insert paths. Unloaded == server says hasChildren but none are
+// present locally (canonical form `children: []`, also `undefined`). A parent
+// without hasChildren is genuinely empty, not unloaded.
+describe("treeModel.isUnloadedBranch", () => {
+  type PH = TreeNode<{ name: string; hasChildren?: boolean }>;
+  it("true for hasChildren + empty array (canonical unloaded form)", () => {
+    const n: PH = { id: "p", name: "P", hasChildren: true, children: [] };
+    expect(treeModel.isUnloadedBranch(n)).toBe(true);
+  });
+  it("true for hasChildren + undefined children", () => {
+    const n: PH = { id: "p", name: "P", hasChildren: true };
+    expect(treeModel.isUnloadedBranch(n)).toBe(true);
+  });
+  it("false for hasChildren + already-loaded children", () => {
+    const n: PH = {
+      id: "p",
+      name: "P",
+      hasChildren: true,
+      children: [{ id: "c", name: "C" }],
+    };
+    expect(treeModel.isUnloadedBranch(n)).toBe(false);
+  });
+  it("false for a genuinely-empty parent (no hasChildren)", () => {
+    expect(
+      treeModel.isUnloadedBranch({
+        id: "p",
+        name: "P",
+        hasChildren: false,
+        children: [],
+      } as PH),
+    ).toBe(false);
+    expect(
+      treeModel.isUnloadedBranch({ id: "p", name: "P" } as PH),
+    ).toBe(false);
+  });
+  it("false for null/undefined", () => {
+    expect(treeModel.isUnloadedBranch(null)).toBe(false);
+    expect(treeModel.isUnloadedBranch(undefined)).toBe(false);
+  });
+});
+
 describe("treeModel.visible", () => {
   it("returns only root nodes when no openIds", () => {
     const v = treeModel.visible(fixture, new Set());
@@ -197,43 +239,64 @@ describe("treeModel.insertByPosition", () => {
     ]);
   });
 
-  // #159 #1: inserting/moving a node under a parent whose children are NOT
-  // loaded (`children === undefined`, e.g. a collapsed page) must NOT materialize
-  // a partial `[node]` list — that would defeat the lazy-load gate and hide the
-  // parent's other real children. The node is left to be lazy-loaded; only
-  // `hasChildren` is flagged so the chevron appears.
-  it("does NOT materialize a child under an UNLOADED parent (children undefined)", () => {
-    type PH = TreeNode<{
-      name: string;
-      position?: string;
-      hasChildren?: boolean;
-    }>;
+  type PH = TreeNode<{
+    name: string;
+    position?: string;
+    hasChildren?: boolean;
+  }>;
+
+  // #159 #1 / #525: inserting/moving a node under an UNLOADED parent must NOT
+  // materialize a partial `[node]` list — that would defeat the lazy-load gate and
+  // hide the parent's other real children. The canonical unloaded form here is
+  // `children: []` + `hasChildren: true` (from `pageToTreeNode` /
+  // `pruneCollapsedChildren`), which the pre-#525 `=== undefined` guard MISSED.
+  // The node is left to be lazy-loaded; the chevron stays enabled.
+  it("does NOT materialize a child under an UNLOADED parent (children: [], hasChildren: true)", () => {
     const tree: PH[] = [
-      { id: "p", name: "P", position: "a0", hasChildren: false }, // children: undefined
+      { id: "p", name: "P", position: "a0", hasChildren: true, children: [] },
     ];
     const node: PH = { id: "x", name: "X", position: "a1" };
     const t = treeModel.insertByPosition(tree, "p", node);
     const parent = treeModel.find(t, "p");
     // The node was NOT inserted (children stay unloaded -> lazy-load fetches the
-    // full set, including this node, on expand).
-    expect(parent?.children).toBeUndefined();
+    // full set, including this node, on expand). MUTATION: the pre-#525 predicate
+    // `children === undefined` does not fire for `[]`, so it would insert `[x]`
+    // here and reredden this expectation.
+    expect(parent?.children).toEqual([]);
     expect(treeModel.find(t, "x")).toBeNull();
-    // ...but the chevron is enabled so the user can expand to load it.
+    // ...and the chevron stays enabled so the user can expand to load it.
     expect((parent as PH).hasChildren).toBe(true);
   });
 
-  it("DOES insert under a LOADED-but-empty parent (children: [])", () => {
-    type PH = TreeNode<{
-      name: string;
-      position?: string;
-      hasChildren?: boolean;
-    }>;
+  it("does NOT materialize a child under an UNLOADED parent (children undefined, hasChildren: true)", () => {
+    const tree: PH[] = [
+      { id: "p", name: "P", position: "a0", hasChildren: true }, // children: undefined
+    ];
+    const node: PH = { id: "x", name: "X", position: "a1" };
+    const t = treeModel.insertByPosition(tree, "p", node);
+    const parent = treeModel.find(t, "p");
+    expect(parent?.children).toBeUndefined();
+    expect(treeModel.find(t, "x")).toBeNull();
+    expect((parent as PH).hasChildren).toBe(true);
+  });
+
+  it("DOES insert under a genuinely-empty parent (children: [], hasChildren: false)", () => {
     const tree: PH[] = [
       { id: "p", name: "P", position: "a0", hasChildren: false, children: [] },
     ];
     const node: PH = { id: "x", name: "X", position: "a1" };
     const t = treeModel.insertByPosition(tree, "p", node);
-    // A loaded (empty) child list is complete, so the node IS inserted.
+    // No server children (`hasChildren: false`), so materializing the first child
+    // is correct — nothing is hidden.
+    expect(treeModel.find(t, "p")?.children?.map((n) => n.id)).toEqual(["x"]);
+  });
+
+  it("DOES insert under a genuinely-empty parent (children undefined, hasChildren: false)", () => {
+    const tree: PH[] = [
+      { id: "p", name: "P", position: "a0", hasChildren: false }, // children: undefined
+    ];
+    const node: PH = { id: "x", name: "X", position: "a1" };
+    const t = treeModel.insertByPosition(tree, "p", node);
     expect(treeModel.find(t, "p")?.children?.map((n) => n.id)).toEqual(["x"]);
   });
 

apps/client/src/features/page/tree/model/tree-model.ts

@@ -43,6 +43,26 @@ export const treeModel = {
     };
   },
 
+  // A branch is "unloaded" when the server says it HAS children (`hasChildren`)
+  // but none are present locally. The canonical unloaded form in this codebase
+  // is `children: []` (produced by `pageToTreeNode` and by `pruneCollapsedChildren`
+  // resetting collapsed branches), NOT `children: undefined` — so a predicate that
+  // only checks `=== undefined` misses the real case and materializes a misleading
+  // partial list (#525). This is the SINGLE source of truth for "should a
+  // fetch/materialize be deferred?", shared by the lazy-load gate (`handleToggle`)
+  // and the realtime insert paths (`insertByPosition` / `placeByPosition`), so they
+  // can never drift apart again. (The local raw `insert` primitive and its DnD/
+  // create-page callers do NOT yet route through this predicate — see #525
+  // follow-up.) A parent WITHOUT `hasChildren` is genuinely empty
+  // (no server children) — inserting its first child is correct, not deferred.
+  isUnloadedBranch<T extends object>(
+    node: TreeNode<T> | null | undefined,
+  ): boolean {
+    if (!node) return false;
+    const hasChildren = (node as { hasChildren?: boolean }).hasChildren === true;
+    return hasChildren && (node.children == null || node.children.length === 0);
+  },
+
   isDescendant<T extends object>(
     tree: TreeNode<T>[],
     ancestorId: string,
@@ -127,14 +147,15 @@ export const treeModel = {
     }
     const parent = treeModel.find(tree, parentId);
     // The parent is in the tree but its children have NOT been lazy-loaded yet
-    // (`children === undefined`, distinct from a loaded-but-empty `[]`). Inserting
+    // (`hasChildren` set + children absent/empty — see `isUnloadedBranch`; the
+    // canonical unloaded form is `children: []`, NOT just `undefined`). Inserting
     // here would MATERIALIZE a misleading partial child list (`[node]`) that
     // defeats the lazy-load gate — which fetches only when children are
     // absent/empty — so the parent's OTHER real children would never load and the
     // moved/added node would be the only one shown (a silent data loss, #159 #1).
     // Instead, leave the children unloaded and just flag `hasChildren` so the
     // chevron appears; expanding fetches the FULL set (including this node).
-    if (parent && parent.children === undefined) {
+    if (parent && treeModel.isUnloadedBranch(parent)) {
       return treeModel.update(
         tree,
         parentId,

apps/client/src/features/websocket/tree-socket-reducers.test.ts

@@ -82,17 +82,19 @@ describe("applyMoveTreeNode", () => {
     ]);
   });
 
-  it("does NOT create a partial child list when the destination is loaded-but-collapsed (children unloaded) — keeps it lazy-loadable (#159)", () => {
-    // `dstCollapsed` is in the tree but its children were never lazy-loaded
-    // (children === undefined). The OLD behavior inserted `src` as the ONLY
-    // child ([src]), which defeated the lazy-load gate and HID the parent's
-    // other real children. Now the move leaves children unloaded (so expanding
-    // fetches the FULL set, including src) and just flags hasChildren.
+  it("does NOT create a partial child list when the destination is loaded-but-collapsed (children unloaded) — keeps it lazy-loadable (#159 #525)", () => {
+    // `dstCollapsed` is in the tree but its children were never lazy-loaded. The
+    // CANONICAL unloaded form here is `hasChildren: true` + `children: []` (from
+    // `pageToTreeNode` / `pruneCollapsedChildren`), NOT `children: undefined`.
+    // The pre-#525 predicate (`children === undefined`) missed this form and
+    // inserted `src` as the ONLY child ([src]), defeating the lazy-load gate and
+    // HIDING the parent's other real children. Now the move leaves children
+    // unloaded (so expanding fetches the FULL set, including src).
     const tree: SpaceTreeNode[] = [
       node("dstCollapsed", {
         position: "a0",
-        hasChildren: false,
-        children: undefined as unknown as SpaceTreeNode[],
+        hasChildren: true,
+        children: [],
       }),
       node("src", { position: "a9" }),
     ];
@@ -105,9 +107,10 @@ describe("applyMoveTreeNode", () => {
       pageData: {},
     });
     const dst = treeModel.find(next, "dstCollapsed");
-    // Children stay unloaded -> the lazy-load gate fetches the FULL set (incl.
-    // src) on expand, rather than showing a misleading partial [src] list.
-    expect(dst?.children).toBeUndefined();
+    // Children stay unloaded ([] not materialized to [src]) -> the lazy-load gate
+    // fetches the FULL set (incl. src) on expand. MUTATION: the pre-#525
+    // `=== undefined` predicate would insert [src] here and redden this.
+    expect(dst?.children).toEqual([]);
     expect(dst?.hasChildren).toBe(true);
     // src moved away from its old root slot (it lives under dstCollapsed
     // server-side and reappears when the parent is expanded/loaded).

apps/server/src/collaboration/collaboration.module.ts

@@ -16,6 +16,7 @@ import { TransclusionService } from '../core/page/transclusion/transclusion.serv
 import { TransclusionModule } from '../core/page/transclusion/transclusion.module';
 import { StorageModule } from '../integrations/storage/storage.module';
 import { EnvironmentModule } from '../integrations/environment/environment.module';
+import { ApiKeyModule } from '../core/api-key/api-key.module';
 
 @Module({
   providers: [
@@ -31,6 +32,7 @@ import { EnvironmentModule } from '../integrations/environment/environment.modul
   exports: [CollaborationGateway],
   imports: [
     TokenModule,
+    ApiKeyModule,
     WatcherModule,
     StorageModule.forRootAsync({
       imports: [EnvironmentModule],

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

@@ -141,7 +141,57 @@ export function htmlToJson(html: string) {
   }
 }
 
-export function jsonToText(tiptapJson: JSONContent) {
+/**
+ * Deterministic text-serializer overrides for the `format:"text"` page read
+ * (#502). Non-text nodes render to a STABLE placeholder instead of their
+ * (structure-dependent) inner text, so a machine diff of two text reads is
+ * driven only by the page's actual prose — output stability across package
+ * versions IS the contract (pinned by a snapshot test). Returning a string from
+ * a `textSerializer` also stops `generateText` descending into the node, so a
+ * table renders as ONE token rather than its flattened cell text.
+ *
+ * Only nodes with no meaningful flat-text form are overridden; every other node
+ * (paragraph/heading/list/code/blockquote/callout/…) keeps its natural text so
+ * a config written as markdown reads back byte-identical.
+ */
+const TEXT_READ_SERIALIZERS: Record<string, (props: { node: any }) => string> =
+  {
+    // Image atom: no inner text -> a fixed placeholder.
+    image: () => '[image]',
+    // Table: `[table RxC]` where R = row count, C = the first row's cell count
+    // (a table's columns are uniform per the schema). Computed from the PM node,
+    // so it is independent of cell contents.
+    table: ({ node }) => {
+      const rows = node?.childCount ?? 0;
+      const cols = rows > 0 ? (node.child(0)?.childCount ?? 0) : 0;
+      return `[table ${rows}x${cols}]`;
+    },
+  };
+
+/**
+ * Serialize a ProseMirror/TipTap document to plain text.
+ *
+ * Default (no options): the long-standing search-index behavior — bare
+ * concatenated node text with `generateText`'s default `\n\n` block separator.
+ * This feeds the page `textContent` tsvector and MUST NOT change.
+ *
+ * `deterministic:true` (#502 `format:"text"` page read): a flat, machine-diffable
+ * rendering — one line per block (`\n` block separator; `hardBreak` already
+ * serializes to `\n`), inline marks/anchors/autoformat dropped, and non-text
+ * nodes replaced by the stable placeholders above (`[image]`, `[table RxC]`).
+ */
+export function jsonToText(
+  // `any` (like jsonToHtml/jsonToMarkdown) so a loosely-typed DB `page.content`
+  // (JsonValue) can be passed straight through, as the controller does.
+  tiptapJson: any,
+  options?: { deterministic?: boolean },
+) {
+  if (options?.deterministic) {
+    return generateText(tiptapJson, tiptapExtensions, {
+      blockSeparator: '\n',
+      textSerializers: TEXT_READ_SERIALIZERS,
+    });
+  }
   return generateText(tiptapJson, tiptapExtensions);
 }
 

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

@@ -52,6 +52,7 @@ describe('AuthenticationExtension.onAuthenticate', () => {
   let pageRepo: { findById: jest.Mock };
   let spaceMemberRepo: { getUserSpaceRoles: jest.Mock };
   let pagePermissionRepo: { canUserEditPage: jest.Mock };
+  let apiKeyService: { validate: jest.Mock };
 
   // Build the hocuspocus onAuthenticate payload. connectionConfig.readOnly
   // starts false; the extension flips it to true on a read-only downgrade.
@@ -79,12 +80,15 @@ describe('AuthenticationExtension.onAuthenticate', () => {
       }),
     };
 
+    apiKeyService = { validate: jest.fn().mockResolvedValue({ user: {}, workspace: {} }) };
+
     ext = new AuthenticationExtension(
       tokenService as any,
       userRepo as any,
       pageRepo as any,
       spaceMemberRepo as any,
       pagePermissionRepo as any,
+      apiKeyService as any,
     );
     // Silence the extension's logger (it warns/debugs on denial branches).
     jest.spyOn(ext['logger'], 'warn').mockImplementation(() => undefined);
@@ -231,4 +235,73 @@ describe('AuthenticationExtension.onAuthenticate', () => {
     // No internal ai_chats row for an MCP/service-account collab edit → null.
     expect(ctx.aiChatId).toBeNull();
   });
+
+  // --- #501: api-key laundering guard (fail-closed discriminator) ----------
+  describe('api-key laundering guard', () => {
+    it('api_key principal → row-checks the key on connect (valid key proceeds)', async () => {
+      tokenService.verifyJwt.mockResolvedValue(
+        buildJwt({ principal: 'api_key', apiKeyId: 'key-1' }),
+      );
+      const data = buildData();
+      await ext.onAuthenticate(data as any);
+
+      expect(apiKeyService.validate).toHaveBeenCalledTimes(1);
+      expect(apiKeyService.validate).toHaveBeenCalledWith(
+        expect.objectContaining({ apiKeyId: 'key-1', type: JwtType.API_KEY }),
+      );
+    });
+
+    it('REVOKED api_key → Unauthorized on connect, BEFORE any page/user lookup', async () => {
+      tokenService.verifyJwt.mockResolvedValue(
+        buildJwt({ principal: 'api_key', apiKeyId: 'key-1' }),
+      );
+      // The shared validator denies a revoked key.
+      apiKeyService.validate.mockRejectedValue(new UnauthorizedException());
+
+      await expect(ext.onAuthenticate(buildData() as any)).rejects.toThrow(
+        UnauthorizedException,
+      );
+      // No new collab connection: the key check gates before page access.
+      expect(pageRepo.findById).not.toHaveBeenCalled();
+    });
+
+    it('api_key principal missing apiKeyId → Unauthorized (malformed)', async () => {
+      tokenService.verifyJwt.mockResolvedValue(buildJwt({ principal: 'api_key' }));
+      await expect(ext.onAuthenticate(buildData() as any)).rejects.toThrow(
+        UnauthorizedException,
+      );
+      expect(apiKeyService.validate).not.toHaveBeenCalled();
+    });
+
+    it('session principal → NO api-key check (session-backed, incl. internal agent)', async () => {
+      tokenService.verifyJwt.mockResolvedValue(buildJwt({ principal: 'session' }));
+      await ext.onAuthenticate(buildData() as any);
+      expect(apiKeyService.validate).not.toHaveBeenCalled();
+    });
+
+    it('claimless token WITHIN the grace window → trusted (legacy pre-rollout)', async () => {
+      // Default rolloutAt = now, so we are inside the grace window.
+      tokenService.verifyJwt.mockResolvedValue(buildJwt()); // no principal
+      await expect(ext.onAuthenticate(buildData() as any)).resolves.toBeDefined();
+      expect(apiKeyService.validate).not.toHaveBeenCalled();
+    });
+
+    it('claimless token AFTER the grace window → Unauthorized (fail-closed)', async () => {
+      // Move the rollout reference far into the past so the grace has elapsed.
+      (ext as any).rolloutAt = Date.now() - 25 * 60 * 60 * 1000;
+      tokenService.verifyJwt.mockResolvedValue(buildJwt()); // no principal
+      await expect(ext.onAuthenticate(buildData() as any)).rejects.toThrow(
+        UnauthorizedException,
+      );
+    });
+
+    it('infra error from the api-key row-check propagates (not masked)', async () => {
+      tokenService.verifyJwt.mockResolvedValue(
+        buildJwt({ principal: 'api_key', apiKeyId: 'key-1' }),
+      );
+      const boom = new Error('db down');
+      apiKeyService.validate.mockRejectedValue(boom);
+      await expect(ext.onAuthenticate(buildData() as any)).rejects.toBe(boom);
+    });
+  });
 });

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

@@ -14,20 +14,37 @@ import { findHighestUserSpaceRole } from '@docmost/db/repos/space/utils';
 import { SpaceRole } from '../../common/helpers/types/permission';
 import { isUserDisabled } from '../../common/helpers';
 import { getPageId } from '../collaboration.util';
-import { JwtCollabPayload, JwtType } from '../../core/auth/dto/jwt-payload';
+import {
+  JwtApiKeyPayload,
+  JwtCollabPayload,
+  JwtType,
+} from '../../core/auth/dto/jwt-payload';
 import { resolveProvenance } from '../../common/decorators/auth-provenance.decorator';
 import { observeCollabAuth } from '../../integrations/metrics/metrics.registry';
+import { ApiKeyService } from '../../core/api-key/api-key.service';
+
+// Max lifetime of a collab token (generateCollabToken uses expiresIn '24h'). Used
+// as the rollout grace window below: once this long has elapsed since this
+// process started serving the #501 code, every STILL-VALID collab token was
+// necessarily minted post-rollout and MUST carry the `principal` discriminator,
+// so a claimless one is a bug and is rejected (fail-closed) rather than trusted.
+const COLLAB_TOKEN_GRACE_MS = 24 * 60 * 60 * 1000;
 
 @Injectable()
 export class AuthenticationExtension implements Extension {
   private readonly logger = new Logger(AuthenticationExtension.name);
 
+  // Reference instant for the claimless-rejection grace window. Overridable so a
+  // unit test can drive the pre-/post-grace boundary without wall-clock waits.
+  protected rolloutAt = Date.now();
+
   constructor(
     private tokenService: TokenService,
     private userRepo: UserRepo,
     private pageRepo: PageRepo,
     private readonly spaceMemberRepo: SpaceMemberRepo,
     private readonly pagePermissionRepo: PagePermissionRepo,
+    private readonly apiKeyService: ApiKeyService,
   ) {}
 
   async onAuthenticate(data: onAuthenticatePayload) {
@@ -54,6 +71,36 @@ export class AuthenticationExtension implements Extension {
       throw new UnauthorizedException('Invalid collab token');
     }
 
+    // #501 — fail-closed api-key laundering guard. A collab token minted by an
+    // api-key principal carries principal='api_key' + apiKeyId; re-check the key
+    // on connect so a REVOKED key gets NO new collab connections (a collab token
+    // outlives its 24h, but a revoked key can no longer open fresh ones). An
+    // api-key token missing its apiKeyId is malformed → reject. A claimless token
+    // (no recognized principal) is trusted only DURING the rollout grace window
+    // (a legacy pre-rollout session token, which api keys could never mint);
+    // once the grace has elapsed every valid token must carry the discriminator,
+    // so a claimless one is a bug and is rejected (not silently trusted for 24h).
+    const principal = jwtPayload.principal;
+    if (principal === 'api_key') {
+      if (!jwtPayload.apiKeyId) {
+        throw new UnauthorizedException();
+      }
+      // Row-check via the SHARED validator: throws Unauthorized on a revoked/
+      // expired/disabled key; an infra error propagates (not masked). No new
+      // connection for a dead key.
+      await this.apiKeyService.validate({
+        sub: jwtPayload.sub,
+        workspaceId: jwtPayload.workspaceId,
+        apiKeyId: jwtPayload.apiKeyId,
+        type: JwtType.API_KEY,
+      } as JwtApiKeyPayload);
+    } else if (principal !== 'session') {
+      // Unrecognized/absent discriminator: reject once past the grace window.
+      if (Date.now() - this.rolloutAt >= COLLAB_TOKEN_GRACE_MS) {
+        throw new UnauthorizedException();
+      }
+    }
+
     const userId = jwtPayload.sub;
     const workspaceId = jwtPayload.workspaceId;
 

apps/server/src/collaboration/json-to-text-deterministic.spec.ts

@@ -0,0 +1,116 @@
+import { jsonToText } from './collaboration.util';
+
+// #502 READ contract: `jsonToText(json, { deterministic: true })` — the flat,
+// machine-diffable text rendering behind getPage `format:"text"`. Block-per-line
+// (`\n` separator), inline marks/anchors dropped, hardBreak -> `\n`, and non-text
+// nodes replaced by STABLE placeholders (`[image]`, `[table RxC]`). Output
+// stability across package versions IS the contract, so it is pinned by a
+// snapshot below. The DEFAULT (no options) path is the search-index serializer
+// and MUST be unchanged — asserted separately.
+
+const doc = (...content: any[]) => ({ type: 'doc', content });
+const para = (...content: any[]) => ({ type: 'paragraph', content });
+const text = (t: string, marks?: any[]) =>
+  marks ? { type: 'text', text: t, marks } : { type: 'text', text: t };
+
+describe('jsonToText — default (search index) behavior is unchanged', () => {
+  it('uses the `\\n\\n` block separator and drops non-text nodes to empty', () => {
+    const d = doc(para(text('alpha')), para(text('beta')));
+    expect(jsonToText(d)).toBe('alpha\n\nbeta');
+  });
+
+  it('an image contributes no text in the default (tsvector) mode', () => {
+    const d = doc(para(text('cap')), { type: 'image', attrs: { src: 's' } });
+    // No `[image]` placeholder leaks into the search index.
+    expect(jsonToText(d)).not.toContain('[image]');
+  });
+});
+
+describe('jsonToText — deterministic:true (getPage format:"text")', () => {
+  it('renders one line per block with `\\n` separators, marks dropped', () => {
+    const d = doc(
+      { type: 'heading', attrs: { level: 2 }, content: [text('Title')] },
+      para(
+        text('hello ', [{ type: 'bold' }]),
+        text('world', [{ type: 'italic' }]),
+      ),
+    );
+    expect(jsonToText(d, { deterministic: true })).toBe('Title\nhello world');
+  });
+
+  it('a hardBreak renders as a newline', () => {
+    const d = doc(para(text('a'), { type: 'hardBreak' }, text('b')));
+    expect(jsonToText(d, { deterministic: true })).toBe('a\nb');
+  });
+
+  it('an image node -> the stable `[image]` placeholder', () => {
+    const d = doc(para(text('before')), { type: 'image', attrs: { src: 's' } });
+    expect(jsonToText(d, { deterministic: true })).toBe('before\n[image]');
+  });
+
+  it('a table -> `[table RxC]` (rows x columns) and its cell text is NOT flattened in', () => {
+    const cell = (t: string) => ({
+      type: 'tableCell',
+      content: [para(text(t))],
+    });
+    const row = (...cells: any[]) => ({ type: 'tableRow', content: cells });
+    const table = {
+      type: 'table',
+      content: [
+        row(cell('CELLONE'), cell('CELLTWO'), cell('CELLTHREE')),
+        row(cell('CELLFOUR'), cell('CELLFIVE'), cell('CELLSIX')),
+      ],
+    };
+    const d = doc(para(text('grid:')), table);
+    const out = jsonToText(d, { deterministic: true });
+    expect(out).toBe('grid:\n[table 2x3]');
+    expect(out).not.toContain('CELL'); // cell text is not flattened into the read
+  });
+
+  it('SNAPSHOT: a mixed document renders to a stable, deterministic string', () => {
+    const cell = (t: string) => ({
+      type: 'tableCell',
+      content: [para(text(t))],
+    });
+    const d = doc(
+      { type: 'heading', attrs: { level: 1 }, content: [text('Config')] },
+      para(text('key = ', [{ type: 'bold' }]), text('value')),
+      {
+        type: 'bulletList',
+        content: [
+          { type: 'listItem', content: [para(text('one'))] },
+          { type: 'listItem', content: [para(text('two'))] },
+        ],
+      },
+      { type: 'image', attrs: { src: 's' } },
+      {
+        type: 'table',
+        content: [{ type: 'tableRow', content: [cell('x'), cell('y')] }],
+      },
+    );
+    expect(jsonToText(d, { deterministic: true })).toMatchInlineSnapshot(`
+     "Config
+     key = value
+
+
+     one
+
+     two
+     [image]
+     [table 1x2]"
+    `);
+  });
+
+  it('SCENARIO: a config written as a code block reads back byte-identical (diff empty)', () => {
+    const config =
+      'export TICKET_LIFETIME=$2592000\nservers:\n  - www.internal.host';
+    const d = doc({
+      type: 'codeBlock',
+      attrs: { language: 'yaml' },
+      content: [text(config)],
+    });
+    // The code block is one block; its text (dollars, bare domain, newlines) is
+    // preserved verbatim, so a read-as-text of a stored config diffs empty.
+    expect(jsonToText(d, { deterministic: true })).toBe(config);
+  });
+});

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

@@ -189,10 +189,11 @@ export function stepBudgetWarning(stepNumber: number): string {
 //
 // `system` is the in-scope system prompt; we CONCATENATE so the original
 // persona/context is preserved — a bare `system` override would REPLACE the
-// whole system prompt for the step. `activatedTools` is PER-TURN mutable state
-// owned by the streaming loop (a closure Set grown by loadTools); it is passed
-// in (not module-global, not persisted) so this stays a pure function of its
-// arguments.
+// whole system prompt for the step. `activatedTools` is a closure Set grown by
+// loadTools and owned by the streaming loop; the caller seeds it from and
+// persists it to the chat's metadata across turns (#490), but this function only
+// READS the Set it is handed, so it stays a pure function of its arguments (not
+// module-global).
 //
 // NOTE: at AI SDK v7 the per-step `system` field is renamed to `instructions`.
 // On v6 (`^6.0.134`) `system` is the correct field — adjust when bumping.
@@ -1410,10 +1411,11 @@ export class AiChatService implements OnModuleInit, OnModuleDestroy {
       const baseTools = { ...external.tools, ...docmostTools };
 
       // Deferred tool loading state (#332), scoped to THIS streaming loop:
-      //  - `activatedTools` is per-TURN mutable state — a fresh closure Set created
-      //    per streamText call, NOT module-global and NOT persisted, so a new turn
-      //    starts cold. loadTools.execute adds to it; prepareAgentStep reads it to
-      //    widen `activeTools` on the NEXT step.
+      //  - `activatedTools` is a fresh closure Set per streamText call (not
+      //    module-global), SEEDED from the chat's persisted metadata.activatedTools
+      //    (#490, just below) so activation carries across turns. loadTools.execute
+      //    adds to it; prepareAgentStep reads it to widen `activeTools` on the NEXT
+      //    step; turn end persists it back.
       //  - `validDeferredNames` = every tool that is NOT core (the in-app deferred
       //    tools + ALL external MCP tools), computed from the ACTUAL toolset so an
       //    external tool is loadable by its namespaced name. loadTools rejects any

apps/server/src/core/api-key/api-key.controller.spec.ts

@@ -0,0 +1,193 @@
+import { ForbiddenException, NotFoundException } from '@nestjs/common';
+import { ApiKeyController } from './api-key.controller';
+import {
+  WorkspaceCaslAction,
+  WorkspaceCaslSubject,
+} from '../casl/interfaces/workspace-ability.type';
+
+/**
+ * Authorization contract for the /api-keys management surface.
+ *
+ *  - A token cannot manage tokens (an api_key PRINCIPAL is 403 on every method)
+ *    — GitHub-PAT semantics closing post-revocation laundering.
+ *  - admin (CASL Manage on API) sees/revokes all workspace keys; a member only
+ *    their own.
+ *  - kill-switch OFF -> the surface 404s (looks like the feature does not exist).
+ */
+
+function makeController(over: any = {}) {
+  const apiKeyService = {
+    create: jest.fn().mockResolvedValue({
+      token: 'tok',
+      key: { id: 'k1', name: 'n', expiresAt: null, createdAt: new Date() },
+    }),
+    revoke: jest.fn().mockResolvedValue(undefined),
+    ...(over.apiKeyService ?? {}),
+  };
+  const apiKeyRepo = {
+    findAllInWorkspace: jest.fn().mockResolvedValue([]),
+    findByCreator: jest.fn().mockResolvedValue([]),
+    findById: jest.fn(),
+    ...(over.apiKeyRepo ?? {}),
+  };
+  const workspaceAbility = {
+    createForUser: jest.fn().mockReturnValue({
+      can: (_a: any, _s: any) => over.canManage ?? false,
+    }),
+    ...(over.workspaceAbility ?? {}),
+  };
+  const environmentService = {
+    isApiKeysEnabled: jest.fn().mockReturnValue(over.enabled ?? true),
+    ...(over.environmentService ?? {}),
+  };
+  const auditService = { log: jest.fn() };
+  const controller = new ApiKeyController(
+    apiKeyService as any,
+    apiKeyRepo as any,
+    workspaceAbility as any,
+    environmentService as any,
+    auditService as any,
+  );
+  return {
+    controller,
+    apiKeyService,
+    apiKeyRepo,
+    workspaceAbility,
+    environmentService,
+    auditService,
+  };
+}
+
+const user = { id: 'u-1', workspaceId: 'ws-1' } as any;
+const workspace = { id: 'ws-1' } as any;
+const reqAccess = () => ({ raw: {}, ip: '1.2.3.4', socket: {} }) as any;
+const reqApiKey = () =>
+  ({ raw: { authType: 'api_key', apiKeyId: 'k-self' }, ip: '1.2.3.4', socket: {} }) as any;
+
+describe('ApiKeyController — a token cannot manage tokens', () => {
+  it('403 on create for an api_key principal', async () => {
+    const { controller, apiKeyService } = makeController();
+    await expect(
+      controller.create({ name: 'x' } as any, user, reqApiKey()),
+    ).rejects.toBeInstanceOf(ForbiddenException);
+    expect(apiKeyService.create).not.toHaveBeenCalled();
+  });
+
+  it('403 on list for an api_key principal', async () => {
+    const { controller } = makeController();
+    await expect(
+      controller.list(user, workspace, reqApiKey()),
+    ).rejects.toBeInstanceOf(ForbiddenException);
+  });
+
+  it('403 on revoke for an api_key principal', async () => {
+    const { controller } = makeController();
+    await expect(
+      controller.revoke({ id: 'k1' } as any, user, workspace, reqApiKey()),
+    ).rejects.toBeInstanceOf(ForbiddenException);
+  });
+});
+
+describe('ApiKeyController — kill-switch OFF → 404', () => {
+  it('create/list/revoke all 404 when disabled', async () => {
+    const { controller } = makeController({ enabled: false });
+    await expect(
+      controller.create({ name: 'x' } as any, user, reqAccess()),
+    ).rejects.toBeInstanceOf(NotFoundException);
+    await expect(
+      controller.list(user, workspace, reqAccess()),
+    ).rejects.toBeInstanceOf(NotFoundException);
+    await expect(
+      controller.revoke({ id: 'k1' } as any, user, workspace, reqAccess()),
+    ).rejects.toBeInstanceOf(NotFoundException);
+  });
+});
+
+describe('ApiKeyController — list scoping', () => {
+  it('admin (Manage on API) lists ALL workspace keys', async () => {
+    const { controller, apiKeyRepo } = makeController({ canManage: true });
+    await controller.list(user, workspace, reqAccess());
+    expect(apiKeyRepo.findAllInWorkspace).toHaveBeenCalledWith('ws-1');
+    expect(apiKeyRepo.findByCreator).not.toHaveBeenCalled();
+  });
+
+  it('member lists ONLY their own keys', async () => {
+    const { controller, apiKeyRepo } = makeController({ canManage: false });
+    await controller.list(user, workspace, reqAccess());
+    expect(apiKeyRepo.findByCreator).toHaveBeenCalledWith('u-1', 'ws-1');
+    expect(apiKeyRepo.findAllInWorkspace).not.toHaveBeenCalled();
+  });
+});
+
+describe('ApiKeyController — revoke scoping', () => {
+  it("member cannot revoke another user's key (403)", async () => {
+    const { controller, apiKeyRepo, apiKeyService } = makeController({
+      canManage: false,
+    });
+    apiKeyRepo.findById.mockResolvedValue({
+      id: 'k1',
+      creatorId: 'someone-else',
+      workspaceId: 'ws-1',
+    });
+    await expect(
+      controller.revoke({ id: 'k1' } as any, user, workspace, reqAccess()),
+    ).rejects.toBeInstanceOf(ForbiddenException);
+    expect(apiKeyService.revoke).not.toHaveBeenCalled();
+  });
+
+  it('member CAN revoke their own key', async () => {
+    const { controller, apiKeyRepo, apiKeyService } = makeController({
+      canManage: false,
+    });
+    apiKeyRepo.findById.mockResolvedValue({
+      id: 'k1',
+      creatorId: 'u-1',
+      workspaceId: 'ws-1',
+    });
+    await controller.revoke({ id: 'k1' } as any, user, workspace, reqAccess());
+    expect(apiKeyService.revoke).toHaveBeenCalledWith('k1', 'ws-1');
+  });
+
+  it("admin CAN revoke another user's key", async () => {
+    const { controller, apiKeyRepo, apiKeyService } = makeController({
+      canManage: true,
+    });
+    apiKeyRepo.findById.mockResolvedValue({
+      id: 'k1',
+      creatorId: 'someone-else',
+      workspaceId: 'ws-1',
+    });
+    await controller.revoke({ id: 'k1' } as any, user, workspace, reqAccess());
+    expect(apiKeyService.revoke).toHaveBeenCalledWith('k1', 'ws-1');
+  });
+
+  it('404 when the key does not exist', async () => {
+    const { controller, apiKeyRepo } = makeController({ canManage: true });
+    apiKeyRepo.findById.mockResolvedValue(undefined);
+    await expect(
+      controller.revoke({ id: 'k1' } as any, user, workspace, reqAccess()),
+    ).rejects.toBeInstanceOf(NotFoundException);
+  });
+});
+
+describe('ApiKeyController — create emits audit + returns token once', () => {
+  it('logs API_KEY_CREATED and returns the token + computed expiry', async () => {
+    const { controller, auditService } = makeController();
+    const res = await controller.create(
+      { name: 'ci' } as any,
+      user,
+      reqAccess(),
+    );
+    expect(res.token).toBe('tok');
+    expect(res.apiKey).toMatchObject({ id: 'k1', name: 'n' });
+    expect(auditService.log).toHaveBeenCalledWith(
+      expect.objectContaining({ event: 'api_key.created' }),
+    );
+  });
+});
+
+// Sanity: the CASL subject used is the workspace API subject.
+it('uses WorkspaceCaslSubject.API with the Manage action', () => {
+  expect(WorkspaceCaslSubject.API).toBe('api_key');
+  expect(WorkspaceCaslAction.Manage).toBeDefined();
+});

apps/server/src/core/api-key/api-key.controller.ts

@@ -0,0 +1,201 @@
+import {
+  Body,
+  Controller,
+  ForbiddenException,
+  HttpCode,
+  HttpStatus,
+  Inject,
+  Logger,
+  NotFoundException,
+  Post,
+  Req,
+  UseGuards,
+} from '@nestjs/common';
+import { Throttle } from '@nestjs/throttler';
+import { FastifyRequest } from 'fastify';
+import { ApiKeyService } from './api-key.service';
+import { ApiKeyRepo } from '@docmost/db/repos/api-key/api-key.repo';
+import { CreateApiKeyDto } from './dto/create-api-key.dto';
+import { RevokeApiKeyDto } from './dto/revoke-api-key.dto';
+import { AuthUser } from '../../common/decorators/auth-user.decorator';
+import { AuthWorkspace } from '../../common/decorators/auth-workspace.decorator';
+import { JwtAuthGuard } from '../../common/guards/jwt-auth.guard';
+import { User, Workspace } from '@docmost/db/types/entity.types';
+import WorkspaceAbilityFactory from '../casl/abilities/workspace-ability.factory';
+import {
+  WorkspaceCaslAction,
+  WorkspaceCaslSubject,
+} from '../casl/interfaces/workspace-ability.type';
+import { AuditEvent, AuditResource } from '../../common/events/audit-events';
+import {
+  AUDIT_SERVICE,
+  IAuditService,
+} from '../../integrations/audit/audit.service';
+import { EnvironmentService } from '../../integrations/environment/environment.service';
+import { UserThrottlerGuard } from '../../integrations/throttle/user-throttler.guard';
+import { AUTH_THROTTLER } from '../../integrations/throttle/throttler-names';
+
+@UseGuards(JwtAuthGuard)
+@Controller('api-keys')
+export class ApiKeyController {
+  private readonly logger = new Logger(ApiKeyController.name);
+
+  constructor(
+    private readonly apiKeyService: ApiKeyService,
+    private readonly apiKeyRepo: ApiKeyRepo,
+    private readonly workspaceAbility: WorkspaceAbilityFactory,
+    private readonly environmentService: EnvironmentService,
+    @Inject(AUDIT_SERVICE) private readonly auditService: IAuditService,
+  ) {}
+
+  // Kill-switch OFF: the issuance surface disappears entirely (404), not a 403 —
+  // it must look like the feature does not exist.
+  private assertEnabled(): void {
+    if (!this.environmentService.isApiKeysEnabled()) {
+      throw new NotFoundException();
+    }
+  }
+
+  // A token cannot manage tokens (GitHub-PAT semantics): an api-key principal is
+  // refused on the management surface, so a leaked key cannot mint a replacement
+  // or revoke the keys that would lock it out (closes post-revocation laundering).
+  private rejectApiKeyPrincipal(req: FastifyRequest): void {
+    if ((req.raw as { authType?: string }).authType === 'api_key') {
+      throw new ForbiddenException('API keys cannot manage API keys');
+    }
+  }
+
+  private clientIp(req: FastifyRequest): string {
+    return req.ip ?? req.socket?.remoteAddress ?? 'unknown';
+  }
+
+  @HttpCode(HttpStatus.OK)
+  @UseGuards(JwtAuthGuard, UserThrottlerGuard)
+  @Throttle({ [AUTH_THROTTLER]: { limit: 10, ttl: 60_000 } })
+  @Post('create')
+  async create(
+    @Body() dto: CreateApiKeyDto,
+    @AuthUser() user: User,
+    @Req() req: FastifyRequest,
+  ) {
+    this.assertEnabled();
+    this.rejectApiKeyPrincipal(req);
+
+    // undefined -> service default (1 year); null -> unlimited; string -> Date.
+    const expiresAt =
+      dto.expiresAt === undefined
+        ? undefined
+        : dto.expiresAt === null
+          ? null
+          : new Date(dto.expiresAt);
+
+    const { token, key } = await this.apiKeyService.create(
+      user,
+      dto.name,
+      expiresAt,
+    );
+
+    this.auditService.log({
+      event: AuditEvent.API_KEY_CREATED,
+      resourceType: AuditResource.API_KEY,
+      resourceId: key.id,
+    });
+    // The durable trail lives in container logs (AUDIT_SERVICE is a Noop in this
+    // build). No token material — the JWT is only ever returned in the response.
+    this.logger.log(
+      `API key created: id=${key.id} name=${JSON.stringify(
+        key.name,
+      )} actor=${user.id} expiresAt=${
+        key.expiresAt ? new Date(key.expiresAt).toISOString() : 'never'
+      } ip=${this.clientIp(req)}`,
+    );
+
+    // Return the token ONCE (never retrievable again) and the computed expiry so
+    // the caller/UI can surface "expires <date>" (the year-default time-bomb
+    // early-warning).
+    return {
+      token,
+      apiKey: {
+        id: key.id,
+        name: key.name,
+        expiresAt: key.expiresAt,
+        createdAt: key.createdAt,
+      },
+    };
+  }
+
+  @HttpCode(HttpStatus.OK)
+  @Post('list')
+  async list(
+    @AuthUser() user: User,
+    @AuthWorkspace() workspace: Workspace,
+    @Req() req: FastifyRequest,
+  ) {
+    this.assertEnabled();
+    this.rejectApiKeyPrincipal(req);
+
+    const ability = this.workspaceAbility.createForUser(user, workspace);
+    // Admin (CASL Manage on API): every key in the workspace, attributed to its
+    // creator (closes "a leaked key of a departed employee is invisible"). A
+    // member sees only their own.
+    const keys = ability.can(
+      WorkspaceCaslAction.Manage,
+      WorkspaceCaslSubject.API,
+    )
+      ? await this.apiKeyRepo.findAllInWorkspace(workspace.id)
+      : await this.apiKeyRepo.findByCreator(user.id, workspace.id);
+
+    return keys.map((k) => ({
+      id: k.id,
+      name: k.name,
+      expiresAt: k.expiresAt,
+      lastUsedAt: k.lastUsedAt,
+      createdAt: k.createdAt,
+      creator: k.creator,
+    }));
+  }
+
+  @HttpCode(HttpStatus.OK)
+  @Post('revoke')
+  async revoke(
+    @Body() dto: RevokeApiKeyDto,
+    @AuthUser() user: User,
+    @AuthWorkspace() workspace: Workspace,
+    @Req() req: FastifyRequest,
+  ) {
+    this.assertEnabled();
+    this.rejectApiKeyPrincipal(req);
+
+    const key = await this.apiKeyRepo.findById(dto.id, workspace.id);
+    // Uniform 404 for a missing/already-revoked key regardless of who asks — no
+    // existence oracle for keys the caller may not own.
+    if (!key) {
+      throw new NotFoundException();
+    }
+
+    const ability = this.workspaceAbility.createForUser(user, workspace);
+    const canManageAll = ability.can(
+      WorkspaceCaslAction.Manage,
+      WorkspaceCaslSubject.API,
+    );
+    // Admin may revoke any key in the workspace; a member only their own.
+    if (!canManageAll && key.creatorId !== user.id) {
+      throw new ForbiddenException();
+    }
+
+    await this.apiKeyService.revoke(key.id, workspace.id);
+
+    this.auditService.log({
+      event: AuditEvent.API_KEY_DELETED,
+      resourceType: AuditResource.API_KEY,
+      resourceId: key.id,
+    });
+    this.logger.log(
+      `API key revoked: id=${key.id} name=${JSON.stringify(
+        key.name,
+      )} actor=${user.id} ip=${this.clientIp(req)}`,
+    );
+
+    return { success: true };
+  }
+}

apps/server/src/core/api-key/api-key.module.ts

@@ -0,0 +1,19 @@
+import { Module } from '@nestjs/common';
+import { ApiKeyService } from './api-key.service';
+import { ApiKeyController } from './api-key.controller';
+import { TokenModule } from '../auth/token.module';
+
+// Core (non-EE) API-key feature: issuance REST endpoints + the shared validator
+// consumed by jwt.strategy (REST) and McpService (the /mcp Bearer router).
+// DatabaseModule (global) provides ApiKeyRepo/UserRepo/WorkspaceRepo; CaslModule
+// (global) provides WorkspaceAbilityFactory; TokenModule provides TokenService
+// (the no-exp api-key signer). ApiKeyService is exported so AuthModule (for
+// jwt.strategy) and McpModule (for the /mcp router) can inject it directly,
+// replacing the absent EE `ee/api-key` dynamic require.
+@Module({
+  imports: [TokenModule],
+  controllers: [ApiKeyController],
+  providers: [ApiKeyService],
+  exports: [ApiKeyService],
+})
+export class ApiKeyModule {}

apps/server/src/core/api-key/api-key.service.spec.ts

@@ -0,0 +1,299 @@
+import { UnauthorizedException } from '@nestjs/common';
+import { ApiKeyService } from './api-key.service';
+import { JwtType } from '../auth/dto/jwt-payload';
+
+/**
+ * Security contract for ApiKeyService.validate — the single validator shared by
+ * jwt.strategy (REST) and the /mcp Bearer router.
+ *
+ * Invariants under test:
+ *  - Anti-enumeration: every DEFINITE deny (missing/revoked/expired row, disabled
+ *    user, workspace mismatch, kill-switch off) throws the SAME bare
+ *    UnauthorizedException — an agent cannot distinguish expired from revoked.
+ *  - deny-on-decision / 5xx-on-infra: an UNEXPECTED (infra) error PROPAGATES as
+ *    itself (→ 5xx), never masked as a 401.
+ *  - Expiry is read from the ROW, never a JWT exp claim.
+ *  - No validate cache (each call re-reads the row → immediate revocation).
+ */
+
+const APP_SECRET = 'secret';
+
+function makeDeps(over: Partial<Record<string, any>> = {}) {
+  const apiKeyRepo = {
+    findById: jest.fn(),
+    insert: jest.fn(),
+    softDelete: jest.fn(),
+    touchLastUsed: jest.fn().mockResolvedValue(undefined),
+    ...(over.apiKeyRepo ?? {}),
+  };
+  const userRepo = {
+    findById: jest.fn(),
+    ...(over.userRepo ?? {}),
+  };
+  const workspaceRepo = {
+    findById: jest.fn().mockResolvedValue({ id: 'ws-1' }),
+    ...(over.workspaceRepo ?? {}),
+  };
+  const tokenService = {
+    generateApiToken: jest.fn().mockResolvedValue('minted.jwt.token'),
+    ...(over.tokenService ?? {}),
+  };
+  const environmentService = {
+    isApiKeysEnabled: jest.fn().mockReturnValue(true),
+    getApiKeysEnabledRaw: jest.fn().mockReturnValue(undefined),
+    getAppSecret: jest.fn().mockReturnValue(APP_SECRET),
+    ...(over.environmentService ?? {}),
+  };
+  const service = new (ApiKeyService as unknown as new (...a: any[]) => ApiKeyService)(
+    apiKeyRepo,
+    userRepo,
+    workspaceRepo,
+    tokenService,
+    environmentService,
+  );
+  return { service, apiKeyRepo, userRepo, workspaceRepo, tokenService, environmentService };
+}
+
+const payload = (over: Record<string, any> = {}) => ({
+  sub: 'u-1',
+  workspaceId: 'ws-1',
+  apiKeyId: 'key-1',
+  type: JwtType.API_KEY,
+  ...over,
+});
+
+const activeRow = (over: Record<string, any> = {}) => ({
+  id: 'key-1',
+  name: 'k',
+  creatorId: 'u-1',
+  workspaceId: 'ws-1',
+  expiresAt: null,
+  lastUsedAt: null,
+  deletedAt: null,
+  ...over,
+});
+
+const activeUser = (over: Record<string, any> = {}) => ({
+  id: 'u-1',
+  workspaceId: 'ws-1',
+  deactivatedAt: null,
+  deletedAt: null,
+  isAgent: false,
+  ...over,
+});
+
+describe('ApiKeyService.validate', () => {
+  it('returns { user, workspace } for a valid active key', async () => {
+    const { service, apiKeyRepo, userRepo } = makeDeps();
+    apiKeyRepo.findById.mockResolvedValue(activeRow());
+    userRepo.findById.mockResolvedValue(activeUser());
+
+    const res = await service.validate(payload() as any);
+
+    expect(res.user).toMatchObject({ id: 'u-1' });
+    expect(res.workspace).toMatchObject({ id: 'ws-1' });
+    // Loads isAgent so downstream provenance does not silently degrade.
+    expect(userRepo.findById).toHaveBeenCalledWith('u-1', 'ws-1', {
+      includeIsAgent: true,
+    });
+  });
+
+  // --- Anti-enumeration: every deny is the SAME bare 401 -------------------
+  const denyCases: Array<[string, (d: ReturnType<typeof makeDeps>) => void]> = [
+    [
+      'missing/orphaned row',
+      (d) => d.apiKeyRepo.findById.mockResolvedValue(undefined),
+    ],
+    [
+      'revoked (soft-deleted → findById returns undefined)',
+      (d) => d.apiKeyRepo.findById.mockResolvedValue(undefined),
+    ],
+    [
+      'expired (expires_at in the past)',
+      (d) => {
+        d.apiKeyRepo.findById.mockResolvedValue(
+          activeRow({ expiresAt: new Date(Date.now() - 1000) }),
+        );
+        d.userRepo.findById.mockResolvedValue(activeUser());
+      },
+    ],
+    [
+      'disabled user',
+      (d) => {
+        d.apiKeyRepo.findById.mockResolvedValue(activeRow());
+        d.userRepo.findById.mockResolvedValue(
+          activeUser({ deactivatedAt: new Date() }),
+        );
+      },
+    ],
+    [
+      'user not found',
+      (d) => {
+        d.apiKeyRepo.findById.mockResolvedValue(activeRow());
+        d.userRepo.findById.mockResolvedValue(undefined);
+      },
+    ],
+    [
+      'creator/sub mismatch',
+      (d) => {
+        d.apiKeyRepo.findById.mockResolvedValue(activeRow({ creatorId: 'other' }));
+        d.userRepo.findById.mockResolvedValue(activeUser());
+      },
+    ],
+    [
+      'workspace row missing',
+      (d) => {
+        d.apiKeyRepo.findById.mockResolvedValue(activeRow());
+        d.userRepo.findById.mockResolvedValue(activeUser());
+        d.workspaceRepo.findById.mockResolvedValue(undefined);
+      },
+    ],
+    [
+      'kill-switch OFF',
+      (d) => d.environmentService.isApiKeysEnabled.mockReturnValue(false),
+    ],
+    [
+      'malformed payload (missing apiKeyId)',
+      () => undefined,
+    ],
+  ];
+
+  it.each(denyCases)(
+    'throws a bare UnauthorizedException with NO message for: %s',
+    async (label, arrange) => {
+      const deps = makeDeps();
+      arrange(deps);
+      const p =
+        label === 'malformed payload (missing apiKeyId)'
+          ? (payload({ apiKeyId: undefined }) as any)
+          : (payload() as any);
+
+      const err = await deps.service.validate(p).catch((e) => e);
+      expect(err).toBeInstanceOf(UnauthorizedException);
+      // Anti-enumeration: identical, class-less message for every failure mode.
+      expect(err.message).toBe('Unauthorized');
+    },
+  );
+
+  it('kill-switch OFF denies BEFORE any DB read', async () => {
+    const { service, apiKeyRepo, environmentService } = makeDeps();
+    environmentService.isApiKeysEnabled.mockReturnValue(false);
+
+    await expect(service.validate(payload() as any)).rejects.toBeInstanceOf(
+      UnauthorizedException,
+    );
+    expect(apiKeyRepo.findById).not.toHaveBeenCalled();
+  });
+
+  // --- Infra error propagates (5xx), NOT masked as 401 ---------------------
+  it('PROPAGATES an infra (DB) error instead of masking it as 401', async () => {
+    const { service, apiKeyRepo } = makeDeps();
+    const boom = new Error('connection terminated');
+    apiKeyRepo.findById.mockRejectedValue(boom);
+
+    await expect(service.validate(payload() as any)).rejects.toBe(boom);
+  });
+
+  // --- No cache: revocation is immediate on the next call ------------------
+  it('re-reads the row on every call (no validate cache → immediate revocation)', async () => {
+    const { service, apiKeyRepo, userRepo } = makeDeps();
+    apiKeyRepo.findById.mockResolvedValue(activeRow());
+    userRepo.findById.mockResolvedValue(activeUser());
+    await service.validate(payload() as any);
+
+    // Now the key is revoked (row invisible) — the very next call denies.
+    apiKeyRepo.findById.mockResolvedValue(undefined);
+    await expect(service.validate(payload() as any)).rejects.toBeInstanceOf(
+      UnauthorizedException,
+    );
+    expect(apiKeyRepo.findById).toHaveBeenCalledTimes(2);
+  });
+
+  // --- last_used_at is throttled + fire-and-forget -------------------------
+  it('touches last_used_at when stale and skips when fresh', async () => {
+    const { service, apiKeyRepo, userRepo } = makeDeps();
+    userRepo.findById.mockResolvedValue(activeUser());
+
+    // Stale (never used) -> touch.
+    apiKeyRepo.findById.mockResolvedValue(activeRow({ lastUsedAt: null }));
+    await service.validate(payload() as any);
+    expect(apiKeyRepo.touchLastUsed).toHaveBeenCalledTimes(1);
+
+    // Fresh (used 1 minute ago) -> skip.
+    apiKeyRepo.touchLastUsed.mockClear();
+    apiKeyRepo.findById.mockResolvedValue(
+      activeRow({ lastUsedAt: new Date(Date.now() - 60_000) }),
+    );
+    await service.validate(payload() as any);
+    expect(apiKeyRepo.touchLastUsed).not.toHaveBeenCalled();
+  });
+
+  it('a failing last_used_at touch never fails the request', async () => {
+    const { service, apiKeyRepo, userRepo } = makeDeps();
+    apiKeyRepo.findById.mockResolvedValue(activeRow({ lastUsedAt: null }));
+    userRepo.findById.mockResolvedValue(activeUser());
+    apiKeyRepo.touchLastUsed.mockRejectedValue(new Error('write failed'));
+
+    await expect(service.validate(payload() as any)).resolves.toMatchObject({
+      user: { id: 'u-1' },
+    });
+  });
+});
+
+describe('ApiKeyService.create (mint-then-insert, no exp)', () => {
+  it('mints the JWT BEFORE inserting the row and returns the token once', async () => {
+    const { service, apiKeyRepo, tokenService } = makeDeps();
+    const order: string[] = [];
+    tokenService.generateApiToken.mockImplementation(async () => {
+      order.push('mint');
+      return 'tok';
+    });
+    apiKeyRepo.insert.mockImplementation(async (row: any) => {
+      order.push('insert');
+      return { ...row, createdAt: new Date() };
+    });
+
+    const user = { id: 'u-1', workspaceId: 'ws-1' } as any;
+    const res = await service.create(user, 'my key');
+
+    expect(order).toEqual(['mint', 'insert']);
+    expect(res.token).toBe('tok');
+    // The id is generated before minting and reused for the row.
+    const mintArg = tokenService.generateApiToken.mock.calls[0][0];
+    const insertArg = apiKeyRepo.insert.mock.calls[0][0];
+    expect(mintArg.apiKeyId).toBe(insertArg.id);
+  });
+
+  it('applies the 1-year default when expiresAt is undefined', async () => {
+    const { service, apiKeyRepo } = makeDeps();
+    apiKeyRepo.insert.mockImplementation(async (row: any) => row);
+    const user = { id: 'u-1', workspaceId: 'ws-1' } as any;
+
+    await service.create(user, 'k');
+
+    const insertArg = apiKeyRepo.insert.mock.calls[0][0];
+    const days =
+      (insertArg.expiresAt.getTime() - Date.now()) / (24 * 60 * 60 * 1000);
+    expect(days).toBeGreaterThan(364);
+    expect(days).toBeLessThan(367);
+  });
+
+  it('honors an explicit null (unlimited)', async () => {
+    const { service, apiKeyRepo } = makeDeps();
+    apiKeyRepo.insert.mockImplementation(async (row: any) => row);
+    const user = { id: 'u-1', workspaceId: 'ws-1' } as any;
+
+    await service.create(user, 'k', null);
+
+    expect(apiKeyRepo.insert.mock.calls[0][0].expiresAt).toBeNull();
+  });
+
+  it('does NOT insert a row when minting fails (mint-then-insert → inert)', async () => {
+    const { service, apiKeyRepo, tokenService } = makeDeps();
+    tokenService.generateApiToken.mockRejectedValue(new Error('mint failed'));
+    const user = { id: 'u-1', workspaceId: 'ws-1' } as any;
+
+    await expect(service.create(user, 'k')).rejects.toThrow('mint failed');
+    expect(apiKeyRepo.insert).not.toHaveBeenCalled();
+  });
+});

apps/server/src/core/api-key/api-key.service.ts

@@ -0,0 +1,191 @@
+import {
+  Injectable,
+  Logger,
+  OnModuleInit,
+  UnauthorizedException,
+} from '@nestjs/common';
+import { v7 as uuid7 } from 'uuid';
+import { ApiKeyRepo } from '@docmost/db/repos/api-key/api-key.repo';
+import { UserRepo } from '@docmost/db/repos/user/user.repo';
+import { WorkspaceRepo } from '@docmost/db/repos/workspace/workspace.repo';
+import { TokenService } from '../auth/services/token.service';
+import { EnvironmentService } from '../../integrations/environment/environment.service';
+import { JwtApiKeyPayload } from '../auth/dto/jwt-payload';
+import { ApiKey, User, Workspace } from '@docmost/db/types/entity.types';
+import { isUserDisabled } from '../../common/helpers';
+
+// Default lifetime for a new key when the caller does not specify one: 1 year.
+// The owner runs a homelab where agents live for years; forcing rotation is
+// operational pain, so an explicit `null` (unlimited) is also allowed.
+const DEFAULT_LIFETIME_MS = 365 * 24 * 60 * 60 * 1000;
+
+// last_used_at is a best-effort forensics stamp, not an access record; we only
+// refresh it when it is older than this to avoid a write on every request. The
+// 1h resolution is a deliberate constant (forensics granularity, not accounting).
+const LAST_USED_THROTTLE_MS = 60 * 60 * 1000;
+
+/**
+ * Core API-key lifecycle service. Owns minting (create), the single validator
+ * shared by BOTH the REST jwt.strategy path and the /mcp Bearer path (validate),
+ * and revocation (revoke). The `api_keys` ROW is the sole source of truth for a
+ * key's lifetime and revocation — never the JWT, which carries no `exp` claim.
+ */
+@Injectable()
+export class ApiKeyService implements OnModuleInit {
+  private readonly logger = new Logger(ApiKeyService.name);
+
+  constructor(
+    private readonly apiKeyRepo: ApiKeyRepo,
+    private readonly userRepo: UserRepo,
+    private readonly workspaceRepo: WorkspaceRepo,
+    private readonly tokenService: TokenService,
+    private readonly environmentService: EnvironmentService,
+  ) {}
+
+  onModuleInit() {
+    // Boot log so the kill-switch state after each deploy is verifiable in logs.
+    const enabled = this.environmentService.isApiKeysEnabled();
+    const raw = this.environmentService.getApiKeysEnabledRaw();
+    this.logger.log(
+      `API keys: ${enabled ? 'ENABLED' : 'DISABLED'} (API_KEYS_ENABLED=${
+        raw ?? 'unset'
+      })`,
+    );
+  }
+
+  /**
+   * Mint a new key for `user`. mint-then-insert ordering (R1):
+   *   1. generate the id first — it must be in the JWT payload before the row.
+   *   2. mint the JWT (no `exp` claim). A mint failure aborts before any row is
+   *      written (inert), so a half-created key cannot exist.
+   *   3. insert the row last. A lost response leaves an orphaned row that is
+   *      visible in `list` and self-heals (the user revokes it).
+   * The token is returned ONCE and never stored — the JWT is self-contained, so
+   * no token material lives in the table.
+   *
+   * `expiresAt`: `undefined` -> default 1 year; `null` -> unlimited (explicit);
+   * a Date -> that instant (a past date is rejected at the DTO layer).
+   */
+  async create(
+    user: User,
+    name: string,
+    expiresAt?: Date | null,
+  ): Promise<{ token: string; key: ApiKey }> {
+    const resolvedExpiresAt =
+      expiresAt === undefined
+        ? new Date(Date.now() + DEFAULT_LIFETIME_MS)
+        : expiresAt;
+
+    const apiKeyId = uuid7();
+
+    const token = await this.tokenService.generateApiToken({
+      apiKeyId,
+      user,
+      workspaceId: user.workspaceId,
+    });
+
+    const key = await this.apiKeyRepo.insert({
+      id: apiKeyId,
+      name,
+      creatorId: user.id,
+      workspaceId: user.workspaceId,
+      expiresAt: resolvedExpiresAt,
+    });
+
+    return { token, key };
+  }
+
+  /**
+   * The single validator for an api-key principal, shared by jwt.strategy and the
+   * /mcp Bearer router. Returns `{ user, workspace }` (the same shape the access
+   * path returns) so the AuthUser/AuthWorkspace decorators and MCP identity work
+   * unchanged.
+   *
+   * Failure semantics (R4, anti-enumeration): a DEFINITE negative fact — feature
+   * disabled, missing/revoked/expired row, workspace mismatch, disabled user —
+   * throws a bare `UnauthorizedException` (a single generic 401 for every case;
+   * an agent cannot distinguish expired from revoked, and its reaction is
+   * identical). An UNEXPECTED (infra) error is NOT caught here: it propagates so
+   * the surface returns 5xx, never a masked 401 (deny-on-decision / 5xx-on-infra).
+   * There is NO validate cache: it is 2–3 PK lookups (~1ms), two orders of
+   * magnitude cheaper than the bcrypt it replaces; a cache would only add a
+   * Date-serialization trap and a revocation lag. Revocation is immediate.
+   */
+  async validate(
+    payload: JwtApiKeyPayload,
+  ): Promise<{ user: User; workspace: Workspace }> {
+    // Kill-switch OFF: deny unconditionally (same generic 401). Note the
+    // endpoints additionally 404 at the controller; here we deny the token.
+    if (!this.environmentService.isApiKeysEnabled()) {
+      throw new UnauthorizedException();
+    }
+
+    if (!payload?.apiKeyId || !payload?.sub || !payload?.workspaceId) {
+      throw new UnauthorizedException();
+    }
+
+    const row = await this.apiKeyRepo.findById(
+      payload.apiKeyId,
+      payload.workspaceId,
+    );
+    // Absent row = revoked (soft-deleted, invisible to findById), orphaned
+    // (creator/workspace cascade-deleted), or never existed. All terminal deny.
+    if (!row) {
+      throw new UnauthorizedException();
+    }
+
+    // Expiry is read from the ROW, never an `exp` JWT claim.
+    if (row.expiresAt && row.expiresAt.getTime() <= Date.now()) {
+      throw new UnauthorizedException();
+    }
+
+    const user = await this.userRepo.findById(
+      payload.sub,
+      payload.workspaceId,
+      { includeIsAgent: true },
+    );
+    if (!user || isUserDisabled(user)) {
+      throw new UnauthorizedException();
+    }
+
+    // The key acts only as its creator (defence in depth against a token whose
+    // signed `sub` ever drifted from the row's owner).
+    if (row.creatorId !== user.id) {
+      throw new UnauthorizedException();
+    }
+
+    const workspace = await this.workspaceRepo.findById(payload.workspaceId);
+    if (!workspace) {
+      throw new UnauthorizedException();
+    }
+
+    // Best-effort, throttled, fire-and-forget forensics stamp AFTER all checks.
+    this.touchLastUsed(row);
+
+    return { user, workspace };
+  }
+
+  /**
+   * Revoke (soft-delete) a key. Authorization/ownership is decided by the caller
+   * (the controller, via CASL); this only performs the terminal write. Idempotent:
+   * a second revoke is a no-op (the row is already invisible).
+   */
+  async revoke(id: string, workspaceId: string): Promise<void> {
+    await this.apiKeyRepo.softDelete(id, workspaceId);
+  }
+
+  // Throttled best-effort last_used_at bump: skip if it was touched within the
+  // window; otherwise fire-and-forget so a stamp write never fails or slows the
+  // request (mirrors SessionActivityService.trackActivity).
+  private touchLastUsed(row: ApiKey): void {
+    const last = row.lastUsedAt ? new Date(row.lastUsedAt).getTime() : 0;
+    if (Date.now() - last < LAST_USED_THROTTLE_MS) return;
+    void this.apiKeyRepo.touchLastUsed(row.id).catch((err) => {
+      this.logger.warn(
+        `Failed to update api_key last_used_at for ${row.id}: ${
+          (err as Error)?.message ?? err
+        }`,
+      );
+    });
+  }
+}

apps/server/src/core/api-key/dto/create-api-key.dto.ts

@@ -0,0 +1,51 @@
+import {
+  IsDateString,
+  IsNotEmpty,
+  IsOptional,
+  IsString,
+  MaxLength,
+  registerDecorator,
+  ValidationOptions,
+} from 'class-validator';
+
+/**
+ * `expiresAt` must be strictly in the future. Skips validation for `null`
+ * (explicit "unlimited") and `undefined` (server applies the 1-year default),
+ * so only an actually-supplied date is range-checked. Rejecting a PAST date at
+ * the DTO layer means a caller cannot mint an already-dead key.
+ */
+function IsFutureDateString(options?: ValidationOptions) {
+  return function (object: object, propertyName: string) {
+    registerDecorator({
+      name: 'isFutureDateString',
+      target: object.constructor,
+      propertyName,
+      options: {
+        message: 'expiresAt must be a date in the future',
+        ...options,
+      },
+      validator: {
+        validate(value: unknown) {
+          if (value === null || value === undefined) return true;
+          if (typeof value !== 'string') return false;
+          const t = Date.parse(value);
+          return !Number.isNaN(t) && t > Date.now();
+        },
+      },
+    });
+  };
+}
+
+export class CreateApiKeyDto {
+  @IsString()
+  @IsNotEmpty()
+  @MaxLength(255)
+  name: string;
+
+  // undefined -> default 1 year (applied server-side); null -> unlimited
+  // (explicit); an ISO date string -> that instant, which must be in the future.
+  @IsOptional()
+  @IsDateString()
+  @IsFutureDateString()
+  expiresAt?: string | null;
+}

apps/server/src/core/api-key/dto/revoke-api-key.dto.ts

@@ -0,0 +1,6 @@
+import { IsUUID } from 'class-validator';
+
+export class RevokeApiKeyDto {
+  @IsUUID()
+  id: string;
+}

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

@@ -20,3 +20,71 @@ describe('AuthController', () => {
     expect(controller).toBeDefined();
   });
 });
+
+// The collab-token handler is the ARM-SEAM of the #501 anti-laundering defense:
+// it derives the api-key origin args ({ apiKeyId }) from the SIGNED-derived
+// `req.raw` fields (stamped by jwt.strategy) and threads them into the collab
+// token mint, forcing principal='api_key' so a later key revoke rejects NEW
+// collab connections. A regression here (reading `body`, dropping `apiKeyId`,
+// or inverting the ternary) would silently mint api-key requests as
+// principal='session' and reopen the laundering hole with a green suite. These
+// tests pin the EXACT args the controller passes to authService.getCollabToken.
+describe('AuthController.collabToken arms the api-key origin (#501)', () => {
+  let controller: AuthController;
+  let getCollabToken: jest.Mock;
+
+  const user = { id: 'u-1', workspaceId: 'ws-1' } as any;
+  const workspace = { id: 'ws-1' } as any;
+
+  beforeEach(() => {
+    getCollabToken = jest.fn().mockResolvedValue({ token: 'ct' });
+    controller = new AuthController(
+      { getCollabToken } as any, // authService
+      {} as any, // sessionService
+      {} as any, // environmentService
+      {} as any, // moduleRef
+      {} as any, // auditService
+    );
+  });
+
+  it('threads { apiKeyId } when req.raw marks an api_key principal (ARMED)', async () => {
+    const req = { raw: { authType: 'api_key', apiKeyId: 'k-1' } } as any;
+
+    await controller.collabToken(user, workspace, req);
+
+    expect(getCollabToken).toHaveBeenCalledTimes(1);
+    expect(getCollabToken).toHaveBeenCalledWith(user, 'ws-1', {
+      apiKeyId: 'k-1',
+    });
+  });
+
+  it('passes undefined for a normal session request (NOT armed)', async () => {
+    const req = { raw: {} } as any;
+
+    await controller.collabToken(user, workspace, req);
+
+    expect(getCollabToken).toHaveBeenCalledTimes(1);
+    expect(getCollabToken).toHaveBeenCalledWith(user, 'ws-1', undefined);
+  });
+
+  it('does NOT arm when api_key authType lacks an apiKeyId', async () => {
+    const req = { raw: { authType: 'api_key' } } as any;
+
+    await controller.collabToken(user, workspace, req);
+
+    expect(getCollabToken).toHaveBeenCalledWith(user, 'ws-1', undefined);
+  });
+
+  it('reads the SIGNED req.raw, never a spoofable client body', async () => {
+    // A client-supplied body claiming api_key must be ignored: only the
+    // jwt.strategy-stamped req.raw can arm the api-key origin.
+    const req = {
+      raw: {},
+      body: { authType: 'api_key', apiKeyId: 'attacker' },
+    } as any;
+
+    await controller.collabToken(user, workspace, req);
+
+    expect(getCollabToken).toHaveBeenCalledWith(user, 'ws-1', undefined);
+  });
+});

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

@@ -207,8 +207,20 @@ export class AuthController {
   async collabToken(
     @AuthUser() user: User,
     @AuthWorkspace() workspace: Workspace,
+    @Req() req: FastifyRequest,
   ) {
-    return this.authService.getCollabToken(user, workspace.id);
+    // Thread the api-key origin (#501): when the requester authenticated with an
+    // api key (jwt.strategy stamped req.raw.authType/apiKeyId), the minted collab
+    // token carries principal='api_key' + apiKeyId so a later revoke of the key
+    // rejects NEW collab connections. A normal session request mints a
+    // principal='session' token. Reading the SIGNED-derived req.raw fields (never
+    // a client body) keeps it unspoofable.
+    const raw = req.raw as { authType?: string; apiKeyId?: string };
+    const apiKey =
+      raw.authType === 'api_key' && raw.apiKeyId
+        ? { apiKeyId: raw.apiKeyId }
+        : undefined;
+    return this.authService.getCollabToken(user, workspace.id, apiKey);
   }
 
   @SkipThrottle({ [AUTH_THROTTLER]: true })

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

@@ -5,9 +5,13 @@ import { JwtStrategy } from './strategies/jwt.strategy';
 import { WorkspaceModule } from '../workspace/workspace.module';
 import { SignupService } from './services/signup.service';
 import { TokenModule } from './token.module';
+import { ApiKeyModule } from '../api-key/api-key.module';
 
 @Module({
-  imports: [TokenModule, WorkspaceModule],
+  // ApiKeyModule supplies ApiKeyService, injected into JwtStrategy so an
+  // api_key Bearer/cookie token is validated directly (replacing the absent EE
+  // `ee/api-key` dynamic require).
+  imports: [TokenModule, WorkspaceModule, ApiKeyModule],
   controllers: [AuthController],
   providers: [AuthService, SignupService, JwtStrategy],
   exports: [SignupService, AuthService],

apps/server/src/core/auth/dto/jwt-payload.ts

@@ -33,6 +33,17 @@ export type JwtPayload = {
   aiChatId?: string | null;
 };
 
+// The AUTH-PRINCIPAL kind behind a collab token — distinct from `actor`
+// (provenance). Stamped into EVERY newly-minted collab token (#501): 'session'
+// for a normal user/session (incl. the internal AI agent, which is session-
+// backed), 'api_key' when the token was minted by an api-key principal (an
+// external MCP agent). The discriminator keys on the token's ORIGIN, so the
+// collab seam can re-check a revoked api key on connect and reject a claimless
+// token after the rollout grace window. NOT keyed on `actor:'agent'` — the
+// internal agent is 'agent' but session-backed, so it must stay on the no-check
+// path.
+export type CollabPrincipal = 'session' | 'api_key';
+
 export type JwtCollabPayload = {
   sub: string;
   workspaceId: string;
@@ -44,6 +55,13 @@ export type JwtCollabPayload = {
   // Nullable: an external MCP agent has no internal ai_chats row, so it carries
   // an 'agent' actor with a null aiChatId.
   aiChatId?: string | null;
+  // Auth-principal discriminator (#501). Present on every post-rollout token;
+  // its absence on a still-valid token past the grace window is treated as an
+  // error, not trust (fail-closed).
+  principal?: CollabPrincipal;
+  // Only when principal === 'api_key': the minting key's id, so the collab seam
+  // can row-check (and reject) a revoked key on connect.
+  apiKeyId?: string;
 };
 
 export type JwtExchangePayload = {

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

@@ -375,10 +375,20 @@ export class AuthService {
     }
   }
 
-  async getCollabToken(user: User, workspaceId: string) {
+  async getCollabToken(
+    user: User,
+    workspaceId: string,
+    // Origin of the request minting this collab token (#501). When the caller is
+    // an api-key principal, its apiKeyId is threaded into the token so the collab
+    // seam can re-check the key on connect (closing api-key -> long-lived-collab
+    // laundering). Absent for a normal session/human request.
+    apiKey?: { apiKeyId: string },
+  ) {
     const token = await this.tokenService.generateCollabToken(
       user,
       workspaceId,
+      undefined,
+      apiKey,
     );
     return { token };
   }

apps/server/src/core/auth/services/token.service.behavior.spec.ts

@@ -1,4 +1,5 @@
 import { ForbiddenException, UnauthorizedException } from '@nestjs/common';
+import * as jwt from 'jsonwebtoken';
 import { TokenService } from './token.service';
 import { JwtType } from '../dto/jwt-payload';
 
@@ -213,4 +214,175 @@ describe('TokenService.generateCollabToken', () => {
       aiChatId: 'chat-456',
     });
   });
+
+  // #501 fail-closed discriminator: EVERY collab token carries a principal.
+  it("defaults principal to 'session' with NO apiKeyId (normal/internal-agent path)", async () => {
+    const { service, jwtService } = makeTokenService();
+    await service.generateCollabToken(makeUser() as never, 'ws-1');
+    const [payload] = jwtService.sign.mock.calls[0];
+    expect(payload.principal).toBe('session');
+    expect(payload).not.toHaveProperty('apiKeyId');
+  });
+
+  it("the internal agent (provenance, NO apiKey) still gets principal='session'", async () => {
+    const { service, jwtService } = makeTokenService();
+    await service.generateCollabToken(
+      makeUser() as never,
+      'ws-1',
+      { actor: 'agent', aiChatId: 'chat-1' },
+    );
+    const [payload] = jwtService.sign.mock.calls[0];
+    // Keyed on api-key ORIGIN, not actor: an is_agent session token is 'session'.
+    expect(payload.principal).toBe('session');
+    expect(payload).not.toHaveProperty('apiKeyId');
+  });
+
+  it("stamps principal='api_key' + apiKeyId when minted by an api-key principal", async () => {
+    const { service, jwtService } = makeTokenService();
+    await service.generateCollabToken(
+      makeUser() as never,
+      'ws-1',
+      undefined,
+      { apiKeyId: 'key-9' },
+    );
+    const [payload] = jwtService.sign.mock.calls[0];
+    expect(payload.principal).toBe('api_key');
+    expect(payload.apiKeyId).toBe('key-9');
+  });
 });
+
+/**
+ * API-key token minting MUST carry NO `exp` claim — the ONLY source of truth for
+ * a key's lifetime/revocation is its `api_keys` row, checked on every request.
+ *
+ * This is a LIVE-bug regression: the shared JwtService is registered with a
+ * global `signOptions.expiresIn` (default '90d') that merges into every sign(),
+ * so an api-key minted through it silently gets exp=now+90d and an "unlimited"
+ * key dies in 90 days. TokenService.generateApiToken mints through a dedicated
+ * no-expiry signer instead. These tests construct the REAL signer (a real secret
+ * via the stubbed EnvironmentService) and decode the produced JWT to assert the
+ * observable property: no `exp`.
+ */
+describe('TokenService.generateApiToken (no exp claim ever)', () => {
+  const APP_SECRET_LOCAL = 'apikey-secret';
+
+  function makeRealSignerService() {
+    // Give the SHARED jwtService a global expiresIn so a regression (minting
+    // through it) would show up as an exp claim — the exact live bug.
+    const { JwtService } = require('@nestjs/jwt');
+    const sharedJwt = new JwtService({
+      secret: APP_SECRET_LOCAL,
+      signOptions: { expiresIn: '90d', issuer: 'Docmost' },
+    });
+    const environmentService = {
+      getAppSecret: () => APP_SECRET_LOCAL,
+    };
+    const service = new (TokenService as unknown as new (
+      ...args: unknown[]
+    ) => TokenService)(sharedJwt, environmentService);
+    return { service };
+  }
+
+  const user = makeUser({ id: 'svc-1', workspaceId: 'ws-1' });
+
+  it('mints an api-key JWT with NO exp claim and issuer Docmost', async () => {
+    const { service } = makeRealSignerService();
+
+    const token = await service.generateApiToken({
+      apiKeyId: 'key-1',
+      user: user as never,
+      workspaceId: 'ws-1',
+    });
+
+    const decoded = jwt.decode(token) as Record<string, unknown>;
+    // The observable security property: no expiry lives in the JWT.
+    expect(decoded.exp).toBeUndefined();
+    expect(decoded).toMatchObject({
+      sub: 'svc-1',
+      apiKeyId: 'key-1',
+      workspaceId: 'ws-1',
+      type: JwtType.API_KEY,
+      iss: 'Docmost',
+    });
+  });
+
+  it('demonstrates the live bug it guards: the SHARED signer WOULD add exp', () => {
+    const { JwtService } = require('@nestjs/jwt');
+    const sharedJwt = new JwtService({
+      secret: APP_SECRET_LOCAL,
+      signOptions: { expiresIn: '90d', issuer: 'Docmost' },
+    });
+    // Even with empty per-call options the global expiresIn merges in.
+    const leaky = sharedJwt.sign({ sub: 'x', type: JwtType.API_KEY }, {});
+    expect((jwt.decode(leaky) as Record<string, unknown>).exp).toBeDefined();
+  });
+
+  it('refuses to mint for a disabled user', async () => {
+    const { service } = makeRealSignerService();
+    await expect(
+      service.generateApiToken({
+        apiKeyId: 'key-1',
+        user: makeUser({ deactivatedAt: new Date() }) as never,
+        workspaceId: 'ws-1',
+      }),
+    ).rejects.toBeInstanceOf(ForbiddenException);
+  });
+});
+
+/**
+ * verifyJwtOneOf is the type-routing primitive: verify the signature once and
+ * assert the token type is on an explicit allowlist. It must NOT degrade into a
+ * "return whatever type" helper — a token whose type is off the allowlist is
+ * rejected with the same generic error as a single-type mismatch.
+ */
+describe('TokenService.verifyJwtOneOf (allowlist type-routing)', () => {
+  it('returns the payload when the type is on the allowlist', async () => {
+    const verifyAsync = jest
+      .fn()
+      .mockResolvedValue({ type: JwtType.API_KEY, sub: 'u-1' });
+    const { service } = makeTokenService({ verifyAsync });
+
+    const payload = await service.verifyJwtOneOf(token123(), [
+      JwtType.ACCESS,
+      JwtType.API_KEY,
+    ]);
+
+    expect(payload).toMatchObject({ type: JwtType.API_KEY, sub: 'u-1' });
+    expect(verifyAsync).toHaveBeenCalledTimes(1);
+  });
+
+  it('accepts the OTHER allowed type too', async () => {
+    const verifyAsync = jest
+      .fn()
+      .mockResolvedValue({ type: JwtType.ACCESS, sub: 'u-1' });
+    const { service } = makeTokenService({ verifyAsync });
+
+    await expect(
+      service.verifyJwtOneOf(token123(), [JwtType.ACCESS, JwtType.API_KEY]),
+    ).resolves.toMatchObject({ type: JwtType.ACCESS });
+  });
+
+  it('rejects a token whose type is OFF the allowlist (confused-deputy guard)', async () => {
+    const verifyAsync = jest
+      .fn()
+      .mockResolvedValue({ type: JwtType.COLLAB, sub: 'u-1' });
+    const { service } = makeTokenService({ verifyAsync });
+
+    await expect(
+      service.verifyJwtOneOf(token123(), [JwtType.ACCESS, JwtType.API_KEY]),
+    ).rejects.toBeInstanceOf(UnauthorizedException);
+  });
+
+  it('verifies the signature exactly ONCE', async () => {
+    const verifyAsync = jest
+      .fn()
+      .mockResolvedValue({ type: JwtType.ACCESS });
+    const { service } = makeTokenService({ verifyAsync });
+    await service.verifyJwtOneOf(token123(), [JwtType.ACCESS]);
+    expect(verifyAsync).toHaveBeenCalledTimes(1);
+  });
+});
+
+function token123(): string {
+  return 'a.b.c';
+}

apps/server/src/core/auth/services/token.service.ts

@@ -4,7 +4,6 @@ import {
   UnauthorizedException,
 } from '@nestjs/common';
 import { JwtService } from '@nestjs/jwt';
-import type { StringValue } from 'ms';
 import { EnvironmentService } from '../../../integrations/environment/environment.service';
 import {
   JwtApiKeyPayload,
@@ -62,6 +61,12 @@ export class TokenService {
     // token carries no actor/aiChatId and is treated as 'user' downstream.
     // aiChatId is nullable for an external agent with no internal ai_chats row.
     provenance?: { actor: 'agent'; aiChatId: string | null },
+    // Optional api-key origin (#501). When the collab token is minted by an
+    // api-key principal (an external MCP agent), the caller passes the key id so
+    // the token carries principal='api_key' + apiKeyId and the collab seam can
+    // re-check the key on connect. Absent -> principal='session' (a normal
+    // user/session, including the internal session-backed AI agent).
+    apiKey?: { apiKeyId: string },
   ): Promise<string> {
     if (isUserDisabled(user)) {
       throw new ForbiddenException();
@@ -71,6 +76,10 @@ export class TokenService {
       sub: user.id,
       workspaceId,
       type: JwtType.COLLAB,
+      // Fail-closed discriminator on EVERY minted token: 'api_key' when minted by
+      // an api-key principal, else 'session'.
+      principal: apiKey ? 'api_key' : 'session',
+      ...(apiKey ? { apiKeyId: apiKey.apiKeyId } : {}),
       ...(provenance
         ? { actor: provenance.actor, aiChatId: provenance.aiChatId }
         : {}),
@@ -123,9 +132,8 @@ export class TokenService {
     apiKeyId: string;
     user: User;
     workspaceId: string;
-    expiresIn?: StringValue | number;
   }): Promise<string> {
-    const { apiKeyId, user, workspaceId, expiresIn } = opts;
+    const { apiKeyId, user, workspaceId } = opts;
     if (isUserDisabled(user)) {
       throw new ForbiddenException();
     }
@@ -137,7 +145,32 @@ export class TokenService {
       type: JwtType.API_KEY,
     };
 
-    return this.jwtService.sign(payload, expiresIn ? { expiresIn } : {});
+    // API-key tokens carry NO `exp` claim EVER — the ONLY source of truth for a
+    // key's lifetime and revocation is its `api_keys` row (checked on every
+    // request), not the JWT. This CANNOT use `this.jwtService`: TokenModule
+    // registers it with a global `signOptions.expiresIn` (JWT_TOKEN_EXPIRES_IN,
+    // default '90d'), which merges into EVERY sign() call — even `sign(payload,
+    // {})` — and `{ expiresIn: undefined }` THROWS rather than stripping it
+    // (verified empirically). So an "unlimited" key minted through the shared
+    // signer would silently get exp=now+90d and die in 90 days regardless of its
+    // row. We mint through a dedicated no-expiry signer, re-stamping only
+    // `issuer: 'Docmost'` for claim parity with the shared signer.
+    return this.apiKeyJwtService().sign(payload);
+  }
+
+  // Lazily-built JWT signer for API-key tokens: same APP_SECRET, same 'Docmost'
+  // issuer, but WITHOUT the global `expiresIn` — so minted API-key tokens have no
+  // `exp` claim. Built once and cached. Verification still goes through the
+  // shared verifier (same secret); `verifyAsync` does not require an `exp`.
+  private _apiKeyJwtService?: JwtService;
+  private apiKeyJwtService(): JwtService {
+    if (!this._apiKeyJwtService) {
+      this._apiKeyJwtService = new JwtService({
+        secret: this.environmentService.getAppSecret(),
+        signOptions: { issuer: 'Docmost' },
+      });
+    }
+    return this._apiKeyJwtService;
   }
 
   async generatePdfRenderToken(
@@ -177,4 +210,31 @@ export class TokenService {
 
     return payload;
   }
+
+  /**
+   * Verify a token's signature ONCE and assert its `type` is one of `allowed`.
+   *
+   * This is the type-routing primitive for surfaces that legitimately accept
+   * more than one token type on the same Bearer slot (the /mcp Bearer path
+   * accepts both an ACCESS and an API_KEY token). It is deliberately NOT a
+   * "verify-and-return-whatever-type" helper — that would be a reusable
+   * confused-deputy footgun (any caller could then feed an attachment/collab
+   * token where an access token is expected). An explicit allowlist preserves
+   * the type-pinning property of `verifyJwt`: a token whose `type` is not in the
+   * allowlist is rejected with the SAME generic error as a type mismatch, and
+   * the signature is verified exactly once (no double-verify).
+   */
+  async verifyJwtOneOf(token: string, allowed: JwtType[]) {
+    const payload = await this.jwtService.verifyAsync(token, {
+      secret: this.environmentService.getAppSecret(),
+    });
+
+    if (!allowed.includes(payload.type)) {
+      throw new UnauthorizedException(
+        'Invalid JWT token. Token type does not match.',
+      );
+    }
+
+    return payload;
+  }
 }

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

@@ -22,7 +22,8 @@ describe('JwtStrategy — provenance derivation', () => {
     const userSessionRepo: any = { findActiveById: jest.fn() };
     const sessionActivityService: any = { trackActivity: jest.fn() };
     const environmentService: any = { getAppSecret: () => 'test-secret' };
-    const moduleRef: any = {};
+    // ACCESS-path tests never touch the api-key seam; a bare stub suffices.
+    const apiKeyService: any = { validate: jest.fn() };
 
     const strategy = new JwtStrategy(
       userRepo,
@@ -30,7 +31,7 @@ describe('JwtStrategy — provenance derivation', () => {
       userSessionRepo,
       sessionActivityService,
       environmentService,
-      moduleRef,
+      apiKeyService,
     );
     return { strategy, userRepo };
   }
@@ -122,25 +123,29 @@ describe('JwtStrategy — provenance derivation', () => {
 });
 
 /**
- * Provenance derivation on the API-KEY path (jwt.strategy.validateApiKey, #486).
+ * Provenance derivation on the API-KEY path (jwt.strategy.validateApiKey, #486
+ * + #501).
  *
  * The access-token path stamped provenance; the API-key path returned early
  * WITHOUT it, so an is_agent API key's REST writes recorded no 'agent' marker.
  * The API-key payload carries no signed claim, so provenance is resolved from the
- * SERVER-SIDE user returned by ApiKeyService.validateApiKey: isAgent -> 'agent',
+ * SERVER-SIDE user returned by ApiKeyService.validate: isAgent -> 'agent',
  * otherwise 'user'; aiChatId is always null (an API key has no ai_chats row).
  *
- * The enterprise ApiKeyService is not bundled in the OSS build, so the strategy
- * loads it through an overridable `resolveApiKeyService` seam that we stub here.
+ * #501 wires the CORE ApiKeyService (the EE `ee/api-key` module is absent in the
+ * fork) directly into the strategy — no dynamic require. The strategy also stamps
+ * `req.raw.authType='api_key'` + `req.raw.apiKeyId` for the "a token cannot manage
+ * tokens" guard on the /api-keys surface.
  */
-describe('JwtStrategy — API-key provenance derivation (#486)', () => {
-  function makeApiKeyStrategy(validateApiKeyImpl: (p: any) => Promise<any>) {
+describe('JwtStrategy — API-key provenance derivation (#486/#501)', () => {
+  function makeApiKeyStrategy(validateImpl: (p: any) => Promise<any>) {
     const userRepo: any = { findById: jest.fn() };
     const workspaceRepo: any = { findById: jest.fn() };
     const userSessionRepo: any = { findActiveById: jest.fn() };
     const sessionActivityService: any = { trackActivity: jest.fn() };
     const environmentService: any = { getAppSecret: () => 'test-secret' };
-    const moduleRef: any = {};
+    const validate = jest.fn(validateImpl);
+    const apiKeyService: any = { validate };
 
     const strategy = new JwtStrategy(
       userRepo,
@@ -148,14 +153,9 @@ describe('JwtStrategy — API-key provenance derivation (#486)', () => {
       userSessionRepo,
       sessionActivityService,
       environmentService,
-      moduleRef,
+      apiKeyService,
     );
-    // Stub the EE ApiKeyService seam (the real module is not in the OSS build).
-    const validateApiKey = jest.fn(validateApiKeyImpl);
-    jest
-      .spyOn(strategy as any, 'resolveApiKeyService')
-      .mockReturnValue({ validateApiKey });
-    return { strategy, validateApiKey };
+    return { strategy, validate };
   }
 
   const makeReq = () => ({ raw: {} as Record<string, any> });
@@ -166,22 +166,23 @@ describe('JwtStrategy — API-key provenance derivation (#486)', () => {
     type: JwtType.API_KEY,
   });
 
-  it("stamps actor='agent' for an is_agent API key (from the validated user)", async () => {
+  it("stamps actor='agent' + authType/apiKeyId for an is_agent API key", async () => {
     const validated = {
       user: { id: 'svc-1', isAgent: true },
       workspace: { id: 'ws-1' },
     };
-    const { strategy, validateApiKey } = makeApiKeyStrategy(
-      async () => validated,
-    );
+    const { strategy, validate } = makeApiKeyStrategy(async () => validated);
     const req = makeReq();
 
     const result = await strategy.validate(req, apiKeyPayload() as any);
 
-    expect(validateApiKey).toHaveBeenCalledTimes(1);
+    expect(validate).toHaveBeenCalledTimes(1);
     expect(req.raw.actor).toBe('agent');
     // API keys carry no internal ai_chats row -> null.
     expect(req.raw.aiChatId).toBeNull();
+    // Principal-kind markers for the management-surface guard.
+    expect(req.raw.authType).toBe('api_key');
+    expect(req.raw.apiKeyId).toBe('key-1');
     // The validated auth object is returned unchanged (req.user shape preserved).
     expect(result).toBe(validated);
   });
@@ -197,25 +198,19 @@ describe('JwtStrategy — API-key provenance derivation (#486)', () => {
 
     expect(req.raw.actor).toBe('user');
     expect(req.raw.aiChatId).toBeNull();
+    expect(req.raw.authType).toBe('api_key');
   });
 
-  it('throws Unauthorized (and stamps nothing) when the EE module is missing', async () => {
-    const userRepo: any = { findById: jest.fn() };
-    const strategy = new JwtStrategy(
-      userRepo,
-      { findById: jest.fn() } as any,
-      { findActiveById: jest.fn() } as any,
-      { trackActivity: jest.fn() } as any,
-      { getAppSecret: () => 'test-secret' } as any,
-      {} as any,
-    );
-    // EE not bundled: the seam returns null.
-    jest.spyOn(strategy as any, 'resolveApiKeyService').mockReturnValue(null);
+  it('propagates a validate() rejection and stamps nothing', async () => {
+    const { strategy } = makeApiKeyStrategy(async () => {
+      throw new UnauthorizedException();
+    });
     const req = makeReq();
 
     await expect(
       strategy.validate(req, apiKeyPayload() as any),
     ).rejects.toThrow(UnauthorizedException);
     expect(req.raw.actor).toBeUndefined();
+    expect(req.raw.authType).toBeUndefined();
   });
 });

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

@@ -1,4 +1,4 @@
-import { Injectable, Logger, UnauthorizedException } from '@nestjs/common';
+import { Injectable, UnauthorizedException } from '@nestjs/common';
 import { PassportStrategy } from '@nestjs/passport';
 import { Strategy } from 'passport-jwt';
 import { EnvironmentService } from '../../../integrations/environment/environment.service';
@@ -9,20 +9,18 @@ import { UserSessionRepo } from '@docmost/db/repos/session/user-session.repo';
 import { SessionActivityService } from '../../session/session-activity.service';
 import { FastifyRequest } from 'fastify';
 import { extractBearerTokenFromHeader, isUserDisabled } from '../../../common/helpers';
-import { ModuleRef } from '@nestjs/core';
 import { resolveProvenance } from '../../../common/decorators/auth-provenance.decorator';
+import { ApiKeyService } from '../../api-key/api-key.service';
 
 @Injectable()
 export class JwtStrategy extends PassportStrategy(Strategy, 'jwt') {
-  private logger = new Logger('JwtStrategy');
-
   constructor(
     private userRepo: UserRepo,
     private workspaceRepo: WorkspaceRepo,
     private userSessionRepo: UserSessionRepo,
     private sessionActivityService: SessionActivityService,
     private readonly environmentService: EnvironmentService,
-    private moduleRef: ModuleRef,
+    private readonly apiKeyService: ApiKeyService,
   ) {
     super({
       jwtFromRequest: (req: FastifyRequest) => {
@@ -102,12 +100,17 @@ export class JwtStrategy extends PassportStrategy(Strategy, 'jwt') {
   }
 
   private async validateApiKey(req: any, payload: JwtApiKeyPayload) {
-    const apiKeyService = this.resolveApiKeyService();
-    if (!apiKeyService) {
-      throw new UnauthorizedException('Enterprise API Key module missing');
-    }
+    // The fork ships the core `ApiKeyService` (the EE `ee/api-key` module is
+    // absent). `validate` throws a bare UnauthorizedException on any definite
+    // deny (missing/revoked/expired row, disabled user, kill-switch off) and
+    // propagates infra errors (→ 5xx) rather than masking them as a 401.
+    const result = await this.apiKeyService.validate(payload);
 
-    const result = await apiKeyService.validateApiKey(payload);
+    // Stamp the principal kind + key id so the /api-keys management surface can
+    // enforce "a token cannot manage tokens". Done in this branch because it
+    // returns before the shared ACCESS-path stamping below.
+    req.raw.authType = 'api_key';
+    req.raw.apiKeyId = payload.apiKeyId;
 
     // Stamp the agent-edit provenance for the API-KEY path too (#486). Unlike the
     // access-token path above, it CANNOT be resolved before this point: the
@@ -119,32 +122,10 @@ export class JwtStrategy extends PassportStrategy(Strategy, 'jwt') {
     // SERVER-SIDE user (never a client field), so an 'agent' badge is unspoofable
     // — mirroring the access-token path. Passing `null` for the claim means the
     // actor is decided solely by user.isAgent.
-    const provenance = resolveProvenance((result as any)?.user, null);
+    const provenance = resolveProvenance(result.user, null);
     req.raw.actor = provenance.actor;
     req.raw.aiChatId = provenance.aiChatId;
 
     return result;
   }
-
-  /**
-   * Resolve the enterprise ApiKeyService, or `null` when the EE module is not
-   * bundled in this build (community build). Extracted as an overridable seam so
-   * the API-key provenance stamping can be unit-tested without the EE package
-   * present (docmost is OSS + a separate EE bundle; `require` of the EE path
-   * throws here). Any load/resolve error is treated as "module missing".
-   */
-  protected resolveApiKeyService(): {
-    validateApiKey: (payload: JwtApiKeyPayload) => Promise<unknown>;
-  } | null {
-    try {
-      // eslint-disable-next-line @typescript-eslint/no-require-imports
-      const ApiKeyModule = require('./../../../ee/api-key/api-key.service');
-      return this.moduleRef.get(ApiKeyModule.ApiKeyService, { strict: false });
-    } catch (err) {
-      this.logger.debug(
-        'API Key module requested but enterprise module not bundled in this build',
-      );
-      return null;
-    }
-  }
 }

apps/server/src/core/core.module.ts

@@ -6,6 +6,7 @@ import {
 } from '@nestjs/common';
 import { UserModule } from './user/user.module';
 import { AuthModule } from './auth/auth.module';
+import { ApiKeyModule } from './api-key/api-key.module';
 import { WorkspaceModule } from './workspace/workspace.module';
 import { PageModule } from './page/page.module';
 import { AttachmentModule } from './attachment/attachment.module';
@@ -29,6 +30,7 @@ import { ClsMiddleware } from 'nestjs-cls';
   imports: [
     UserModule,
     AuthModule,
+    ApiKeyModule,
     WorkspaceModule,
     PageModule,
     AttachmentModule,

apps/server/src/core/page/dto/create-page.dto.ts

@@ -10,6 +10,12 @@ import { Transform } from 'class-transformer';
 
 export type ContentFormat = 'json' | 'markdown' | 'html';
 
+// READ-only rendering formats for `getPage` (#502). A superset of the writable
+// `ContentFormat` with `text` — a flat, deterministic, machine-diffable text
+// rendering — added. Kept SEPARATE from `ContentFormat` so the write path
+// (createPage/updatePage `parseProsemirrorContent`) can never be handed `text`.
+export type PageReadFormat = ContentFormat | 'text';
+
 export class CreatePageDto {
   @IsOptional()
   @IsString()

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

@@ -8,7 +8,7 @@ import {
 } from 'class-validator';
 import { Transform } from 'class-transformer';
 
-import { ContentFormat } from './create-page.dto';
+import { PageReadFormat } from './create-page.dto';
 import { IsPageIdOrSlugId } from './page-identity.validator';
 
 export class PageIdDto {
@@ -43,8 +43,8 @@ export class PageInfoDto extends PageIdDto {
 
   @IsOptional()
   @Transform(({ value }) => value?.toLowerCase())
-  @IsIn(['json', 'markdown', 'html'])
-  format?: ContentFormat;
+  @IsIn(['json', 'markdown', 'html', 'text'])
+  format?: PageReadFormat;
 }
 
 export class DeletePageDto extends PageIdDto {

apps/server/src/core/page/page.controller.getpage-format.spec.ts

@@ -0,0 +1,76 @@
+import { NotFoundException } from '@nestjs/common';
+import { PageController } from './page.controller';
+import { jsonToText, jsonToMarkdown } from '../../collaboration/collaboration.util';
+
+// #502 READ: getPage `format:"text"` routes through the deterministic jsonToText
+// path (placeholders for non-text nodes, block-per-line), while `format:"json"`
+// (or none) returns the raw content and `format:"markdown"` still converts. This
+// pins the CONTROLLER wiring with lightweight mocks (no DB needed — the jsonToText
+// output contract itself is pinned in json-to-text-deterministic.spec.ts).
+
+const CONTENT = {
+  type: 'doc',
+  content: [
+    { type: 'heading', attrs: { level: 1 }, content: [{ type: 'text', text: 'Config' }] },
+    {
+      type: 'paragraph',
+      content: [
+        { type: 'text', text: 'key=', marks: [{ type: 'bold' }] },
+        { type: 'text', text: 'value' },
+      ],
+    },
+    { type: 'image', attrs: { src: 's' } },
+  ],
+};
+
+function makeController(page: any): PageController {
+  const pageRepo = { findById: jest.fn().mockResolvedValue(page) } as any;
+  const pageAccessService = {
+    validateCanViewWithPermissions: jest
+      .fn()
+      .mockResolvedValue({ canEdit: true, hasRestriction: false }),
+  } as any;
+  // Only pageRepo + pageAccessService are exercised by getPage; the rest are
+  // never touched on this path, so undefined placeholders are fine.
+  return new PageController(
+    undefined as any, // pageService
+    pageRepo,
+    undefined as any, // pageHistoryService
+    undefined as any, // spaceAbility
+    pageAccessService,
+    undefined as any, // backlinkService
+    undefined as any, // labelService
+    undefined as any, // auditService
+  );
+}
+
+const user = { id: 'u1' } as any;
+
+describe('PageController.getPage — format:"text" (#502)', () => {
+  it('returns deterministic flat text with placeholders for non-text nodes', async () => {
+    const controller = makeController({ id: 'p1', content: CONTENT });
+    const res: any = await controller.getPage({ pageId: 'p1', format: 'text' } as any, user);
+    expect(res.content).toBe(jsonToText(CONTENT, { deterministic: true }));
+    expect(res.content).toBe('Config\nkey=value\n[image]');
+    expect(res.permissions).toEqual({ canEdit: true, hasRestriction: false });
+  });
+
+  it('markdown format still converts to markdown (unchanged)', async () => {
+    const controller = makeController({ id: 'p1', content: CONTENT });
+    const res: any = await controller.getPage({ pageId: 'p1', format: 'markdown' } as any, user);
+    expect(res.content).toBe(jsonToMarkdown(CONTENT));
+  });
+
+  it('json / no format returns the raw ProseMirror content object', async () => {
+    const controller = makeController({ id: 'p1', content: CONTENT });
+    const res: any = await controller.getPage({ pageId: 'p1' } as any, user);
+    expect(res.content).toEqual(CONTENT); // untouched object, not a string
+  });
+
+  it('missing page -> NotFoundException', async () => {
+    const controller = makeController(null);
+    await expect(
+      controller.getPage({ pageId: 'nope', format: 'text' } as any, user),
+    ).rejects.toBeInstanceOf(NotFoundException);
+  });
+});

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

@@ -49,6 +49,7 @@ import { AddLabelsDto, RemoveLabelDto } from '../label/dto/label.dto';
 import {
   jsonToHtml,
   jsonToMarkdown,
+  jsonToText,
 } from '../../collaboration/collaboration.util';
 import { AuditEvent, AuditResource } from '../../common/events/audit-events';
 import {
@@ -93,10 +94,16 @@ export class PageController {
     const permissions = { canEdit, hasRestriction };
 
     if (dto.format && dto.format !== 'json' && page.content) {
-      const contentOutput =
-        dto.format === 'markdown'
-          ? jsonToMarkdown(page.content)
-          : jsonToHtml(page.content);
+      let contentOutput: string;
+      if (dto.format === 'markdown') {
+        contentOutput = jsonToMarkdown(page.content);
+      } else if (dto.format === 'text') {
+        // #502: flat, deterministic, machine-diffable text (block-per-line,
+        // inline marks/anchors dropped, non-text nodes -> stable placeholders).
+        contentOutput = jsonToText(page.content, { deterministic: true });
+      } else {
+        contentOutput = jsonToHtml(page.content);
+      }
       return {
         ...page,
         content: contentOutput,

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

@@ -37,6 +37,7 @@ import { AiProviderCredentialsRepo } from '@docmost/db/repos/ai-chat/ai-provider
 import { AiMcpServerRepo } from '@docmost/db/repos/ai-chat/ai-mcp-server.repo';
 import { AiAgentRoleRepo } from '@docmost/db/repos/ai-agent-roles/ai-agent-roles.repo';
 import { PageEmbeddingRepo } from '@docmost/db/repos/ai-chat/page-embedding.repo';
+import { ApiKeyRepo } from '@docmost/db/repos/api-key/api-key.repo';
 import { PageListener } from '@docmost/db/listeners/page.listener';
 import { PostgresJSDialect } from 'kysely-postgres-js';
 import * as postgres from 'postgres';
@@ -129,6 +130,7 @@ import { firstSqlToken } from '../integrations/metrics/metrics.constants';
     AiMcpServerRepo,
     AiAgentRoleRepo,
     PageEmbeddingRepo,
+    ApiKeyRepo,
     PageListener,
   ],
   exports: [
@@ -164,6 +166,7 @@ import { firstSqlToken } from '../integrations/metrics/metrics.constants';
     AiMcpServerRepo,
     AiAgentRoleRepo,
     PageEmbeddingRepo,
+    ApiKeyRepo,
   ],
 })
 export class DatabaseModule implements OnApplicationBootstrap {

apps/server/src/database/repos/api-key/api-key.repo.ts

@@ -0,0 +1,110 @@
+import { Injectable } from '@nestjs/common';
+import { InjectKysely } from 'nestjs-kysely';
+import { KyselyDB, KyselyTransaction } from '@docmost/db/types/kysely.types';
+import { DB, Users } from '@docmost/db/types/db';
+import { dbOrTx } from '@docmost/db/utils';
+import { ApiKey, InsertableApiKey } from '@docmost/db/types/entity.types';
+import { jsonObjectFrom } from 'kysely/helpers/postgres';
+import { ExpressionBuilder } from 'kysely';
+
+// Public-facing shape: the api_keys row plus a compact creator attribution used
+// by the admin list (the workspace-wide view attributes each key to its author).
+export type ApiKeyWithCreator = ApiKey & {
+  creator: Pick<Users, 'id' | 'name' | 'email' | 'avatarUrl'> | null;
+};
+
+@Injectable()
+export class ApiKeyRepo {
+  constructor(@InjectKysely() private readonly db: KyselyDB) {}
+
+  // Compact creator attribution embedded in the admin list rows. A nested
+  // subquery (jsonObjectFrom) keeps it one round-trip; the token material is
+  // never stored, so nothing sensitive is joined in.
+  private withCreator(eb: ExpressionBuilder<DB, 'apiKeys'>) {
+    return jsonObjectFrom(
+      eb
+        .selectFrom('users')
+        .select(['users.id', 'users.name', 'users.email', 'users.avatarUrl'])
+        .whereRef('users.id', '=', 'apiKeys.creatorId'),
+    ).as('creator');
+  }
+
+  async findById(
+    id: string,
+    workspaceId: string,
+    trx?: KyselyTransaction,
+  ): Promise<ApiKey | undefined> {
+    const db = dbOrTx(this.db, trx);
+    return db
+      .selectFrom('apiKeys')
+      .selectAll()
+      .where('id', '=', id)
+      .where('workspaceId', '=', workspaceId)
+      // Convention (soft-delete): a revoked key is invisible to reads.
+      .where('deletedAt', 'is', null)
+      .executeTakeFirst();
+  }
+
+  async findByCreator(
+    creatorId: string,
+    workspaceId: string,
+  ): Promise<ApiKeyWithCreator[]> {
+    return this.db
+      .selectFrom('apiKeys')
+      .selectAll('apiKeys')
+      .select((eb) => this.withCreator(eb))
+      .where('creatorId', '=', creatorId)
+      .where('workspaceId', '=', workspaceId)
+      .where('deletedAt', 'is', null)
+      .orderBy('createdAt', 'desc')
+      .execute() as unknown as Promise<ApiKeyWithCreator[]>;
+  }
+
+  async findAllInWorkspace(
+    workspaceId: string,
+  ): Promise<ApiKeyWithCreator[]> {
+    return this.db
+      .selectFrom('apiKeys')
+      .selectAll('apiKeys')
+      .select((eb) => this.withCreator(eb))
+      .where('workspaceId', '=', workspaceId)
+      .where('deletedAt', 'is', null)
+      .orderBy('createdAt', 'desc')
+      .execute() as unknown as Promise<ApiKeyWithCreator[]>;
+  }
+
+  async insert(
+    insertable: InsertableApiKey,
+    trx?: KyselyTransaction,
+  ): Promise<ApiKey> {
+    const db = dbOrTx(this.db, trx);
+    return db
+      .insertInto('apiKeys')
+      .values(insertable)
+      .returningAll()
+      .executeTakeFirst();
+  }
+
+  // Soft-delete = revoke. Terminal: the row stays for forensics but is invisible
+  // to every read above, so validate() denies it immediately (no grace window).
+  async softDelete(id: string, workspaceId: string): Promise<void> {
+    await this.db
+      .updateTable('apiKeys')
+      .set({ deletedAt: new Date(), updatedAt: new Date() })
+      .where('id', '=', id)
+      .where('workspaceId', '=', workspaceId)
+      .where('deletedAt', 'is', null)
+      .execute();
+  }
+
+  // Throttled best-effort forensics stamp. Not on the critical path: callers
+  // fire-and-forget and swallow errors, so it never fails a request.
+  async touchLastUsed(id: string): Promise<void> {
+    await this.db
+      .updateTable('apiKeys')
+      .set({ lastUsedAt: new Date() })
+      .where('id', '=', id)
+      .where('deletedAt', 'is', null)
+      .execute();
+  }
+}

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

@@ -70,6 +70,23 @@ export class EnvironmentService {
     return this.configService.get<string>('JWT_TOKEN_EXPIRES_IN', '90d');
   }
 
+  // Kill-switch for the agent API-key feature. Default ON (unset -> enabled): a
+  // deploy that never sets the variable must NOT silently kill every agent. The
+  // parse is STRICT — the value is validated by environment.validation to be
+  // exactly 'true' or 'false' (or absent), so a typo like `=0`/`=off`/`=False`
+  // fails at boot rather than being read as "enabled" (which would leave an
+  // operator who yanked the switch during an incident with it still on). When
+  // OFF: validate() denies every api-key token and the issuance endpoints 404.
+  isApiKeysEnabled(): boolean {
+    return this.configService.get<string>('API_KEYS_ENABLED', 'true') !== 'false';
+  }
+
+  // Raw value (or undefined) for the boot log, so the state after each deploy is
+  // verifiable in container logs: `API keys: ENABLED/DISABLED (API_KEYS_ENABLED=...)`.
+  getApiKeysEnabledRaw(): string | undefined {
+    return this.configService.get<string>('API_KEYS_ENABLED');
+  }
+
   getCookieExpiresIn(): Date {
     const expiresInStr = this.getJwtTokenExpiresIn();
     let msUntilExpiry: number;

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

@@ -103,6 +103,15 @@ export class EnvironmentVariables {
   @IsString()
   TYPESENSE_LOCALE: string;
 
+  // Agent API-key kill-switch. Optional (absent -> default ON). STRICT: only the
+  // literals 'true'/'false' are accepted, so `=0`/`=off`/`=False` fail at boot
+  // instead of being silently read as "enabled" — the switch must actually flip
+  // when an operator flips it. See EnvironmentService.isApiKeysEnabled.
+  @IsOptional()
+  @IsIn(['true', 'false'])
+  @IsString()
+  API_KEYS_ENABLED: string;
+
   @IsOptional()
   @ValidateIf((obj) => obj.AI_DRIVER)
   @IsIn(['openai', 'openai-compatible', 'gemini', 'ollama'])

apps/server/src/integrations/import/import.controller.ts

@@ -85,6 +85,14 @@ export class ImportController {
       throw new BadRequestException('spaceId is required');
     }
 
+    // #502: optional multipart field. Only the MCP agent `createPage` path sends
+    // `disableMarkdownExtensions=true` (its body is agent-authored plain prose /
+    // config, so a `$…$` span must stay literal and a bare `www.host` must not
+    // autolink). A HUMAN file upload omits the field, so it stays false and math
+    // + autolink remain ON for human imports. Settable ONLY via this API param.
+    const disableMarkdownExtensions =
+      file.fields?.disableMarkdownExtensions?.value === 'true';
+
     const ability = await this.spaceAbility.createForUser(user, spaceId);
     if (ability.cannot(SpaceCaslAction.Edit, SpaceCaslSubject.Page)) {
       throw new ForbiddenException();
@@ -95,6 +103,7 @@ export class ImportController {
       user.id,
       spaceId,
       workspace.id,
+      disableMarkdownExtensions,
     );
 
     const ext = path.extname(file.filename).toLowerCase();

apps/server/src/integrations/import/services/import-attachment.service.drawio-svg.spec.ts

@@ -0,0 +1,131 @@
+// p-limit and @sindresorhus/slugify are ESM-only and not in jest's transform
+// allowlist; both are irrelevant to createDrawioSvg (a pure fs + string method),
+// so they are mocked out to keep the module graph loadable under ts-jest.
+jest.mock('p-limit', () => ({
+  __esModule: true,
+  default: () => (fn: () => unknown) => fn(),
+}));
+jest.mock('@sindresorhus/slugify', () => ({
+  __esModule: true,
+  default: (input: string) => String(input),
+}));
+
+import { promises as fs } from 'fs';
+import * as os from 'os';
+import * as path from 'path';
+import { ImportAttachmentService } from './import-attachment.service';
+
+/**
+ * Unit test for ImportAttachmentService.createDrawioSvg (issue #507).
+ *
+ * The Confluence import wraps a `.drawio` file into a `.drawio.svg` attachment.
+ * The `content=` payload MUST be the mxfile XML entity-escaped (draw.io's native
+ * form), NOT base64 — draw.io's editor decodes a base64 content= via Latin-1
+ * atob, mangling every non-ASCII char into mojibake. createDrawioSvg touches no
+ * injected dependency, so the service is built with placeholder deps.
+ */
+describe('ImportAttachmentService.createDrawioSvg (#507)', () => {
+  const service = new ImportAttachmentService(
+    {} as any,
+    {} as any,
+    {} as any,
+  );
+  const call = (p: string): Promise<Buffer> =>
+    (service as any).createDrawioSvg(p);
+
+  let tmpDir: string;
+  beforeAll(async () => {
+    tmpDir = await fs.mkdtemp(path.join(os.tmpdir(), 'drawio-507-'));
+  });
+  afterAll(async () => {
+    await fs.rm(tmpDir, { recursive: true, force: true });
+  });
+
+  const writeDrawio = async (name: string, xml: string): Promise<string> => {
+    const p = path.join(tmpDir, name);
+    await fs.writeFile(p, xml, 'utf-8');
+    return p;
+  };
+
+  it('writes content= as entity-encoded XML, not base64', async () => {
+    const drawio =
+      '<mxfile host="Confluence"><diagram name="Схема — ёж">' +
+      '<mxGraphModel><root><mxCell id="0"/>' +
+      '<mxCell id="2" value="Старт-бит" vertex="1" parent="0"/>' +
+      '</root></mxGraphModel></diagram></mxfile>';
+    const p = await writeDrawio('cyrillic.drawio', drawio);
+
+    const svg = (await call(p)).toString('utf-8');
+    const content = /content="([^"]*)"/.exec(svg)?.[1];
+    expect(content).toBeDefined();
+
+    // Entity-encoded XML form, starting with &lt;mxfile — never a base64 blob.
+    expect(content).toMatch(/^&lt;mxfile/);
+    expect(content).toContain('&lt;');
+    // Non-ASCII survives as raw UTF-8, with no Latin-1 mojibake.
+    expect(content).toContain('Старт-бит');
+    expect(content).toContain('Схема — ёж');
+    expect(content).not.toContain('Ð');
+
+    // Decoding the attribute (un-escaping) yields the original drawio file.
+    const decoded = content!
+      .replace(/&lt;/g, '<')
+      .replace(/&gt;/g, '>')
+      .replace(/&quot;/g, '"')
+      .replace(/&amp;/g, '&');
+    expect(decoded).toBe(drawio);
+  });
+
+  it('encodes literal tab/newline/CR as numeric char-refs, not literal control chars (#507 F1)', async () => {
+    // A literal tab/newline/CR inside the mxfile XML would be collapsed to a
+    // single space by XML attribute-value normalization when the draw.io editor
+    // reads content=, silently flattening multi-line labels and tab-bearing
+    // values. They must be emitted as numeric char-refs instead.
+    const drawio =
+      '<mxfile><diagram name="p">' +
+      '<mxGraphModel><root><mxCell id="0"/>' +
+      '<mxCell id="2" value="col1\tcol2" style="html=1;\nshadow=0" vertex="1" parent="0"/>' +
+      '<mxCell id="3" value="Line1\nLine2\rLine3" vertex="1" parent="0"/>' +
+      '</root></mxGraphModel></diagram></mxfile>';
+    const p = await writeDrawio('ctrl.drawio', drawio);
+
+    const svg = (await call(p)).toString('utf-8');
+    const content = /content="([^"]*)"/.exec(svg)?.[1];
+    expect(content).toBeDefined();
+    // No literal control chars survive in the attribute value.
+    expect(content).not.toMatch(/[\t\n\r]/);
+    // They round-trip as numeric char-refs.
+    expect(content).toContain('&#x9;');
+    expect(content).toContain('&#xa;');
+    expect(content).toContain('&#xd;');
+    // Decoding (char-refs back to literal, entities back) recovers the file.
+    const decoded = content!
+      .replace(/&lt;/g, '<')
+      .replace(/&gt;/g, '>')
+      .replace(/&quot;/g, '"')
+      .replace(/&#39;/g, "'")
+      .replace(/&#x9;/gi, '\t')
+      .replace(/&#xa;/gi, '\n')
+      .replace(/&#xd;/gi, '\r')
+      .replace(/&amp;/g, '&');
+    expect(decoded).toBe(drawio);
+  });
+
+  it('escapes XML metacharacters in the drawio payload', async () => {
+    const drawio = '<mxfile><diagram name="a &amp; b">"q" &lt;x&gt;</diagram></mxfile>';
+    const p = await writeDrawio('meta.drawio', drawio);
+
+    const svg = (await call(p)).toString('utf-8');
+    const content = /content="([^"]*)"/.exec(svg)?.[1];
+    expect(content).toBeDefined();
+    // The attribute value must contain no bare `<`, `>` or `"` that would break
+    // out of the content="..." attribute or the SVG element.
+    expect(content).not.toMatch(/[<>"]/);
+    const decoded = content!
+      .replace(/&lt;/g, '<')
+      .replace(/&gt;/g, '>')
+      .replace(/&quot;/g, '"')
+      .replace(/&amp;/g, '&');
+    expect(decoded).toBe(drawio);
+  });
+});

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

@@ -8,6 +8,7 @@ import { createReadStream } from 'node:fs';
 import { promises as fs } from 'fs';
 import { Readable } from 'stream';
 import { getMimeType, sanitizeFileName } from '../../../common/helpers';
+import { htmlEscape } from '../../../common/helpers/html-escaper';
 import { v7 } from 'uuid';
 import { FileTask } from '@docmost/db/types/entity.types';
 import { getAttachmentFolderPath } from '../../../core/attachment/attachment.utils';
@@ -849,7 +850,12 @@ export class ImportAttachmentService {
   ): Promise<Buffer> {
     try {
       const drawioContent = await fs.readFile(drawioPath, 'utf-8');
-      const drawioBase64 = Buffer.from(drawioContent).toString('base64');
+      // Write the mxfile XML XML-entity-escaped (draw.io's native content= form),
+      // NOT base64. draw.io's editor decodes a base64 content= via Latin-1 atob
+      // (no UTF-8 step), turning every non-ASCII char (Cyrillic, ё, —) into
+      // mojibake; the entity-encoded form is decoded by the DOM as UTF-8 and
+      // opens intact. Docmost's own decoder reads both forms.
+      const drawioEscaped = this.xmlEscapeContent(drawioContent);
 
       let imageElement = '';
       // If we have a PNG, include it in the SVG
@@ -875,7 +881,7 @@ export class ImportAttachmentService {
       width="600"
       height="400"
       viewBox="0 0 600 400"
-      content="${drawioBase64}">${imageElement}</svg>`;
+      content="${drawioEscaped}">${imageElement}</svg>`;
 
       return Buffer.from(svgContent, 'utf-8');
     } catch (error) {
@@ -884,6 +890,24 @@ export class ImportAttachmentService {
     }
   }
 
+  /**
+   * Escape a string so it is safe as the value of a double-quoted XML attribute
+   * (the `content=` payload of a `.drawio.svg`). The shared `htmlEscape` covers
+   * `& < > " '` (a strict superset of what this attribute needs; the extra `'`
+   * escape is harmless in a `"`-delimited value). On top of that, the numeric
+   * char-refs for tab/newline/CR are required: a literal tab/newline/CR inside
+   * an attribute value is collapsed to a single space by XML attribute-value
+   * normalization on DOM read (both our decoder and the real draw.io editor),
+   * silently flattening multi-line labels and tab-bearing values. Char-refs
+   * survive that normalization (#507).
+   */
+  private xmlEscapeContent(s: string): string {
+    return htmlEscape(s)
+      .replace(/\t/g, '&#x9;')
+      .replace(/\n/g, '&#xa;')
+      .replace(/\r/g, '&#xd;');
+  }
+
   private async uploadWithRetry(opts: {
     abs: string;
     storageFilePath: string;

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

@@ -0,0 +1,67 @@
+// Importing ImportService transitively loads import-formatter.ts, which imports
+// the ESM-only @sindresorhus/slugify (not in jest's transform allowlist). It is
+// irrelevant to this path, so mock it to keep the module graph loadable (mirrors
+// the sibling import.service specs).
+jest.mock('@sindresorhus/slugify', () => ({
+  __esModule: true,
+  default: (input: string) => String(input),
+}));
+
+import { ImportService } from './import.service';
+
+// #502 BLOCKER 1: the server markdown import path (`/pages/import`) now accepts an
+// optional `disableMarkdownExtensions` flag threaded into `processMarkdown`.
+//   - MCP agent `createPage` sends it TRUE  -> extensions OFF (a `$…$` config span
+//     stays literal, a schemeless `www.host` is not autolinked).
+//   - a HUMAN file upload omits it (default FALSE) -> extensions ON, so a real
+//     `$x^2$` still becomes a formula (human imports unaffected).
+// `processMarkdown` only uses the imported converter (no injected deps on this
+// path), so the service is constructed with null deps for this focused unit test.
+
+function makeService(): ImportService {
+  return new ImportService(null as any, null as any, null as any, null as any);
+}
+
+function findAll(node: any, type: string, acc: any[] = []): any[] {
+  if (!node || typeof node !== 'object') return acc;
+  if (node.type === type) acc.push(node);
+  if (Array.isArray(node.content)) for (const c of node.content) findAll(c, type, acc);
+  return acc;
+}
+function hasLink(node: any): boolean {
+  return findAll(node, 'text').some((t: any) =>
+    t.marks?.some((m: any) => m.type === 'link'),
+  );
+}
+
+describe('ImportService.processMarkdown — #502 disableMarkdownExtensions', () => {
+  it('disableMarkdownExtensions=true (MCP createPage): `$…$` stays literal, no math', async () => {
+    const svc = makeService();
+    const doc = await svc.processMarkdown('export A=$FOO and B=$BAR done', true);
+    expect(findAll(doc, 'mathInline')).toHaveLength(0);
+  });
+
+  it('disableMarkdownExtensions=true: a schemeless www is NOT autolinked', async () => {
+    const svc = makeService();
+    const doc = await svc.processMarkdown('see www.example.com here', true);
+    expect(hasLink(doc)).toBe(false);
+  });
+
+  it('disableMarkdownExtensions=true: an explicit https:// STILL links', async () => {
+    const svc = makeService();
+    const doc = await svc.processMarkdown('see https://example.com here', true);
+    expect(hasLink(doc)).toBe(true);
+  });
+
+  it('DEFAULT (human upload): a real `$x^2$` DOES become a math node', async () => {
+    const svc = makeService();
+    const doc = await svc.processMarkdown('$x^2$');
+    expect(findAll(doc, 'mathInline')).toHaveLength(1);
+  });
+
+  it('DEFAULT (human upload): a schemeless www IS autolinked', async () => {
+    const svc = makeService();
+    const doc = await svc.processMarkdown('see www.example.com here');
+    expect(hasLink(doc)).toBe(true);
+  });
+});

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

@@ -52,6 +52,12 @@ export class ImportService {
     userId: string,
     spaceId: string,
     workspaceId: string,
+    // #502: when true, the markdown importer runs with the two layered
+    // extensions OFF (a `$…$` span stays literal text; a schemeless `www.host` is
+    // NOT autolinked). ONLY the MCP agent `createPage` path sets this; a HUMAN
+    // file upload never passes it, so it defaults false and math/autolink stay ON
+    // for human imports (their `$x^2$` still becomes a formula).
+    disableMarkdownExtensions = false,
   ) {
     const file = await filePromise;
     const fileBuffer = await file.toBuffer();
@@ -66,7 +72,10 @@ export class ImportService {
 
     try {
       if (fileExtension.endsWith('.md')) {
-        prosemirrorState = await this.processMarkdown(fileContent);
+        prosemirrorState = await this.processMarkdown(
+          fileContent,
+          disableMarkdownExtensions,
+        );
       } else if (fileExtension.endsWith('.html')) {
         prosemirrorState = await this.processHTML(fileContent);
       }
@@ -138,7 +147,12 @@ export class ImportService {
     return createdPage;
   }
 
-  async processMarkdown(markdownInput: string): Promise<any> {
+  async processMarkdown(
+    markdownInput: string,
+    // #502: forwarded to the importer. DEFAULT false keeps math + fuzzy autolink
+    // ON (human uploads unaffected); the MCP agent `createPage` path passes true.
+    disableMarkdownExtensions = false,
+  ): Promise<any> {
     // 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
@@ -147,7 +161,12 @@ export class ImportService {
     // 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));
+    return markdownToProseMirror(
+      normalizeForeignMarkdown(markdownInput),
+      disableMarkdownExtensions
+        ? { parseMath: false, fuzzyLinkify: false }
+        : undefined,
+    );
   }
 
   async processHTML(htmlInput: string): Promise<any> {

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

@@ -304,37 +304,102 @@ export function clientIp(req: ClientIpRequest): string {
   return 'unknown';
 }
 
-// Minimal structural shape of the TokenService.verifyJwt method we depend on,
-// so this module never imports the concrete TokenService (heavy graph).
-export interface AccessJwtVerifier {
-  verifyJwt: (
-    token: string,
-    type: JwtType,
-  ) => Promise<{
-    sub?: string;
-    email?: string;
-    workspaceId?: string;
-    sessionId?: string;
-  }>;
-}
-
-/**
- * Bind a TokenService-like verifier into a one-arg `verifyJwt(token)` that
- * ALWAYS enforces `JwtType.ACCESS`. This is the single place where the /mcp
- * Bearer path pins the token type: a Bearer access token must be verified AS an
- * access token (not refresh/exchange/collab/etc.), so the type literal is fixed
- * here rather than at the call site. McpService.verifyMcpBearer delegates to
- * this, keeping the `JwtType.ACCESS` choice testable without the heavy graph.
- */
-export function bindAccessJwtVerifier(
-  tokenService: AccessJwtVerifier,
-): (token: string) => Promise<{
+// The decoded payload shared by the /mcp Bearer allowlist. Carries the `type`
+// discriminator and the API-key `apiKeyId`, on top of the access-token fields.
+export interface McpBearerPayload {
+  type?: JwtType;
   sub?: string;
   email?: string;
   workspaceId?: string;
   sessionId?: string;
-}> {
-  return (token: string) => tokenService.verifyJwt(token, JwtType.ACCESS);
+  apiKeyId?: string;
+}
+
+// Minimal structural shape of the TokenService.verifyJwtOneOf method.
+export interface OneOfJwtVerifier {
+  verifyJwtOneOf: (
+    token: string,
+    allowed: JwtType[],
+  ) => Promise<McpBearerPayload>;
+}
+
+/**
+ * Bind a TokenService-like verifier into a one-arg `verifyJwtOneOf(token)` that
+ * pins the /mcp Bearer ALLOWLIST to exactly {ACCESS, API_KEY}. This is the single
+ * place the /mcp Bearer path pins the token type: the /mcp Bearer slot
+ * legitimately accepts either an ACCESS token (a
+ * human's session token) OR an API_KEY token (an agent's key), but NOTHING else
+ * (collab/exchange/attachment/etc. are rejected with the generic type error).
+ * The allowlist is fixed here rather than at the call site, and the signature is
+ * verified exactly once (see verifyMcpBearer).
+ */
+export function bindMcpBearerVerifier(
+  tokenService: OneOfJwtVerifier,
+): (token: string) => Promise<McpBearerPayload> {
+  return (token: string) =>
+    tokenService.verifyJwtOneOf(token, [JwtType.ACCESS, JwtType.API_KEY]);
+}
+
+// Deps for the /mcp Bearer router. `verifyJwtOneOf` is the one-arg verifier bound
+// above (allowlist {ACCESS, API_KEY}); the ACCESS-specific revocation/disabled
+// deps mirror BearerVerifyDeps; `validateApiKey` is the SHARED api-key row-check.
+export interface McpBearerDeps
+  extends Omit<BearerVerifyDeps, 'verifyJwt'> {
+  verifyJwtOneOf: (token: string) => Promise<McpBearerPayload>;
+  // Row-check for an API_KEY principal — the SAME validator REST uses. Throws
+  // UnauthorizedException on a definite deny; PROPAGATES an infra error (→ 5xx),
+  // never masking it as a 401. Not a login attempt: the Basic limiter is not
+  // involved on this path.
+  validateApiKey: (payload: McpBearerPayload) => Promise<unknown>;
+}
+
+/**
+ * Verify a /mcp Bearer token that may be an ACCESS token OR an API_KEY token, and
+ * route by type. The signature is verified EXACTLY ONCE (verifyJwtOneOf); the
+ * result is reused so the ACCESS branch does not re-verify.
+ *
+ *   - API_KEY -> bind to THIS instance's workspace FIRST (a token for another
+ *     workspace is rejected), THEN run the shared `validateApiKey` row-check.
+ *     No session/limiter involvement (an API key is not a login).
+ *   - ACCESS  -> the unchanged `verifyBearerAccess` (session-active + not-disabled
+ *     checks), fed a closure over the already-verified payload so "verify once"
+ *     and "helper unchanged" coexist.
+ *
+ * Throws UnauthorizedException on any auth failure (uniform generic message — no
+ * enumeration of why); propagates an infra error from `validateApiKey` as itself.
+ */
+export async function verifyMcpBearer(
+  token: string,
+  deps: McpBearerDeps,
+): Promise<{ sub?: string; email?: string }> {
+  const generic = 'Invalid or expired token';
+  const payload = await deps.verifyJwtOneOf(token);
+
+  if (payload.type === JwtType.API_KEY) {
+    if (!payload.sub || !payload.workspaceId) {
+      throw new UnauthorizedException(generic);
+    }
+    // Instance-binding (mirrors verifyBearerAccess): reject an API_KEY token
+    // minted for a different workspace before touching the DB.
+    if (
+      deps.expectedWorkspaceId &&
+      payload.workspaceId !== deps.expectedWorkspaceId
+    ) {
+      throw new UnauthorizedException(generic);
+    }
+    // Shared row-check. A definite deny throws Unauthorized; an infra error
+    // propagates (→ 5xx), which the caller must NOT convert to a 401.
+    await deps.validateApiKey(payload);
+    return { sub: payload.sub };
+  }
+
+  // ACCESS: reuse verifyBearerAccess WITHOUT re-verifying the signature.
+  return verifyBearerAccess(token, {
+    verifyJwt: async () => payload,
+    expectedWorkspaceId: deps.expectedWorkspaceId,
+    findUser: deps.findUser,
+    findActiveSession: deps.findActiveSession,
+  });
 }
 
 // Minimal shapes for the Bearer revocation/disabled check. Kept structural so
@@ -728,18 +793,24 @@ export async function resolveMcpSessionConfig(
     };
   }
 
-  // --- 2) fallback A: Bearer access-JWT (user-supplied token) ---
+  // --- 2) fallback A: Bearer JWT (user-supplied ACCESS or agent API_KEY) ---
   const bearer = extractBearer(authHeader);
   if (bearer) {
     let payload: { sub?: string; email?: string };
     try {
       payload = await deps.verifyAccessJwt(bearer);
     } catch (err) {
-      const message =
-        err instanceof Error && err.message
-          ? err.message
-          : 'Invalid or expired token';
-      throw new UnauthorizedException(message);
+      // Anti-enumeration (Bearer leg): EVERY auth failure surfaces the SAME
+      // generic 401 — expired/revoked/wrong-type/unknown are indistinguishable
+      // to the caller (its reaction is identical either way). But an UNEXPECTED
+      // (infra) error is NOT an auth verdict: rethrow it AS ITSELF so the surface
+      // maps it to 5xx (mapAuthResultToResponse), never masking a DB/Redis
+      // outage as a bad token. verifyMcpBearer throws UnauthorizedException on a
+      // definite deny and lets an infra error from validateApiKey propagate.
+      if (err instanceof UnauthorizedException) {
+        throw new UnauthorizedException('Invalid or expired token');
+      }
+      throw err;
     }
     return {
       config: { apiUrl, getToken: async () => bearer },

apps/server/src/integrations/mcp/mcp-basic-login-gate.spec.ts

@@ -115,6 +115,7 @@ function makeService(opts: {
     undefined as never, // userRepo
     undefined as never, // userSessionRepo
     moduleRef as never, // moduleRef (read by the MFA branch)
+    undefined as never, // apiKeyService (unused by the login-gate path)
     undefined as never, // sandboxStore (unused by the login-gate path)
   );
   // Stop the constructor's unref'd sweep timer leaking across tests.

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

@@ -4,13 +4,16 @@ import { McpService } from './mcp.service';
 import { DatabaseModule } from '@docmost/db/database.module';
 import { AuthModule } from '../../core/auth/auth.module';
 import { TokenModule } from '../../core/auth/token.module';
+import { ApiKeyModule } from '../../core/api-key/api-key.module';
 
 // Community MCP feature: the server itself serves the Model Context Protocol
 // over HTTP at /mcp. DatabaseModule (global) provides WorkspaceRepo. AuthModule
 // supplies AuthService (per-user HTTP-Basic login validation) and TokenModule
-// supplies TokenService (Bearer access-JWT verification for the token fallback).
+// supplies TokenService (Bearer JWT verification for the token path). ApiKeyModule
+// supplies ApiKeyService (the shared api-key row-check for the API_KEY Bearer
+// branch, so an agent authenticates with a key instead of the bcrypt Basic path).
 @Module({
-  imports: [DatabaseModule, AuthModule, TokenModule],
+  imports: [DatabaseModule, AuthModule, TokenModule, ApiKeyModule],
   controllers: [McpController],
   providers: [McpService],
 })

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

@@ -6,9 +6,10 @@ import {
   isCredentialsFailure,
   isInitializeRequestBody,
   verifyBearerAccess,
+  verifyMcpBearer,
+  bindMcpBearerVerifier,
   sharedTokenMatches,
   clientIp,
-  bindAccessJwtVerifier,
   extractBearer,
   decideBasicGate,
   mapAuthResultToResponse,
@@ -524,13 +525,28 @@ describe('resolveMcpSessionConfig', () => {
     expect(resolved.identity).toBe('bearer:user-9');
   });
 
-  it('Bearer invalid -> specific 401 from verifyAccessJwt', async () => {
+  it('Bearer invalid -> UNIFORM generic 401 (anti-enumeration, reason not leaked)', async () => {
+    // #501: the Bearer leg no longer surfaces the specific reason. Whether the
+    // token is expired, revoked, wrong-type or unknown, the caller sees ONE bare
+    // 'Invalid or expired token' — an agent's reaction is identical, and a leaked
+    // class would be an enumeration oracle.
     const verifyAccessJwt = jest
       .fn()
       .mockRejectedValue(new UnauthorizedException('jwt expired'));
     await expect(
       resolveMcpSessionConfig('Bearer expired', makeDeps({ verifyAccessJwt })),
-    ).rejects.toThrow('jwt expired');
+    ).rejects.toThrow('Invalid or expired token');
+  });
+
+  it('Bearer INFRA error -> propagates (NOT masked as 401)', async () => {
+    // A non-UnauthorizedException (e.g. a DB outage in the api-key row-check) is
+    // not an auth verdict: it must propagate so the surface maps it to 5xx.
+    const verifyAccessJwt = jest
+      .fn()
+      .mockRejectedValue(new Error('connection terminated'));
+    await expect(
+      resolveMcpSessionConfig('Bearer x', makeDeps({ verifyAccessJwt })),
+    ).rejects.toThrow('connection terminated');
   });
 
   it('no creds + env service account configured -> service-account config', async () => {
@@ -1001,48 +1017,104 @@ describe('clientIp (XFF-fallback precedence, item 5)', () => {
   });
 });
 
-describe('bindAccessJwtVerifier enforces JwtType.ACCESS (item 3)', () => {
-  it('calls TokenService.verifyJwt with JwtType.ACCESS as the second argument', async () => {
-    // Mock TokenService: assert the type literal is pinned to ACCESS so swapping
-    // to REFRESH (or omitting the type) breaks this test.
-    const verifyJwt = jest
+describe('bindMcpBearerVerifier pins the {ACCESS, API_KEY} allowlist (#501)', () => {
+  it('calls verifyJwtOneOf with exactly [ACCESS, API_KEY]', async () => {
+    const verifyJwtOneOf = jest
       .fn()
-      .mockResolvedValue({ sub: 'user-1', workspaceId: 'ws-1' });
-    const verify = bindAccessJwtVerifier({ verifyJwt });
+      .mockResolvedValue({ type: JwtType.API_KEY, sub: 'u-1' });
+    await bindMcpBearerVerifier({ verifyJwtOneOf })('the.jwt');
+    expect(verifyJwtOneOf).toHaveBeenCalledWith('the.jwt', [
+      JwtType.ACCESS,
+      JwtType.API_KEY,
+    ]);
+    // Pin the concrete enum values too.
+    expect(verifyJwtOneOf.mock.calls[0][1]).toEqual(['access', 'api_key']);
+  });
+});
 
-    await verify('the.access.jwt');
-
-    expect(verifyJwt).toHaveBeenCalledTimes(1);
-    expect(verifyJwt).toHaveBeenCalledWith('the.access.jwt', JwtType.ACCESS);
-    // Pin the real enum value too, so renaming/repointing the enum member is caught.
-    expect(verifyJwt.mock.calls[0][1]).toBe('access');
+describe('verifyMcpBearer routes by token type (#501)', () => {
+  const accessDeps = (over: any = {}) => ({
+    verifyJwtOneOf: jest.fn(),
+    expectedWorkspaceId: 'ws-1',
+    findUser: jest.fn().mockResolvedValue({ deactivatedAt: null }),
+    findActiveSession: jest
+      .fn()
+      .mockResolvedValue({ userId: 'u-1', workspaceId: 'ws-1' }),
+    validateApiKey: jest.fn(),
+    ...over,
   });
 
-  it('passes through the verified payload', async () => {
-    const payload = { sub: 'user-9', email: 'u@e.com', workspaceId: 'ws-1' };
-    const verifyJwt = jest.fn().mockResolvedValue(payload);
-    await expect(
-      bindAccessJwtVerifier({ verifyJwt })('t'),
-    ).resolves.toBe(payload);
+  it('API_KEY -> row-checks via validateApiKey and does NOT touch session/limiter', async () => {
+    const deps = accessDeps({
+      verifyJwtOneOf: jest.fn().mockResolvedValue({
+        type: JwtType.API_KEY,
+        sub: 'svc-1',
+        workspaceId: 'ws-1',
+        apiKeyId: 'k-1',
+      }),
+      validateApiKey: jest.fn().mockResolvedValue({ user: { id: 'svc-1' } }),
+    });
+    const res = await verifyMcpBearer('tok', deps);
+    expect(deps.validateApiKey).toHaveBeenCalledTimes(1);
+    // No session lookup on the api-key path (not a login).
+    expect(deps.findActiveSession).not.toHaveBeenCalled();
+    expect(res).toEqual({ sub: 'svc-1' });
   });
 
-  // The Bearer revocation/disabled checks (verifyBearerAccess) are covered above;
-  // this binds the ACCESS-type enforcement that verifyMcpBearer wires in.
-  it('feeds verifyBearerAccess so the whole Bearer chain enforces ACCESS', async () => {
-    const verifyJwt = jest.fn().mockResolvedValue({
-      sub: 'user-1',
+  it('API_KEY for ANOTHER workspace -> rejected before the row-check', async () => {
+    const deps = accessDeps({
+      verifyJwtOneOf: jest.fn().mockResolvedValue({
+        type: JwtType.API_KEY,
+        sub: 'svc-1',
+        workspaceId: 'ws-OTHER',
+        apiKeyId: 'k-1',
+      }),
+      validateApiKey: jest.fn(),
+    });
+    await expect(verifyMcpBearer('tok', deps)).rejects.toBeInstanceOf(
+      UnauthorizedException,
+    );
+    expect(deps.validateApiKey).not.toHaveBeenCalled();
+  });
+
+  it('API_KEY infra error from validateApiKey PROPAGATES (not masked)', async () => {
+    const boom = new Error('db down');
+    const deps = accessDeps({
+      verifyJwtOneOf: jest.fn().mockResolvedValue({
+        type: JwtType.API_KEY,
+        sub: 'svc-1',
+        workspaceId: 'ws-1',
+        apiKeyId: 'k-1',
+      }),
+      validateApiKey: jest.fn().mockRejectedValue(boom),
+    });
+    await expect(verifyMcpBearer('tok', deps)).rejects.toBe(boom);
+  });
+
+  it('ACCESS -> runs the session/disabled checks and does NOT call validateApiKey', async () => {
+    const deps = accessDeps({
+      verifyJwtOneOf: jest.fn().mockResolvedValue({
+        type: JwtType.ACCESS,
+        sub: 'u-1',
+        workspaceId: 'ws-1',
+        sessionId: 'sess-1',
+        email: 'u@e.com',
+      }),
+    });
+    const res = await verifyMcpBearer('tok', deps);
+    expect(deps.findActiveSession).toHaveBeenCalledWith('sess-1');
+    expect(deps.validateApiKey).not.toHaveBeenCalled();
+    expect(res).toEqual({ sub: 'u-1', email: 'u@e.com' });
+  });
+
+  it('verifies the signature exactly ONCE (single verifyJwtOneOf, no re-verify)', async () => {
+    const verifyJwtOneOf = jest.fn().mockResolvedValue({
+      type: JwtType.ACCESS,
+      sub: 'u-1',
       workspaceId: 'ws-1',
-      sessionId: 'sess-1',
     });
-    const res = await verifyBearerAccess('t', {
-      verifyJwt: bindAccessJwtVerifier({ verifyJwt }),
-      findUser: jest.fn().mockResolvedValue({ deactivatedAt: null }),
-      findActiveSession: jest
-        .fn()
-        .mockResolvedValue({ userId: 'user-1', workspaceId: 'ws-1' }),
-    });
-    expect(verifyJwt).toHaveBeenCalledWith('t', JwtType.ACCESS);
-    expect(res).toEqual({ sub: 'user-1', email: undefined });
+    await verifyMcpBearer('tok', accessDeps({ verifyJwtOneOf }));
+    expect(verifyJwtOneOf).toHaveBeenCalledTimes(1);
   });
 });
 
@@ -1198,6 +1270,7 @@ describe('McpService.onModuleDestroy — CollabSession teardown (#486)', () => {
       {} as any,
       {} as any,
       {} as any,
+      {} as any,
     );
   }
 

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

@@ -14,16 +14,17 @@ import { UserSessionRepo } from '@docmost/db/repos/session/user-session.repo';
 import { AuthService } from '../../core/auth/services/auth.service';
 import { TokenService } from '../../core/auth/services/token.service';
 import { validateSsoEnforcement } from '../../core/auth/auth.util';
-import { JwtPayload } from '../../core/auth/dto/jwt-payload';
+import { JwtApiKeyPayload } from '../../core/auth/dto/jwt-payload';
 import { Workspace } from '@docmost/db/types/entity.types';
+import { ApiKeyService } from '../../core/api-key/api-key.service';
 import {
   FailedLoginLimiter,
   resolveMcpSessionConfig,
-  verifyBearerAccess,
+  verifyMcpBearer,
   isInitializeRequestBody,
   sharedTokenMatches,
   clientIp,
-  bindAccessJwtVerifier,
+  bindMcpBearerVerifier,
   decideBasicGate,
   mapAuthResultToResponse,
   DocmostMcpConfig,
@@ -105,6 +106,10 @@ export class McpService implements OnModuleDestroy {
     private readonly userRepo: UserRepo,
     private readonly userSessionRepo: UserSessionRepo,
     private readonly moduleRef: ModuleRef,
+    // Shared api-key row-check for the /mcp API_KEY Bearer branch (same validator
+    // REST uses). Also lets an agent authenticate to /mcp with an api key instead
+    // of the bcrypt Basic path, so parallel reads stop starving the limiter.
+    private readonly apiKeyService: ApiKeyService,
     // Shared singleton in-RAM blob store backing the stash tool.
     private readonly sandboxStore: SandboxStore,
   ) {
@@ -194,37 +199,41 @@ export class McpService implements OnModuleDestroy {
     }
   }
 
-  // Bearer access-JWT verification for the /mcp token fallback. verifyJwt only
-  // checks signature/exp/type, but a logged-out (revoked) or disabled user can
-  // still hold an unexpired access JWT. JwtStrategy additionally checks the
-  // session is active and the user is not disabled; we mirror those exact checks
-  // here so the MCP Bearer path is not weaker than the normal cookie/header path.
+  // Bearer verification for the /mcp token path. The Bearer slot accepts EITHER
+  // an ACCESS token (a human session token) OR an API_KEY token (an agent's key)
+  // — the allowlist is pinned in bindMcpBearerVerifier. An ACCESS token is
+  // checked exactly as JwtStrategy does (signature/exp/type + session-active +
+  // not-disabled), so the MCP path is not weaker than the cookie/header path. An
+  // API_KEY token is HMAC-verified (microseconds) then row-checked via the shared
+  // ApiKeyService.validate — NOT a login attempt, so the Basic bcrypt path and
+  // its anti-brute-force limiter are never touched (the parallel-reads fix).
   private async verifyMcpBearer(
     token: string,
   ): Promise<{ sub?: string; email?: string }> {
-    // Resolve THIS instance's workspace so verifyBearerAccess can bind the
-    // token's `workspaceId` claim to it (mirrors JwtStrategy). The community
-    // build is single-workspace (findFirst), so this is the default workspace
-    // and the check is a no-op here; it only rejects a foreign-workspace token
-    // in a multi-workspace deployment. Undefined (no workspace configured) means
-    // no check — the credentials path would already have failed with no
-    // workspace, and an undefined here keeps the helper a no-op rather than
-    // rejecting every token.
+    // Resolve THIS instance's workspace so the router can bind the token's
+    // `workspaceId` claim to it (mirrors JwtStrategy). The community build is
+    // single-workspace (findFirst), so this is the default workspace and the
+    // check is a no-op here; it only rejects a foreign-workspace token in a
+    // multi-workspace deployment. Undefined (no workspace configured) means no
+    // check — the credentials path would already have failed with no workspace.
     const instanceWorkspace = await this.workspaceRepo.findFirst();
-    // The revocation/disabled decision logic lives in the framework-free
-    // verifyBearerAccess helper (unit-testable without the heavy auth graph);
-    // this method only wires in the concrete TokenService + repos.
-    return verifyBearerAccess(token, {
-      // The JwtType.ACCESS enforcement lives in bindAccessJwtVerifier (a pure,
-      // testable seam) so the type literal cannot silently drift to REFRESH.
-      verifyJwt: bindAccessJwtVerifier(this.tokenService) as (
-        t: string,
-      ) => Promise<JwtPayload>,
+    // The type-routing + revocation/disabled decision logic lives in the
+    // framework-free verifyMcpBearer helper (unit-testable without the heavy auth
+    // graph); this method only wires in the concrete TokenService + repos + the
+    // shared api-key validator.
+    return verifyMcpBearer(token, {
+      // The {ACCESS, API_KEY} allowlist enforcement lives in bindMcpBearerVerifier
+      // (a pure, testable seam) so the type set cannot silently drift.
+      verifyJwtOneOf: bindMcpBearerVerifier(this.tokenService),
       expectedWorkspaceId: instanceWorkspace?.id,
       findUser: (sub, workspaceId) =>
         this.userRepo.findById(sub, workspaceId),
       findActiveSession: (sessionId) =>
         this.userSessionRepo.findActiveById(sessionId),
+      // Shared with REST: a definite deny throws Unauthorized, an infra error
+      // propagates (→ 5xx). The /mcp bearer catch must preserve that distinction.
+      validateApiKey: (payload) =>
+        this.apiKeyService.validate(payload as JwtApiKeyPayload),
     });
   }
 

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

@@ -322,20 +322,21 @@ describe('AiChatService.stream [integration]', () => {
   });
 
   /**
-   * #332 deferred tool loading, the ON path. The riskiest property is that the
-   * per-turn `activatedTools` Set is created FRESH inside each stream() call, so a
-   * tool a previous turn activated via loadTools is NOT still active when the next
-   * turn starts — the new turn begins "cold" (CORE + loadTools only). The unit
-   * tests only exercise pure prepareAgentStep with hand-fed Sets; this pins the
-   * real wiring end-to-end (loadTools.execute -> activatedTools -> prepareStep ->
-   * per-step activeTools) against the real streamText loop, and proves there is no
-   * cross-turn leak. We drive a MockLanguageModelV3 whose step 1 calls
-   * loadTools(['createPage']) and assert, via the model's recorded per-step
-   * CallOptions.tools (the AI SDK filters the provider tool list by activeTools),
-   * that the deferred tool becomes active on the SAME turn's next step but NOT on a
-   * fresh turn's first step.
+   * #332 + #490 deferred tool loading, the ON path. Turn 1 starts COLD (CORE +
+   * loadTools only) and activates a deferred tool via loadTools; that activation
+   * is PERSISTED into the chat's metadata.activatedTools (#490) so the NEXT turn
+   * SEEDS from it and the tool is active from the fresh turn's FIRST step — the
+   * model never re-runs loadTools to re-activate the same tool. The unit tests
+   * only exercise pure prepareAgentStep with hand-fed Sets; this pins the real
+   * wiring end-to-end (loadTools.execute -> activatedTools -> persist -> next-turn
+   * seed -> prepareStep -> per-step activeTools) against the real streamText loop.
+   * We drive a MockLanguageModelV3 whose step 1 calls loadTools(['createPage'])
+   * and assert, via the model's recorded per-step CallOptions.tools (the AI SDK
+   * filters the provider tool list by activeTools), that the deferred tool becomes
+   * active on the SAME turn's next step AND, seeded from metadata, on the next
+   * turn's first step.
    */
-  describe('deferred tool loading ON — per-turn activation, no leak (#332)', () => {
+  describe('deferred tool loading ON — cross-turn activation persistence (#332 + #490)', () => {
     // A stub deferred (non-core) tool the agent can activate. Its execute is never
     // called — the model only needs to SEE it become active — but it must be a
     // valid AI-SDK tool so the SDK includes it in a step's tool list once active.
@@ -451,7 +452,7 @@ describe('AiChatService.stream [integration]', () => {
       } as any);
     }
 
-    it('activates a deferred tool for the SAME turn, and a NEW turn starts cold (no leak)', async () => {
+    it('activates a deferred tool for the SAME turn, and a NEW turn SEEDS it from persisted chat metadata (#490)', async () => {
       const chatId = (await createChat(db, { workspaceId, creatorId: userId })).id;
 
       // --- Turn 1: loadTools(createPage) on step 1, then answer on step 2. ---
@@ -474,7 +475,7 @@ describe('AiChatService.stream [integration]', () => {
       // Step 2 of the SAME turn sees the just-activated deferred tool.
       expect(step2Tools).toContain('createPage');
 
-      // --- Turn 2 on the SAME chat: must start cold again. ---
+      // --- Turn 2 on the SAME chat: seeds the persisted activation (#490). ---
       const model2 = new MockLanguageModelV3({
         doStream: async () => ({ stream: successStream() }),
       } as any);
@@ -485,9 +486,10 @@ describe('AiChatService.stream [integration]', () => {
 
       const nextTurnFirstStep = toolNames(model2.doStreamCalls[0]);
       expect(nextTurnFirstStep).toContain('loadTools');
-      // The activated set is per-turn: the prior turn's createPage did NOT leak,
-      // so the fresh turn's first step sees it deferred again.
-      expect(nextTurnFirstStep).not.toContain('createPage');
+      // #490: activation PERSISTS across turns — turn 1 wrote createPage into the
+      // chat's metadata.activatedTools, so the next turn seeds from it and the
+      // deferred tool is active from the FIRST step (no need to re-run loadTools).
+      expect(nextTurnFirstStep).toContain('createPage');
     });
   });
 });

packages/mcp/README.md

@@ -118,7 +118,10 @@ All 41 tools, grouped by what you'd reach for them.
 - **`getPage`** — A page's content as clean **Markdown** (canonical for text; drops only
   block ids, resolved-comment anchors, and a fixed no-Markdown-representation attr set —
   table spans/colwidth/background, indent, `callout.icon`, `orderedList.type`, and link
-  `internal`/`target`/`rel`/`class`; use `getPageJson` when you need those).
+  `internal`/`target`/`rel`/`class`; use `getPageJson` when you need those). Pass
+  `format:"text"` for a flat, deterministic plain-text rendering (one line per block,
+  marks dropped, stable `[image]`/`[table RxC]` placeholders) to machine-diff what you
+  wrote against what was stored.
 - **`getPageJson`** — A page's **lossless ProseMirror/TipTap JSON**, including every
   block's `attrs.id` and the `slugId` used in URLs. This is what the per-block editing
   tools consume.

packages/mcp/README.ru.md

@@ -123,7 +123,10 @@ Docmost-MCP не сочетают:
   лишь id блоков, якоря разрешённых комментариев и фиксированный набор атрибутов без
   markdown-представления — спаны/colwidth/фон ячеек таблиц, отступы (indent),
   `callout.icon`, `orderedList.type` и `internal`/`target`/`rel`/`class` у ссылок;
-  используйте `getPageJson`, когда они нужны).
+  используйте `getPageJson`, когда они нужны). Передайте `format:"text"` для плоского
+  детерминированного plain-text рендера (одна строка на блок, маркировка убрана,
+  стабильные плейсхолдеры `[image]`/`[table RxC]`) — чтобы machine-diff'ом сверить то,
+  что вы записали, с тем, что сохранилось.
 - **`getPageJson`** — **Lossless ProseMirror/TipTap JSON** страницы, включая `attrs.id`
   каждого блока и `slugId`, используемый в URL. Именно его потребляют инструменты
   поблочного редактирования.

packages/mcp/src/client/context.ts

@@ -701,10 +701,20 @@ export abstract class DocmostClientContext {
   }
 
 
-  /** Raw page info including the ProseMirror JSON content and slugId. */
-  async getPageRaw(pageId: string) {
+  /**
+   * Raw page info including the ProseMirror JSON content and slugId.
+   *
+   * With `format:"text"` (#502) the server instead renders `content` as a flat,
+   * deterministic text string (its `jsonToText` path — the SAME serializer that
+   * feeds search), so the MCP text read reuses the server's ONE serializer
+   * rather than shipping a second one. Every other caller omits `format` and
+   * gets the JSON content unchanged.
+   */
+  async getPageRaw(pageId: string, format?: "text") {
     await this.ensureAuthenticated();
-    const response = await this.client.post("/pages/info", { pageId });
+    const body: Record<string, unknown> = { pageId };
+    if (format) body.format = format;
+    const response = await this.client.post("/pages/info", body);
     return response.data?.data ?? response.data;
   }
 

packages/mcp/src/client/pages.ts

@@ -93,6 +93,13 @@ export function PagesMixin<TBase extends GConstructor<DocmostClientContext>>(Bas
     const buildForm = () => {
       const form = new FormData();
       form.append("spaceId", spaceId);
+      // #502: this is an AGENT-authored body (plain prose / config), so tell the
+      // server import path to run the markdown importer with the two layered
+      // extensions OFF — a `$…$` span stays literal text (real math via
+      // `update_page_json`) and a schemeless `www.host`/email is not autolinked
+      // (an explicit `https://…` still links). A human file upload never sends
+      // this field, so human imports keep math + autolink ON.
+      form.append("disableMarkdownExtensions", "true");
       form.append("file", fileContent, {
         filename: `${title || "import"}.md`,
         contentType: "text/markdown",

packages/mcp/src/client/read.ts

@@ -72,7 +72,7 @@ export interface IReadMixin {
   getTree(spaceId: string, rootPageId?: string, maxDepth?: number): any;
   getPageContext(pageId: string): any;
   listSidebarPages(spaceId: string, pageId?: string): any;
-  getPage(pageId: string): any;
+  getPage(pageId: string, format?: "markdown" | "text"): any;
   getPageJson(pageId: string): any;
   getOutline(pageId: string): any;
   getNode(pageId: string, nodeId: string, format?: "markdown" | "json"): any;
@@ -420,8 +420,34 @@ export function ReadMixin<TBase extends GConstructor<DocmostClientContext>>(Base
     return convertProseMirrorToMarkdown(content, options);
   }
 
-  async getPage(pageId: string) {
+  async getPage(pageId: string, format: "markdown" | "text" = "markdown") {
     await this.ensureAuthenticated();
+
+    // #502 `format:"text"`: a flat, deterministic, machine-diffable rendering
+    // (block-per-line, inline marks/comment anchors dropped, non-text nodes ->
+    // stable placeholders like `[image]` / `[table RxC]`). The server produces
+    // it via its `jsonToText` path (the SAME serializer that feeds search), so
+    // there is no second serializer here — we just request it and pass the
+    // string through. Distinct from the markdown default: no PM->markdown walk,
+    // no markdown conversion cache, and no `{{SUBPAGES}}` substitution (the text
+    // renderer emits no such placeholder). Use it to diff a page you wrote as a
+    // config/prose against what was stored.
+    if (format === "text") {
+      const textData = await this.getPageRaw(pageId, "text");
+      let subpages: any[] = [];
+      try {
+        subpages = await this.listSidebarPages(textData.spaceId, textData.id);
+      } catch (e: any) {
+        console.warn("Failed to fetch subpages:", e);
+      }
+      const textContent =
+        typeof textData.content === "string" ? textData.content : "";
+      return {
+        data: filterPage(textData, textContent, subpages),
+        success: true,
+      };
+    }
+
     const resultData = await this.getPageRaw(pageId);
 
     // Agent read: hide resolved-comment anchors so the agent sees only active

packages/mcp/src/lib/collaboration.ts

@@ -14,6 +14,7 @@ import {
   markdownToProseMirror,
   normalizeAgentMarkdown,
 } from "@docmost/prosemirror-markdown";
+import type { MarkdownImportOptions } from "@docmost/prosemirror-markdown";
 import { docmostExtensions, docmostSchema } from "./docmost-schema.js";
 import { withPageLock } from "./page-lock.js";
 import type { PageId } from "./page-id.js";
@@ -111,16 +112,31 @@ global.WebSocket = WebSocket;
  * horizontalRule the serializer emitted, and stripping it would silently drop the
  * page's leading content (#493 review). The front-matter strip stays on the
  * server FILE-import boundary only (`normalizeForeignMarkdown`).
+ *
+ * #502 IMPORTANT — the two layered markdown extensions (`$…$` math, schemeless
+ * fuzzy autolink) are NOT decided here; they are the CALLER's choice via
+ * `options`, because the two callers of this wrapper need OPPOSITE behavior:
+ *   - AGENT-authored plain markdown (`updatePageMarkdown`) → both OFF, so a
+ *     `$…$` config span stays literal and a bare `www.host` is not autolinked
+ *     (real math is authored via `update_page_json`).
+ *   - FULL-FILE round-trip import (`import_page_markdown`, #328 lossless) →
+ *     DEFAULTS (both ON), because the exporter serializes a math node as readable
+ *     `$x^2$`; re-importing with math OFF would degrade it to literal text and
+ *     BREAK the lossless export→import pair.
+ * So `options` DEFAULTS to `undefined` → the package importer's defaults (ON),
+ * which is the safe round-trip behavior; the agent-write caller opts OUT
+ * explicitly. (The fragment path `importMarkdownFragment` opts out on its own.)
  */
 export async function markdownToProseMirrorCanonical(
   markdownContent: string,
+  options?: MarkdownImportOptions,
 ): Promise<any> {
   // #419: normalize + merge glyph-forked footnote definitions BEFORE
   // canonicalizing, so the canonicalizer re-hangs references and drops the
   // now-orphaned duplicate definitions.
   return canonicalizeFootnotes(
     normalizeAndMergeFootnotes(
-      await markdownToProseMirror(normalizeAgentMarkdown(markdownContent)),
+      await markdownToProseMirror(normalizeAgentMarkdown(markdownContent), options),
     ),
   );
 }
@@ -358,7 +374,17 @@ export async function updatePageContentRealtime(
 ): Promise<MutationResult> {
   // PAGE write: canonicalize footnotes (markdown import builds the bottom list in
   // definition order; numbering is reference-ordered).
-  const tiptapJson = await markdownToProseMirrorCanonical(markdownContent);
+  //
+  // #502: this is the AGENT-authored `updatePageMarkdown` body — plain prose /
+  // config — so the two layered markdown extensions are turned OFF: a `$…$` span
+  // stays literal text (real math via `update_page_json`) and a SCHEMELESS
+  // `www.host`/email is not autolinked (an explicit `https://…` still links).
+  // Contrast `import_page_markdown`, which keeps DEFAULTS for the #328 lossless
+  // round-trip.
+  const tiptapJson = await markdownToProseMirrorCanonical(markdownContent, {
+    parseMath: false,
+    fuzzyLinkify: false,
+  });
   return await mutatePageContent(
     pageId,
     collabToken,

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

@@ -178,10 +178,11 @@ function sliceModel(xml: string): string | null {
 // --- decode chain ----------------------------------------------------------
 
 /**
- * Read the `content=` attribute out of a `.drawio.svg` string. Docmost stores a
- * base64 payload there (createDrawioSvg); draw.io's own SVG export may store the
- * XML entity-encoded instead. The DOM decodes entities for us, so the caller
- * only has to distinguish "starts with '<'" (raw XML) from base64.
+ * Read the `content=` attribute out of a `.drawio.svg` string. Docmost writes
+ * the mxfile XML entity-encoded there (buildDrawioSvg / createDrawioSvg), which
+ * is also how draw.io's own SVG export stores it; older attachments stored a
+ * base64 payload instead. The DOM decodes entities for us, so the caller only
+ * has to distinguish "starts with '<'" (raw XML) from base64.
  */
 export function extractContentAttr(svg: string): string {
   const { doc, error } = parseXml(svg);
@@ -195,12 +196,23 @@ export function extractContentAttr(svg: string): string {
   // value itself never contains a double-quote (base64 / entity-encoded XML).
   const m = /content="([^"]*)"/.exec(svg);
   if (m) {
-    // Decode the handful of XML entities a raw regex would leave encoded.
+    // Decode the handful of XML entities a raw regex would leave encoded. The
+    // numeric char-refs for tab/newline/CR MUST be decoded here too: the DOM
+    // path above turns them back into the literal control chars, so this
+    // regex fallback has to agree or the two decode paths diverge (#507).
+    // `&amp;` is decoded last so an escaped `&amp;#x9;` reads back as the
+    // literal text `&#x9;`, not a tab.
     return m[1]
       .replace(/&lt;/g, "<")
       .replace(/&gt;/g, ">")
       .replace(/&quot;/g, '"')
       .replace(/&#39;/g, "'")
+      .replace(/&#x9;/gi, "\t")
+      .replace(/&#9;/g, "\t")
+      .replace(/&#xa;/gi, "\n")
+      .replace(/&#10;/g, "\n")
+      .replace(/&#xd;/gi, "\r")
+      .replace(/&#13;/g, "\r")
       .replace(/&amp;/g, "&");
   }
   throw new Error("drawio: SVG has no content= attribute to decode");
@@ -307,9 +319,16 @@ export function encodeDrawioFile(modelXml: string, title = "Page-1"): string {
 /**
  * Build the `diagram.drawio.svg` attachment. Mirrors the import service's
  * createDrawioSvg contract exactly:
- *   <svg xmlns=… xmlns:xlink=… content="${base64(drawioFile)}">${inner}</svg>
+ *   <svg xmlns=… xmlns:xlink=… content="${xmlEscape(drawioFile)}">${inner}</svg>
  * plus width/height/viewBox from the diagram bounding box and the schematic
  * preview as the visible children (`inner`).
+ *
+ * The `content=` value is the mxfile XML XML-entity-escaped (draw.io's own
+ * native form), NOT base64. draw.io's editor decodes a base64 content= via
+ * Latin-1 atob (no UTF-8 step), turning every non-ASCII char (e.g. Cyrillic,
+ * ё, —) into mojibake; the entity-encoded form is decoded by the DOM as UTF-8
+ * and opens intact. Our decoder (decodeDrawioSvg) reads both forms, so old
+ * base64 attachments still round-trip.
  */
 export function buildDrawioSvg(
   modelXml: string,
@@ -318,14 +337,14 @@ export function buildDrawioSvg(
   title = "Page-1",
 ): string {
   const file = encodeDrawioFile(modelXml, title);
-  const base64 = Buffer.from(file, "utf-8").toString("base64");
+  const content = xmlEscape(file);
   const w = Math.max(1, Math.round(bbox.width));
   const h = Math.max(1, Math.round(bbox.height));
   return (
     `<svg xmlns="http://www.w3.org/2000/svg" ` +
     `xmlns:xlink="http://www.w3.org/1999/xlink" ` +
     `width="${w}" height="${h}" viewBox="0 0 ${w} ${h}" ` +
-    `content="${base64}">${inner}</svg>`
+    `content="${content}">${inner}</svg>`
   );
 }
 
@@ -334,7 +353,15 @@ function xmlEscape(s: string): string {
     .replace(/&/g, "&amp;")
     .replace(/</g, "&lt;")
     .replace(/>/g, "&gt;")
-    .replace(/"/g, "&quot;");
+    .replace(/"/g, "&quot;")
+    // A literal tab/newline/CR inside an attribute value is collapsed to a
+    // single space by XML attribute-value normalization on DOM read (both jsdom
+    // here and the real draw.io editor), silently flattening multi-line labels
+    // and tab-bearing values. Numeric char-refs survive that normalization, so
+    // emit them the way draw.io's own native export does (#507).
+    .replace(/\t/g, "&#x9;")
+    .replace(/\n/g, "&#xa;")
+    .replace(/\r/g, "&#xd;");
 }
 
 // --- normalization + hash --------------------------------------------------

packages/mcp/src/lib/markdown-fragment.ts

@@ -135,7 +135,17 @@ export interface MarkdownFragment {
 export async function importMarkdownFragment(
   markdown: string,
 ): Promise<MarkdownFragment> {
-  const doc = await markdownToProseMirror(markdown);
+  // #502: the fragment path is an MCP agent WRITE (patch_node/insert_node
+  // markdown), so it uses the SAME extensions-OFF importer options as the
+  // full-page write (markdownToProseMirrorCanonical): a `$…$` span stays literal
+  // and a schemeless domain/email is not autolinked. This keeps a block written
+  // via markdown canonically identical to the same content in a full-page write
+  // (no "second canon"). Explicit `https://…` links and block structure are
+  // unaffected.
+  const doc = await markdownToProseMirror(markdown, {
+    parseMath: false,
+    fuzzyLinkify: false,
+  });
   const content: any[] = Array.isArray(doc?.content) ? doc.content : [];
 
   const blocks: any[] = [];

packages/mcp/src/tool-specs.ts

@@ -469,7 +469,11 @@ export const SHARED_TOOL_SPECS = {
       '(markdown). The fragment may be SEVERAL blocks (a "1 → N" splice: rewrite a ' +
       'whole section in one call) — the first block inherits this block id, the ' +
       'rest get fresh ids. `^[...]` footnotes are supported (their definitions ' +
-      "merge into the page's footnote list). REJECTED when the target is a table " +
+      "merge into the page's footnote list). Markdown is taken LITERALLY — " +
+      '`$...$`/`$$...$$` are NOT parsed as math and schemeless `www.host` / bare ' +
+      'emails are NOT auto-linked (an explicit `https://` URL still links); for a ' +
+      'real formula pass a `mathInline`/`mathBlock` ProseMirror node via `node` ' +
+      '(or updatePageJson). REJECTED when the target is a table ' +
       'cell with attributes markdown cannot represent (merged/colored/fixed-width) ' +
       '— use the table tools or `node`. ' +
       '`node` (for precise attr/mark work): a raw ProseMirror node, e.g. a ' +
@@ -535,6 +539,10 @@ export const SHARED_TOOL_SPECS = {
       'Provide EXACTLY ONE of `markdown` or `node`. ' +
       '`markdown` (RECOMMENDED): a canonical markdown fragment — may be SEVERAL ' +
       'blocks, inserted in order at the anchor; `^[...]` footnotes supported. ' +
+      'Markdown is taken LITERALLY — `$...$`/`$$...$$` are NOT parsed as math and ' +
+      'schemeless `www.host` / bare emails are NOT auto-linked (an explicit ' +
+      '`https://` URL still links); for a real formula pass a ' +
+      '`mathInline`/`mathBlock` ProseMirror node via `node` (or updatePageJson). ' +
       '`node` (for precise attr/mark work OR table structure): a raw ProseMirror ' +
       'node. Table structure is JSON-only (not expressible in markdown): to add a ' +
       'tableRow, pass a tableRow node with position before/after and anchor INSIDE ' +
@@ -913,28 +921,46 @@ export const SHARED_TOOL_SPECS = {
     inAppKey: 'getPage',
     writeClass: 'readOnly',
     description:
-      'Fetch a single page as Markdown by its id. Returns the page title and ' +
-      'its Markdown content. The converter is canonical (round-trips text and ' +
-      'block structure), so this is sufficient for text edits; use the ' +
-      'page-JSON read tool only when you need what Markdown cannot carry. The ' +
-      'Markdown drops exactly: (1) block ids (not visible in Markdown); ' +
-      '(2) resolved-comment anchors (hidden here; only active <span ' +
-      'data-comment-id> anchors remain); (3) a fixed set of attributes with no ' +
-      'Markdown representation — table-cell colspan/rowspan/colwidth/' +
-      'backgroundColor/backgroundColorName, heading/paragraph indent, ' +
-      'callout.icon, orderedList.type, and link internal/target/rel/class. ' +
-      'Inline <span data-comment-id> tags in the markdown are comment highlight ' +
-      'anchors — treat them as markup, not page text.',
+      'Fetch a single page by its id. Returns the page title and its content. ' +
+      'format:"markdown" (DEFAULT) returns canonical Markdown (round-trips text ' +
+      'and block structure), sufficient for text edits; use the page-JSON read ' +
+      'tool only when you need what Markdown cannot carry. The Markdown drops ' +
+      'exactly: (1) block ids (not visible in Markdown); (2) resolved-comment ' +
+      'anchors (hidden here; only active <span data-comment-id> anchors remain); ' +
+      '(3) a fixed set of attributes with no Markdown representation — table-cell ' +
+      'colspan/rowspan/colwidth/backgroundColor/backgroundColorName, ' +
+      'heading/paragraph indent, callout.icon, orderedList.type, and link ' +
+      'internal/target/rel/class. Inline <span data-comment-id> tags in the ' +
+      'markdown are comment highlight anchors — treat them as markup, not page ' +
+      'text. format:"text" returns a FLAT, DETERMINISTIC plain-text rendering ' +
+      'for machine diffing: one line per block, ALL inline marks/formatting and ' +
+      'comment anchors dropped, a hardBreak is a newline, and non-text nodes ' +
+      'become STABLE placeholders — an image is "[image]" and a table is ' +
+      '"[table RxC]" (R rows x C columns). This output is stable across versions ' +
+      '(pinned by a snapshot test); use it to diff a config/prose you wrote ' +
+      'against what was stored (an empty diff means it was stored verbatim).',
     tier: 'core',
-    catalogLine: 'getPage — fetch a page as Markdown by its id.',
+    catalogLine:
+      'getPage — fetch a page by its id (format:"markdown" default, or "text" for a flat machine-diffable read).',
     // Reconciled: MCP's stricter .min(1) kept; in-app's more-informative
     // "(or slugId)" describe kept.
     buildShape: (z) => ({
       pageId: z.string().min(1).describe('The id (or slugId) of the page.'),
+      format: z
+        .enum(['markdown', 'text'])
+        .optional()
+        .describe(
+          'Output format: "markdown" (default, canonical round-trippable) or ' +
+            '"text" (flat deterministic plain text for machine diffing).',
+        ),
     }),
     // MCP wraps the raw `{ data, success }` as JSON. The in-app host instead
     // projects a token-efficient `{ title, markdown }` (its long-standing shape).
-    execute: (client, { pageId }) => client.getPage(pageId as string),
+    execute: (client, { pageId, format }) =>
+      client.getPage(
+        pageId as string,
+        (format as 'markdown' | 'text' | undefined) ?? 'markdown',
+      ),
     inAppExecute: async (client, { pageId }) => {
       // getPage(pageId) -> { data: filterPage(page, markdown), success }.
       const result = (await client.getPage(pageId as string)) as {
@@ -1077,8 +1103,12 @@ export const SHARED_TOOL_SPECS = {
     description:
       'Create a new page with a Markdown body in a space, optionally under a ' +
       'parent page (omit parentPageId to create at the space root). Returns ' +
-      'the new page id and title. Reversible: a page can be moved to trash ' +
-      'later.',
+      'the new page id and title. Body text is taken LITERALLY — ' +
+      '`$...$`/`$$...$$` are NOT parsed into a math formula and schemeless ' +
+      '`www.host` / bare emails are NOT auto-linked (an explicit `https://` URL ' +
+      'still links); for a real formula use updatePageJson with ' +
+      '`mathInline`/`mathBlock` nodes instead. Reversible: a page can be moved ' +
+      'to trash later.',
     tier: 'deferred',
     catalogLine: 'createPage — create a new page with a Markdown body in a space.',
     // Reconciled schema DRIFT: the MCP copy pinned `content` to .min(1) while
@@ -1337,7 +1367,11 @@ export const SHARED_TOOL_SPECS = {
       'title). The whole body is re-imported from the markdown (block ids ' +
       'regenerate — for surgical or id-preserving edits use the find/replace, ' +
       'node-patch or page-JSON tools instead). Docmost-flavoured markdown is ' +
-      'parsed, including `^[...]` inline footnotes. Reversible: the previous ' +
+      'parsed, including `^[...]` inline footnotes. Text is taken LITERALLY — ' +
+      '`$...$`/`$$...$$` are NOT parsed into a math formula and schemeless ' +
+      '`www.host` / bare emails are NOT auto-linked (an explicit `https://` URL ' +
+      'still links); for a real formula use updatePageJson with ' +
+      '`mathInline`/`mathBlock` nodes instead. Reversible: the previous ' +
       'version is kept in page history.',
     tier: 'deferred',
     catalogLine:

packages/mcp/test/mock/createpage-import-flag.test.mjs

@@ -0,0 +1,83 @@
+// #502 BLOCKER 1 (client half): the MCP `createPage` tool builds its body as an
+// AGENT-authored markdown file and POSTs it to the server `/pages/import`
+// endpoint. It must send the `disableMarkdownExtensions=true` multipart field so
+// the SERVER importer runs with math + fuzzy-autolink OFF (a human file upload
+// omits the field and keeps them ON). This mock http server captures the raw
+// multipart body and asserts the field is present.
+import { test, after } from "node:test";
+import assert from "node:assert/strict";
+import http from "node:http";
+import { DocmostClient } from "../../build/client.js";
+
+function sendJson(res, status, obj, extra = {}) {
+  res.writeHead(status, { "Content-Type": "application/json", ...extra });
+  res.end(JSON.stringify(obj));
+}
+function readRaw(req) {
+  return new Promise((resolve) => {
+    const chunks = [];
+    req.on("data", (c) => chunks.push(c));
+    req.on("end", () => resolve(Buffer.concat(chunks).toString("utf-8")));
+  });
+}
+
+const openServers = [];
+after(async () => {
+  await Promise.all(openServers.map((s) => new Promise((r) => s.close(r))));
+});
+
+const NEW_ID = "00000000-0000-4000-8000-000000000042";
+const SPACE = "00000000-0000-4000-8000-0000000000aa";
+
+function spawn(state) {
+  return new Promise((resolve) => {
+    const server = http.createServer(async (req, res) => {
+      const raw = await readRaw(req);
+      if (req.url === "/api/auth/login") {
+        return sendJson(res, 200, { success: true }, { "Set-Cookie": "authToken=t; Path=/; HttpOnly" });
+      }
+      if (req.url === "/api/pages/import") {
+        state.importBody = raw; // the raw multipart payload
+        return sendJson(res, 200, { data: { id: NEW_ID } });
+      }
+      if (req.url === "/api/pages/update") {
+        return sendJson(res, 200, { data: { id: NEW_ID } });
+      }
+      if (req.url === "/api/pages/info") {
+        return sendJson(res, 200, {
+          data: {
+            id: NEW_ID,
+            slugId: "slugnew1234",
+            title: "T",
+            spaceId: SPACE,
+            updatedAt: "2026-01-01T00:00:00Z",
+            content: { type: "doc", content: [{ type: "paragraph", content: [{ type: "text", text: "x" }] }] },
+          },
+        });
+      }
+      if (req.url === "/api/pages/sidebar-pages") {
+        return sendJson(res, 200, { data: { items: [], meta: { hasNextPage: false, nextCursor: null } } });
+      }
+      return sendJson(res, 404, { message: "not found" });
+    });
+    server.listen(0, "127.0.0.1", () => {
+      openServers.push(server);
+      resolve(`http://127.0.0.1:${server.address().port}/api`);
+    });
+  });
+}
+
+test("createPage sends disableMarkdownExtensions=true in the /pages/import multipart", async () => {
+  const state = {};
+  const baseURL = await spawn(state);
+  const client = new DocmostClient(baseURL, "e@x.com", "pw");
+
+  await client.createPage("My Config", "ticket $x=1$ at www.host.com", SPACE);
+
+  assert.ok(state.importBody, "the import endpoint received a body");
+  // The multipart payload carries the field name and its "true" value.
+  assert.match(state.importBody, /name="disableMarkdownExtensions"/);
+  assert.match(state.importBody, /name="disableMarkdownExtensions"[\s\S]*?\r?\n\r?\ntrue\r?\n/);
+  // The agent body itself is still sent as the file part.
+  assert.match(state.importBody, /ticket \$x=1\$ at www\.host\.com/);
+});

packages/mcp/test/mock/getpage-text-format.test.mjs

@@ -0,0 +1,116 @@
+// #502 READ: the getPage tool gains a `format:"text"` mode. It requests the
+// server's flat, deterministic text rendering (the server's jsonToText path — the
+// SAME serializer that feeds search), passing it through unchanged. This mock
+// stands up a local http server (same harness style as getpage-conversion-cache)
+// and asserts end-to-end that:
+//   - format:"text" sends `format:"text"` in the /pages/info body and returns the
+//     server's text string verbatim (no client-side markdown conversion);
+//   - the DEFAULT (no format) still returns markdown-converted content;
+//   - the text read resolves page + subpages like the markdown read.
+import { test, after } from "node:test";
+import assert from "node:assert/strict";
+import http from "node:http";
+import { DocmostClient } from "../../build/client.js";
+
+function readBody(req) {
+  return new Promise((resolve) => {
+    let raw = "";
+    req.on("data", (c) => (raw += c));
+    req.on("end", () => resolve(raw));
+  });
+}
+function sendJson(res, status, obj, extra = {}) {
+  res.writeHead(status, { "Content-Type": "application/json", ...extra });
+  res.end(JSON.stringify(obj));
+}
+
+const openServers = [];
+after(async () => {
+  await Promise.all(openServers.map((s) => new Promise((r) => s.close(r))));
+});
+
+const PAGE_UUID = "00000000-0000-4000-8000-000000000010";
+const SPACE_UUID = "00000000-0000-4000-8000-0000000000aa";
+const CHILD_UUID = "00000000-0000-4000-8000-0000000000bb";
+
+// The deterministic text the SERVER's jsonToText would produce for this page.
+const SERVER_TEXT = "Title line\nsecond block\n[image]\n[table 2x3]";
+
+function makeDoc(text) {
+  return { type: "doc", content: [{ type: "paragraph", content: [{ type: "text", text }] }] };
+}
+
+function spawn(state) {
+  return new Promise((resolve) => {
+    const server = http.createServer(async (req, res) => {
+      const body = await readBody(req);
+      if (req.url === "/api/auth/login") {
+        return sendJson(res, 200, { success: true }, { "Set-Cookie": "authToken=t; Path=/; HttpOnly" });
+      }
+      if (req.url === "/api/pages/info") {
+        const parsed = body ? JSON.parse(body) : {};
+        state.lastInfoBody = parsed;
+        // Emulate the server: when format:"text" is requested, `content` is the
+        // flat text string; otherwise it is the raw ProseMirror JSON.
+        const content = parsed.format === "text" ? SERVER_TEXT : makeDoc("Title line");
+        return sendJson(res, 200, {
+          success: true,
+          data: {
+            id: PAGE_UUID,
+            slugId: "slug123456",
+            title: "Text Page",
+            parentPageId: null,
+            spaceId: SPACE_UUID,
+            updatedAt: "2026-01-01T00:00:00Z",
+            content,
+          },
+        });
+      }
+      if (req.url === "/api/pages/sidebar-pages") {
+        return sendJson(res, 200, {
+          success: true,
+          data: {
+            items: [{ id: CHILD_UUID, title: "Child", hasChildren: false }],
+            meta: { hasNextPage: false, nextCursor: null },
+          },
+        });
+      }
+      return sendJson(res, 404, { message: "not found" });
+    });
+    server.listen(0, "127.0.0.1", () => {
+      openServers.push(server);
+      resolve(`http://127.0.0.1:${server.address().port}/api`);
+    });
+  });
+}
+
+function makeClient(baseURL) {
+  return new DocmostClient({ apiUrl: baseURL, getToken: async () => "access" });
+}
+
+test('getPage(format:"text") requests text and returns the server text verbatim', async () => {
+  const state = {};
+  const client = makeClient(await spawn(state));
+
+  const result = await client.getPage(PAGE_UUID, "text");
+  assert.equal(state.lastInfoBody.format, "text", "the info request carried format:text");
+  assert.equal(result.success, true);
+  assert.equal(result.data.content, SERVER_TEXT, "returns the server's flat text unchanged");
+  // Deterministic placeholders are surfaced to the agent.
+  assert.ok(result.data.content.includes("[image]"));
+  assert.ok(result.data.content.includes("[table 2x3]"));
+  // No client-side markdown artifacts leaked in.
+  assert.ok(!result.data.content.includes("{{SUBPAGES}}"));
+  // Subpages still resolve for context.
+  assert.deepEqual(result.data.subpages, [{ id: CHILD_UUID, title: "Child" }]);
+});
+
+test('getPage default (no format) still returns markdown, not text', async () => {
+  const state = {};
+  const client = makeClient(await spawn(state));
+
+  const result = await client.getPage(PAGE_UUID);
+  assert.equal(state.lastInfoBody.format, undefined, "default read sends no format");
+  assert.ok(result.data.content.includes("Title line"), "markdown content converted client-side");
+  assert.notEqual(result.data.content, SERVER_TEXT);
+});

packages/mcp/test/mock/write-path-extensions-wiring.test.mjs

@@ -0,0 +1,181 @@
+// #502 caller-WIRING: end-to-end through a live Hocuspocus collab stack (same
+// harness style as markdown-patch-insert), driving the REAL client methods and
+// reading the persisted document back, so the test proves each write tool passes
+// the RIGHT importer options — not just that the shared wrapper can:
+//   - updatePageMarkdown (client.updatePage)      -> extensions OFF  (`$…$` literal, www not linked)
+//   - import_page_markdown (client.importPageMarkdown) -> DEFAULTS   (`$x^2$` -> math node, #328)
+// Mutating either caller's option flips the matching assertion (see the coder's
+// mutation note), so this file guards the wiring, not only the wrapper.
+import { test, after } from "node:test";
+import assert from "node:assert/strict";
+import http from "node:http";
+import { WebSocketServer } from "ws";
+import { Hocuspocus } from "@hocuspocus/server";
+import { DocmostClient } from "../../build/client.js";
+import { buildYDoc } from "../../build/lib/collaboration.js";
+import { serializeDocmostMarkdown } from "@docmost/prosemirror-markdown";
+
+const PAGE = "11111111-1111-4111-8111-111111111111";
+
+function findAll(node, type, acc = []) {
+  if (!node || typeof node !== "object") return acc;
+  if (node.type === type) acc.push(node);
+  if (Array.isArray(node.content)) for (const c of node.content) findAll(c, type, acc);
+  return acc;
+}
+function allText(node, acc = []) {
+  if (!node || typeof node !== "object") return acc.join("");
+  if (node.type === "text" && typeof node.text === "string") acc.push(node.text);
+  if (Array.isArray(node.content)) for (const c of node.content) allText(c, acc);
+  return acc.join("");
+}
+function hasLink(node) {
+  return findAll(node, "text").some((t) => t.marks?.some((m) => m.type === "link"));
+}
+
+function fragmentToJson(frag) {
+  const decodeNode = (el) => {
+    if (el.constructor.name === "YXmlText") {
+      const delta = el.toDelta();
+      return delta.map((d) => {
+        const node = { type: "text", text: d.insert };
+        if (d.attributes && Object.keys(d.attributes).length) {
+          node.marks = Object.entries(d.attributes).map(([type, attrs]) =>
+            attrs && typeof attrs === "object" && Object.keys(attrs).length
+              ? { type, attrs }
+              : { type },
+          );
+        }
+        return node;
+      });
+    }
+    const node = { type: el.nodeName };
+    const attrs = el.getAttributes();
+    if (attrs && Object.keys(attrs).length) node.attrs = attrs;
+    const children = [];
+    for (const child of el.toArray()) {
+      const decoded = decodeNode(child);
+      if (Array.isArray(decoded)) children.push(...decoded);
+      else children.push(decoded);
+    }
+    if (children.length) node.content = children;
+    return node;
+  };
+  const content = [];
+  for (const child of frag.toArray()) content.push(decodeNode(child));
+  return { type: "doc", content };
+}
+
+const openStacks = [];
+after(async () => {
+  await Promise.all(
+    openStacks.map(
+      ({ server, hocuspocus }) =>
+        new Promise((resolve) => {
+          server.close(() => {
+            Promise.resolve(hocuspocus.destroy?.()).finally(resolve);
+          });
+        }),
+    ),
+  );
+});
+
+async function spawnCollabStack(seedDoc) {
+  const state = { lastDoc: null };
+  const hocuspocus = new Hocuspocus({
+    quiet: true,
+    async onLoadDocument() {
+      return buildYDoc(seedDoc);
+    },
+    async onChange(data) {
+      try {
+        state.lastDoc = fragmentToJson(data.document.getXmlFragment("default"));
+      } catch {
+        /* ignore teardown-race decode errors */
+      }
+    },
+  });
+  const wss = new WebSocketServer({ noServer: true });
+  const server = http.createServer((req, res) => {
+    let raw = "";
+    req.on("data", (c) => (raw += c));
+    req.on("end", () => {
+      if (req.url === "/api/auth/login") {
+        res.writeHead(200, {
+          "Content-Type": "application/json",
+          "Set-Cookie": "authToken=t; Path=/; HttpOnly",
+        });
+        res.end(JSON.stringify({ success: true }));
+        return;
+      }
+      if (req.url === "/api/auth/collab-token") {
+        res.writeHead(200, { "Content-Type": "application/json" });
+        res.end(JSON.stringify({ data: { token: "collab-jwt" } }));
+        return;
+      }
+      res.writeHead(404, { "Content-Type": "application/json" });
+      res.end(JSON.stringify({ message: "not found" }));
+    });
+  });
+  server.on("upgrade", (request, socket, head) => {
+    if (!request.url || !request.url.startsWith("/collab")) {
+      socket.destroy();
+      return;
+    }
+    wss.handleUpgrade(request, socket, head, (ws) => {
+      hocuspocus.handleConnection(ws, request);
+    });
+  });
+  const baseURL = await new Promise((resolve) => {
+    server.listen(0, "127.0.0.1", () => {
+      resolve(`http://127.0.0.1:${server.address().port}/api`);
+    });
+  });
+  openStacks.push({ server, hocuspocus });
+  return { state, baseURL };
+}
+
+function seed() {
+  return {
+    type: "doc",
+    content: [
+      { type: "paragraph", attrs: { id: "p-id" }, content: [{ type: "text", text: "seed" }] },
+    ],
+  };
+}
+
+test("updatePageMarkdown wiring: extensions OFF — `$…$` literal, www not linked, https links", async () => {
+  const { state, baseURL } = await spawnCollabStack(seed());
+  const client = new DocmostClient(baseURL, "e@x.com", "pw");
+
+  await client.updatePage(PAGE, "cfg $x=1$ and www.host.com and https://ex.com");
+
+  assert.ok(state.lastDoc, "a document was persisted");
+  assert.equal(findAll(state.lastDoc, "mathInline").length, 0, "no phantom math from an agent write");
+  assert.ok(allText(state.lastDoc).includes("$x=1$"), "literal dollars preserved");
+  assert.ok(allText(state.lastDoc).includes("www.host.com"), "bare domain preserved as text");
+  // The explicit https URL still links (only the schemeless autolink is off).
+  const links = findAll(state.lastDoc, "text").filter((t) =>
+    t.marks?.some((m) => m.type === "link"),
+  );
+  assert.ok(links.some((t) => t.text?.includes("ex.com")), "explicit https still links");
+});
+
+test("import_page_markdown wiring: DEFAULTS — exported `$x^2$` re-imports AS a math node (#328)", async () => {
+  const { state, baseURL } = await spawnCollabStack(seed());
+  const client = new DocmostClient(baseURL, "e@x.com", "pw");
+
+  // A self-contained docmost markdown file whose body carries a math span (as the
+  // exporter emits it). import_page_markdown must import it with math ON.
+  const meta = { version: 1, pageId: PAGE, slugId: "s", title: "T", spaceId: "sp", parentPageId: null };
+  const fullMd = serializeDocmostMarkdown(meta, "energy is $x^2$ here", []);
+
+  await client.importPageMarkdown(PAGE, fullMd);
+
+  assert.ok(state.lastDoc, "a document was persisted");
+  assert.equal(
+    findAll(state.lastDoc, "mathInline").length,
+    1,
+    "the lossless round-trip is intact: math survives import_page_markdown",
+  );
+});

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

@@ -51,6 +51,14 @@ const hasRule = (issues, rule, cellId) =>
     (i) => i.rule === rule && (cellId === undefined || i.cellId === cellId),
   );
 
+// Reverse the attribute-value XML escaping used in the `content=` payload.
+const unescapeAttr = (s) =>
+  s
+    .replace(/&lt;/g, "<")
+    .replace(/&gt;/g, ">")
+    .replace(/&quot;/g, '"')
+    .replace(/&amp;/g, "&");
+
 // --- style parsing ---------------------------------------------------------
 
 test("parseStyle: base stylename + key=value pairs", () => {
@@ -335,16 +343,20 @@ test("encode/build: a title with < > \" & round-trips without corrupting the SVG
 
   // The outer content="..." attribute must not be broken by the title: the raw
   // title metacharacters never appear literally in the SVG markup (they are
-  // base64-encoded inside content=, and escaped inside the file XML).
+  // entity-escaped inside content=, doubly so where the file XML already escaped
+  // them inside name="...").
   const contentMatch = /content="([^"]*)"/.exec(svg);
   assert.ok(contentMatch, "SVG has a single well-formed content= attribute");
 
   // The diagram model still decodes losslessly despite the exotic title.
   assert.equal(decodeDrawioSvg(svg), model);
 
+  // content= is now entity-encoded XML (draw.io's native form), never base64.
+  assert.match(contentMatch[1], /^&lt;mxfile/);
+
   // The file XML is well-formed: the title lives in name="..." as escaped
   // entities, so unescaping recovers the original title byte-for-byte.
-  const fileXml = Buffer.from(contentMatch[1], "base64").toString("utf-8");
+  const fileXml = unescapeAttr(contentMatch[1]);
   const nameMatch = /<diagram id="[^"]*" name="([^"]*)">/.exec(fileXml);
   assert.ok(nameMatch, "the diagram name attribute is intact and quote-safe");
   const decodedTitle = nameMatch[1]
@@ -358,3 +370,112 @@ test("encode/build: a title with < > \" & round-trips without corrupting the SVG
   const file = encodeDrawioFile(model, title);
   assert.match(file, /name="A &lt; B &gt; C &quot; D &amp; E">/);
 });
+
+// --- #507: content= is entity-encoded XML, never base64 --------------------
+
+// A model whose cell values carry Cyrillic, ё and an em dash — exactly the
+// characters draw.io's Latin-1 atob mangles when content= is base64.
+const CYRILLIC_MODEL =
+  "<mxGraphModel><root>" +
+  '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+  '<mxCell id="2" value="Старт-бит — ёж" style="rounded=1;html=1;" vertex="1" parent="1">' +
+  '<mxGeometry x="100" y="100" width="120" height="60" as="geometry"/></mxCell>' +
+  "</root></mxGraphModel>";
+
+test("#507: buildDrawioSvg writes content= as entity-encoded XML (not base64)", () => {
+  const model = normalizeXml(CYRILLIC_MODEL);
+  const svg = buildDrawioSvg(model, "<g/>", { width: 200, height: 120 }, "Диаграмма");
+
+  const contentMatch = /content="([^"]*)"/.exec(svg);
+  assert.ok(contentMatch, "SVG has a single well-formed content= attribute");
+  const content = contentMatch[1];
+
+  // The content= value is the entity-encoded mxfile XML — starts with `&lt;mxfile`.
+  assert.match(content, /^&lt;mxfile/, "content= is entity-encoded mxfile XML");
+  // It must NOT be a base64 blob: base64 has no XML entities and no literal `<`.
+  assert.ok(content.includes("&lt;"), "content= carries XML entities, not base64");
+
+  // Cyrillic / ё / — survive verbatim in the attribute (raw UTF-8, not atob-mangled).
+  assert.ok(content.includes("Старт-бит — ёж"), "non-ASCII value is raw UTF-8 in content=");
+  assert.ok(content.includes("Диаграмма"), "non-ASCII title is raw UTF-8 in content=");
+  // The mojibake that base64+atob would have produced must be absent.
+  assert.ok(!content.includes("Ð"), "no Latin-1 mojibake in content=");
+});
+
+test("#507: Cyrillic model round-trips byte-stable through buildDrawioSvg -> decodeDrawioSvg", () => {
+  const model = normalizeXml(CYRILLIC_MODEL);
+  const svg = buildDrawioSvg(model, "<g/>", { width: 200, height: 120 }, "Заголовок — ё");
+  assert.equal(decodeDrawioSvg(svg), model);
+});
+
+test("#507 back-compat: an OLD base64-form .drawio.svg still decodes losslessly", () => {
+  const model = normalizeXml(CYRILLIC_MODEL);
+  // Reproduce the pre-fix write path: encodeDrawioFile -> base64 in content=.
+  const file = encodeDrawioFile(model, "Старая диаграмма");
+  const base64 = Buffer.from(file, "utf-8").toString("base64");
+  const svg =
+    `<svg xmlns="http://www.w3.org/2000/svg" content="${base64}"><g/></svg>`;
+  // No XML entities, purely base64 alphabet — this is the legacy form.
+  assert.ok(!base64.includes("<") && !base64.includes("&"));
+  assert.equal(decodeDrawioSvg(svg), model);
+});
+
+test("#507 negative: non-ASCII in a cell value AND in the title round-trip clean", () => {
+  const model = normalizeXml(CYRILLIC_MODEL);
+  const title = "Тест — ёмкость № 5";
+  const svg = buildDrawioSvg(model, "<g/>", { width: 200, height: 120 }, title);
+
+  // Model recovered byte-for-byte.
+  assert.equal(decodeDrawioSvg(svg), model);
+
+  // Title lands in the <diagram name="..."> of the decoded file XML, intact.
+  const content = /content="([^"]*)"/.exec(svg)[1];
+  const fileXml = unescapeAttr(content);
+  const nameMatch = /<diagram id="[^"]*" name="([^"]*)">/.exec(fileXml);
+  assert.ok(nameMatch, "diagram name attribute present");
+  assert.equal(unescapeAttr(nameMatch[1]), title);
+});
+
+// --- #507 F1: literal tab/newline/CR in an attribute value survive the
+// content= round-trip. The whole mxfile XML lives in one content="..." attr;
+// XML attribute-value normalization collapses a LITERAL tab/newline/CR to a
+// single space on DOM read, so the escape must emit numeric char-refs instead.
+const CTRL_MODEL =
+  "<mxGraphModel><root>" +
+  '<mxCell id="0"/><mxCell id="1" parent="0"/>' +
+  '<mxCell id="2" value="col1\tcol2" style="html=1;\nshadow=0" vertex="1" parent="1">' +
+  '<mxGeometry x="10" y="10" width="120" height="60" as="geometry"/></mxCell>' +
+  '<mxCell id="3" value="Line1\nLine2\rLine3" vertex="1" parent="1">' +
+  '<mxGeometry x="10" y="100" width="120" height="60" as="geometry"/></mxCell>' +
+  "</root></mxGraphModel>";
+
+test("#507 F1: literal tab/newline/CR in a value round-trip byte-stable (DOM decode)", () => {
+  const svg = buildDrawioSvg(CTRL_MODEL, "<g/>", { width: 200, height: 200 });
+  const content = /content="([^"]*)"/.exec(svg)[1];
+  // The tab/newline/CR must be emitted as numeric char-refs, never as literal
+  // control chars (which DOM attribute-value normalization would eat).
+  assert.ok(
+    !/[\t\n\r]/.test(content),
+    "no literal tab/newline/CR survive in the content= attribute",
+  );
+  assert.ok(
+    content.includes("&#x9;") &&
+      content.includes("&#xa;") &&
+      content.includes("&#xd;"),
+    "tab/newline/CR are emitted as numeric char-refs",
+  );
+  // Full DOM decode recovers the model byte-for-byte, control chars intact.
+  assert.equal(decodeDrawioSvg(svg), CTRL_MODEL);
+});
+
+test("#507 F1: regex fallback decodes tab/newline/CR char-refs (agrees with DOM path)", () => {
+  const svg = buildDrawioSvg(CTRL_MODEL, "<g/>", { width: 200, height: 200 });
+  const content = /content="([^"]*)"/.exec(svg)[1];
+  // A bare `&` makes the SVG wrapper malformed, forcing extractContentAttr onto
+  // its regex fallback branch. That branch must decode the tab/newline/CR
+  // char-refs exactly like the DOM path, or the two decoders diverge.
+  const malformedSvg = `<svg content="${content}">&</svg>`;
+  assert.equal(decodeDrawioSvg(malformedSvg), CTRL_MODEL);
+  // The well-formed (DOM) path yields the identical result.
+  assert.equal(decodeDrawioSvg(svg), CTRL_MODEL);
+});

packages/mcp/test/unit/mcp-write-extensions-off.test.mjs

@@ -0,0 +1,108 @@
+// #502: the two layered markdown extensions (`$…$` math, schemeless fuzzy
+// autolink) are decided PER CALLER of the shared write importer, not hardcoded in
+// the wrapper — because the callers need OPPOSITE behavior:
+//   - AGENT-authored plain markdown (updatePageMarkdown, patch_node/insert_node)
+//     -> extensions OFF: a `$…$` config span stays literal, a bare `www.host` is
+//     not autolinked, an explicit `https://…` still links.
+//   - FULL-FILE round-trip import (import_page_markdown, #328 lossless) ->
+//     DEFAULTS (extensions ON): an exported math node's `$x^2$` re-imports AS a
+//     math node, so the export→import pair is NOT broken.
+// This unit file pins the importer contract at each of those semantics. The
+// caller-WIRING (that each client method passes the right options) is pinned by
+// the collab-backed test in mock/write-path-extensions-wiring.test.mjs.
+import { test } from "node:test";
+import assert from "node:assert/strict";
+import { markdownToProseMirrorCanonical } from "../../build/lib/collaboration.js";
+import { importMarkdownFragment } from "../../build/lib/markdown-fragment.js";
+import {
+  markdownToProseMirror,
+  convertProseMirrorToMarkdown,
+} from "@docmost/prosemirror-markdown";
+
+const OFF = { parseMath: false, fuzzyLinkify: false };
+
+function findAll(node, type, acc = []) {
+  if (!node || typeof node !== "object") return acc;
+  if (node.type === type) acc.push(node);
+  if (Array.isArray(node.content)) for (const c of node.content) findAll(c, type, acc);
+  return acc;
+}
+function allText(node, acc = []) {
+  if (!node || typeof node !== "object") return acc.join("");
+  if (node.type === "text" && typeof node.text === "string") acc.push(node.text);
+  if (Array.isArray(node.content)) for (const c of node.content) allText(c, acc);
+  return acc.join("");
+}
+function hasLink(node) {
+  return findAll(node, "text").some((t) => t.marks?.some((m) => m.type === "link"));
+}
+
+// --- AGENT-write semantics (updatePageMarkdown): extensions OFF -----------------
+
+test("agent-write importer (OFF): `$…$` config stays literal, no math node", async () => {
+  const doc = await markdownToProseMirrorCanonical("export A=$FOO and B=$BAR done", OFF);
+  assert.equal(findAll(doc, "mathInline").length, 0);
+  assert.equal(allText(doc), "export A=$FOO and B=$BAR done");
+});
+
+test("agent-write importer (OFF): schemeless www NOT linked; explicit https STILL linked", async () => {
+  const bare = await markdownToProseMirrorCanonical("see www.example.com here", OFF);
+  assert.equal(hasLink(bare), false);
+  assert.equal(allText(bare), "see www.example.com here");
+
+  const explicit = await markdownToProseMirrorCanonical("see https://example.com here", OFF);
+  assert.equal(hasLink(explicit), true);
+});
+
+test("agent-write importer (OFF): heading + list structure preserved", async () => {
+  const doc = await markdownToProseMirrorCanonical("## Heading\n\n- one\n- two", OFF);
+  assert.equal(findAll(doc, "heading").length, 1);
+  assert.equal(findAll(doc, "bulletList").length, 1);
+});
+
+test("fragment importer (patch_node/insert_node) is OFF: `$x=1$` literal, https links", async () => {
+  const { blocks } = await importMarkdownFragment("cfg $x=1$ and https://ex.com");
+  const doc = { type: "doc", content: blocks };
+  assert.equal(findAll(doc, "mathInline").length, 0);
+  assert.equal(hasLink(doc), true);
+  assert.ok(allText(doc).includes("$x=1$"));
+});
+
+// --- FULL-FILE import semantics (import_page_markdown): DEFAULTS (math ON) ------
+
+test("import_page_markdown importer (DEFAULTS): `$x^2$` DOES create a math node", async () => {
+  // markdownToProseMirrorCanonical WITHOUT options == what import_page_markdown
+  // passes. Math must survive (this is the REAL importer, not the package default).
+  const doc = await markdownToProseMirrorCanonical("$x^2$");
+  assert.equal(findAll(doc, "mathInline").length, 1);
+  assert.equal(findAll(doc, "mathInline")[0].attrs.text, "x^2");
+});
+
+test("import_page_markdown (DEFAULTS): #328 lossless export->import keeps math (round-trip)", async () => {
+  // The exporter serializes a math node as readable `$x^2$`; re-importing through
+  // the REAL import_page_markdown importer (markdownToProseMirrorCanonical, no
+  // options) must yield a math node again and be byte-stable. Under the BUGGY code
+  // (canonical hardcoded parseMath:false) doc2 would be literal text -> this test
+  // would REDDEN.
+  const source = {
+    type: "doc",
+    content: [{ type: "paragraph", content: [{ type: "mathInline", attrs: { text: "x^2" } }] }],
+  };
+  const md1 = convertProseMirrorToMarkdown(source);
+  const doc2 = await markdownToProseMirrorCanonical(md1); // real import path, defaults
+  assert.equal(findAll(doc2, "mathInline").length, 1, "math survives the round-trip import");
+  const md2 = convertProseMirrorToMarkdown(doc2);
+  assert.equal(md2, md1, "export is byte-stable across the round-trip");
+});
+
+test("import_page_markdown (DEFAULTS): a schemeless www IS autolinked", async () => {
+  const doc = await markdownToProseMirrorCanonical("see www.example.com here");
+  assert.equal(hasLink(doc), true);
+});
+
+// --- Package default importer (editor/file-import/git-sync) is UNCHANGED --------
+
+test("PACKAGE default importer keeps math ON (editor/file/git-sync path)", async () => {
+  const doc = await markdownToProseMirror("$x^2$");
+  assert.equal(findAll(doc, "mathInline").length, 1);
+});

packages/prosemirror-markdown/src/lib/index.ts

@@ -25,6 +25,7 @@ export {
   markdownToProseMirror,
   markdownToProseMirrorSync,
 } from "./markdown-to-prosemirror.js";
+export type { MarkdownImportOptions } from "./markdown-to-prosemirror.js";
 
 // Foreign-markdown normalizer (#493): the input-liberal pre-pass that rewrites
 // GFM `[^id]` reference footnotes to canonical inline `^[body]`. Two variants:

packages/prosemirror-markdown/src/lib/markdown-to-prosemirror.ts

@@ -7,7 +7,7 @@
  * natively through the collab gateway, so no websocket/Yjs write-path lives
  * here.
  */
-import { Marked } from "marked";
+import { Marked, Tokenizer } from "marked";
 import { parseHtmlDocument, generateJsonWith } from "./dom-parser.js";
 import type { TokenizerExtension, RendererExtension } from "marked";
 import { docmostExtensions } from "./docmost-schema.js";
@@ -230,19 +230,88 @@ function escapeFootnoteAttr(value: string): string {
   return String(value).replace(/&/g, "&").replace(/"/g, """);
 }
 
-// Dedicated marked instance: default (GFM) options plus the `==` highlight
-// inline extension, the `$…$` / `$$…$$` math extensions (#293 canon #6), and the
-// `^[…]` inline-footnote extension (#293 canon #2). Constructed once at module
-// load so the extensions are registered exactly once and never mutate the global
-// `marked` singleton.
-const markedInstance = new Marked().use({
-  extensions: [
+/**
+ * Options controlling which of the two *layered* markdown extensions the
+ * canonical importer applies. Both default to `true`, so the human editor,
+ * file-import and git-sync paths keep their existing behavior byte-for-byte;
+ * ONLY the MCP markdown-write path opts OUT (see #502).
+ *
+ * The extensions are optional because they are the SOURCE of two silent
+ * corruptions when an AGENT writes plain prose/config as markdown:
+ *   - `parseMath`: a `$…$` span becomes a `mathInline` node. An agent writing a
+ *     config like `export A=$FOO and B=$BAR` gets `$FOO and B=$` silently turned
+ *     into a formula. With `parseMath:false` the `$` stays literal text (real
+ *     formulas go through `update_page_json` with `mathInline`/`mathBlock`).
+ *   - `fuzzyLinkify`: marked's GFM autolinker turns a SCHEMELESS `www.foo.com`
+ *     (and email) into a link. With `fuzzyLinkify:false` a schemeless domain
+ *     stays literal text; an EXPLICIT `https://…` STILL becomes a link (only the
+ *     fuzzy, schemeless autolink is suppressed).
+ */
+export interface MarkdownImportOptions {
+  /** Apply the `$…$` / `$$…$$` math extensions (default true). */
+  parseMath?: boolean;
+  /** Apply marked's GFM schemeless (fuzzy) autolinker (default true). */
+  fuzzyLinkify?: boolean;
+}
+
+/**
+ * `fuzzyLinkify:false` override of marked's built-in GFM `url` inline tokenizer.
+ *
+ * The stock tokenizer autolinks THREE shapes: a schemeless `www.host` domain, a
+ * bare email, and an EXPLICIT `scheme://…` URL. #502 wants only the last kept —
+ * a schemeless domain/email an agent typed as prose must stay literal text, but
+ * a deliberate `https://…` still links. We delegate to the original tokenizer
+ * and, when it matched, DROP the token (returning `undefined`, so the run stays
+ * literal text) unless the matched RAW text carries an explicit `scheme:` prefix.
+ * `www.`/email matches have no scheme in their raw text, so they are dropped;
+ * `https://…`/`ftp://…` keep their link.
+ */
+const SCHEME_PREFIX_RE = /^[a-zA-Z][a-zA-Z0-9+.-]*:/;
+const noFuzzyUrlTokenizer = {
+  url(this: any, src: string) {
+    const token = Tokenizer.prototype.url.call(this, src) as any;
+    if (!token) return token;
+    // Keep only explicit-scheme URLs; schemeless `www.`/email matches -> literal.
+    return SCHEME_PREFIX_RE.test(token.raw) ? token : undefined;
+  },
+};
+
+/**
+ * Build a dedicated `marked` instance for a given extension combination: default
+ * (GFM) options plus the `==` highlight and `^[…]` footnote inline extensions
+ * ALWAYS, the `$…$`/`$$…$$` math extensions only when `parseMath`, and the
+ * schemeless-autolink suppressor only when `!fuzzyLinkify`. Built on a private
+ * `Marked` instance so nothing leaks into the global `marked` singleton.
+ */
+function buildMarkedInstance(parseMath: boolean, fuzzyLinkify: boolean): Marked {
+  const extensions: (TokenizerExtension & RendererExtension)[] = [
     highlightMarkExtension,
-    mathInlineExtension,
-    mathBlockExtension,
     footnoteInlineExtension,
-  ],
-});
+  ];
+  if (parseMath) {
+    extensions.push(mathInlineExtension, mathBlockExtension);
+  }
+  const instance = new Marked().use({ extensions });
+  if (!fuzzyLinkify) {
+    instance.use({ tokenizer: noFuzzyUrlTokenizer as any });
+  }
+  return instance;
+}
+
+// Memoize one instance per (parseMath, fuzzyLinkify) combination so the
+// extensions are registered exactly once per combo (never on the global
+// singleton). The default `(true, true)` instance preserves the pre-#502
+// behavior exactly for the editor/file-import/git-sync paths.
+const markedInstanceCache = new Map<string, Marked>();
+function getMarkedInstance(parseMath: boolean, fuzzyLinkify: boolean): Marked {
+  const key = `${parseMath}:${fuzzyLinkify}`;
+  let instance = markedInstanceCache.get(key);
+  if (!instance) {
+    instance = buildMarkedInstance(parseMath, fuzzyLinkify);
+    markedInstanceCache.set(key, instance);
+  }
+  return instance;
+}
 
 // NOTE: this module no longer installs a module-level `global.window`/`document`
 // jsdom shim. The HTML->DOM passes below (bridgeTaskLists / applyCommentDirectives
@@ -301,7 +370,7 @@ const CODE_FENCE_RE = /^(\s*)(`{3,}|~{3,})/;
 // preprocess is sync. Keeping it sync lets a sync converter entry
 // (`markdownToProseMirrorSync`, used by the client's chat renderer which must
 // stay synchronous) share this exact logic with the async entry.
-function preprocessCallouts(markdown: string): string {
+function preprocessCallouts(markdown: string, markedInstance: Marked): string {
   // Defensive cap: skip preprocessing for pathologically large inputs.
   if (markdown.length > MAX_CALLOUT_PREPROCESS_BYTES) {
     return markdown;
@@ -955,7 +1024,7 @@ function applyCommentDirectives(html: string): string {
 // sups stay inert) rather than hang.
 const MAX_FOOTNOTE_ROUNDS = 10000;
 
-function assembleFootnotes(html: string): string {
+function assembleFootnotes(html: string, markedInstance: Marked): string {
   // Cheap early-out: nothing carries a footnote body -> nothing to assemble.
   if (!html.includes("data-fn-text")) return html;
   const document = parseHtmlDocument(html);
@@ -1081,8 +1150,18 @@ function stripEmptyParagraphs(node: any): any {
  * for every existing Node consumer). A sync entry is REQUIRED by the client's
  * chat renderer, which runs inside a React render/useMemo and cannot await.
  */
-export function markdownToProseMirrorSync(markdownContent: string): any {
-  const withCallouts = preprocessCallouts(markdownContent);
+export function markdownToProseMirrorSync(
+  markdownContent: string,
+  options?: MarkdownImportOptions,
+): any {
+  // Select the marked instance for this call's extension combination. Defaults
+  // (math + fuzzy autolink ON) preserve the editor/file-import/git-sync paths;
+  // the MCP markdown-write path passes both false (#502).
+  const markedInstance = getMarkedInstance(
+    options?.parseMath ?? true,
+    options?.fuzzyLinkify ?? true,
+  );
+  const withCallouts = preprocessCallouts(markdownContent, markedInstance);
   const html = markedInstance.parse(withCallouts) as string;
   // Materialize comment directives (#293 #9 attached textAlign; #5 standalone
   // subpages/pageBreak) while the comment nodes still exist, before generateJSON
@@ -1091,7 +1170,7 @@ export function markdownToProseMirrorSync(markdownContent: string): any {
   // #293 canon #2: assemble the doc-level footnote list from the `<sup
   // data-fn-text>` markers (from `^[…]` or the raw-HTML column form) before
   // generateJSON, so references + definitions materialize into the schema model.
-  const withFootnotes = assembleFootnotes(withAttrs);
+  const withFootnotes = assembleFootnotes(withAttrs, markedInstance);
   const bridged = bridgeTaskLists(withFootnotes);
   const doc = generateJsonWith(bridged, docmostExtensions);
   return stripEmptyParagraphs(doc);
@@ -1104,6 +1183,7 @@ export function markdownToProseMirrorSync(markdownContent: string): any {
  */
 export async function markdownToProseMirror(
   markdownContent: string,
+  options?: MarkdownImportOptions,
 ): Promise<any> {
-  return markdownToProseMirrorSync(markdownContent);
+  return markdownToProseMirrorSync(markdownContent, options);
 }

packages/prosemirror-markdown/test/markdown-import-options.test.ts

@@ -0,0 +1,170 @@
+import { describe, expect, it } from 'vitest';
+// Import DIRECTLY from src (like math.test.ts) so we exercise the real
+// converter and its module-load jsdom setup.
+import { convertProseMirrorToMarkdown } from '../src/lib/markdown-converter.js';
+import { markdownToProseMirror } from '../src/lib/markdown-to-prosemirror.js';
+
+// ---------------------------------------------------------------------------
+// #502: the canonical importer is parameterized with `{ parseMath, fuzzyLinkify }`
+// (both DEFAULT true). The MCP markdown-WRITE path passes both false so an agent's
+// plain prose/config is imported LITERALLY:
+//   - parseMath:false  -> a `$…$` span stays literal text (no phantom mathInline)
+//   - fuzzyLinkify:false -> a SCHEMELESS `www.host`/email stays literal text; an
+//     EXPLICIT `https://…` STILL links (only the fuzzy autolink is suppressed).
+// The DEFAULTS (editor/file-import/git-sync) keep math + fuzzy autolink ON, so
+// this file also pins that the defaults are UNCHANGED.
+// ---------------------------------------------------------------------------
+
+const OFF = { parseMath: false, fuzzyLinkify: false } as const;
+
+// Collect the first paragraph's inline children (the common assertion target).
+function firstParaInline(doc: any): any[] {
+  const p = doc.content?.find((n: any) => n.type === 'paragraph');
+  return p?.content ?? [];
+}
+
+function findAll(node: any, type: string, acc: any[] = []): any[] {
+  if (!node || typeof node !== 'object') return acc;
+  if (node.type === type) acc.push(node);
+  if (Array.isArray(node.content)) {
+    for (const c of node.content) findAll(c, type, acc);
+  }
+  return acc;
+}
+
+// Flatten every text node's text (ignoring marks/structure) into one string.
+function allText(node: any, acc: string[] = []): string {
+  if (!node || typeof node !== 'object') return acc.join('');
+  if (node.type === 'text' && typeof node.text === 'string') acc.push(node.text);
+  if (Array.isArray(node.content)) {
+    for (const c of node.content) allText(c, acc);
+  }
+  return acc.join('');
+}
+
+describe('#502 importer options — extensions OFF (MCP write path)', () => {
+  it('a `$…$` config span stays literal text (no mathInline node)', async () => {
+    const md = 'export A=$FOO and B=$BAR done';
+    const doc = await markdownToProseMirror(md, OFF);
+    expect(findAll(doc, 'mathInline')).toHaveLength(0);
+    expect(allText(doc)).toBe('export A=$FOO and B=$BAR done');
+  });
+
+  it('a real-looking `$x=1$` span stays literal text', async () => {
+    const doc = await markdownToProseMirror('$x=1$', OFF);
+    expect(findAll(doc, 'mathInline')).toHaveLength(0);
+    expect(allText(doc)).toBe('$x=1$');
+  });
+
+  it('the reported `($ticket_lifetime=2592000)` config stays literal', async () => {
+    const doc = await markdownToProseMirror('($ticket_lifetime=2592000)', OFF);
+    expect(findAll(doc, 'mathInline')).toHaveLength(0);
+    expect(allText(doc)).toBe('($ticket_lifetime=2592000)');
+  });
+
+  it('a `$$…$$` block stays literal (no mathBlock node)', async () => {
+    const doc = await markdownToProseMirror('$$\nx^2\n$$', OFF);
+    expect(findAll(doc, 'mathBlock')).toHaveLength(0);
+    expect(allText(doc)).toContain('x^2');
+  });
+
+  it('a SCHEMELESS `www.example.com` is NOT autolinked', async () => {
+    const doc = await markdownToProseMirror('see www.example.com here', OFF);
+    const inline = firstParaInline(doc);
+    expect(inline.some((n: any) => n.marks?.some((m: any) => m.type === 'link'))).toBe(false);
+    expect(allText(doc)).toBe('see www.example.com here');
+  });
+
+  it('a bare dotted domain `gitea.vvzvlad.xyz` stays literal text', async () => {
+    const doc = await markdownToProseMirror('see gitea.vvzvlad.xyz here', OFF);
+    expect(findAll(doc, 'text').every((t: any) => !t.marks?.some((m: any) => m.type === 'link'))).toBe(true);
+  });
+
+  it('an EXPLICIT `https://…` STILL becomes a link', async () => {
+    const doc = await markdownToProseMirror('see https://example.com here', OFF);
+    const linked = firstParaInline(doc).find((n: any) =>
+      n.marks?.some((m: any) => m.type === 'link'),
+    );
+    expect(linked?.text).toBe('https://example.com');
+    const link = linked.marks.find((m: any) => m.type === 'link');
+    expect(link.attrs.href).toBe('https://example.com');
+  });
+
+  it('`foo_bar_baz` is not italicized (CommonMark, unaffected by options)', async () => {
+    const doc = await markdownToProseMirror('foo_bar_baz', OFF);
+    expect(findAll(doc, 'text').some((t: any) => t.marks?.some((m: any) => m.type === 'italic' || m.type === 'em'))).toBe(false);
+    expect(allText(doc)).toBe('foo_bar_baz');
+  });
+
+  it('block STRUCTURE (headings, lists, code fence) is preserved with extensions off', async () => {
+    const md = '## Heading\n\n- one\n- two\n\n```\ncode $x$ here\n```';
+    const doc = await markdownToProseMirror(md, OFF);
+    expect(findAll(doc, 'heading')).toHaveLength(1);
+    expect(findAll(doc, 'bulletList')).toHaveLength(1);
+    expect(findAll(doc, 'codeBlock')).toHaveLength(1);
+    // The `$x$` inside the code fence never becomes math regardless.
+    expect(findAll(doc, 'mathInline')).toHaveLength(0);
+  });
+});
+
+describe('#502 importer options — DEFAULTS unchanged (editor/file/git-sync)', () => {
+  it('DEFAULT: `$x^2$` DOES create a mathInline node (file-import unaffected)', async () => {
+    const doc = await markdownToProseMirror('$x^2$');
+    expect(findAll(doc, 'mathInline')).toHaveLength(1);
+    expect(findAll(doc, 'mathInline')[0].attrs.text).toBe('x^2');
+  });
+
+  it('DEFAULT: a schemeless `www.example.com` IS autolinked', async () => {
+    const doc = await markdownToProseMirror('see www.example.com here');
+    const linked = firstParaInline(doc).find((n: any) =>
+      n.marks?.some((m: any) => m.type === 'link'),
+    );
+    expect(linked?.text).toBe('www.example.com');
+  });
+
+  it('DEFAULT: explicitly passing {parseMath:true, fuzzyLinkify:true} equals no-options', async () => {
+    const a = await markdownToProseMirror('$x^2$ and www.foo.com');
+    const b = await markdownToProseMirror('$x^2$ and www.foo.com', {
+      parseMath: true,
+      fuzzyLinkify: true,
+    });
+    expect(JSON.stringify(b)).toBe(JSON.stringify(a));
+  });
+
+  it('round-trip export->import at the PACKAGE-DEFAULT layer keeps math (file-import / #328)', async () => {
+    // The package DEFAULT importer is what the server file-import path uses. A
+    // page holding real math is exported, then re-imported with DEFAULTS (math
+    // ON): the mathInline survives. (The tool-level import_page_markdown round-
+    // trip, which goes through mcp's markdownToProseMirrorCanonical, is pinned
+    // authoritatively in @docmost/mcp's mcp-write-extensions-off test.)
+    const source = {
+      type: 'doc',
+      content: [
+        { type: 'paragraph', content: [{ type: 'mathInline', attrs: { text: 'x^2' } }] },
+      ],
+    };
+    const md1 = convertProseMirrorToMarkdown(source);
+    const doc2 = await markdownToProseMirror(md1); // DEFAULTS -> math on
+    expect(findAll(doc2, 'mathInline')).toHaveLength(1);
+    const md2 = convertProseMirrorToMarkdown(doc2);
+    expect(md2).toBe(md1); // byte-stable
+  });
+});
+
+describe('#502 mutation guard', () => {
+  // If a future change silently flipped the MCP write path back to parseMath:true,
+  // the OFF assertion below would go RED — this pins the discriminating behavior.
+  it('with parseMath:true the same span DOES become math (proves the flag drives it)', async () => {
+    const on = await markdownToProseMirror('$x=1$', { parseMath: true, fuzzyLinkify: false });
+    expect(findAll(on, 'mathInline')).toHaveLength(1);
+    const off = await markdownToProseMirror('$x=1$', OFF);
+    expect(findAll(off, 'mathInline')).toHaveLength(0);
+  });
+
+  it('with fuzzyLinkify:true the same www domain DOES link (proves the flag drives it)', async () => {
+    const on = await markdownToProseMirror('www.example.com', { parseMath: false, fuzzyLinkify: true });
+    expect(findAll(on, 'text').some((t: any) => t.marks?.some((m: any) => m.type === 'link'))).toBe(true);
+    const off = await markdownToProseMirror('www.example.com', OFF);
+    expect(findAll(off, 'text').some((t: any) => t.marks?.some((m: any) => m.type === 'link'))).toBe(false);
+  });
+});