test(#522): make the internal-link subset invariant a real cross-package drift guard

Reviewer follow-up on the #522 internal-link import fix. The fix itself is
confirmed correct; these three changes harden its load-bearing subset invariant
and fix a stale doc.

Finding 1 (drift guard): the in-package test only compared isInternalPagePath
against a HAND-COPIED server regex, so a later narrowing of the real server
INTERNAL_LINK_REGEX would leave the test green while the client silently became
WIDER than the server. Add apps/server/.../export/internal-link-parity.spec.ts:
the top layer already depends on @docmost/prosemirror-markdown and exports
isInternalPagePath, so this spec imports the LIVE server INTERNAL_LINK_REGEX AND
the LIVE isInternalPagePath and asserts subset over an accept-corpus — a server
narrowing now reddens CI. The in-package manual copy is demoted from its
"drift guard" role (comment updated to say so; it stays as local documentation).

Finding 2 (charset non-vacuity): the REJECT list was purely structural, so the
mutation widening the slug charset [a-zA-Z0-9-] -> [a-zA-Z0-9-.] survived the
whole suite. Add REJECT cases whose ONLY defect is a forbidden slug character
(abc.def / abc_def / abc%20 / abc~x); assert both isInternalPagePath and the
server regex reject them. The mutation now reddens the new reject test.

Finding 3 (stale JSDoc): canonicalize.ts KNOWN_DEFAULTS module blurb claimed
every entry was read from docmost-schema and import-materialized. The new
link.internal default breaks both claims (source is editor-ext/src/lib/link.ts;
external links leave internal absent/null, never false). Add a bullet documenting
the one editor-sourced, non-materialized default (false ≡ absent/null).

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
 

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/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/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/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/export/internal-link-parity.spec.ts

@@ -0,0 +1,70 @@
+import { INTERNAL_LINK_REGEX } from './utils';
+import { isInternalPagePath } from '@docmost/prosemirror-markdown';
+
+/**
+ * Cross-package DRIFT GUARD for the internal-link subset invariant (#522).
+ *
+ * The client-side `isInternalPagePath`
+ * (`packages/prosemirror-markdown/src/lib/internal-links.ts`) promotes a markdown
+ * link to `internal: true` on import. Every link it marks internal MUST be one
+ * the server would backlink and export-rewrite — i.e. the client matcher MUST be
+ * a STRICT SUBSET of the server's canonical `INTERNAL_LINK_REGEX`
+ * (`./utils.ts`). If the client ever accepts a path the server rejects, that link
+ * is stored internal but silently dropped from the backlink graph and broken on
+ * export — the exact bug #522 fixed.
+ *
+ * This spec is the load-bearing guard: it imports the LIVE server regex AND the
+ * LIVE `isInternalPagePath` (no hand-copied regex on either side). A narrowing of
+ * EITHER — most dangerously the server regex — reddens here. The in-package
+ * accept/reject test documents the client's behaviour but cannot see the server
+ * regex; this top-layer spec is what makes the subset relation mechanical
+ * (AGENTS.md rule #7: a CI test that fails on drift of the source of truth).
+ */
+describe('internal-link subset parity (client isInternalPagePath ⊆ server INTERNAL_LINK_REGEX)', () => {
+  // Every path the CLIENT accepts. Kept deliberately broad across the risky
+  // dimensions — the slug charset (digits, hyphens, mixed case, leading/trailing
+  // hyphen), the space charset, and the optional trailing slash — so a narrowing
+  // of the server regex on any of them reddens the subset assertion below.
+  const CLIENT_ACCEPTS = [
+    '/s/eng/p/abc123',
+    '/s/eng/p/abc123/', // trailing slash
+    '/s/My-Space/p/A-b-C-9', // hyphens + mixed case in both segments
+    '/s/x/p/z', // shortest
+    '/s/eng/p/my-page-abc123', // slug with hyphens (extractPageSlugId shape)
+    '/s/eng/p/-lead', // leading hyphen in slug
+    '/s/eng/p/trail-', // trailing hyphen in slug
+    '/s/eng/p/0123456789', // all-digit slug
+    '/s/a.b/p/abc', // dot in the SPACE segment (space charset is [^/]+)
+    '/s/space with space/p/abc', // space char in the SPACE segment
+  ];
+
+  it('every corpus path is actually client-accepted (guards the corpus itself)', () => {
+    // If a path here stopped being client-accepted the subset test would pass
+    // vacuously; assert acceptance up front so the corpus stays meaningful. The
+    // filter-to-empty form names the offending paths on failure.
+    const notAccepted = CLIENT_ACCEPTS.filter((h) => !isInternalPagePath(h));
+    expect(notAccepted).toEqual([]);
+  });
+
+  it('every client-accepted path also matches the LIVE server regex (subset)', () => {
+    // The mechanical drift guard: narrow the server INTERNAL_LINK_REGEX and at
+    // least one hyphen/charset/structure case appears here.
+    const notInServer = CLIENT_ACCEPTS.filter((h) => !INTERNAL_LINK_REGEX.test(h));
+    expect(notInServer).toEqual([]);
+  });
+
+  it('the client rejects forbidden-slug-char paths the server also rejects', () => {
+    // Documents the subset BOUNDARY: correct shape, forbidden slug char. The
+    // client and the LIVE server regex must agree on rejection.
+    const forbidden = [
+      '/s/eng/p/abc.def',
+      '/s/eng/p/abc_def',
+      '/s/eng/p/abc%20',
+      '/s/eng/p/abc~x',
+    ];
+    const clientAccepts = forbidden.filter((h) => isInternalPagePath(h));
+    const serverAccepts = forbidden.filter((h) => INTERNAL_LINK_REGEX.test(h));
+    expect(clientAccepts).toEqual([]);
+    expect(serverAccepts).toEqual([]);
+  });
+});

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),
     });
   }
 

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

@@ -25,13 +25,22 @@
  * drop any attr whose value equals its known schema default. A non-default
  * value (e.g. `orderedList.start: 5`) is NOT a default, so it is KEPT.
  *
- * Every entry below was read from `packages/docmost-client/src/lib/
+ * Every entry below — with the single documented exception of the `link.internal`
+ * marker (see its own bullet) — was read from `packages/docmost-client/src/lib/
  * docmost-schema.ts` (the line refs are the exact `default:` declarations) and
  * confirmed to be materialized by an export→import→export round-trip:
  *   - mark `link`    target / rel  — DocmostAttributes + StarterKit link.
  *       StarterKit's link extension defaults `target: "_blank"` and
  *       `rel: "noopener noreferrer nofollow"`; both materialize on import
  *       (empirically confirmed) even when the source had only `href`.
+ *   - mark `link`    internal (#522) — the ONE editor-sourced, NOT-import-
+ *       materialized default here. Its source is `editor-ext/src/lib/link.ts`
+ *       (default `internal: false`), not docmost-schema, and import does NOT
+ *       materialize it (an imported external link leaves `internal` absent/null,
+ *       never `false`). It is listed so that the editor's stored `internal:false`
+ *       normalizes to the same "external" canon as absent/null (`false ≡ absent`),
+ *       keeping a stored external link canonically equal to its re-import. The
+ *       load-bearing `internal:true` is NON-default and therefore KEPT.
  *   - mark `comment` resolved      — docmost-schema.ts L213-214 (`default: false`).
  *   - node `orderedList` start     — provided by StarterKit's orderedList
  *       (`default: 1`); materializes on import (empirically confirmed).
@@ -56,6 +65,14 @@ const KNOWN_DEFAULTS: Record<string, Record<string, unknown>> = {
   link: {
     target: "_blank",
     rel: "noopener noreferrer nofollow",
+    // Editor-authored EXTERNAL links store `internal: false` (editor-ext link
+    // default `packages/editor-ext/src/lib/link.ts`), while an imported external
+    // link leaves `internal` absent/null. Both mean "external", so `internal:
+    // false` must normalize away exactly like `null`/absent — otherwise a stored
+    // `internal:false` link diverges from its re-import under
+    // `docsCanonicallyEqual` (false !== null). The internal marker `internal:true`
+    // is NON-default, so it is KEPT and survives canonicalization (#522 §11).
+    internal: false,
   },
   comment: {
     resolved: false,

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

@@ -38,6 +38,10 @@ export {
   normalizeForeignMarkdown,
   normalizeAgentMarkdown,
 } from "./foreign-markdown.js";
+// Pure primitive: detect the unambiguously-internal wiki-page link path
+// (`/s/<space>/p/<slug>`) and promote such link marks to their native internal
+// form during import (#522). A strict subset of the server's INTERNAL_LINK_REGEX.
+export { isInternalPagePath, markInternalLinks } from "./internal-links.js";
 
 // The Docmost tiptap schema mirror. Exposed so consumers (and the sync
 // engine's schema-validity regression tests) can build the exact ProseMirror

packages/prosemirror-markdown/src/lib/internal-links.ts

@@ -0,0 +1,112 @@
+/**
+ * Detect and mark unambiguously-internal wiki-page links during markdown import.
+ *
+ * WHY THIS EXISTS
+ * ---------------
+ * The markdown converter (`markdownToProseMirrorSync`) materializes every link
+ * with StarterKit's external defaults — `internal: null`, `target: "_blank"`,
+ * `rel: "noopener noreferrer nofollow"`. A markdown link that points at an
+ * internal wiki page written in its host-less, root-relative form
+ * (`[text](/s/<space>/p/<slugId>)`) is therefore stored as EXTERNAL: it opens in
+ * a new tab, gets no hover-preview, and is invisible to the backlink graph
+ * (`extractInternalLinkSlugIds` only counts links whose mark carries
+ * `internal: true`). This module supplies the pure primitive that a post-walk in
+ * the converter uses to promote such links to their native internal form.
+ *
+ * WHERE THE CANON LIVES (a strict subset, on purpose)
+ * ---------------------------------------------------
+ * The authoritative definition of "what is an internal link path" is the
+ * server's `INTERNAL_LINK_REGEX`
+ * (`apps/server/src/integrations/export/utils.ts`):
+ *   /^(https?:\/\/)?([^\/]+)?(\/s\/([^\/]+)\/)?p\/([a-zA-Z0-9-]+)\/?$/
+ * This package is a lower layer than the server app and cannot import it, so the
+ * matcher below is a DOCUMENTED, STRICT SUBSET of that regex: it accepts only the
+ * space-qualified, root-relative page path `/s/<space>/p/<slug>` (with optional
+ * trailing slash). Because it is a subset, every link we mark internal here is
+ * guaranteed to also satisfy the server regex, hence guaranteed backlink-able and
+ * export-rewritable. A unit test pins the exact accept/reject set as the guard
+ * against drift.
+ *
+ * FAIL-TOWARD-EXTERNAL
+ * --------------------
+ * We mark a link internal ONLY on an unambiguous anchored match. Any ambiguity
+ * (a scheme/host, `#anchor`, `?query`, a space-less `/p/<slug>`, a relative
+ * `p/<slug>`, a non-string href) leaves the link external. A false-external is a
+ * soft degradation (a new tab); a false-internal would produce broken SPA
+ * navigation, so "external" is the conservative default.
+ *
+ * Precedent for the target internal shape: the file importer already promotes
+ * internal anchors (`apps/server/src/integrations/import/utils/import-formatter.ts`
+ * `$a.attr('data-internal','true')`) and editor-ext reads it
+ * (`packages/editor-ext/src/lib/link.ts`).
+ */
+
+/**
+ * Matches ONLY the space-qualified, root-relative internal page path
+ * `/s/<space>/p/<slug>` (with optional trailing slash). A STRICT SUBSET of the
+ * server's `INTERNAL_LINK_REGEX`:
+ *   - `<space>` = `[^/]+`   (any non-slash segment, as in the server's group 4)
+ *   - `<slug>`  = `[a-zA-Z0-9-]+`  (as in the server's group 5 / `extractPageSlugId`)
+ * Anchored on both ends so a scheme/host, a trailing `#anchor`/`?query`, or any
+ * extra path segment fails to match.
+ */
+const INTERNAL_PAGE_PATH = /^\/s\/[^/]+\/p\/[a-zA-Z0-9-]+\/?$/;
+
+/**
+ * True iff `href` is the unambiguous, space-qualified, root-relative internal
+ * page path. Pure and side-effect-free. Non-string input returns false.
+ */
+export function isInternalPagePath(href: unknown): boolean {
+  return typeof href === "string" && INTERNAL_PAGE_PATH.test(href);
+}
+
+/**
+ * The native internal-link attribute overrides applied to a link mark whose href
+ * is an internal page path. Mirrors the manual JSON-patch form
+ * (`{internal:true, target:null, rel:null}`) and the editor-ext/file-importer
+ * precedent: internal links carry no `target`/`rel` (same-tab SPA navigation).
+ */
+const INTERNAL_LINK_ATTRS = { internal: true, target: null, rel: null } as const;
+
+/**
+ * In-place post-walk of a finished ProseMirror doc that promotes every
+ * unambiguously-internal link mark to its native internal form.
+ *
+ * A link that spans several text nodes (e.g. `[**bold** word](/s/x/p/abc)`)
+ * stores an equivalent link mark on EACH covered text node — and a covered node
+ * may carry nested marks (bold/italic) alongside the link. We therefore walk the
+ * entire tree and rewrite EVERY `link` mark whose href passes
+ * `isInternalPagePath`, so no covered segment is left external.
+ *
+ * Pure of external effects and IDEMPOTENT: re-running on an already-marked doc
+ * leaves it unchanged (an internal-path href always maps to the same attrs).
+ * External links are never touched — their `target:_blank`/`rel:noopener…` stay.
+ *
+ * The doc is mutated in place (the converter owns the freshly-built doc and
+ * returns it directly); the same node reference is returned for convenience.
+ */
+export function markInternalLinks<T>(node: T): T {
+  walk(node);
+  return node;
+}
+
+function walk(node: any): void {
+  if (!node || typeof node !== "object") return;
+  if (Array.isArray(node)) {
+    for (const child of node) walk(child);
+    return;
+  }
+  if (Array.isArray(node.marks)) {
+    for (const mark of node.marks) {
+      if (
+        mark &&
+        mark.type === "link" &&
+        mark.attrs &&
+        isInternalPagePath(mark.attrs.href)
+      ) {
+        mark.attrs = { ...mark.attrs, ...INTERNAL_LINK_ATTRS };
+      }
+    }
+  }
+  if (Array.isArray(node.content)) walk(node.content);
+}

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

@@ -12,6 +12,7 @@ import { parseHtmlDocument, generateJsonWith } from "./dom-parser.js";
 import type { TokenizerExtension, RendererExtension } from "marked";
 import { docmostExtensions } from "./docmost-schema.js";
 import { parseAttachedComment } from "./attached-comment.js";
+import { markInternalLinks } from "./internal-links.js";
 import { splitFootnoteParagraphs } from "./footnote.js";
 import {
   decodeInlineMathLatex,
@@ -1094,7 +1095,12 @@ export function markdownToProseMirrorSync(markdownContent: string): any {
   const withFootnotes = assembleFootnotes(withAttrs);
   const bridged = bridgeTaskLists(withFootnotes);
   const doc = generateJsonWith(bridged, docmostExtensions);
-  return stripEmptyParagraphs(doc);
+  // Promote unambiguously-internal wiki-page links (`[t](/s/<space>/p/<slug>)`)
+  // to their native internal form (`internal:true, target:null, rel:null`) so
+  // they get same-tab SPA navigation, hover-preview, and backlink participation.
+  // Every markdown import path funnels through here, so all of them are fixed at
+  // once; external links are left untouched (#522).
+  return markInternalLinks(stripEmptyParagraphs(doc));
 }
 
 /**

packages/prosemirror-markdown/test/internal-links.test.ts

@@ -0,0 +1,345 @@
+import { describe, expect, it } from 'vitest';
+import {
+  isInternalPagePath,
+  markInternalLinks,
+} from '../src/lib/internal-links.js';
+import { markdownToProseMirrorSync } from '../src/lib/markdown-to-prosemirror.js';
+import {
+  canonicalizeContent,
+  docsCanonicallyEqual,
+} from '../src/lib/canonicalize.js';
+
+// A LOCAL, illustrative copy of the server's INTERNAL_LINK_REGEX
+// (apps/server/src/integrations/export/utils.ts) used only to document the
+// subset boundary WITHIN this package (this layer cannot import the server).
+// It is NOT the cross-package drift guard: a hand copy can silently go stale if
+// the server regex is later narrowed. The real, mechanical drift guard lives in
+// the top layer, `apps/server/src/integrations/export/internal-link-parity.spec.ts`,
+// which imports BOTH the LIVE server `INTERNAL_LINK_REGEX` and the LIVE
+// `isInternalPagePath` and reddens if the client ever ceases to be a subset.
+const SERVER_INTERNAL_LINK_REGEX =
+  /^(https?:\/\/)?([^\/]+)?(\/s\/([^\/]+)\/)?p\/([a-zA-Z0-9-]+)\/?$/;
+
+// Walk a doc collecting every link mark (across all text nodes).
+const linkMarks = (doc: any): any[] => {
+  const out: any[] = [];
+  const walk = (n: any): void => {
+    if (!n || typeof n !== 'object') return;
+    if (Array.isArray(n)) return n.forEach(walk);
+    if (Array.isArray(n.marks))
+      for (const m of n.marks) if (m?.type === 'link') out.push(m);
+    if (Array.isArray(n.content)) walk(n.content);
+  };
+  walk(doc);
+  return out;
+};
+
+describe('isInternalPagePath', () => {
+  const ACCEPT = [
+    '/s/eng/p/abc123',
+    '/s/eng/p/abc123/', // trailing slash
+    '/s/My-Space/p/A-b-C-9', // hyphens + mixed case in both segments
+    '/s/x/p/z',
+  ];
+  const REJECT = [
+    'https://example.com/p/x', // scheme + host
+    'http://host/s/eng/p/abc', // scheme + host, even on the internal shape
+    '//host/s/eng/p/abc', // protocol-relative host
+    '/p/abc123', // space-less form (server does NOT backlink it)
+    'p/abc123', // relative
+    's/eng/p/abc123', // missing leading slash
+    '/s/eng/p/abc#section', // anchor
+    '/s/eng/p/abc?q=1', // query
+    '/s/eng/p/abc/extra', // extra segment
+    '/s//p/abc', // empty space segment
+    '/s/eng/p/', // empty slug
+    '/s/eng/p', // no slug at all
+    '/api/pages/abc', // other internal route
+    '/s/eng/x/abc', // wrong middle segment
+    '/s/a/b/p/abc', // space contains slash -> extra segment
+    '',
+  ];
+  // Structurally VALID `/s/<space>/p/<slug>` shapes whose ONLY defect is a
+  // forbidden character in the slug segment. These pin the slug charset
+  // `[a-zA-Z0-9-]` itself (not just the surrounding structure): drop them and a
+  // mutation widening the charset (e.g. adding `.`) survives the suite. Each is
+  // ALSO rejected by the server regex — documenting that the subset boundary
+  // holds precisely on the charset, not just on structure.
+  const REJECT_SLUG_CHARSET = [
+    '/s/eng/p/abc.def', // dot
+    '/s/eng/p/abc_def', // underscore
+    '/s/eng/p/abc%20', // percent-encoded space
+    '/s/eng/p/abc~x', // tilde
+  ];
+
+  it('accepts the space-qualified root-relative page path (+trailing slash)', () => {
+    for (const href of ACCEPT)
+      expect(isInternalPagePath(href), href).toBe(true);
+  });
+
+  it('rejects external URLs, ambiguous, and non-page forms', () => {
+    for (const href of REJECT)
+      expect(isInternalPagePath(href), href).toBe(false);
+  });
+
+  it('rejects a correctly-shaped path with a forbidden slug character', () => {
+    // Pins the slug charset itself: a mutation widening `[a-zA-Z0-9-]` reddens.
+    for (const href of REJECT_SLUG_CHARSET)
+      expect(isInternalPagePath(href), href).toBe(false);
+  });
+
+  it('the forbidden-slug-char paths are rejected by the server regex too', () => {
+    // The subset boundary holds on the charset, not just the structure: none of
+    // these match the server regex, so the client must not accept them either.
+    for (const href of REJECT_SLUG_CHARSET)
+      expect(SERVER_INTERNAL_LINK_REGEX.test(href), href).toBe(false);
+  });
+
+  it('rejects non-string input (fail-toward-external)', () => {
+    for (const v of [null, undefined, 123, {}, [], true])
+      expect(isInternalPagePath(v as unknown)).toBe(false);
+  });
+
+  it('is a STRICT SUBSET of the server INTERNAL_LINK_REGEX', () => {
+    // Every accepted href must also satisfy the server regex (so it is
+    // guaranteed backlink-able / export-rewritable).
+    for (const href of ACCEPT)
+      expect(SERVER_INTERNAL_LINK_REGEX.test(href), href).toBe(true);
+  });
+});
+
+describe('markInternalLinks', () => {
+  const linkNode = (text: string, href: string, extraMarks: any[] = []) => ({
+    type: 'text',
+    text,
+    marks: [
+      {
+        type: 'link',
+        attrs: {
+          href,
+          internal: null,
+          title: null,
+          target: '_blank',
+          rel: 'noopener noreferrer nofollow',
+          class: null,
+        },
+      },
+      ...extraMarks,
+    ],
+  });
+
+  it('marks an internal-path link internal:true, target:null, rel:null', () => {
+    const doc = {
+      type: 'doc',
+      content: [
+        { type: 'paragraph', content: [linkNode('hi', '/s/eng/p/abc123')] },
+      ],
+    };
+    markInternalLinks(doc);
+    const m = linkMarks(doc)[0];
+    expect(m.attrs.internal).toBe(true);
+    expect(m.attrs.target).toBeNull();
+    expect(m.attrs.rel).toBeNull();
+    expect(m.attrs.href).toBe('/s/eng/p/abc123'); // href untouched
+  });
+
+  it('leaves external links untouched', () => {
+    const doc = {
+      type: 'doc',
+      content: [
+        {
+          type: 'paragraph',
+          content: [linkNode('ext', 'https://example.com/p/x')],
+        },
+      ],
+    };
+    markInternalLinks(doc);
+    const m = linkMarks(doc)[0];
+    expect(m.attrs.internal).toBeNull();
+    expect(m.attrs.target).toBe('_blank');
+    expect(m.attrs.rel).toBe('noopener noreferrer nofollow');
+  });
+
+  it('marks EVERY text node a multi-node link spans (incl. nested bold/italic)', () => {
+    // A link `[**bold** plain *ital*](/s/x/p/abc)` stores the link mark on each
+    // covered text node; some also carry bold/italic. All must become internal.
+    const bold = { type: 'bold' };
+    const italic = { type: 'italic' };
+    const doc = {
+      type: 'doc',
+      content: [
+        {
+          type: 'paragraph',
+          content: [
+            linkNode('bold', '/s/x/p/abc', [bold]),
+            linkNode(' plain ', '/s/x/p/abc'),
+            linkNode('ital', '/s/x/p/abc', [italic]),
+          ],
+        },
+      ],
+    };
+    markInternalLinks(doc);
+    const marks = linkMarks(doc);
+    expect(marks).toHaveLength(3);
+    for (const m of marks) {
+      expect(m.attrs.internal).toBe(true);
+      expect(m.attrs.target).toBeNull();
+      expect(m.attrs.rel).toBeNull();
+    }
+    // Nested bold/italic marks are preserved alongside the promoted link.
+    const nested = doc.content[0].content;
+    expect(nested[0].marks.some((m: any) => m.type === 'bold')).toBe(true);
+    expect(nested[2].marks.some((m: any) => m.type === 'italic')).toBe(true);
+  });
+
+  it('is idempotent', () => {
+    const doc = {
+      type: 'doc',
+      content: [
+        { type: 'paragraph', content: [linkNode('hi', '/s/eng/p/abc')] },
+      ],
+    };
+    markInternalLinks(doc);
+    const once = JSON.stringify(doc);
+    markInternalLinks(doc);
+    expect(JSON.stringify(doc)).toBe(once);
+  });
+});
+
+describe('markdown import (full converter) — #522 acceptance', () => {
+  it('promotes an internal link and leaves an external one external', () => {
+    const doc = markdownToProseMirrorSync(
+      '[t](/s/eng/p/abc123) and [ext](https://example.com/p/x)',
+    );
+    const marks = linkMarks(doc);
+    const internal = marks.find((m) => m.attrs.href === '/s/eng/p/abc123');
+    const external = marks.find(
+      (m) => m.attrs.href === 'https://example.com/p/x',
+    );
+    expect(internal.attrs).toMatchObject({
+      internal: true,
+      target: null,
+      rel: null,
+    });
+    expect(external.attrs).toMatchObject({
+      internal: null,
+      target: '_blank',
+      rel: 'noopener noreferrer nofollow',
+    });
+  });
+
+  it('does NOT promote the space-less /p/<slug> form (documented limit)', () => {
+    const doc = markdownToProseMirrorSync('[t](/p/abc123)');
+    const m = linkMarks(doc)[0];
+    expect(m.attrs.internal).toBeNull();
+    expect(m.attrs.target).toBe('_blank');
+  });
+
+  it('the promoted link is backlink-extractable (matches server regex + true)', () => {
+    // Mirrors extractInternalLinkSlugIds: internal flag AND server-regex match.
+    const doc = markdownToProseMirrorSync('[t](/s/eng/p/my-page-abc123)');
+    const m = linkMarks(doc)[0];
+    expect(m.attrs.internal).toBe(true);
+    const match = m.attrs.href.match(SERVER_INTERNAL_LINK_REGEX);
+    expect(match).not.toBeNull();
+    // group 5 is the slug segment the server feeds to extractPageSlugId.
+    expect(match![5]).toBe('my-page-abc123');
+  });
+
+  it('comment-body markdown gets the same treatment (shared converter path)', () => {
+    // Comment bodies go through the same markdownToProseMirrorSync; a spot-check
+    // that the shared path (not a comment-only branch) does the promotion.
+    const doc = markdownToProseMirrorSync('see [here](/s/team/p/xyz789)');
+    const m = linkMarks(doc).find((x) => x.attrs.href === '/s/team/p/xyz789');
+    expect(m.attrs.internal).toBe(true);
+  });
+});
+
+describe('canonicalize — internal:false ≡ external (#522 §11)', () => {
+  it('drops editor-authored internal:false so external stays canonically equal', () => {
+    // Editor stores external links with internal:false; import leaves it absent.
+    const stored = {
+      type: 'doc',
+      content: [
+        {
+          type: 'paragraph',
+          content: [
+            {
+              type: 'text',
+              text: 'x',
+              marks: [
+                {
+                  type: 'link',
+                  attrs: {
+                    href: 'https://example.com',
+                    internal: false,
+                    target: '_blank',
+                    rel: 'noopener noreferrer nofollow',
+                  },
+                },
+              ],
+            },
+          ],
+        },
+      ],
+    };
+    const reimport = {
+      type: 'doc',
+      content: [
+        {
+          type: 'paragraph',
+          content: [
+            {
+              type: 'text',
+              text: 'x',
+              marks: [
+                {
+                  type: 'link',
+                  attrs: {
+                    href: 'https://example.com',
+                    internal: null, // import default
+                    target: '_blank',
+                    rel: 'noopener noreferrer nofollow',
+                  },
+                },
+              ],
+            },
+          ],
+        },
+      ],
+    };
+    expect(docsCanonicallyEqual(stored, reimport)).toBe(true);
+    // internal:false / target / rel all drop as defaults; only the non-default
+    // href survives.
+    const canon = canonicalizeContent(stored);
+    const mark = canon.content[0].content[0].marks[0];
+    expect(mark.attrs).toEqual({ href: 'https://example.com' });
+  });
+
+  it('keeps internal:true through canonicalization (non-default, load-bearing)', () => {
+    const doc = {
+      type: 'doc',
+      content: [
+        {
+          type: 'paragraph',
+          content: [
+            {
+              type: 'text',
+              text: 'x',
+              marks: [
+                {
+                  type: 'link',
+                  attrs: { href: '/s/x/p/abc', internal: true },
+                },
+              ],
+            },
+          ],
+        },
+      ],
+    };
+    const canon = canonicalizeContent(doc);
+    const mark = canon.content[0].content[0].marks[0];
+    expect(mark.attrs.internal).toBe(true);
+    expect(mark.attrs.href).toBe('/s/x/p/abc');
+  });
+});