feat(api-key): distinguish expired from expiring-soon + cover service unwrap

Fix 1: an already-expired key rendered the forward-looking "Expiring soon"
badge/tooltip ("expires within 30 days"), which is false for a past expiry.
Add a pure isExpired() helper and, in ApiKeysManager, render a red "Expired"
badge ("This key has expired") for past expiries; keep the orange "Expiring
soon" badge only for keys expiring in the future within 30 days (the two
states are made mutually exclusive at the call site). Extend utils.test.ts
with isExpired coverage (past/future/null/exact-now boundary) and add a
component assertion that an expired key shows "Expired" and NOT "Expiring
soon".

Fix 2: the response-contract unwrap (res.data turning the server envelope
{data:{token,apiKey},success,status} into {token,apiKey}) was exercised by no
test — component tests fully mock the service. Add a service-layer unit test
that mocks the api-client (axios instance) and asserts createApiKey unwraps to
the inner {token,apiKey} payload and getApiKeys resolves to the row array.

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

apps/client/src/App.tsx

@@ -44,6 +44,12 @@ const AccountSettings = lazy(
 const AccountPreferences = lazy(
   () => import("@/pages/settings/account/account-preferences.tsx"),
 );
+// #506 — lazy leaf (own chunk): the API-keys management page is route-split so
+// its code (Mantine table/modals + the create/revoke flow) stays out of the
+// entry bundle (post-#342 bundle discipline).
+const AccountApiKeys = lazy(
+  () => import("@/pages/settings/account/account-api-keys.tsx"),
+);
 const WorkspaceSettings = lazy(
   () => import("@/pages/settings/workspace/workspace-settings"),
 );
@@ -105,6 +111,7 @@ export default function App() {
               path={"account/preferences"}
               element={<AccountPreferences />}
             />
+            <Route path={"account/api-keys"} element={<AccountApiKeys />} />
             <Route path={"workspace"} element={<WorkspaceSettings />} />
             <Route path={"ai"} element={<AiSettings />} />
             <Route path={"members"} element={<WorkspaceMembers />} />

apps/client/src/components/settings/settings-sidebar.tsx

@@ -10,6 +10,7 @@ import {
   IconBrush,
   IconWorld,
   IconSparkles,
+  IconKey,
 } from "@tabler/icons-react";
 import { Link, useLocation } from "react-router-dom";
 import classes from "./settings.module.css";
@@ -46,6 +47,11 @@ const groupedData: DataGroup[] = [
         icon: IconBrush,
         path: "/settings/account/preferences",
       },
+      {
+        label: "API keys",
+        icon: IconKey,
+        path: "/settings/account/api-keys",
+      },
     ],
   },
   {

apps/client/src/features/api-key/components/api-keys-manager.test.tsx

@@ -0,0 +1,234 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import {
+  render,
+  screen,
+  fireEvent,
+  waitFor,
+  within,
+} from "@testing-library/react";
+import { MantineProvider } from "@mantine/core";
+import { ModalsProvider } from "@mantine/modals";
+import { QueryClient, QueryClientProvider } from "@tanstack/react-query";
+import { Provider, createStore } from "jotai";
+import { UserRole } from "@/lib/types";
+import { currentUserAtom } from "@/features/user/atoms/current-user-atom";
+import { IApiKey } from "@/features/api-key/types/api-key.types";
+
+// Mock the service layer so no real HTTP is attempted; every test drives the
+// component through these three functions.
+vi.mock("@/features/api-key/services/api-key-service", () => ({
+  getApiKeys: vi.fn(),
+  createApiKey: vi.fn(),
+  revokeApiKey: vi.fn(),
+}));
+
+import {
+  getApiKeys,
+  createApiKey,
+  revokeApiKey,
+} from "@/features/api-key/services/api-key-service";
+import ApiKeysManager from "./api-keys-manager";
+
+// matchMedia (read by MantineProvider) is stubbed globally in vitest.setup.ts.
+
+const ISO_SOON = new Date(Date.now() + 10 * 864e5).toISOString();
+const ISO_FAR = new Date(Date.now() + 200 * 864e5).toISOString();
+const ISO_EXPIRED = new Date(Date.now() - 3 * 864e5).toISOString();
+
+// Dump the storage stub via the Web Storage API — its data lives in a closure
+// (see vitest.setup.ts), so JSON.stringify(localStorage) would be vacuous.
+function storageDump(): string {
+  let out = "";
+  for (let i = 0; i < localStorage.length; i++) {
+    const k = localStorage.key(i) as string;
+    out += `${k}=${localStorage.getItem(k)};`;
+  }
+  return out;
+}
+
+function makeKey(overrides: Partial<IApiKey> = {}): IApiKey {
+  return {
+    id: "key-1",
+    name: "CI token",
+    expiresAt: ISO_FAR,
+    lastUsedAt: null,
+    createdAt: "2026-01-01T00:00:00.000Z",
+    creator: { id: "u1", name: "Alice", email: "a@x.io", avatarUrl: null },
+    ...overrides,
+  };
+}
+
+function renderManager(role: UserRole) {
+  const store = createStore();
+  store.set(currentUserAtom, {
+    user: { id: "me", role } as never,
+    workspace: {} as never,
+  });
+  const queryClient = new QueryClient({
+    defaultOptions: { queries: { retry: false } },
+  });
+  const utils = render(
+    <Provider store={store}>
+      <QueryClientProvider client={queryClient}>
+        <MantineProvider>
+          <ModalsProvider>
+            <ApiKeysManager />
+          </ModalsProvider>
+        </MantineProvider>
+      </QueryClientProvider>
+    </Provider>,
+  );
+  return { store, queryClient, ...utils };
+}
+
+beforeEach(() => {
+  vi.clearAllMocks();
+  localStorage.clear();
+});
+
+describe("ApiKeysManager — list rendering", () => {
+  it("renders an explicit expiry date and highlights a <30-day key (acceptance #3)", async () => {
+    vi.mocked(getApiKeys).mockResolvedValue([
+      makeKey({ id: "k-soon", name: "Soon key", expiresAt: ISO_SOON }),
+      makeKey({ id: "k-far", name: "Far key", expiresAt: ISO_FAR }),
+    ]);
+
+    renderManager(UserRole.MEMBER);
+
+    await screen.findByText("Soon key");
+    // Explicit dates, not "in N days": the year is rendered verbatim.
+    const soonYear = new Date(ISO_SOON).getFullYear().toString();
+    expect(screen.getAllByText(new RegExp(soonYear)).length).toBeGreaterThan(0);
+    // Exactly one key is inside the 30-day warning window.
+    expect(screen.getAllByText("Expiring soon")).toHaveLength(1);
+  });
+
+  it('shows "Expired" (not "Expiring soon") for an already-expired key', async () => {
+    vi.mocked(getApiKeys).mockResolvedValue([
+      makeKey({ id: "k-dead", name: "Dead key", expiresAt: ISO_EXPIRED }),
+    ]);
+    renderManager(UserRole.MEMBER);
+    await screen.findByText("Dead key");
+    // A past expiry is labelled "Expired", never the forward-looking badge.
+    expect(screen.getByText("Expired")).toBeDefined();
+    expect(screen.queryByText("Expiring soon")).toBeNull();
+  });
+
+  it('shows "Never" for an unlimited key and no highlight', async () => {
+    vi.mocked(getApiKeys).mockResolvedValue([
+      makeKey({ id: "k-forever", name: "Forever", expiresAt: null }),
+    ]);
+    renderManager(UserRole.MEMBER);
+    await screen.findByText("Forever");
+    expect(screen.getByText("Never")).toBeDefined();
+    expect(screen.queryByText("Expiring soon")).toBeNull();
+  });
+
+  it("empty list shows the empty state", async () => {
+    vi.mocked(getApiKeys).mockResolvedValue([]);
+    renderManager(UserRole.MEMBER);
+    expect(await screen.findByText("No API keys yet")).toBeDefined();
+  });
+});
+
+describe("ApiKeysManager — admin vs member view (acceptance #6)", () => {
+  it("a member does NOT see the author column", async () => {
+    vi.mocked(getApiKeys).mockResolvedValue([
+      makeKey({ creator: { id: "me", name: "Me", email: "m@x.io", avatarUrl: null } }),
+    ]);
+    renderManager(UserRole.MEMBER);
+    await screen.findByText("CI token");
+    // Author header absent + creator name not rendered (no author column).
+    expect(screen.queryByText("Author")).toBeNull();
+    expect(screen.queryByText("Me")).toBeNull();
+  });
+
+  it("an admin sees the author column with the creator's name", async () => {
+    vi.mocked(getApiKeys).mockResolvedValue([
+      makeKey({ creator: { id: "u1", name: "Alice", email: "a@x.io", avatarUrl: null } }),
+    ]);
+    renderManager(UserRole.ADMIN);
+    await screen.findByText("CI token");
+    expect(screen.getByText("Author")).toBeDefined();
+    expect(screen.getByText("Alice")).toBeDefined();
+  });
+});
+
+describe("ApiKeysManager — revoke (acceptance #4)", () => {
+  it("revoke removes the row from the list", async () => {
+    vi.mocked(getApiKeys)
+      .mockResolvedValueOnce([
+        makeKey({ id: "k1", name: "Doomed" }),
+        makeKey({ id: "k2", name: "Survivor" }),
+      ])
+      // After revoke, invalidation refetches the reduced list.
+      .mockResolvedValue([makeKey({ id: "k2", name: "Survivor" })]);
+    vi.mocked(revokeApiKey).mockResolvedValue();
+
+    renderManager(UserRole.MEMBER);
+    await screen.findByText("Doomed");
+
+    fireEvent.click(screen.getByLabelText("Revoke Doomed"));
+    // Confirm modal → click the destructive confirm button.
+    const confirm = await screen.findByRole("button", { name: "Revoke" });
+    fireEvent.click(confirm);
+
+    await waitFor(() =>
+      expect(screen.queryByText("Doomed")).toBeNull(),
+    );
+    expect(screen.getByText("Survivor")).toBeDefined();
+    expect(revokeApiKey).toHaveBeenCalledWith("k1");
+  });
+});
+
+describe("ApiKeysManager — show-once token (acceptance #1 & #2)", () => {
+  it("shows the token once, then discards it from the UI, localStorage and query cache", async () => {
+    const SECRET = "gm_secret-token-value-xyz";
+    vi.mocked(getApiKeys).mockResolvedValue([]);
+    vi.mocked(createApiKey).mockResolvedValue({
+      token: SECRET,
+      apiKey: {
+        id: "new-1",
+        name: "My key",
+        expiresAt: ISO_FAR,
+        createdAt: new Date().toISOString(),
+      },
+    });
+
+    const { queryClient } = renderManager(UserRole.MEMBER);
+    await screen.findByText("No API keys yet");
+
+    // Open create modal (use the header CTA), fill the name, submit.
+    fireEvent.click(
+      screen.getAllByRole("button", { name: "Create API key" })[0],
+    );
+    const nameInput = await screen.findByLabelText(/Name/);
+    fireEvent.change(nameInput, { target: { value: "My key" } });
+    fireEvent.click(screen.getByRole("button", { name: "Create" }));
+
+    // Token is shown exactly once in the show-once modal.
+    const tokenEl = await screen.findByTestId("api-key-token");
+    expect(tokenEl.textContent).toBe(SECRET);
+
+    // Close the modal → token discarded from the DOM.
+    fireEvent.click(screen.getByRole("button", { name: "Done" }));
+    await waitFor(() =>
+      expect(screen.queryByTestId("api-key-token")).toBeNull(),
+    );
+
+    // Acceptance #2: the secret is nowhere in localStorage or the react-query
+    // caches (query cache never carried it; the mutation copy was reset()).
+    // Non-vacuous: currentUser IS in storage, so the dump is exercised.
+    const dump = storageDump();
+    expect(dump).toContain("currentUser");
+    expect(dump).not.toContain(SECRET);
+    const cacheDump = JSON.stringify(
+      queryClient.getQueryCache().getAll().map((q) => q.state.data),
+    );
+    expect(cacheDump).not.toContain(SECRET);
+    const mutationDump = JSON.stringify(
+      queryClient.getMutationCache().getAll().map((m) => m.state.data),
+    );
+    expect(mutationDump).not.toContain(SECRET);
+  });
+});

apps/client/src/features/api-key/components/api-keys-manager.tsx

@@ -0,0 +1,264 @@
+import { useState } from "react";
+import {
+  ActionIcon,
+  Badge,
+  Button,
+  Center,
+  Group,
+  Loader,
+  Stack,
+  Table,
+  Text,
+  Tooltip,
+} from "@mantine/core";
+import { modals } from "@mantine/modals";
+import { notifications } from "@mantine/notifications";
+import { IconAlertTriangle, IconKey, IconTrash } from "@tabler/icons-react";
+import { useTranslation } from "react-i18next";
+import useUserRole from "@/hooks/use-user-role.tsx";
+import { formatLocalized, useDateFnsLocale } from "@/lib/date-locale";
+import { timeAgo } from "@/lib/time";
+import {
+  useApiKeysQuery,
+  useCreateApiKeyMutation,
+  useRevokeApiKeyMutation,
+} from "@/features/api-key/queries/api-key-query";
+import {
+  IApiKey,
+  ICreateApiKeyResponse,
+} from "@/features/api-key/types/api-key.types";
+import {
+  isExpired,
+  isExpiringSoon,
+  lastUsedBucket,
+} from "@/features/api-key/utils";
+import { CreateApiKeyModal } from "./create-api-key-modal";
+import { ShowTokenModal } from "./show-token-modal";
+
+export default function ApiKeysManager() {
+  const { t } = useTranslation();
+  const locale = useDateFnsLocale();
+  // Manage-on-API === Owner/Admin server-side, so the admin (workspace-wide)
+  // list + "author" column mirror exactly the roles the server serves the
+  // whole-workspace response to.
+  const { isAdmin } = useUserRole();
+
+  const { data: keys, isLoading, isError } = useApiKeysQuery();
+  const createMutation = useCreateApiKeyMutation();
+  const revokeMutation = useRevokeApiKeyMutation();
+
+  const [createOpened, setCreateOpened] = useState(false);
+  // SECURITY: the show-once token lives ONLY here, in this component's local
+  // state. It is never written to localStorage, the query cache or a log. Closing
+  // the modal sets it back to null (handleCloseToken) — discarded forever.
+  const [createdKey, setCreatedKey] = useState<ICreateApiKeyResponse | null>(
+    null,
+  );
+
+  const handleCreate = async (values: {
+    name: string;
+    expiresAt: string | null;
+  }): Promise<boolean> => {
+    try {
+      const res = await createMutation.mutateAsync(values);
+      setCreateOpened(false);
+      // Move the token into local state, then immediately purge react-query's
+      // own copy of the mutation result so the secret does not linger in the
+      // mutation cache.
+      setCreatedKey(res);
+      createMutation.reset();
+      return true;
+    } catch {
+      notifications.show({
+        message: t("Failed to create API key"),
+        color: "red",
+      });
+      return false;
+    }
+  };
+
+  const handleCloseToken = () => {
+    // Token discarded — the only copy the UI ever held is dropped here.
+    setCreatedKey(null);
+  };
+
+  const openRevokeModal = (key: IApiKey) =>
+    modals.openConfirmModal({
+      title: t("Revoke API key"),
+      centered: true,
+      children: (
+        <Text size="sm">
+          {t(
+            'Are you sure you want to revoke "{{name}}"? Any client using this key will immediately lose access. This cannot be undone.',
+            { name: key.name },
+          )}
+        </Text>
+      ),
+      labels: { confirm: t("Revoke"), cancel: t("Cancel") },
+      confirmProps: { color: "red" },
+      onConfirm: () => revokeMutation.mutate(key.id),
+    });
+
+  const formatDate = (iso: string) =>
+    formatLocalized(new Date(iso), "MMM dd, yyyy", "PP", locale);
+
+  const renderLastUsed = (lastUsedAt: string | null) => {
+    switch (lastUsedBucket(lastUsedAt)) {
+      case "never":
+        return t("Never used");
+      case "recent":
+        return t("Within the last hour");
+      case "stale":
+        // Coarse relative time — last_used_at is throttled to ~1h server-side,
+        // so we don't promise finer precision.
+        return timeAgo(new Date(lastUsedAt as string));
+    }
+  };
+
+  if (isLoading) {
+    return (
+      <Center py="xl">
+        <Loader size="sm" />
+      </Center>
+    );
+  }
+
+  const rows = (keys ?? []).map((key) => {
+    // Mutually exclusive: an already-expired key is labelled "Expired" (a past
+    // expiry) rather than the forward-looking "Expiring soon". isExpiringSoon
+    // also matches past expiries, so gate "soon" on !expired.
+    const expired = isExpired(key.expiresAt);
+    const soon = !expired && isExpiringSoon(key.expiresAt);
+    return (
+      <Table.Tr key={key.id}>
+        <Table.Td>
+          <Text fw={500}>{key.name}</Text>
+        </Table.Td>
+        <Table.Td>{formatDate(key.createdAt)}</Table.Td>
+        <Table.Td>
+          {key.expiresAt ? (
+            <Group gap={6} wrap="nowrap">
+              <Text size="sm">{formatDate(key.expiresAt)}</Text>
+              {expired && (
+                <Tooltip label={t("This key has expired")} withArrow>
+                  <Badge
+                    color="red"
+                    variant="light"
+                    size="sm"
+                    leftSection={<IconAlertTriangle size={12} />}
+                  >
+                    {t("Expired")}
+                  </Badge>
+                </Tooltip>
+              )}
+              {soon && (
+                <Tooltip
+                  label={t("This key expires within 30 days")}
+                  withArrow
+                >
+                  <Badge
+                    color="orange"
+                    variant="light"
+                    size="sm"
+                    leftSection={<IconAlertTriangle size={12} />}
+                  >
+                    {t("Expiring soon")}
+                  </Badge>
+                </Tooltip>
+              )}
+            </Group>
+          ) : (
+            <Text size="sm" c="dimmed">
+              {t("Never")}
+            </Text>
+          )}
+        </Table.Td>
+        <Table.Td>
+          <Text size="sm" c="dimmed">
+            {renderLastUsed(key.lastUsedAt)}
+          </Text>
+        </Table.Td>
+        {isAdmin && (
+          <Table.Td>
+            <Text size="sm">
+              {key.creator?.name ?? key.creator?.email ?? t("Unknown")}
+            </Text>
+          </Table.Td>
+        )}
+        <Table.Td style={{ textAlign: "right" }}>
+          <Tooltip label={t("Revoke")} withArrow>
+            <ActionIcon
+              variant="subtle"
+              color="red"
+              aria-label={t("Revoke {{name}}", { name: key.name })}
+              onClick={() => openRevokeModal(key)}
+            >
+              <IconTrash size={16} />
+            </ActionIcon>
+          </Tooltip>
+        </Table.Td>
+      </Table.Tr>
+    );
+  });
+
+  return (
+    <>
+      <Group justify="space-between" mb="md">
+        <Text size="sm" c="dimmed">
+          {isAdmin
+            ? t("API keys across the workspace.")
+            : t("Your personal API keys.")}
+        </Text>
+        <Button
+          leftSection={<IconKey size={16} />}
+          onClick={() => setCreateOpened(true)}
+        >
+          {t("Create API key")}
+        </Button>
+      </Group>
+
+      {isError ? (
+        <Text c="red" size="sm">
+          {t("Failed to load API keys.")}
+        </Text>
+      ) : rows.length === 0 ? (
+        <Stack align="center" gap="xs" py="xl">
+          <IconKey size={32} opacity={0.4} />
+          <Text c="dimmed">{t("No API keys yet")}</Text>
+          <Button
+            variant="light"
+            leftSection={<IconKey size={16} />}
+            onClick={() => setCreateOpened(true)}
+          >
+            {t("Create API key")}
+          </Button>
+        </Stack>
+      ) : (
+        <Table.ScrollContainer minWidth={600}>
+          <Table verticalSpacing="sm" highlightOnHover>
+            <Table.Thead>
+              <Table.Tr>
+                <Table.Th>{t("Name")}</Table.Th>
+                <Table.Th>{t("Created")}</Table.Th>
+                <Table.Th>{t("Expires")}</Table.Th>
+                <Table.Th>{t("Last used")}</Table.Th>
+                {isAdmin && <Table.Th>{t("Author")}</Table.Th>}
+                <Table.Th />
+              </Table.Tr>
+            </Table.Thead>
+            <Table.Tbody>{rows}</Table.Tbody>
+          </Table>
+        </Table.ScrollContainer>
+      )}
+
+      <CreateApiKeyModal
+        opened={createOpened}
+        onClose={() => setCreateOpened(false)}
+        onSubmit={handleCreate}
+        loading={createMutation.isPending}
+      />
+
+      <ShowTokenModal created={createdKey} onClose={handleCloseToken} />
+    </>
+  );
+}

apps/client/src/features/api-key/components/create-api-key-modal.tsx

@@ -0,0 +1,104 @@
+import { Button, Group, Modal, Select, Stack, TextInput } from "@mantine/core";
+import { useForm } from "@mantine/form";
+import { useTranslation } from "react-i18next";
+import {
+  ApiKeyLifetime,
+  DEFAULT_LIFETIME,
+  lifetimeToExpiresAt,
+} from "@/features/api-key/utils";
+
+interface Props {
+  opened: boolean;
+  onClose: () => void;
+  // Resolves the create request, returning true on success. The parent owns the
+  // mutation (and the token it returns); this modal only collects the name +
+  // lifetime. On failure (false) the form state is kept so the user can retry.
+  onSubmit: (values: {
+    name: string;
+    expiresAt: string | null;
+  }) => Promise<boolean>;
+  loading?: boolean;
+}
+
+interface FormValues {
+  name: string;
+  lifetime: ApiKeyLifetime;
+}
+
+export function CreateApiKeyModal({
+  opened,
+  onClose,
+  onSubmit,
+  loading,
+}: Props) {
+  const { t } = useTranslation();
+
+  const form = useForm<FormValues>({
+    initialValues: {
+      name: "",
+      lifetime: DEFAULT_LIFETIME,
+    },
+    validate: {
+      name: (value) =>
+        value.trim().length === 0 ? t("Name is required") : null,
+    },
+  });
+
+  const lifetimeOptions: { value: ApiKeyLifetime; label: string }[] = [
+    { value: "30d", label: t("30 days") },
+    { value: "90d", label: t("90 days") },
+    { value: "1y", label: t("1 year") },
+    { value: "never", label: t("No expiration") },
+  ];
+
+  const handleSubmit = form.onSubmit(async (values) => {
+    const ok = await onSubmit({
+      name: values.name.trim(),
+      expiresAt: lifetimeToExpiresAt(values.lifetime),
+    });
+    // Reset only after a successful submit so a failed create keeps the form
+    // state (the parent surfaces the error via a notification).
+    if (ok) form.reset();
+  });
+
+  const handleClose = () => {
+    form.reset();
+    onClose();
+  };
+
+  return (
+    <Modal
+      opened={opened}
+      onClose={handleClose}
+      title={t("Create API key")}
+      centered
+    >
+      <form onSubmit={handleSubmit}>
+        <Stack gap="sm">
+          <TextInput
+            label={t("Name")}
+            placeholder={t("e.g. CI deploy token")}
+            data-autofocus
+            withAsterisk
+            {...form.getInputProps("name")}
+          />
+          <Select
+            label={t("Expiration")}
+            data={lifetimeOptions}
+            allowDeselect={false}
+            checkIconPosition="right"
+            {...form.getInputProps("lifetime")}
+          />
+          <Group justify="flex-end" mt="xs">
+            <Button variant="default" onClick={handleClose} type="button">
+              {t("Cancel")}
+            </Button>
+            <Button type="submit" loading={loading}>
+              {t("Create")}
+            </Button>
+          </Group>
+        </Stack>
+      </form>
+    </Modal>
+  );
+}

apps/client/src/features/api-key/components/show-token-modal.tsx

@@ -0,0 +1,107 @@
+import {
+  Alert,
+  Button,
+  Code,
+  Group,
+  Modal,
+  Stack,
+  Text,
+} from "@mantine/core";
+import { IconAlertTriangle, IconCheck, IconCopy } from "@tabler/icons-react";
+import { useTranslation } from "react-i18next";
+import { CopyButton } from "@/components/common/copy-button";
+import { formatLocalized, useDateFnsLocale } from "@/lib/date-locale";
+import { ICreateApiKeyResponse } from "@/features/api-key/types/api-key.types";
+
+interface Props {
+  // The freshly-created key incl. its token. Owned by the parent; this modal
+  // only renders it and never copies it into its own persistent state.
+  created: ICreateApiKeyResponse | null;
+  // Closing MUST discard the token in the parent (set the `created` prop back to
+  // null) — the token is shown exactly once.
+  onClose: () => void;
+}
+
+export function ShowTokenModal({ created, onClose }: Props) {
+  const { t } = useTranslation();
+  const locale = useDateFnsLocale();
+
+  const expiresAt = created?.apiKey.expiresAt ?? null;
+
+  return (
+    <Modal
+      opened={created !== null}
+      onClose={onClose}
+      title={t("API key created")}
+      centered
+      // No dismiss-on-outside-click: the token is irretrievable, so closing is a
+      // deliberate act (the user confirms they have saved it).
+      closeOnClickOutside={false}
+    >
+      {created && (
+        <Stack gap="sm">
+          <Alert
+            color="orange"
+            icon={<IconAlertTriangle size={18} />}
+            variant="light"
+          >
+            {t(
+              "Copy your API key now and store it somewhere safe. For security reasons it will not be shown again.",
+            )}
+          </Alert>
+
+          <div>
+            <Text size="sm" c="dimmed" mb={4}>
+              {t("Token")}
+            </Text>
+            <Group gap="xs" wrap="nowrap" align="flex-start">
+              <Code
+                block
+                data-testid="api-key-token"
+                style={{ flex: 1, wordBreak: "break-all" }}
+              >
+                {created.token}
+              </Code>
+              <CopyButton value={created.token}>
+                {({ copied, copy }) => (
+                  <Button
+                    variant="light"
+                    size="xs"
+                    color={copied ? "teal" : "blue"}
+                    leftSection={
+                      copied ? (
+                        <IconCheck size={16} />
+                      ) : (
+                        <IconCopy size={16} />
+                      )
+                    }
+                    onClick={copy}
+                  >
+                    {copied ? t("Copied") : t("Copy")}
+                  </Button>
+                )}
+              </CopyButton>
+            </Group>
+          </div>
+
+          <Text size="sm" c="dimmed">
+            {expiresAt
+              ? t("Expires {{date}}", {
+                  date: formatLocalized(
+                    new Date(expiresAt),
+                    "MMM dd, yyyy",
+                    "PP",
+                    locale,
+                  ),
+                })
+              : t("This key never expires")}
+          </Text>
+
+          <Group justify="flex-end" mt="xs">
+            <Button onClick={onClose}>{t("Done")}</Button>
+          </Group>
+        </Stack>
+      )}
+    </Modal>
+  );
+}

apps/client/src/features/api-key/queries/api-key-query.ts

@@ -0,0 +1,66 @@
+import {
+  useMutation,
+  useQuery,
+  useQueryClient,
+  UseQueryResult,
+} from "@tanstack/react-query";
+import { notifications } from "@mantine/notifications";
+import { useTranslation } from "react-i18next";
+import {
+  createApiKey,
+  getApiKeys,
+  revokeApiKey,
+} from "@/features/api-key/services/api-key-service";
+import {
+  IApiKey,
+  ICreateApiKey,
+  ICreateApiKeyResponse,
+} from "@/features/api-key/types/api-key.types";
+
+export const API_KEYS_QUERY_KEY = ["api-keys"];
+
+export function useApiKeysQuery(): UseQueryResult<IApiKey[], Error> {
+  return useQuery({
+    queryKey: API_KEYS_QUERY_KEY,
+    queryFn: () => getApiKeys(),
+  });
+}
+
+/**
+ * Create mutation.
+ *
+ * SECURITY: the response contains the token exactly once. This hook deliberately
+ * does NOT stash it anywhere — the caller reads it from `mutateAsync`'s resolved
+ * value, moves it into the show-once modal's local state, then calls
+ * `mutation.reset()` to purge react-query's own copy immediately. `gcTime: 0`
+ * is a second belt so nothing lingers in the mutation cache after the observer
+ * unmounts. The list is invalidated here (the list carries no token).
+ */
+export function useCreateApiKeyMutation() {
+  const queryClient = useQueryClient();
+  return useMutation<ICreateApiKeyResponse, Error, ICreateApiKey>({
+    mutationFn: (data) => createApiKey(data),
+    gcTime: 0,
+    onSuccess: () => {
+      queryClient.invalidateQueries({ queryKey: API_KEYS_QUERY_KEY });
+    },
+  });
+}
+
+export function useRevokeApiKeyMutation() {
+  const { t } = useTranslation();
+  const queryClient = useQueryClient();
+  return useMutation<void, Error, string>({
+    mutationFn: (id) => revokeApiKey(id),
+    onSuccess: () => {
+      queryClient.invalidateQueries({ queryKey: API_KEYS_QUERY_KEY });
+      notifications.show({ message: t("API key revoked") });
+    },
+    onError: () => {
+      notifications.show({
+        message: t("Failed to revoke API key"),
+        color: "red",
+      });
+    },
+  });
+}

apps/client/src/features/api-key/services/api-key-service.test.ts

@@ -0,0 +1,78 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+
+// Mock the api-client (axios instance). vi.mock replaces the whole module, so
+// the real response interceptor — which returns `response.data`, i.e. the
+// server envelope { data, success, status } — is bypassed. Our mocked post/get
+// therefore resolve to that post-interceptor envelope shape directly, and the
+// service under test reads `.data` off it to unwrap the inner payload. This is
+// the one bug-prone line the component tests (which fully mock the service)
+// never exercise.
+const { post, get } = vi.hoisted(() => ({ post: vi.fn(), get: vi.fn() }));
+vi.mock("@/lib/api-client", () => ({
+  default: { post, get },
+}));
+
+import {
+  createApiKey,
+  getApiKeys,
+} from "@/features/api-key/services/api-key-service";
+
+beforeEach(() => {
+  vi.clearAllMocks();
+});
+
+describe("api-key-service response-contract unwrap", () => {
+  it("createApiKey unwraps the envelope to { token, apiKey }", async () => {
+    const payload = {
+      token: "gm_secret-abc",
+      apiKey: {
+        id: "key-1",
+        name: "CI token",
+        expiresAt: "2027-07-11T12:00:00.000Z",
+        createdAt: "2026-07-11T12:00:00.000Z",
+      },
+    };
+    // The server envelope as the interceptor hands it to the service.
+    post.mockResolvedValue({ data: payload, success: true, status: 200 });
+
+    const result = await createApiKey({
+      name: "CI token",
+      expiresAt: "2027-07-11T12:00:00.000Z",
+    });
+
+    // The inner payload only — not the { data, success, status } wrapper.
+    expect(result).toEqual(payload);
+    expect(result.token).toBe("gm_secret-abc");
+    expect(result.apiKey).toEqual(payload.apiKey);
+    expect(post).toHaveBeenCalledWith("/api-keys/create", {
+      name: "CI token",
+      expiresAt: "2027-07-11T12:00:00.000Z",
+    });
+  });
+
+  it("getApiKeys unwraps the envelope to the array of rows", async () => {
+    const rows = [
+      {
+        id: "key-1",
+        name: "CI token",
+        expiresAt: null,
+        lastUsedAt: null,
+        createdAt: "2026-01-01T00:00:00.000Z",
+      },
+      {
+        id: "key-2",
+        name: "Deploy token",
+        expiresAt: "2027-01-01T00:00:00.000Z",
+        lastUsedAt: null,
+        createdAt: "2026-02-01T00:00:00.000Z",
+      },
+    ];
+    post.mockResolvedValue({ data: rows, success: true, status: 200 });
+
+    const result = await getApiKeys();
+
+    expect(result).toEqual(rows);
+    expect(result).toHaveLength(2);
+    expect(post).toHaveBeenCalledWith("/api-keys/list");
+  });
+});

apps/client/src/features/api-key/services/api-key-service.ts

@@ -0,0 +1,28 @@
+import api from "@/lib/api-client";
+import {
+  IApiKey,
+  ICreateApiKey,
+  ICreateApiKeyResponse,
+} from "@/features/api-key/types/api-key.types";
+
+// Mint a new key. The response carries the token ONCE — the caller must move it
+// straight into the show-once modal's local state and never cache it (see
+// use-api-key-query / create-api-key-modal for the reset()-after-read pattern).
+export async function createApiKey(
+  data: ICreateApiKey,
+): Promise<ICreateApiKeyResponse> {
+  const res = await api.post<ICreateApiKeyResponse>("/api-keys/create", data);
+  return res.data as ICreateApiKeyResponse;
+}
+
+// List the caller's keys (or, for an admin, every key in the workspace with
+// creator attribution). Never returns token material.
+export async function getApiKeys(): Promise<IApiKey[]> {
+  const res = await api.post<IApiKey[]>("/api-keys/list");
+  return res.data as IApiKey[];
+}
+
+// Revocation is server-side immediate; the caller drops the row on success.
+export async function revokeApiKey(id: string): Promise<void> {
+  await api.post("/api-keys/revoke", { id });
+}

apps/client/src/features/api-key/types/api-key.types.ts

@@ -0,0 +1,48 @@
+// Compact creator attribution embedded in the admin (workspace-wide) list. A
+// normal member's list only ever contains their own keys, so the field is
+// present but redundant; the author column is only rendered for admins.
+export interface IApiKeyCreator {
+  id: string;
+  name: string;
+  email: string;
+  avatarUrl: string | null;
+}
+
+// A single api-key row as returned by `POST /api/api-keys/list`. Note: the list
+// NEVER carries token material — only metadata.
+export interface IApiKey {
+  id: string;
+  name: string;
+  // ISO string, or null for an unlimited ("never expires") key.
+  expiresAt: string | null;
+  // ISO string, or null if the key was never used. Throttled to ~1h server-side
+  // (#501), so the UI must not promise sub-hour precision.
+  lastUsedAt: string | null;
+  createdAt: string;
+  creator?: IApiKeyCreator | null;
+}
+
+// Payload for `POST /api/api-keys/create`. `expiresAt`: an ISO date string for a
+// bounded lifetime, or null for an unlimited key. (undefined would let the
+// server apply its 1-year default, but the form always sends an explicit value.)
+export interface ICreateApiKey {
+  name: string;
+  expiresAt: string | null;
+}
+
+// The metadata half of the create response. The token itself is carried
+// separately (see ICreateApiKeyResponse) and is shown exactly once.
+export interface ICreatedApiKey {
+  id: string;
+  name: string;
+  expiresAt: string | null;
+  createdAt: string;
+}
+
+// Response of `POST /api/api-keys/create`. `token` is the ONLY time the secret
+// is ever returned — it must live only in the show-once modal's local state and
+// must never be cached, persisted or logged.
+export interface ICreateApiKeyResponse {
+  token: string;
+  apiKey: ICreatedApiKey;
+}

apps/client/src/features/api-key/utils.test.ts

@@ -0,0 +1,100 @@
+import { describe, it, expect } from "vitest";
+import {
+  DEFAULT_LIFETIME,
+  EXPIRY_WARNING_DAYS,
+  isExpired,
+  isExpiringSoon,
+  lastUsedBucket,
+  lifetimeToExpiresAt,
+} from "./utils";
+
+const NOW = new Date("2026-07-11T12:00:00.000Z");
+const daysFromNow = (n: number) =>
+  new Date(NOW.getTime() + n * 24 * 60 * 60 * 1000).toISOString();
+
+describe("lifetimeToExpiresAt", () => {
+  it("default lifetime is 1 year (acceptance #7)", () => {
+    expect(DEFAULT_LIFETIME).toBe("1y");
+    const iso = lifetimeToExpiresAt("1y", NOW);
+    expect(iso).toBe("2027-07-11T12:00:00.000Z");
+  });
+
+  it('"never" sends null (acceptance #7)', () => {
+    expect(lifetimeToExpiresAt("never", NOW)).toBeNull();
+  });
+
+  it("30d / 90d map to the exact future instant", () => {
+    expect(lifetimeToExpiresAt("30d", NOW)).toBe(daysFromNow(30));
+    expect(lifetimeToExpiresAt("90d", NOW)).toBe(daysFromNow(90));
+  });
+});
+
+describe("isExpiringSoon (acceptance #3 highlight)", () => {
+  it("an unlimited key is never 'soon'", () => {
+    expect(isExpiringSoon(null, NOW)).toBe(false);
+  });
+
+  it("highlights a key expiring within the 30-day window", () => {
+    expect(isExpiringSoon(daysFromNow(EXPIRY_WARNING_DAYS - 1), NOW)).toBe(true);
+    expect(isExpiringSoon(daysFromNow(10), NOW)).toBe(true);
+  });
+
+  it("does not highlight a key well outside the window", () => {
+    expect(isExpiringSoon(daysFromNow(EXPIRY_WARNING_DAYS + 1), NOW)).toBe(
+      false,
+    );
+    expect(isExpiringSoon(daysFromNow(200), NOW)).toBe(false);
+  });
+
+  it("an already-expired key is highlighted", () => {
+    expect(isExpiringSoon(daysFromNow(-3), NOW)).toBe(true);
+  });
+});
+
+describe("isExpired (past vs future expiry)", () => {
+  it("an unlimited key is never expired", () => {
+    expect(isExpired(null, NOW)).toBe(false);
+  });
+
+  it("a past expiry is expired", () => {
+    expect(isExpired(daysFromNow(-3), NOW)).toBe(true);
+    expect(isExpired(daysFromNow(-1), NOW)).toBe(true);
+  });
+
+  it("a future expiry is not expired (even within the warning window)", () => {
+    expect(isExpired(daysFromNow(1), NOW)).toBe(false);
+    expect(isExpired(daysFromNow(EXPIRY_WARNING_DAYS - 1), NOW)).toBe(false);
+    expect(isExpired(daysFromNow(200), NOW)).toBe(false);
+  });
+
+  it("an expiry exactly at 'now' counts as expired (boundary is inclusive)", () => {
+    expect(isExpired(NOW.toISOString(), NOW)).toBe(true);
+  });
+
+  it("is mutually distinguishable from isExpiringSoon: expired vs soon-but-future", () => {
+    // A key 3 days in the past: expired, and (by design) also matches
+    // isExpiringSoon — the UI resolves this by checking isExpired first.
+    expect(isExpired(daysFromNow(-3), NOW)).toBe(true);
+    // A key 10 days in the future: NOT expired, but expiring soon.
+    expect(isExpired(daysFromNow(10), NOW)).toBe(false);
+    expect(isExpiringSoon(daysFromNow(10), NOW)).toBe(true);
+  });
+});
+
+describe("lastUsedBucket (within-the-last-hour semantics)", () => {
+  const minutesAgo = (n: number) =>
+    new Date(NOW.getTime() - n * 60 * 1000).toISOString();
+
+  it("null last-used is 'never'", () => {
+    expect(lastUsedBucket(null, NOW)).toBe("never");
+  });
+
+  it("under an hour is 'recent' (no sub-hour precision promised)", () => {
+    expect(lastUsedBucket(minutesAgo(5), NOW)).toBe("recent");
+    expect(lastUsedBucket(minutesAgo(59), NOW)).toBe("recent");
+  });
+
+  it("over an hour is 'stale'", () => {
+    expect(lastUsedBucket(minutesAgo(90), NOW)).toBe("stale");
+  });
+});

apps/client/src/features/api-key/utils.ts

@@ -0,0 +1,76 @@
+import { addDays, addYears, differenceInMinutes } from "date-fns";
+
+// The single early-warning window (#501/#506): keys whose expiry is closer than
+// this are visually highlighted in the list. Also used to classify a key as
+// already-expired (a negative "days until" is < 30 too).
+export const EXPIRY_WARNING_DAYS = 30;
+
+// last_used_at is throttled to ~1h server-side, so anything under an hour is
+// shown as the coarse "within the last hour" rather than a false-precise
+// "5 minutes ago".
+export const LAST_USED_THROTTLE_MINUTES = 60;
+
+export type ApiKeyLifetime = "30d" | "90d" | "1y" | "never";
+
+export const DEFAULT_LIFETIME: ApiKeyLifetime = "1y";
+
+// Maps a lifetime choice to the `expiresAt` payload sent to the server: an ISO
+// string for a bounded lifetime, or null for an explicit unlimited key.
+export function lifetimeToExpiresAt(
+  lifetime: ApiKeyLifetime,
+  now: Date = new Date(),
+): string | null {
+  switch (lifetime) {
+    case "30d":
+      return addDays(now, 30).toISOString();
+    case "90d":
+      return addDays(now, 90).toISOString();
+    case "1y":
+      return addYears(now, 1).toISOString();
+    case "never":
+      return null;
+  }
+}
+
+// True when a bounded key's expiry is already in the past (or exactly now). An
+// unlimited key (null) is never expired. This is distinct from "expiring soon":
+// the two states are mutually exclusive at the call site (see api-keys-manager),
+// so an already-expired key is labelled "Expired", not "Expiring soon".
+export function isExpired(
+  expiresAt: string | null,
+  now: Date = new Date(),
+): boolean {
+  if (!expiresAt) return false;
+  const expiry = new Date(expiresAt).getTime();
+  if (Number.isNaN(expiry)) return false;
+  return expiry <= now.getTime();
+}
+
+// True when a bounded key expires within the warning window (or is already
+// expired). An unlimited key (null) is never "expiring soon". Callers that need
+// to distinguish an already-past expiry should check isExpired() first, as this
+// predicate deliberately also covers the already-expired case.
+export function isExpiringSoon(
+  expiresAt: string | null,
+  now: Date = new Date(),
+): boolean {
+  if (!expiresAt) return false;
+  const expiry = new Date(expiresAt).getTime();
+  if (Number.isNaN(expiry)) return false;
+  const msLeft = expiry - now.getTime();
+  return msLeft < EXPIRY_WARNING_DAYS * 24 * 60 * 60 * 1000;
+}
+
+// Classifies last-used recency so the caller can pick the honest label without
+// promising sub-hour precision. Returns "never", "recent" (< 1h) or "stale".
+export function lastUsedBucket(
+  lastUsedAt: string | null,
+  now: Date = new Date(),
+): "never" | "recent" | "stale" {
+  if (!lastUsedAt) return "never";
+  const used = new Date(lastUsedAt);
+  if (Number.isNaN(used.getTime())) return "never";
+  return differenceInMinutes(now, used) < LAST_USED_THROTTLE_MINUTES
+    ? "recent"
+    : "stale";
+}

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

@@ -36,6 +36,7 @@ const STATIC_ROUTES = new Set<string>([
   '/setup/register',
   '/settings/account/profile',
   '/settings/account/preferences',
+  '/settings/account/api-keys',
   '/settings/workspace',
   '/settings/ai',
   '/settings/members',

apps/client/src/pages/settings/account/account-api-keys.tsx

@@ -0,0 +1,22 @@
+import SettingsTitle from "@/components/settings/settings-title.tsx";
+import ApiKeysManager from "@/features/api-key/components/api-keys-manager";
+import { getAppName } from "@/lib/config.ts";
+import { Helmet } from "react-helmet-async";
+import { useTranslation } from "react-i18next";
+
+export default function AccountApiKeys() {
+  const { t } = useTranslation();
+
+  return (
+    <>
+      <Helmet>
+        <title>
+          {t("API keys")} - {getAppName()}
+        </title>
+      </Helmet>
+      <SettingsTitle title={t("API keys")} />
+
+      <ApiKeysManager />
+    </>
+  );
+}

apps/client/vitest.setup.ts

@@ -63,3 +63,15 @@ vi.stubGlobal("matchMedia", (query: string) => ({
   removeEventListener: vi.fn(),
   dispatchEvent: vi.fn(),
 }));
+
+// Mantine's ScrollArea (used by Table.ScrollContainer, ScrollArea, etc.) reads
+// `ResizeObserver` in a layout effect on mount, which jsdom does not implement.
+// A no-op stub lets any test rendering those components mount cleanly.
+vi.stubGlobal(
+  "ResizeObserver",
+  class {
+    observe() {}
+    unobserve() {}
+    disconnect() {}
+  },
+);

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.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/mcp/mcp-auth.helpers.ts

@@ -337,6 +337,104 @@ export function bindAccessJwtVerifier(
   return (token: string) => tokenService.verifyJwt(token, JwtType.ACCESS);
 }
 
+// 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;
+  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 REPLACES
+ * `bindAccessJwtVerifier` as the single place the /mcp Bearer path pins the token
+ * type: the /mcp Bearer slot now 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
 // this module never imports the concrete repos/JwtPayload (heavy graph).
 export interface BearerVerifyDeps {
@@ -728,18 +826,24 @@ 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

@@ -6,6 +6,8 @@ import {
   isCredentialsFailure,
   isInitializeRequestBody,
   verifyBearerAccess,
+  verifyMcpBearer,
+  bindMcpBearerVerifier,
   sharedTokenMatches,
   clientIp,
   bindAccessJwtVerifier,
@@ -524,13 +526,28 @@ 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 () => {
@@ -1046,6 +1063,107 @@ describe('bindAccessJwtVerifier enforces JwtType.ACCESS (item 3)', () => {
   });
 });
 
+describe('bindMcpBearerVerifier pins the {ACCESS, API_KEY} allowlist (#501)', () => {
+  it('calls verifyJwtOneOf with exactly [ACCESS, API_KEY]', async () => {
+    const verifyJwtOneOf = jest
+      .fn()
+      .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']);
+  });
+});
+
+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('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' });
+  });
+
+  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',
+    });
+    await verifyMcpBearer('tok', accessDeps({ verifyJwtOneOf }));
+    expect(verifyJwtOneOf).toHaveBeenCalledTimes(1);
+  });
+});
+
 describe('decideBasicGate (pure SSO/MFA pre-token gate, refactor R1)', () => {
   // The pure decision extracted out of McpService.enforceBasicLoginGate. It is
   // tested WITHOUT ModuleRef and WITHOUT an on-disk EE MFA module: the SSO verdict
@@ -1198,6 +1316,7 @@ 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),
     });
   }