fix(ai-chat): open chat window before resolving the bound chat (#191)

Address PR #209 review.

- use-open-ai-chat.ts: call setWindowOpen(true) before awaiting
  getBoundChat so the header button feels instant on slow connections;
  the chat switch (setActiveChatId/setDraft/setSelectedRoleId) is applied
  after the round-trip resolves. Also drop the redundant no-op
  setWindowOpen(true) in the already-open branch (bare early return).
- CHANGELOG.md: document the header AI-chat button auto-opening the
  latest chat bound to the current document under [Unreleased]/Added.

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

CHANGELOG.md

@@ -41,6 +41,16 @@ per-workspace rolling-day token budget.
   foreign key is `ON DELETE SET NULL`, so deleting the target leaves a dangling
   alias any workspace member can reclaim. (#205)
 
+- **Temporary notes — auto-move to Trash after a workspace lifetime.** A note can
+  be marked temporary so it auto-moves to Trash once a configurable workspace
+  lifetime elapses (default `DEFAULT_TEMPORARY_NOTE_HOURS` = 24h) unless made
+  permanent first. The deadline is frozen at creation time, so later changes to
+  the workspace setting never reschedule existing notes; an hourly background
+  sweep trashes notes past their deadline (children ride along). An open
+  temporary note shows a banner with a "Make permanent" rescue action; restoring
+  a note from Trash disarms the timer so it is not immediately re-trashed.
+  Operators configure the lifetime per workspace. (#201)
+
 - **Persistent AI-chat history as the source of truth + server-side export.**
   An assistant turn is now persisted to the database step by step: the row is
   inserted upfront as `streaming` and updated as each agent step finishes, then
@@ -81,9 +91,31 @@ per-workspace rolling-day token budget.
 - **Footnote multi-backlinks.** A footnote referenced more than once now shows a
   back-link per reference (↩ a b c …), each scrolling to its own occurrence, like
   Pandoc/Wikipedia; a single-reference footnote keeps the plain ↩. (#168)
+- **Generate a page title from its content.** A "sparkles" button in the page
+  byline reads the live editor content (including unsaved edits), generates a
+  title via the workspace AI provider (`POST /ai-chat/generate-page-title`), and
+  applies it through the existing `/pages/update` route — reflecting it in the
+  title field and broadcasting to other clients. Gated by the `settings.ai.generative`
+  flag and throttled per user. (#199)
+- **AI chat: header button auto-opens the chat bound to the current document.**
+  Clicking the AI-chat button in the header while viewing a page now reopens the
+  latest chat tied to that document instead of whatever chat was last active,
+  reusing the existing `ai_chats.page_id` provenance (no migration). The newest
+  chat you created on the page wins; with no bound chat — or off a page, or if
+  the lookup fails — it falls soft to a fresh chat and keeps the current
+  selection otherwise. (#191)
 
 ### Changed
 
+- **AI chat now feeds the model the full stored transcript.** The per-turn model
+  conversation was rebuilt from a sliding window of the 50 most recent stored
+  rows, which silently dropped the beginning of any longer chat. It is now
+  rebuilt from the complete non-deleted transcript in chronological order, so
+  the model sees every turn (a 5000-row backstop guards process memory — a
+  safety net far above any realistic chat, not a conversational limit). On a
+  very long chat this can eventually reach the model's context window; the
+  client already surfaces that as "start a new chat". (#202)
+
 - **AI chat default provider is now `openai-compatible` (reasoning surfaced).**
   For the `openai` driver the chat provider defaults to the openai-compatible
   implementation, so a workspace pointing at z.ai/GLM/DeepSeek now streams the

apps/client/public/locales/en-US/translation.json

@@ -598,6 +598,17 @@
   "Are you sure you want to permanently delete '{{title}}'? This action cannot be undone.": "Are you sure you want to permanently delete '{{title}}'? This action cannot be undone.",
   "Restore '{{title}}' and its sub-pages?": "Restore '{{title}}' and its sub-pages?",
   "Move to trash": "Move to trash",
+  "Make temporary": "Make temporary",
+  "Make permanent": "Make permanent",
+  "New temporary note": "New temporary note",
+  "Temporary note": "Temporary note",
+  "Temporary notes": "Temporary notes",
+  "Temporary note — moves to trash unless made permanent": "Temporary note — moves to trash unless made permanent",
+  "Note will move to trash unless made permanent": "Note will move to trash unless made permanent",
+  "Note is now permanent": "Note is now permanent",
+  "Temporary note lifetime (hours)": "Temporary note lifetime (hours)",
+  "A temporary note is automatically moved to trash after this many hours unless it is made permanent. The deadline is fixed when the note is created.": "A temporary note is automatically moved to trash after this many hours unless it is made permanent. The deadline is fixed when the note is created.",
+  "This temporary note moves to trash {{time}} (with its sub-pages) unless made permanent.": "This temporary note moves to trash {{time}} (with its sub-pages) unless made permanent.",
   "Move this page to trash?": "Move this page to trash?",
   "Restore page": "Restore page",
   "Permanently delete": "Permanently delete",
@@ -1330,5 +1341,13 @@
   "The address \"{{alias}}\" currently points to \"{{title}}\". Move it to this page?": "The address \"{{alias}}\" currently points to \"{{title}}\". Move it to this page?",
   "The address \"{{alias}}\" is already in use. Move it to this page?": "The address \"{{alias}}\" is already in use. Move it to this page?",
   "Failed to set custom address": "Failed to set custom address",
-  "Failed to remove custom address": "Failed to remove custom address"
+  "Failed to remove custom address": "Failed to remove custom address",
+  "Generate title with AI": "Generate title with AI",
+  "Title generated": "Title generated",
+  "Failed to generate title": "Failed to generate title",
+  "The note is empty": "The note is empty",
+  "Could not generate a title": "Could not generate a title",
+  "AI title generation is disabled": "AI title generation is disabled",
+  "AI is not configured": "AI is not configured",
+  "Too many requests, please try again later": "Too many requests, please try again later"
 }

apps/client/public/locales/ru-RU/translation.json

@@ -607,6 +607,17 @@
   "Are you sure you want to permanently delete '{{title}}'? This action cannot be undone.": "Вы уверены, что хотите окончательно удалить '{{title}}'? Это действие невозможно отменить.",
   "Restore '{{title}}' and its sub-pages?": "Восстановить '{{title}}' и её подстраницы?",
   "Move to trash": "Переместить в корзину",
+  "Make temporary": "Сделать временной",
+  "Make permanent": "Сделать постоянной",
+  "New temporary note": "Новая временная заметка",
+  "Temporary note": "Временная заметка",
+  "Temporary notes": "Временные заметки",
+  "Temporary note — moves to trash unless made permanent": "Временная заметка — уедет в корзину, если не сделать постоянной",
+  "Note will move to trash unless made permanent": "Заметка уедет в корзину, если не сделать её постоянной",
+  "Note is now permanent": "Заметка теперь постоянная",
+  "Temporary note lifetime (hours)": "Время жизни временной заметки (часы)",
+  "A temporary note is automatically moved to trash after this many hours unless it is made permanent. The deadline is fixed when the note is created.": "Временная заметка автоматически уезжает в корзину через указанное число часов, если не сделать её постоянной. Дедлайн фиксируется при создании заметки.",
+  "This temporary note moves to trash {{time}} (with its sub-pages) unless made permanent.": "Эта временная заметка уедет в корзину {{time}} (вместе с подстраницами), если не сделать её постоянной.",
   "Move this page to trash?": "Переместить эту страницу в корзину?",
   "Restore page": "Восстановить страницу",
   "Permanently delete": "Удалить навсегда",
@@ -1187,5 +1198,13 @@
   "The address \"{{alias}}\" currently points to \"{{title}}\". Move it to this page?": "Адрес «{{alias}}» сейчас указывает на «{{title}}». Переместить его на эту страницу?",
   "The address \"{{alias}}\" is already in use. Move it to this page?": "Адрес «{{alias}}» уже используется. Переместить его на эту страницу?",
   "Failed to set custom address": "Не удалось задать пользовательский адрес",
-  "Failed to remove custom address": "Не удалось удалить пользовательский адрес"
+  "Failed to remove custom address": "Не удалось удалить пользовательский адрес",
+  "Generate title with AI": "Сгенерировать название через AI",
+  "Title generated": "Название сгенерировано",
+  "Failed to generate title": "Не удалось сгенерировать название",
+  "The note is empty": "Заметка пустая",
+  "Could not generate a title": "Не удалось придумать название",
+  "AI title generation is disabled": "Генерация названий через AI отключена",
+  "AI is not configured": "AI не настроен",
+  "Too many requests, please try again later": "Слишком много запросов, попробуйте позже"
 }

apps/client/src/components/layouts/global/app-header.tsx

@@ -10,12 +10,12 @@ import classes from "./app-header.module.css";
 import { BrandLogo } from "@/components/ui/brand-logo";
 import TopMenu from "@/components/layouts/global/top-menu.tsx";
 import { Link } from "react-router-dom";
-import { useAtom, useSetAtom } from "jotai";
+import { useAtom } from "jotai";
 import {
   desktopSidebarAtom,
   mobileSidebarAtom,
 } from "@/components/layouts/global/hooks/atoms/sidebar-atom.ts";
-import { aiChatWindowOpenAtom } from "@/features/ai-chat/atoms/ai-chat-atom.ts";
+import { useOpenAiChatForCurrentPage } from "@/features/ai-chat/hooks/use-open-ai-chat.ts";
 import { workspaceAtom } from "@/features/user/atoms/current-user-atom.ts";
 import { useToggleSidebar } from "@/components/layouts/global/hooks/hooks/use-toggle-sidebar.ts";
 import SidebarToggle from "@/components/ui/sidebar-toggle-button.tsx";
@@ -38,7 +38,9 @@ export function AppHeader() {
   const toggleDesktop = useToggleSidebar(desktopSidebarAtom);
 
   const [workspace] = useAtom(workspaceAtom);
-  const setAiChatWindowOpen = useSetAtom(aiChatWindowOpenAtom);
+  // Opening from the header auto-opens the document's bound chat (last chat
+  // created on the current page); off a page it keeps the current selection.
+  const openAiChat = useOpenAiChatForCurrentPage();
   // AI chat entry point: only shown when the workspace enables it (A7 gate).
   const aiChatEnabled = workspace?.settings?.ai?.chat === true;
 
@@ -105,7 +107,7 @@ export function AppHeader() {
                 color="dark"
                 size="sm"
                 aria-label={t("AI chat")}
-                onClick={() => setAiChatWindowOpen((v) => !v)}
+                onClick={openAiChat}
               >
                 <IconMessage size={20} />
               </ActionIcon>

apps/client/src/features/ai-chat/hooks/use-open-ai-chat.test.tsx

@@ -0,0 +1,135 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import { renderHook, act } from "@testing-library/react";
+import { Provider, createStore } from "jotai";
+import type { ReactNode } from "react";
+import { useOpenAiChatForCurrentPage } from "./use-open-ai-chat";
+import {
+  activeAiChatIdAtom,
+  aiChatWindowOpenAtom,
+  aiChatDraftAtom,
+  selectedAiRoleIdAtom,
+} from "@/features/ai-chat/atoms/ai-chat-atom.ts";
+
+// useMatch is the only react-router-dom export the hook uses; drive its return
+// per test to simulate "on a page" vs "off a page".
+const useMatchMock = vi.fn();
+vi.mock("react-router-dom", () => ({
+  useMatch: () => useMatchMock(),
+}));
+
+// The bound-chat resolver is the network boundary; stub it per test.
+const getBoundChatMock = vi.fn();
+vi.mock("@/features/ai-chat/services/ai-chat-service.ts", () => ({
+  getBoundChat: (pageId: string) => getBoundChatMock(pageId),
+}));
+
+// Put the hook on a page route by default ("doc-p1" -> page id "p1"); individual
+// tests override useMatch to go off-page.
+function onPage(pageSlug = "doc-p1") {
+  useMatchMock.mockReturnValue({ params: { pageSlug } });
+}
+function offPage() {
+  useMatchMock.mockReturnValue(null);
+}
+
+// Render the hook inside an explicit jotai store so atom side effects are
+// assertable; the store is returned for setup + assertions.
+function setup(seed?: (store: ReturnType<typeof createStore>) => void) {
+  const store = createStore();
+  seed?.(store);
+  const wrapper = ({ children }: { children: ReactNode }) => (
+    <Provider store={store}>{children}</Provider>
+  );
+  const { result } = renderHook(() => useOpenAiChatForCurrentPage(), { wrapper });
+  return { store, open: () => act(() => result.current()) };
+}
+
+describe("useOpenAiChatForCurrentPage", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    onPage();
+  });
+
+  it("on a page: resolves the bound chat, selects it, and opens the window", async () => {
+    getBoundChatMock.mockResolvedValue("bound-chat-1");
+    const { store, open } = setup((s) => s.set(aiChatDraftAtom, "stale draft"));
+
+    await open();
+
+    expect(getBoundChatMock).toHaveBeenCalledWith("p1");
+    expect(store.get(activeAiChatIdAtom)).toBe("bound-chat-1");
+    expect(store.get(aiChatWindowOpenAtom)).toBe(true);
+    expect(store.get(aiChatDraftAtom)).toBe(""); // cleared on a real switch
+  });
+
+  it("on a page with no bound chat: opens a fresh chat (null)", async () => {
+    getBoundChatMock.mockResolvedValue(null);
+    const { store, open } = setup((s) => s.set(activeAiChatIdAtom, "previous"));
+
+    await open();
+
+    expect(store.get(activeAiChatIdAtom)).toBeNull();
+    expect(store.get(aiChatWindowOpenAtom)).toBe(true);
+  });
+
+  it("off a page: keeps the current selection and does NOT resolve", async () => {
+    offPage();
+    const { store, open } = setup((s) => {
+      s.set(activeAiChatIdAtom, "keep-me");
+      s.set(aiChatDraftAtom, "untouched");
+    });
+
+    await open();
+
+    expect(getBoundChatMock).not.toHaveBeenCalled();
+    expect(store.get(activeAiChatIdAtom)).toBe("keep-me");
+    expect(store.get(aiChatDraftAtom)).toBe("untouched"); // no switch -> kept
+    expect(store.get(aiChatWindowOpenAtom)).toBe(true);
+  });
+
+  it("window already open: re-click does NOT re-resolve or switch chats", async () => {
+    getBoundChatMock.mockResolvedValue("would-switch");
+    const { store, open } = setup((s) => {
+      s.set(aiChatWindowOpenAtom, true);
+      s.set(activeAiChatIdAtom, "current");
+    });
+
+    await open();
+
+    expect(getBoundChatMock).not.toHaveBeenCalled();
+    expect(store.get(activeAiChatIdAtom)).toBe("current");
+    expect(store.get(aiChatWindowOpenAtom)).toBe(true);
+  });
+
+  it("does NOT clear the draft when the resolved chat equals the current one", async () => {
+    getBoundChatMock.mockResolvedValue("same");
+    const { store, open } = setup((s) => {
+      s.set(activeAiChatIdAtom, "same");
+      s.set(aiChatDraftAtom, "in-progress");
+    });
+
+    await open();
+
+    expect(store.get(aiChatDraftAtom)).toBe("in-progress"); // no switch
+    expect(store.get(aiChatWindowOpenAtom)).toBe(true);
+  });
+
+  it("fail-soft: a resolve error opens a fresh chat (null)", async () => {
+    getBoundChatMock.mockRejectedValue(new Error("network"));
+    const { store, open } = setup((s) => s.set(activeAiChatIdAtom, "previous"));
+
+    await open();
+
+    expect(store.get(activeAiChatIdAtom)).toBeNull();
+    expect(store.get(aiChatWindowOpenAtom)).toBe(true);
+  });
+
+  it("clears the picked role on a real switch", async () => {
+    getBoundChatMock.mockResolvedValue("bound");
+    const { store, open } = setup((s) => s.set(selectedAiRoleIdAtom, "role-1"));
+
+    await open();
+
+    expect(store.get(selectedAiRoleIdAtom)).toBeNull();
+  });
+});

apps/client/src/features/ai-chat/hooks/use-open-ai-chat.ts

@@ -0,0 +1,67 @@
+import { useCallback } from "react";
+import { useAtom, useSetAtom } from "jotai";
+import { useMatch } from "react-router-dom";
+import {
+  aiChatWindowOpenAtom,
+  activeAiChatIdAtom,
+  aiChatDraftAtom,
+  selectedAiRoleIdAtom,
+} from "@/features/ai-chat/atoms/ai-chat-atom.ts";
+import { getBoundChat } from "@/features/ai-chat/services/ai-chat-service.ts";
+import { extractPageSlugId } from "@/lib";
+
+/**
+ * The generic "open the AI chat" action, WITH document binding: when invoked
+ * while viewing a page, it resolves that page's bound chat and selects it before
+ * opening — so the last chat for this document re-opens by itself. With no bound
+ * chat (or off a page) it keeps the current selection / opens a fresh chat. Used
+ * by the app-header entry point; NOT by the provenance badge (which deep-links).
+ */
+export function useOpenAiChatForCurrentPage() {
+  const [windowOpen, setWindowOpen] = useAtom(aiChatWindowOpenAtom);
+  const [activeChatId, setActiveChatId] = useAtom(activeAiChatIdAtom);
+  const setDraft = useSetAtom(aiChatDraftAtom);
+  const setSelectedRoleId = useSetAtom(selectedAiRoleIdAtom);
+
+  // Same route-match trick the window uses: read :pageSlug from the pathname.
+  // AiChatWindow lives in a pathless parent layout route, so useParams() can't
+  // see :pageSlug — match the full path against the authenticated page route.
+  const match = useMatch("/s/:spaceSlug/p/:pageSlug");
+  const pageId = extractPageSlugId(match?.params?.pageSlug);
+
+  return useCallback(async () => {
+    // Re-clicks while the window is already open (incl. minimized) must NOT
+    // re-resolve and yank the user to another chat: resolve only on a genuine
+    // closed -> open transition. (`windowOpen` is already true here, so there
+    // is nothing to set — just bail.)
+    if (windowOpen) return;
+    // Open the window FIRST so the control feels instant: the bound-chat
+    // round-trip below must never gate the window appearing, or on a slow
+    // connection the first click reads as a hung control until the POST returns.
+    setWindowOpen(true);
+    let resolved: string | null = activeChatId; // off-a-page: keep current
+    if (pageId) {
+      try {
+        resolved = await getBoundChat(pageId); // null => fresh chat
+      } catch {
+        resolved = null; // fail-soft: a fresh chat is always a safe fallback
+      }
+    }
+    // Clear the composer draft / picked role ONLY on an actual switch, so
+    // reopening the same chat does not wipe an in-progress draft. Applied after
+    // the resolve so the window is already visible while the switch settles.
+    if (resolved !== activeChatId) {
+      setActiveChatId(resolved);
+      setDraft("");
+      setSelectedRoleId(null);
+    }
+  }, [
+    windowOpen,
+    activeChatId,
+    pageId,
+    setWindowOpen,
+    setActiveChatId,
+    setDraft,
+    setSelectedRoleId,
+  ]);
+}

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

@@ -37,6 +37,17 @@ export async function getAiChatMessages(
   return req.data;
 }
 
+/**
+ * Resolve the chat bound to a document (the current user's most-recent chat
+ * created on that page), or null when there is none. Drives auto-open-on-page.
+ */
+export async function getBoundChat(pageId: string): Promise<string | null> {
+  const req = await api.post<{ chatId: string | null }>("/ai-chat/bound-chat", {
+    pageId,
+  });
+  return req.data.chatId;
+}
+
 /** Rename a chat. */
 export async function renameAiChat(data: {
   chatId: string;
@@ -68,6 +79,19 @@ export async function exportAiChat(
   return req.data.markdown;
 }
 
+/**
+ * Generate a page title from note content (markdown). One-shot, non-streaming
+ * (#199): the server only summarizes the supplied text and returns a suggestion;
+ * it never writes the page. The caller applies the title via /pages/update.
+ */
+export async function generatePageTitle(content: string): Promise<string> {
+  const req = await api.post<{ title: string }>(
+    "/ai-chat/generate-page-title",
+    { content },
+  );
+  return req.data.title;
+}
+
 /**
  * Agent roles API (`/ai-chat/roles`). `list` is available to any workspace
  * member (for the chat-creation picker); create/update/delete are admin-only

apps/client/src/features/editor/components/fixed-toolbar/groups/generate-title-group.tsx

@@ -0,0 +1,39 @@
+import { FC } from "react";
+import { ActionIcon, Tooltip } from "@mantine/core";
+import { IconSparkles } from "@tabler/icons-react";
+import { useTranslation } from "react-i18next";
+import { useGeneratePageTitle } from "@/features/editor/hooks/use-generate-page-title.ts";
+
+interface Props {
+  pageId: string;
+  color?: string;
+  iconSize?: number;
+}
+
+/**
+ * AI "generate title" button (#199). Reads the live editor content and applies a
+ * model-suggested title immediately. Rendered in the page byline, only in edit
+ * mode and when the workspace's generative AI flag is on.
+ */
+export const GenerateTitleGroup: FC<Props> = ({
+  pageId,
+  color = "gray",
+  iconSize = 20,
+}) => {
+  const { t } = useTranslation();
+  const gen = useGeneratePageTitle(pageId);
+
+  return (
+    <Tooltip label={t("Generate title with AI")} withArrow openDelay={250}>
+      <ActionIcon
+        variant="subtle"
+        color={color}
+        aria-label={t("Generate title with AI")}
+        loading={gen.isPending}
+        onClick={() => gen.mutate()}
+      >
+        <IconSparkles size={iconSize} stroke={1.5} />
+      </ActionIcon>
+    </Tooltip>
+  );
+};

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

@@ -26,17 +26,20 @@ import { FixedToolbar } from "@/features/editor/components/fixed-toolbar/fixed-t
 import { PageEditMode } from "@/features/user/types/user.types.ts";
 import { useAsideTriggerProps } from "@/hooks/use-toggle-aside.tsx";
 import { DeletedPageBanner } from "@/features/page/trash/components/deleted-page-banner.tsx";
+import { TemporaryNoteBanner } from "@/features/page/components/temporary-note-banner.tsx";
 import clsx from "clsx";
 import {
   currentPageEditModeAtom,
   pageEditorAtom,
 } from "@/features/editor/atoms/editor-atoms.ts";
 import { DictationGroup } from "@/features/editor/components/fixed-toolbar/groups/dictation-group";
+import { GenerateTitleGroup } from "@/features/editor/components/fixed-toolbar/groups/generate-title-group";
 
 const MemoizedTitleEditor = React.memo(TitleEditor);
 const MemoizedPageEditor = React.memo(PageEditor);
 const MemoizedFixedToolbar = React.memo(FixedToolbar);
 const MemoizedDeletedPageBanner = React.memo(DeletedPageBanner);
+const MemoizedTemporaryNoteBanner = React.memo(TemporaryNoteBanner);
 
 type PageUser = {
   id: string;
@@ -74,6 +77,9 @@ export function FullEditor({
   const [user] = useAtom(userAtom);
   const workspace = useAtomValue(workspaceAtom);
   const isDictationEnabled = workspace?.settings?.ai?.dictation === true;
+  // AI title generation reuses the generative AI flag (same gate as the on-page
+  // generative menu); the server enforces it too (#199).
+  const isTitleGenEnabled = workspace?.settings?.ai?.generative === true;
   const fullPageWidth = user.settings?.preferences?.fullPageWidth;
   const editorToolbarEnabled =
     user.settings?.preferences?.editorToolbar ?? false;
@@ -103,6 +109,7 @@ export function FullEditor({
         <MemoizedFixedToolbar />
       )}
       <MemoizedDeletedPageBanner slugId={slugId} />
+      <MemoizedTemporaryNoteBanner slugId={slugId} />
       <MemoizedTitleEditor
         pageId={pageId}
         slugId={slugId}
@@ -111,11 +118,13 @@ export function FullEditor({
         editable={editable}
       />
       <PageByline
+        pageId={pageId}
         creator={creator}
         contributors={contributors}
         editable={editable}
         isEditMode={isEditMode}
         isDictationEnabled={isDictationEnabled}
+        isTitleGenEnabled={isTitleGenEnabled}
       />
       <MemoizedPageEditor
         pageId={pageId}
@@ -128,19 +137,23 @@ export function FullEditor({
 }
 
 type PageBylineProps = {
+  pageId: string;
   creator?: PageUser;
   contributors?: IContributor[];
   editable?: boolean;
   isEditMode?: boolean;
   isDictationEnabled?: boolean;
+  isTitleGenEnabled?: boolean;
 };
 
 function PageByline({
+  pageId,
   creator,
   contributors,
   editable,
   isEditMode,
   isDictationEnabled,
+  isTitleGenEnabled,
 }: PageBylineProps) {
   const { t } = useTranslation();
   const detailsTriggerProps = useAsideTriggerProps("details");
@@ -148,6 +161,9 @@ function PageByline({
   const showDictation = Boolean(
     isDictationEnabled && editable && isEditMode && editor,
   );
+  const showTitleGen = Boolean(
+    isTitleGenEnabled && editable && isEditMode && editor,
+  );
 
   const otherContributors = (contributors ?? []).filter(
     (c) => c.id !== creator?.id,
@@ -238,6 +254,11 @@ function PageByline({
         {showDictation && editor && (
           <DictationGroup editor={editor} color="gray" iconSize={20} />
         )}
+        {/* Shown only in edit mode when the workspace's generative AI flag is on,
+            so AI title generation stays reachable from the byline (#199). */}
+        {showTitleGen && (
+          <GenerateTitleGroup pageId={pageId} color="gray" iconSize={20} />
+        )}
       </Group>
     </Group>
   );

apps/client/src/features/editor/hooks/use-generate-page-title.test.tsx

@@ -0,0 +1,294 @@
+import { describe, it, expect, vi, beforeEach } from "vitest";
+import { renderHook, act } from "@testing-library/react";
+import type { ReactNode } from "react";
+import { QueryClient, QueryClientProvider } from "@tanstack/react-query";
+import { Provider, createStore } from "jotai";
+import type { Editor } from "@tiptap/core";
+import {
+  pageEditorAtom,
+  titleEditorAtom,
+} from "@/features/editor/atoms/editor-atoms.ts";
+
+// --- Mocks for the hook's collaborators ---------------------------------------
+
+const generatePageTitleMock = vi.fn();
+vi.mock("@/features/ai-chat/services/ai-chat-service.ts", () => ({
+  generatePageTitle: (content: string) => generatePageTitleMock(content),
+}));
+
+const updateTitleMock = vi.fn();
+const updatePageDataMock = vi.fn();
+vi.mock("@/features/page/queries/page-query.ts", () => ({
+  useUpdateTitlePageMutation: () => ({ mutateAsync: updateTitleMock }),
+  updatePageData: (page: unknown) => updatePageDataMock(page),
+}));
+
+const emitMock = vi.fn();
+vi.mock("@/features/websocket/use-query-emit.ts", () => ({
+  useQueryEmit: () => emitMock,
+}));
+
+const localEmitMock = vi.fn();
+vi.mock("@/lib/local-emitter.ts", () => ({
+  default: { emit: (...args: unknown[]) => localEmitMock(...args) },
+}));
+
+// htmlToMarkdown just echoes the editor HTML so each test controls the markdown
+// purely via the fake page editor's getHTML().
+vi.mock("@docmost/editor-ext", () => ({
+  htmlToMarkdown: (html: string) => html,
+}));
+
+const notificationsShowMock = vi.fn();
+vi.mock("@mantine/notifications", () => ({
+  notifications: { show: (opts: unknown) => notificationsShowMock(opts) },
+}));
+
+vi.mock("react-i18next", () => ({
+  useTranslation: () => ({ t: (key: string) => key }),
+}));
+
+// Import after mocks are registered.
+import { useGeneratePageTitle } from "./use-generate-page-title.ts";
+
+// --- Test helpers -------------------------------------------------------------
+
+function makePageEditor(pageId: string, html = "<p>content</p>"): Editor {
+  return {
+    isDestroyed: false,
+    getHTML: () => html,
+    storage: { pageId },
+  } as unknown as Editor;
+}
+
+function makeTitleEditor(): Editor & {
+  commands: { setContent: ReturnType<typeof vi.fn> };
+} {
+  return {
+    isDestroyed: false,
+    isFocused: false,
+    commands: { setContent: vi.fn() },
+  } as unknown as Editor & {
+    commands: { setContent: ReturnType<typeof vi.fn> };
+  };
+}
+
+function setup(pageId: string, store = createStore()) {
+  const queryClient = new QueryClient({
+    defaultOptions: { mutations: { retry: false } },
+  });
+  const wrapper = ({ children }: { children: ReactNode }) => (
+    <QueryClientProvider client={queryClient}>
+      <Provider store={store}>{children}</Provider>
+    </QueryClientProvider>
+  );
+  const { result } = renderHook(() => useGeneratePageTitle(pageId), {
+    wrapper,
+  });
+  return { result, store };
+}
+
+const PAGE_A = {
+  id: "pageA",
+  title: "Generated Title",
+  spaceId: "space1",
+  slugId: "slugA",
+  parentPageId: null,
+  icon: null,
+} as any;
+
+beforeEach(() => {
+  vi.clearAllMocks();
+});
+
+describe("useGeneratePageTitle", () => {
+  it("shows a notice and bails when the editor content is empty", async () => {
+    const store = createStore();
+    store.set(pageEditorAtom as never, makePageEditor("pageA", "   "));
+    store.set(titleEditorAtom as never, makeTitleEditor());
+    const { result } = setup("pageA", store);
+
+    await act(async () => {
+      await result.current.mutateAsync();
+    });
+
+    expect(notificationsShowMock).toHaveBeenCalledWith(
+      expect.objectContaining({ message: "The note is empty", color: "yellow" }),
+    );
+    expect(generatePageTitleMock).not.toHaveBeenCalled();
+    expect(updateTitleMock).not.toHaveBeenCalled();
+  });
+
+  it("leaves the title untouched when the model returns nothing usable", async () => {
+    const store = createStore();
+    store.set(pageEditorAtom as never, makePageEditor("pageA"));
+    store.set(titleEditorAtom as never, makeTitleEditor());
+    generatePageTitleMock.mockResolvedValue("   ");
+    const { result } = setup("pageA", store);
+
+    await act(async () => {
+      await result.current.mutateAsync();
+    });
+
+    expect(updateTitleMock).not.toHaveBeenCalled();
+    expect(notificationsShowMock).toHaveBeenCalledWith(
+      expect.objectContaining({
+        message: "Could not generate a title",
+        color: "yellow",
+      }),
+    );
+  });
+
+  it("happy path: applies the title, refreshes cache, writes the field, broadcasts", async () => {
+    const store = createStore();
+    const titleEditor = makeTitleEditor();
+    store.set(pageEditorAtom as never, makePageEditor("pageA"));
+    store.set(titleEditorAtom as never, titleEditor);
+    generatePageTitleMock.mockResolvedValue("Generated Title");
+    updateTitleMock.mockResolvedValue(PAGE_A);
+    const { result } = setup("pageA", store);
+
+    await act(async () => {
+      await result.current.mutateAsync();
+    });
+
+    expect(updateTitleMock).toHaveBeenCalledWith({
+      pageId: "pageA",
+      title: "Generated Title",
+    });
+    expect(updatePageDataMock).toHaveBeenCalledWith(PAGE_A);
+    expect(titleEditor.commands.setContent).toHaveBeenCalledWith(
+      "Generated Title",
+    );
+    expect(localEmitMock).toHaveBeenCalled();
+    expect(emitMock).toHaveBeenCalled();
+    expect(notificationsShowMock).toHaveBeenCalledWith(
+      expect.objectContaining({ message: "Title generated" }),
+    );
+  });
+
+  it("does NOT write the visible title field when the user navigated away during generation", async () => {
+    const store = createStore();
+    const titleEditor = makeTitleEditor(); // persistent across navigation
+    store.set(pageEditorAtom as never, makePageEditor("pageA"));
+    store.set(titleEditorAtom as never, titleEditor);
+
+    // Control when generation resolves so we can navigate mid-flight.
+    let resolveTitle!: (t: string) => void;
+    generatePageTitleMock.mockReturnValue(
+      new Promise<string>((res) => {
+        resolveTitle = res;
+      }),
+    );
+    updateTitleMock.mockResolvedValue(PAGE_A);
+    const { result } = setup("pageA", store);
+
+    let pending!: Promise<void>;
+    act(() => {
+      pending = result.current.mutateAsync();
+    });
+
+    // User navigates to page B: the live page editor now belongs to pageB.
+    act(() => {
+      store.set(pageEditorAtom as never, makePageEditor("pageB"));
+    });
+
+    await act(async () => {
+      resolveTitle("Generated Title");
+      await pending;
+    });
+
+    // DB write is still correct (keyed by the captured pageId)...
+    expect(updateTitleMock).toHaveBeenCalledWith({
+      pageId: "pageA",
+      title: "Generated Title",
+    });
+    // ...but we must NOT stamp page A's title into page B's visible field.
+    expect(titleEditor.commands.setContent).not.toHaveBeenCalled();
+    // The change is still broadcast to other clients.
+    expect(emitMock).toHaveBeenCalled();
+  });
+
+  it("does NOT write the visible title field when the title editor is focused", async () => {
+    const store = createStore();
+    const titleEditor = makeTitleEditor();
+    store.set(pageEditorAtom as never, makePageEditor("pageA"));
+    store.set(titleEditorAtom as never, titleEditor);
+
+    // Resolve generation under our control so we can mark the live title editor
+    // as focused before the post-generation write runs.
+    let resolveTitle!: (t: string) => void;
+    generatePageTitleMock.mockReturnValue(
+      new Promise<string>((res) => {
+        resolveTitle = res;
+      }),
+    );
+    updateTitleMock.mockResolvedValue(PAGE_A);
+    const { result } = setup("pageA", store);
+
+    let pending!: Promise<void>;
+    act(() => {
+      pending = result.current.mutateAsync();
+    });
+
+    // The user clicked into the title field while the model ran — overwriting it
+    // now would clobber what they are actively typing.
+    act(() => {
+      (titleEditor as { isFocused: boolean }).isFocused = true;
+    });
+
+    await act(async () => {
+      resolveTitle("Generated Title");
+      await pending;
+    });
+
+    // The DB write still persists the value...
+    expect(updateTitleMock).toHaveBeenCalledWith({
+      pageId: "pageA",
+      title: "Generated Title",
+    });
+    expect(updatePageDataMock).toHaveBeenCalledWith(PAGE_A);
+    // ...but the visible field is left alone while it is focused.
+    expect(titleEditor.commands.setContent).not.toHaveBeenCalled();
+    // The change is still broadcast to other clients.
+    expect(localEmitMock).toHaveBeenCalled();
+    expect(emitMock).toHaveBeenCalled();
+  });
+
+  it("bails before calling the model when the page editor is destroyed", async () => {
+    const store = createStore();
+    const pageEditor = makePageEditor("pageA");
+    (pageEditor as { isDestroyed: boolean }).isDestroyed = true;
+    store.set(pageEditorAtom as never, pageEditor);
+    store.set(titleEditorAtom as never, makeTitleEditor());
+    const { result } = setup("pageA", store);
+
+    await act(async () => {
+      await result.current.mutateAsync();
+    });
+
+    expect(generatePageTitleMock).not.toHaveBeenCalled();
+    expect(updateTitleMock).not.toHaveBeenCalled();
+  });
+
+  it.each([
+    [403, "AI title generation is disabled"],
+    [503, "AI is not configured"],
+    [429, "Too many requests, please try again later"],
+    [500, "Failed to generate title"],
+  ])("maps HTTP %s onError to a friendly message", async (status, message) => {
+    const store = createStore();
+    store.set(pageEditorAtom as never, makePageEditor("pageA"));
+    store.set(titleEditorAtom as never, makeTitleEditor());
+    generatePageTitleMock.mockRejectedValue({ response: { status } });
+    const { result } = setup("pageA", store);
+
+    await act(async () => {
+      await expect(result.current.mutateAsync()).rejects.toBeTruthy();
+    });
+
+    expect(notificationsShowMock).toHaveBeenCalledWith(
+      expect.objectContaining({ message, color: "red" }),
+    );
+  });
+});

apps/client/src/features/editor/hooks/use-generate-page-title.ts

@@ -0,0 +1,134 @@
+import { useRef } from "react";
+import { useMutation } from "@tanstack/react-query";
+import { useAtomValue } from "jotai";
+import { notifications } from "@mantine/notifications";
+import { useTranslation } from "react-i18next";
+import { htmlToMarkdown } from "@docmost/editor-ext";
+import {
+  pageEditorAtom,
+  titleEditorAtom,
+} from "@/features/editor/atoms/editor-atoms.ts";
+import {
+  updatePageData,
+  useUpdateTitlePageMutation,
+} from "@/features/page/queries/page-query.ts";
+import { generatePageTitle } from "@/features/ai-chat/services/ai-chat-service.ts";
+import { useQueryEmit } from "@/features/websocket/use-query-emit.ts";
+import { UpdateEvent } from "@/features/websocket/types";
+import localEmitter from "@/lib/local-emitter.ts";
+
+// Maximum length we send to the model. The server truncates again; this is a
+// cheap client-side bound so we never ship a huge body over the wire.
+const MAX_CONTENT_CHARS = 20000;
+
+/**
+ * Generate a title for the given page from the LIVE editor content (#199),
+ * including unsaved edits, then apply it IMMEDIATELY (per product decision). The
+ * server endpoint only summarizes the supplied markdown — it never writes the
+ * page; the actual title write goes through the existing /pages/update mutation
+ * (which enforces edit permission), and is mirrored to the title field + other
+ * clients exactly like TitleEditor.saveTitle. Returns a mutation-like API so the
+ * button can show a loading state via `isPending`.
+ */
+export function useGeneratePageTitle(pageId: string) {
+  const { t } = useTranslation();
+  const pageEditor = useAtomValue(pageEditorAtom);
+  const titleEditor = useAtomValue(titleEditorAtom);
+  const { mutateAsync: updateTitle } = useUpdateTitlePageMutation();
+  const emit = useQueryEmit();
+
+  // The page/title editors come from GLOBAL atoms that re-point when the user
+  // navigates to another page. The mutation below awaits the model for 1-3s, and
+  // its closure captures the editors from the render that started it. Keep a live
+  // reference so the post-generation write targets whatever page is on screen
+  // *now*, not the page the generation was started from.
+  const editorsRef = useRef({ pageEditor, titleEditor });
+  editorsRef.current = { pageEditor, titleEditor };
+
+  return useMutation<void, Error, void>({
+    mutationFn: async () => {
+      if (!pageEditor || pageEditor.isDestroyed) return;
+
+      const markdown = htmlToMarkdown(pageEditor.getHTML()).trim();
+      if (!markdown) {
+        notifications.show({ message: t("The note is empty"), color: "yellow" });
+        return;
+      }
+
+      const title = (
+        await generatePageTitle(markdown.slice(0, MAX_CONTENT_CHARS))
+      ).trim();
+      if (!title) {
+        // The model returned nothing usable — keep the existing title untouched.
+        notifications.show({
+          message: t("Could not generate a title"),
+          color: "yellow",
+        });
+        return;
+      }
+
+      const page = await updateTitle({ pageId, title }); // POST /pages/update
+      updatePageData(page); // refresh the react-query cache
+
+      // Reflect the new title in the field immediately. The button lives in the
+      // byline, so the title editor is not focused — setContent is safe and stays
+      // undoable through its History extension (Ctrl/Cmd+Z reverts the change).
+      //
+      // Guard against navigation during generation: if the user switched pages
+      // while the model ran, the (persistent) title editor now shows ANOTHER
+      // page, so writing here would drop page A's title into page B's visible
+      // field. page-editor.tsx stamps the live page editor with its pageId
+      // (`editor.storage.pageId`), mirroring TitleEditor's `activePageId !==
+      // pageId` guard — bail the visible write unless that live editor still
+      // belongs to the page this title was generated for. The DB write above is
+      // already correct (keyed by the captured `pageId`), and the broadcast below
+      // still propagates page A's change to other clients.
+      const livePageEditor = editorsRef.current.pageEditor;
+      const liveTitleEditor = editorsRef.current.titleEditor;
+      // `storage.pageId` is stamped untyped in page-editor.tsx's onCreate.
+      const livePageId = (livePageEditor?.storage as { pageId?: string })
+        ?.pageId;
+      const stillOnPage = livePageId === pageId;
+      if (
+        stillOnPage &&
+        liveTitleEditor &&
+        !liveTitleEditor.isDestroyed &&
+        !liveTitleEditor.isFocused
+      ) {
+        liveTitleEditor.commands.setContent(page.title);
+      }
+
+      // Broadcast to other clients, mirroring TitleEditor.saveTitle's event shape.
+      const event: UpdateEvent = {
+        operation: "updateOne",
+        spaceId: page.spaceId,
+        entity: ["pages"],
+        id: page.id,
+        payload: {
+          title: page.title,
+          slugId: page.slugId,
+          parentPageId: page.parentPageId,
+          icon: page.icon,
+        },
+      };
+      localEmitter.emit("message", event);
+      emit(event);
+
+      notifications.show({ message: t("Title generated") });
+    },
+    onError: (err) => {
+      // Map known HTTP statuses to friendly messages, falling back to generic.
+      const status = (err as { response?: { status?: number } })?.response
+        ?.status;
+      const message =
+        status === 403
+          ? t("AI title generation is disabled")
+          : status === 503
+            ? t("AI is not configured")
+            : status === 429
+              ? t("Too many requests, please try again later")
+              : t("Failed to generate title");
+      notifications.show({ message, color: "red" });
+    },
+  });
+}

apps/client/src/features/page-embed/queries/page-embed-query.ts

@@ -1,7 +1,40 @@
 import { useMutation } from "@tanstack/react-query";
 import { notifications } from "@mantine/notifications";
-import { toggleTemplate } from "@/features/page-embed/services/page-embed-api";
-import type { ToggleTemplateResponse } from "@/features/page-embed/types/page-embed.types";
+import {
+  toggleTemplate,
+  toggleTemporary,
+} from "@/features/page-embed/services/page-embed-api";
+import type {
+  ToggleTemplateResponse,
+  ToggleTemporaryResponse,
+} from "@/features/page-embed/types/page-embed.types";
+import { queryClient } from "@/main.tsx";
+
+/**
+ * After toggling a note's temporary state, mirror the new deadline into the
+ * shared page cache (keyed by both slugId and id) and refresh the sidebar so the
+ * menu label, the in-page banner, and the tree icon all reflect the change.
+ * Centralised here so the header menu and the banner can't drift apart on the
+ * cache-key plumbing.
+ */
+export function syncTemporaryExpiresInCache(
+  page: { id: string; slugId: string },
+  temporaryExpiresAt: string | null,
+) {
+  for (const key of [page.slugId, page.id]) {
+    const cached = queryClient.getQueryData<any>(["pages", key]);
+    if (cached) {
+      queryClient.setQueryData(["pages", key], {
+        ...cached,
+        temporaryExpiresAt,
+      });
+    }
+  }
+  queryClient.invalidateQueries({
+    predicate: (item) =>
+      ["sidebar-pages"].includes(item.queryKey[0] as string),
+  });
+}
 
 export function useToggleTemplateMutation() {
   return useMutation<
@@ -18,3 +51,20 @@ export function useToggleTemplateMutation() {
     },
   });
 }
+
+export function useToggleTemporaryMutation() {
+  return useMutation<
+    ToggleTemporaryResponse,
+    Error,
+    { pageId: string; temporary?: boolean }
+  >({
+    mutationFn: (data) => toggleTemporary(data),
+    onError: (err: any) => {
+      notifications.show({
+        message:
+          err?.response?.data?.message || "Failed to update temporary note",
+        color: "red",
+      });
+    },
+  });
+}

apps/client/src/features/page-embed/services/page-embed-api.ts

@@ -2,6 +2,7 @@ import api from "@/lib/api-client";
 import type {
   PageTemplateLookup,
   ToggleTemplateResponse,
+  ToggleTemporaryResponse,
 } from "../types/page-embed.types";
 
 export async function lookupTemplate(params: {
@@ -18,3 +19,11 @@ export async function toggleTemplate(params: {
   const r = await api.post("/pages/toggle-template", params);
   return r.data;
 }
+
+export async function toggleTemporary(params: {
+  pageId: string;
+  temporary?: boolean;
+}): Promise<ToggleTemporaryResponse> {
+  const r = await api.post("/pages/toggle-temporary", params);
+  return r.data;
+}

apps/client/src/features/page-embed/types/page-embed.types.ts

@@ -14,3 +14,9 @@ export type ToggleTemplateResponse = {
   pageId: string;
   isTemplate: boolean;
 };
+
+export type ToggleTemporaryResponse = {
+  pageId: string;
+  // null => the note was made permanent; ISO string => armed deadline.
+  temporaryExpiresAt: string | null;
+};

apps/client/src/features/page/components/header/page-header-menu.tsx

@@ -2,6 +2,7 @@ import { ActionIcon, Button, Group, Menu, Text, ThemeIcon, Tooltip } from "@mant
 import {
   IconArrowRight,
   IconArrowsHorizontal,
+  IconClockHour4,
   IconDots,
   IconEye,
   IconEyeOff,
@@ -24,6 +25,10 @@ import { useDisclosure, useHotkeys } from "@mantine/hooks";
 import { useClipboard } from "@/hooks/use-clipboard";
 import { useParams } from "react-router-dom";
 import { usePageQuery } from "@/features/page/queries/page-query.ts";
+import {
+  useToggleTemporaryMutation,
+  syncTemporaryExpiresInCache,
+} from "@/features/page-embed/queries/page-embed-query.ts";
 import { buildPageUrl } from "@/features/page/page.utils.ts";
 import { notifications } from "@mantine/notifications";
 import { getAppUrl } from "@/lib/config.ts";
@@ -160,6 +165,29 @@ function PageActionMenu({ readOnly }: PageActionMenuProps) {
   const { data: watchStatus } = useWatchStatusQuery(page?.id);
   const watchPage = useWatchPageMutation();
   const unwatchPage = useUnwatchPageMutation();
+  const toggleTemporary = useToggleTemporaryMutation();
+  const isTemporary = !!page?.temporaryExpiresAt;
+
+  const handleToggleTemporary = async () => {
+    if (!page?.id) return;
+    const next = !isTemporary;
+    try {
+      const res = await toggleTemporary.mutateAsync({
+        pageId: page.id,
+        temporary: next,
+      });
+      // Reflect the new deadline in the page cache so the menu label flips and
+      // any banner updates. The sidebar icon refreshes via its own query.
+      syncTemporaryExpiresInCache(page, res.temporaryExpiresAt);
+      notifications.show({
+        message: next
+          ? t("Note will move to trash unless made permanent")
+          : t("Note is now permanent"),
+      });
+    } catch {
+      // mutation surfaces the error via notifications
+    }
+  };
 
   const handleCopyLink = () => {
     const pageUrl =
@@ -309,6 +337,12 @@ function PageActionMenu({ readOnly }: PageActionMenuProps) {
           {!readOnly && (
             <>
               <Menu.Divider />
+              <Menu.Item
+                leftSection={<IconClockHour4 size={16} />}
+                onClick={handleToggleTemporary}
+              >
+                {isTemporary ? t("Make permanent") : t("Make temporary")}
+              </Menu.Item>
               <Menu.Item
                 color={"red"}
                 leftSection={<IconTrash size={16} />}

apps/client/src/features/page/components/temporary-note-banner.tsx

@@ -0,0 +1,87 @@
+import { Button, Group, Paper, Text } from "@mantine/core";
+import { IconClockHour4 } from "@tabler/icons-react";
+import { Trans, useTranslation } from "react-i18next";
+import { useTimeAgo } from "@/hooks/use-time-ago.tsx";
+import { usePageQuery } from "@/features/page/queries/page-query.ts";
+import {
+  useToggleTemporaryMutation,
+  syncTemporaryExpiresInCache,
+} from "@/features/page-embed/queries/page-embed-query.ts";
+import { useGetSpaceBySlugQuery } from "@/features/space/queries/space-query.ts";
+import { useSpaceAbility } from "@/features/space/permissions/use-space-ability.ts";
+import {
+  SpaceCaslAction,
+  SpaceCaslSubject,
+} from "@/features/space/permissions/permissions.type.ts";
+
+type TemporaryNoteBannerProps = {
+  slugId: string;
+};
+
+/**
+ * Banner shown on an open temporary note ("structure or die"). Mirrors
+ * DeletedPageBanner: it reads the page from the shared query cache and offers
+ * the explicit rescue action — "Make permanent". Children ride along to trash
+ * with the note, which is noted in the copy.
+ */
+export function TemporaryNoteBanner({ slugId }: TemporaryNoteBannerProps) {
+  const { t } = useTranslation();
+  const { data: page } = usePageQuery({ pageId: slugId });
+  const { data: space } = useGetSpaceBySlugQuery(page?.space?.slug);
+  const spaceAbility = useSpaceAbility(space?.membership?.permissions);
+  const expiresTimeAgo = useTimeAgo(page?.temporaryExpiresAt);
+  const toggleTemporary = useToggleTemporaryMutation();
+
+  // Don't show on a note that is already in trash; the deleted-page banner
+  // owns that state.
+  if (!page?.temporaryExpiresAt || page?.deletedAt) return null;
+
+  const canEdit = spaceAbility.can(SpaceCaslAction.Edit, SpaceCaslSubject.Page);
+
+  const handleMakePermanent = async () => {
+    try {
+      const res = await toggleTemporary.mutateAsync({
+        pageId: page.id,
+        temporary: false,
+      });
+      syncTemporaryExpiresInCache(page, res.temporaryExpiresAt);
+    } catch {
+      // mutation surfaces the error via notifications
+    }
+  };
+
+  return (
+    <Paper radius="sm" mb="md" px="md" py="xs" bg="orange.0">
+      <Group justify="space-between" wrap="wrap" gap="sm">
+        <Group gap="xs" wrap="nowrap" style={{ flex: 1, minWidth: 0 }}>
+          <IconClockHour4
+            size={18}
+            stroke={1.5}
+            style={{
+              flexShrink: 0,
+              color: "var(--mantine-color-orange-7)",
+            }}
+          />
+          <Text size="sm">
+            <Trans
+              i18nKey="This temporary note moves to trash {{time}} (with its sub-pages) unless made permanent."
+              values={{ time: expiresTimeAgo }}
+            />
+          </Text>
+        </Group>
+        {canEdit && (
+          <Button
+            size="xs"
+            variant="light"
+            color="orange"
+            leftSection={<IconClockHour4 size={16} />}
+            onClick={handleMakePermanent}
+            loading={toggleTemporary.isPending}
+          >
+            {t("Make permanent")}
+          </Button>
+        )}
+      </Group>
+    </Paper>
+  );
+}

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

@@ -6,6 +6,7 @@ import { useDisclosure } from "@mantine/hooks";
 import { notifications } from "@mantine/notifications";
 import {
   IconArrowRight,
+  IconClockHour4,
   IconCopy,
   IconDotsVertical,
   IconFileExport,
@@ -30,7 +31,10 @@ import {
   useRemoveFavoriteMutation,
 } from "@/features/favorite/queries/favorite-query";
 
-import { useToggleTemplateMutation } from "@/features/page-embed/queries/page-embed-query";
+import {
+  useToggleTemplateMutation,
+  useToggleTemporaryMutation,
+} from "@/features/page-embed/queries/page-embed-query";
 import { treeDataAtom } from "@/features/page/tree/atoms/tree-data-atom.ts";
 import { treeModel } from "@/features/page/tree/model/tree-model";
 import { useTreeMutation } from "@/features/page/tree/hooks/use-tree-mutation.ts";
@@ -65,6 +69,8 @@ export function NodeMenu({ node, canEdit }: NodeMenuProps) {
   const isFavorited = favoriteIds.has(node.id);
   const toggleTemplate = useToggleTemplateMutation();
   const isTemplate = !!node.isTemplate;
+  const toggleTemporary = useToggleTemporaryMutation();
+  const isTemporary = !!node.temporaryExpiresAt;
 
   const handleToggleTemplate = async () => {
     const next = !isTemplate;
@@ -84,6 +90,29 @@ export function NodeMenu({ node, canEdit }: NodeMenuProps) {
     }
   };
 
+  const handleToggleTemporary = async () => {
+    const next = !isTemporary;
+    try {
+      const res = await toggleTemporary.mutateAsync({
+        pageId: node.id,
+        temporary: next,
+      });
+      // Reflect the new deadline locally so the icon/menu update immediately.
+      setData((prev) =>
+        treeModel.update(prev, node.id, {
+          temporaryExpiresAt: res.temporaryExpiresAt,
+        } as any),
+      );
+      notifications.show({
+        message: next
+          ? t("Note will move to trash unless made permanent")
+          : t("Note is now permanent"),
+      });
+    } catch {
+      // mutation surfaces the error via notifications
+    }
+  };
+
   const handleCopyLink = () => {
     const pageUrl =
       getAppUrl() + buildPageUrl(spaceSlug, node.slugId, node.name);
@@ -248,6 +277,17 @@ export function NodeMenu({ node, canEdit }: NodeMenuProps) {
                 {isTemplate ? t("Unset as template") : t("Make template")}
               </Menu.Item>
 
+              <Menu.Item
+                leftSection={<IconClockHour4 size={16} />}
+                onClick={(e) => {
+                  e.preventDefault();
+                  e.stopPropagation();
+                  handleToggleTemporary();
+                }}
+              >
+                {isTemporary ? t("Make permanent") : t("Make temporary")}
+              </Menu.Item>
+
               <Menu.Divider />
               <Menu.Item
                 c="red"

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

@@ -6,6 +6,7 @@ import { ActionIcon, rem, Tooltip } from "@mantine/core";
 import {
   IconChevronDown,
   IconChevronRight,
+  IconClockHour4,
   IconFileDescription,
   IconPlus,
   IconPointFilled,
@@ -191,6 +192,28 @@ export function SpaceTreeRow({
         </Tooltip>
       )}
 
+      {node.temporaryExpiresAt && (
+        <Tooltip
+          // Children ride along to trash with the note (recursive removePage).
+          label={t("Temporary note — moves to trash unless made permanent")}
+          withArrow
+        >
+          <IconClockHour4
+            size={14}
+            stroke={1.5}
+            // Same visual-only indicator pattern as the template icon, but
+            // orange to flag the impending death timer.
+            style={{
+              flexShrink: 0,
+              marginLeft: rem(4),
+              color: "var(--mantine-color-orange-6)",
+            }}
+            aria-label={t("Temporary note")}
+            role="img"
+          />
+        </Tooltip>
+      )}
+
       <div className={classes.actions}>
         <NodeMenu node={node} canEdit={canEdit} />
 

apps/client/src/features/page/tree/hooks/use-tree-mutation.ts

@@ -22,7 +22,10 @@ import { getSpaceUrl } from "@/lib/config.ts";
 
 export type UseTreeMutation = {
   handleMove: (sourceId: string, op: DropOp) => Promise<void>;
-  handleCreate: (parentId: string | null) => Promise<void>;
+  handleCreate: (
+    parentId: string | null,
+    opts?: { temporary?: boolean },
+  ) => Promise<void>;
   handleRename: (id: string, name: string) => Promise<void>;
   handleDelete: (id: string) => Promise<void>;
 };
@@ -119,9 +122,15 @@ export function useTreeMutation(spaceId: string): UseTreeMutation {
   );
 
   const handleCreate = useCallback(
-    async (parentId: string | null) => {
-      const payload: { spaceId: string; parentPageId?: string } = { spaceId };
+    async (parentId: string | null, opts?: { temporary?: boolean }) => {
+      const payload: {
+        spaceId: string;
+        parentPageId?: string;
+        temporary?: boolean;
+      } = { spaceId };
       if (parentId) payload.parentPageId = parentId;
+      // Ask the server to arm the death timer for a "temporary note".
+      if (opts?.temporary) payload.temporary = true;
 
       let createdPage: IPage;
       try {
@@ -138,6 +147,8 @@ export function useTreeMutation(spaceId: string): UseTreeMutation {
         spaceId: createdPage.spaceId,
         parentPageId: createdPage.parentPageId,
         hasChildren: false,
+        // Show the temporary-note icon immediately on optimistic insert.
+        temporaryExpiresAt: createdPage.temporaryExpiresAt,
         children: [],
       };
 

apps/client/src/features/page/tree/types.ts

@@ -9,5 +9,7 @@ export type SpaceTreeNode = {
   hasChildren: boolean;
   canEdit?: boolean;
   isTemplate?: boolean;
+  // Death-timer deadline. null/absent => permanent; ISO string => temporary note.
+  temporaryExpiresAt?: string | null;
   children: SpaceTreeNode[];
 };

apps/client/src/features/page/tree/utils/utils.ts

@@ -26,6 +26,7 @@ export function buildTree(pages: IPage[]): SpaceTreeNode[] {
       parentPageId: page.parentPageId,
       canEdit: page.canEdit ?? page.permissions?.canEdit,
       isTemplate: page.isTemplate,
+      temporaryExpiresAt: page.temporaryExpiresAt,
       children: [],
     };
   });

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

@@ -13,6 +13,10 @@ export interface IPage {
   workspaceId: string;
   isLocked: boolean;
   isTemplate?: boolean;
+  // Death-timer deadline. null/absent => permanent; ISO string => temporary note.
+  temporaryExpiresAt?: string | null;
+  // Create-only input flag: ask the server to arm the timer on a new page.
+  temporary?: boolean;
   lastUpdatedById: string;
   createdAt: Date;
   updatedAt: Date;

apps/client/src/features/space/components/sidebar/space-sidebar.tsx

@@ -13,6 +13,7 @@ import {
   IconEye,
   IconEyeOff,
   IconFileExport,
+  IconHourglass,
   IconPlus,
   IconSettings,
   IconStar,
@@ -71,6 +72,10 @@ export function SpaceSidebar() {
     handleCreate(null);
   }
 
+  function handleCreateTemporaryPage() {
+    handleCreate(null, { temporary: true });
+  }
+
   return (
     <>
       <div className={classes.navbar}>
@@ -111,16 +116,39 @@ export function SpaceSidebar() {
                 SpaceCaslAction.Manage,
                 SpaceCaslSubject.Page,
               ) && (
-                <Tooltip label={t("Create page")} withArrow position="right">
-                  <ActionIcon
-                    variant="default"
-                    size={18}
-                    onClick={handleCreatePage}
-                    aria-label={t("Create page")}
+                <>
+                  <Tooltip
+                    label={t("Create page")}
+                    withArrow
+                    position="right"
                   >
-                    <IconPlus />
-                  </ActionIcon>
-                </Tooltip>
+                    <ActionIcon
+                      variant="default"
+                      size={18}
+                      onClick={handleCreatePage}
+                      aria-label={t("Create page")}
+                    >
+                      <IconPlus />
+                    </ActionIcon>
+                  </Tooltip>
+
+                  {/* Standalone second button: a "temporary note" auto-moves to
+                      trash after the workspace lifetime unless made permanent. */}
+                  <Tooltip
+                    label={t("New temporary note")}
+                    withArrow
+                    position="right"
+                  >
+                    <ActionIcon
+                      variant="default"
+                      size={18}
+                      onClick={handleCreateTemporaryPage}
+                      aria-label={t("New temporary note")}
+                    >
+                      <IconHourglass />
+                    </ActionIcon>
+                  </Tooltip>
+                </>
               )}
             </Group>
           </Group>

apps/client/src/features/workspace/components/settings/components/temporary-note-settings.tsx

@@ -0,0 +1,86 @@
+import { useState } from "react";
+import { useAtom } from "jotai";
+import {
+  Button,
+  Group,
+  NumberInput,
+  Paper,
+  Stack,
+  Text,
+} from "@mantine/core";
+import { notifications } from "@mantine/notifications";
+import { useTranslation } from "react-i18next";
+import useUserRole from "@/hooks/use-user-role.tsx";
+import { workspaceAtom } from "@/features/user/atoms/current-user-atom.ts";
+import { updateWorkspace } from "@/features/workspace/services/workspace-service.ts";
+import { IWorkspace } from "@/features/workspace/types/workspace.types.ts";
+
+// Mirrors DEFAULT_TEMPORARY_NOTE_HOURS on the server. Shown when the workspace
+// has no explicit value configured yet.
+const DEFAULT_TEMPORARY_NOTE_HOURS = 24;
+
+/**
+ * Workspace-level editor for the temporary-note lifetime, in HOURS. The deadline
+ * is frozen per-note at creation, so changing this only affects notes created
+ * afterwards. `temporaryNoteHours` is a top-level workspace column (like
+ * trashRetentionDays), not a nested setting.
+ */
+export default function TemporaryNoteSettings() {
+  const { t } = useTranslation();
+  const [workspace, setWorkspace] = useAtom(workspaceAtom);
+  const { isAdmin } = useUserRole();
+  const [isLoading, setIsLoading] = useState(false);
+  const [value, setValue] = useState<number>(
+    workspace?.temporaryNoteHours ?? DEFAULT_TEMPORARY_NOTE_HOURS,
+  );
+
+  async function handleSave() {
+    if (!value || value < 1) return;
+    setIsLoading(true);
+    try {
+      const updated = await updateWorkspace({
+        temporaryNoteHours: value,
+      } as Partial<IWorkspace>);
+      setWorkspace({ ...updated, temporaryNoteHours: value });
+      notifications.show({ message: t("Updated successfully") });
+    } catch (err) {
+      notifications.show({
+        message:
+          (err as any)?.response?.data?.message ?? t("Failed to update data"),
+        color: "red",
+      });
+    } finally {
+      setIsLoading(false);
+    }
+  }
+
+  return (
+    <Stack mt="sm">
+      <Text fw={700} size="lg">
+        {t("Temporary notes")}
+      </Text>
+
+      <Paper withBorder radius="md" p="lg">
+        <Text size="xs" c="dimmed" mb="xs">
+          {t(
+            "A temporary note is automatically moved to trash after this many hours unless it is made permanent. The deadline is fixed when the note is created.",
+          )}
+        </Text>
+        <NumberInput
+          label={t("Temporary note lifetime (hours)")}
+          min={1}
+          allowDecimal={false}
+          value={value}
+          onChange={(v) => setValue(typeof v === "number" ? v : Number(v))}
+          disabled={!isAdmin || isLoading}
+          w={220}
+        />
+        <Group justify="flex-end" mt="md">
+          <Button onClick={handleSave} loading={isLoading} disabled={!isAdmin}>
+            {t("Save")}
+          </Button>
+        </Group>
+      </Paper>
+    </Stack>
+  );
+}

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

@@ -28,6 +28,8 @@ export interface IWorkspace {
   aiDictationStreaming?: boolean;
   aiPublicShareAssistant?: boolean;
   trashRetentionDays?: number;
+  // Default lifetime (HOURS) for new temporary notes; frozen per-note at creation.
+  temporaryNoteHours?: number;
   restrictApiToAdmins?: boolean;
   allowMemberTemplates?: boolean;
   isScimEnabled?: boolean;

apps/client/src/pages/settings/workspace/workspace-settings.tsx

@@ -3,6 +3,7 @@ import WorkspaceNameForm from "@/features/workspace/components/settings/componen
 import WorkspaceIcon from "@/features/workspace/components/settings/components/workspace-icon.tsx";
 import HtmlEmbedSettings from "@/features/workspace/components/settings/components/html-embed-settings.tsx";
 import TrackerSettings from "@/features/workspace/components/settings/components/tracker-settings.tsx";
+import TemporaryNoteSettings from "@/features/workspace/components/settings/components/temporary-note-settings.tsx";
 import { useTranslation } from "react-i18next";
 import { getAppName } from "@/lib/config.ts";
 import { Helmet } from "react-helmet-async";
@@ -19,6 +20,7 @@ export default function WorkspaceSettings() {
       <WorkspaceNameForm />
       <HtmlEmbedSettings />
       <TrackerSettings />
+      <TemporaryNoteSettings />
     </>
   );
 }

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

@@ -0,0 +1,44 @@
+import { AiChatController } from './ai-chat.controller';
+import type { User, Workspace } from '@docmost/db/types/entity.types';
+
+/**
+ * Wiring spec for the #191 `POST /ai-chat/bound-chat` endpoint. It must forward
+ * the requesting user + workspace + pageId to findLatestByPage and return the
+ * matched chat's id, or `{ chatId: null }` when there is none. The repo already
+ * scopes to the caller's OWN chats, so a foreign pageId simply yields no match
+ * (null) — no extra page-access check is needed. Exercised with hand-rolled
+ * mocks, no Nest graph and no DB.
+ */
+describe('AiChatController.boundChat', () => {
+  const user = { id: 'u1' } as User;
+  const workspace = { id: 'ws1' } as Workspace;
+
+  function makeController(chat: unknown) {
+    const aiChatRepo = {
+      findLatestByPage: jest.fn().mockResolvedValue(chat),
+    };
+    const controller = new AiChatController(
+      {} as never,
+      aiChatRepo as never,
+      {} as never,
+      {} as never,
+    );
+    return { controller, aiChatRepo };
+  }
+
+  it('returns the owned chat id and scopes the lookup to user + workspace + page', async () => {
+    const { controller, aiChatRepo } = makeController({
+      id: 'c1',
+      creatorId: 'u1',
+    });
+    const res = await controller.boundChat({ pageId: 'p1' }, user, workspace);
+    expect(aiChatRepo.findLatestByPage).toHaveBeenCalledWith('u1', 'ws1', 'p1');
+    expect(res).toEqual({ chatId: 'c1' });
+  });
+
+  it('returns { chatId: null } for a page with no owned chat (incl. foreign pageId)', async () => {
+    const { controller } = makeController(undefined);
+    const res = await controller.boundChat({ pageId: 'foreign' }, user, workspace);
+    expect(res).toEqual({ chatId: null });
+  });
+});

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

@@ -30,8 +30,10 @@ import { FileInterceptor } from '../../common/interceptors/file.interceptor';
 import { AiChatService, AiChatStreamBody } from './ai-chat.service';
 import { AiTranscriptionService } from './ai-transcription.service';
 import {
+  BoundChatDto,
   ChatIdDto,
   ExportChatDto,
+  GeneratePageTitleDto,
   GetChatMessagesDto,
   RenameChatDto,
 } from './dto/ai-chat.dto';
@@ -66,6 +68,28 @@ export class AiChatController {
     return this.aiChatRepo.findByCreator(user.id, workspace.id, pagination);
   }
 
+  /**
+   * Resolve the chat bound to a document for the requesting user: the most-recent
+   * non-deleted chat created on that page (ai_chats.page_id). Returns
+   * { chatId: null } when the page has no owned chat (-> a fresh chat). No page
+   * access check needed: only the caller's OWN chats are matched, so a foreign
+   * pageId reveals nothing.
+   */
+  @HttpCode(HttpStatus.OK)
+  @Post('bound-chat')
+  async boundChat(
+    @Body() dto: BoundChatDto,
+    @AuthUser() user: User,
+    @AuthWorkspace() workspace: Workspace,
+  ): Promise<{ chatId: string | null }> {
+    const chat = await this.aiChatRepo.findLatestByPage(
+      user.id,
+      workspace.id,
+      dto.pageId,
+    );
+    return { chatId: chat?.id ?? null };
+  }
+
   /** Fetch the messages of a chat (oldest first, paginated). */
   @HttpCode(HttpStatus.OK)
   @Post('messages')
@@ -316,6 +340,43 @@ export class AiChatController {
     return { text };
   }
 
+  /**
+   * Generate a page title from supplied note content (#199). One-shot,
+   * non-streaming. Gated by the workspace AI flag (reusing settings.ai.generative,
+   * the same flag that gates the on-page generative AI menu); returns { title }.
+   * The endpoint NEVER writes the page — the client applies the title via the
+   * existing /pages/update route (which enforces edit permission), so access
+   * checks are not duplicated here. Throttled per user via AI_CHAT_THROTTLER.
+   */
+  @HttpCode(HttpStatus.OK)
+  @UseGuards(JwtAuthGuard, UserThrottlerGuard)
+  @Throttle({ [AI_CHAT_THROTTLER]: { limit: 20, ttl: 60000 } })
+  @Post('generate-page-title')
+  async generatePageTitle(
+    @Body() dto: GeneratePageTitleDto,
+    @AuthWorkspace() workspace: Workspace,
+  ): Promise<{ title: string }> {
+    const settings = (workspace.settings ?? {}) as {
+      ai?: { generative?: boolean };
+    };
+    if (settings.ai?.generative !== true) {
+      throw new ForbiddenException('AI title generation is disabled');
+    }
+    try {
+      const title = await this.aiChatService.generatePageTitle(
+        workspace.id,
+        dto.content,
+      );
+      return { title };
+    } catch (err) {
+      // Preserve meaningful HTTP errors (e.g. AiNotConfiguredException -> 503).
+      if (err instanceof HttpException) throw err;
+      // Surface the real provider/transport reason instead of an opaque 500.
+      this.logger.error('AI title generation failed', err as Error);
+      throw new ServiceUnavailableException(describeProviderError(err));
+    }
+  }
+
   /**
    * Ensure the chat exists, belongs to this workspace, AND was created by the
    * requesting user (per-user isolation). Throws ForbiddenException otherwise.

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

@@ -0,0 +1,122 @@
+import {
+  ForbiddenException,
+  HttpException,
+  ServiceUnavailableException,
+} from '@nestjs/common';
+import { AiChatController } from './ai-chat.controller';
+import { cleanGeneratedTitle } from './ai-chat.service';
+import type { Workspace } from '@docmost/db/types/entity.types';
+
+/**
+ * Pure post-processing of a model-generated title (#199): trims, strips a single
+ * pair of surrounding quotes, drops a trailing period, and hard-caps the length.
+ */
+describe('cleanGeneratedTitle', () => {
+  it('trims surrounding whitespace', () => {
+    expect(cleanGeneratedTitle('  Hello world  ')).toBe('Hello world');
+  });
+
+  it('strips a single pair of surrounding double quotes', () => {
+    expect(cleanGeneratedTitle('"My note"')).toBe('My note');
+  });
+
+  it('strips surrounding single quotes', () => {
+    expect(cleanGeneratedTitle("'My note'")).toBe('My note');
+  });
+
+  it('drops a trailing period', () => {
+    expect(cleanGeneratedTitle('A complete sentence.')).toBe(
+      'A complete sentence',
+    );
+  });
+
+  it('caps the result at 255 characters (the page-title column bound)', () => {
+    expect(cleanGeneratedTitle('x'.repeat(400))).toHaveLength(255);
+  });
+
+  it('returns an empty string for blank/garbage input', () => {
+    expect(cleanGeneratedTitle('   ')).toBe('');
+    expect(cleanGeneratedTitle('""')).toBe('');
+  });
+});
+
+/**
+ * Wiring spec for the #199 `POST /ai-chat/generate-page-title` endpoint. It must:
+ * gate on settings.ai.generative (403 when off), delegate to the service when on,
+ * rethrow HttpExceptions verbatim (e.g. AiNotConfiguredException -> 503), and map
+ * any other provider/transport fault to a 503. Exercised by instantiating the
+ * controller with hand-rolled mocks — no Nest graph, no DB.
+ */
+describe('AiChatController.generatePageTitle', () => {
+  const enabledWorkspace = {
+    id: 'ws1',
+    settings: { ai: { generative: true } },
+  } as unknown as Workspace;
+
+  function makeController(generate: jest.Mock) {
+    const aiChatService = { generatePageTitle: generate };
+    const controller = new AiChatController(
+      aiChatService as never,
+      {} as never,
+      {} as never,
+      {} as never,
+    );
+    return { controller, aiChatService };
+  }
+
+  it('forbids when the generative AI flag is off', async () => {
+    const generate = jest.fn();
+    const { controller } = makeController(generate);
+    const disabled = { id: 'ws1', settings: {} } as unknown as Workspace;
+    await expect(
+      controller.generatePageTitle({ content: 'body' }, disabled),
+    ).rejects.toBeInstanceOf(ForbiddenException);
+    expect(generate).not.toHaveBeenCalled();
+  });
+
+  it('forbids when settings.ai.generative is anything but exactly true', async () => {
+    const generate = jest.fn();
+    const { controller } = makeController(generate);
+    const ws = {
+      id: 'ws1',
+      settings: { ai: { generative: 'yes' } },
+    } as unknown as Workspace;
+    await expect(
+      controller.generatePageTitle({ content: 'body' }, ws),
+    ).rejects.toBeInstanceOf(ForbiddenException);
+  });
+
+  it('returns { title } from the service when enabled', async () => {
+    const generate = jest.fn().mockResolvedValue('Generated Title');
+    const { controller } = makeController(generate);
+    const res = await controller.generatePageTitle(
+      { content: 'some markdown body' },
+      enabledWorkspace,
+    );
+    expect(generate).toHaveBeenCalledWith('ws1', 'some markdown body');
+    expect(res).toEqual({ title: 'Generated Title' });
+  });
+
+  it('rethrows an HttpException from the service verbatim (e.g. 503 not configured)', async () => {
+    const notConfigured = new ServiceUnavailableException('AI not configured');
+    const generate = jest.fn().mockRejectedValue(notConfigured);
+    const { controller } = makeController(generate);
+    await expect(
+      controller.generatePageTitle({ content: 'body' }, enabledWorkspace),
+    ).rejects.toBe(notConfigured);
+  });
+
+  it('maps a non-HTTP provider error to a 503', async () => {
+    const generate = jest.fn().mockRejectedValue(new Error('socket hang up'));
+    const { controller } = makeController(generate);
+    // Silence the expected error log.
+    jest
+      .spyOn((controller as unknown as { logger: { error: () => void } }).logger, 'error')
+      .mockImplementation(() => undefined);
+    const err = await controller
+      .generatePageTitle({ content: 'body' }, enabledWorkspace)
+      .catch((e) => e);
+    expect(err).toBeInstanceOf(ServiceUnavailableException);
+    expect(err).toBeInstanceOf(HttpException);
+  });
+});

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

@@ -241,7 +241,7 @@ describe('prepareAgentStep', () => {
  * write path. It runs identically for the upfront insert (empty steps,
  * 'streaming'), every per-step update, and the terminal finalize — so a future
  * background worker can call the same function. These tests pin the four status
- * shapes and the `metadata.parts` shape that rowToUiMessage/findRecent depend on
+ * shapes and the `metadata.parts` shape that rowToUiMessage/findAllByChat depend on
  * (per-step text + tool parts via assistantParts, in-progress text appended).
  */
 describe('flushAssistant', () => {

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

@@ -75,6 +75,18 @@ export function prepareAgentStep(
 
 export { MAX_AGENT_STEPS, FINAL_STEP_INSTRUCTION };
 
+// Pure, unit-testable post-processing for a model-generated title (#199): trim
+// whitespace, strip a single pair of surrounding quotes the model often adds,
+// drop a trailing period, and hard-cap the length to the page-title column.
+export function cleanGeneratedTitle(text: string): string {
+  return text
+    .trim()
+    .replace(/^["']|["']$/g, '')
+    .replace(/\.+$/, '')
+    .trim()
+    .slice(0, 255);
+}
+
 /**
  * Pure, unit-testable (#198): decide whether THIS turn is an interrupt-resume,
  * i.e. it directly follows a user interruption of the previous (still-partial)
@@ -353,12 +365,14 @@ export class AiChatService implements OnModuleInit {
 
     // Rebuild the conversation from persisted history (not the client payload),
     // so the model always sees the authoritative server-side transcript. Load
-    // the most RECENT tail (oldest -> newest) so chats longer than one page do
-    // not drop recent turns (incl. the user message just inserted above).
-    const history = await this.aiChatMessageRepo.findRecent(
+    // the FULL history in chronological order (oldest -> newest, incl. the user
+    // message just inserted above) so NO turns are dropped — there is no
+    // recent-tail window anymore. `findAllByChat` keeps a 5000-row memory-safety
+    // backstop (on overflow it keeps the NEWEST rows and logs a warning); that
+    // is a safety net far above any realistic chat, not a conversational limit.
+    const history = await this.aiChatMessageRepo.findAllByChat(
       chatId,
       workspace.id,
-      50,
     );
     const uiMessages = history.map(rowToUiMessage);
     // convertToModelMessages is async in ai@6.0.134 (returns Promise<ModelMessage[]>).
@@ -834,6 +848,27 @@ export class AiChatService implements OnModuleInit {
     }
   }
 
+  /**
+   * One-shot page-title generation from a note's content (#199). No tools, no
+   * streaming — mirrors generateTitle() but for an arbitrary note body supplied
+   * by the client, and RETURNS the title instead of writing it (the client
+   * applies it via the existing /pages/update route, which enforces edit
+   * permission). The content is truncated to keep the prompt cheap and within
+   * context limits. Throws AiNotConfiguredException (503) if AI is unconfigured.
+   */
+  async generatePageTitle(workspaceId: string, content: string): Promise<string> {
+    const model = await this.ai.getChatModel(workspaceId);
+    const { text } = await generateText({
+      model,
+      system:
+        'You generate a single concise, descriptive title for a note based on ' +
+        'its content. Reply with the title only — at most 8 words, no quotes, ' +
+        'no trailing punctuation, written in the same language as the note.',
+      prompt: content.slice(0, 8000),
+    });
+    return cleanGeneratedTitle(text);
+  }
+
   /**
    * Cheap, non-blocking title generation from the first user message. Uses
    * generateText (async) and writes the result back onto the chat row. Any
@@ -1256,7 +1291,7 @@ export async function applyFinalize(
  *
  * `metadata.parts` is built by assistantParts over the finished steps, then the
  * in-progress text appended as a trailing text part, so rowToUiMessage /
- * findRecent keep replaying the turn unchanged. `metadata.finishReason`,
+ * findAllByChat keep replaying the turn unchanged. `metadata.finishReason`,
  * `metadata.error`, `metadata.usage`, `metadata.contextTokens` and
  * `metadata.maxContextTokens` are attached only when provided/relevant, matching
  * the pre-#183 onFinish/onError records.

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

@@ -17,6 +17,16 @@ export class RenameChatDto {
   title: string;
 }
 
+/** One-shot page-title generation from note content (#199). */
+export class GeneratePageTitleDto {
+  // Note body as markdown/plain text. Capped to bound the prompt cost and
+  // reject abusive payloads; the service truncates again before the model call.
+  @IsString()
+  @MinLength(1)
+  @MaxLength(20000)
+  content: string;
+}
+
 /** Optional chat id for listing messages of a specific chat. */
 export class GetChatMessagesDto {
   @IsString()
@@ -27,6 +37,12 @@ export class GetChatMessagesDto {
   cursor?: string;
 }
 
+/** Resolve the chat bound to a document (the page's most-recent owned chat). */
+export class BoundChatDto {
+  @IsString()
+  pageId: string;
+}
+
 /** Export a chat to Markdown (#183). `lang` localizes the few fixed
  *  role/tool-action labels; defaults to English server-side. */
 export class ExportChatDto {

apps/server/src/core/page/constants/temporary-note.constants.ts

@@ -0,0 +1,5 @@
+// Default lifetime for a temporary note, in HOURS, used when the workspace has
+// no `temporaryNoteHours` configured (NULL). Mirrors the trash-cleanup
+// DEFAULT_RETENTION_DAYS fallback. After this many hours a temporary note is
+// auto-moved to trash unless it was made permanent first.
+export const DEFAULT_TEMPORARY_NOTE_HOURS = 24;

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

@@ -1,4 +1,5 @@
 import {
+  IsBoolean,
   IsIn,
   IsOptional,
   IsString,
@@ -32,4 +33,10 @@ export class CreatePageDto {
   @Transform(({ value }) => value?.toLowerCase() ?? 'json')
   @IsIn(['json', 'markdown', 'html'])
   format?: ContentFormat;
+
+  // When true, create the page as a temporary note: arm its death timer
+  // (now + workspace temporaryNoteHours) at creation.
+  @IsOptional()
+  @IsBoolean()
+  temporary?: boolean;
 }

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

@@ -3,6 +3,7 @@ import { PageService } from './services/page.service';
 import { PageController } from './page.controller';
 import { PageHistoryService } from './services/page-history.service';
 import { TrashCleanupService } from './services/trash-cleanup.service';
+import { TemporaryNoteCleanupService } from './services/temporary-note-cleanup.service';
 import { BacklinkService } from './services/backlink.service';
 import { StorageModule } from '../../integrations/storage/storage.module';
 import { CollaborationModule } from '../../collaboration/collaboration.module';
@@ -16,6 +17,7 @@ import { LabelModule } from '../label/label.module';
     PageService,
     PageHistoryService,
     TrashCleanupService,
+    TemporaryNoteCleanupService,
     BacklinkService,
   ],
   exports: [PageService, PageHistoryService],

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

@@ -2,6 +2,7 @@ import { BadRequestException } from '@nestjs/common';
 import { PageService } from './page.service';
 import { MovePageDto } from '../dto/move-page.dto';
 import { Page } from '@docmost/db/types/entity.types';
+import { DEFAULT_TEMPORARY_NOTE_HOURS } from '../constants/temporary-note.constants';
 
 // Direct instantiation with stub deps. The Test.createTestingModule form failed
 // to resolve the @InjectKysely()/@InjectQueue() tokens at compile(), and this
@@ -420,4 +421,79 @@ describe('PageService', () => {
       });
     });
   });
+
+  describe('create() temporary deadline (#201)', () => {
+    // db stub for the workspaces.temporaryNoteHours lookup:
+    // selectFrom('workspaces').select(['temporaryNoteHours']).where(...).executeTakeFirst()
+    const makeDb = (workspaceRow: any) => {
+      const builder: any = {
+        selectFrom: jest.fn(() => builder),
+        select: jest.fn(() => builder),
+        where: jest.fn(() => builder),
+        executeTakeFirst: jest.fn().mockResolvedValue(workspaceRow),
+      };
+      return builder;
+    };
+
+    const makeGeneralQueue = () =>
+      ({ add: jest.fn().mockReturnValue({ catch: jest.fn() }) }) as any;
+
+    const run = async (dto: any, workspaceRow: any) => {
+      const pageRepo = {
+        insertPage: jest.fn().mockResolvedValue({ id: 'p1' }),
+      };
+      const db = makeDb(workspaceRow);
+      const svc = new PageService(
+        pageRepo as any, // pageRepo
+        {} as any, // pagePermissionRepo
+        {} as any, // attachmentRepo
+        db as any, // db
+        {} as any, // storageService
+        {} as any, // attachmentQueue
+        {} as any, // aiQueue
+        makeGeneralQueue(), // generalQueue
+        {} as any, // eventEmitter
+        {} as any, // collaborationGateway
+        {} as any, // watcherService
+        {} as any, // transclusionService
+      );
+      // nextPagePosition runs a real db query; stub it out.
+      jest.spyOn(svc, 'nextPagePosition').mockResolvedValue('a0' as any);
+      await svc.create('u1', 'w1', dto, undefined);
+      return { payload: pageRepo.insertPage.mock.calls[0][0], db };
+    };
+
+    afterEach(() => jest.useRealTimers());
+
+    it('freezes temporaryExpiresAt at now + workspace hours when temporary', async () => {
+      jest.useFakeTimers().setSystemTime(new Date('2026-06-26T00:00:00.000Z'));
+      const { payload } = await run(
+        { title: 't', spaceId: 's1', temporary: true },
+        { temporaryNoteHours: 5 },
+      );
+      expect(payload.temporaryExpiresAt).toEqual(
+        new Date(Date.now() + 5 * 60 * 60 * 1000),
+      );
+    });
+
+    it('falls back to DEFAULT_TEMPORARY_NOTE_HOURS when the workspace hours are null', async () => {
+      jest.useFakeTimers().setSystemTime(new Date('2026-06-26T00:00:00.000Z'));
+      const { payload } = await run(
+        { title: 't', spaceId: 's1', temporary: true },
+        { temporaryNoteHours: null },
+      );
+      expect(payload.temporaryExpiresAt).toEqual(
+        new Date(Date.now() + DEFAULT_TEMPORARY_NOTE_HOURS * 60 * 60 * 1000),
+      );
+    });
+
+    it('leaves temporaryExpiresAt undefined and skips the workspace lookup for a non-temporary page', async () => {
+      const { payload, db } = await run(
+        { title: 't', spaceId: 's1' },
+        { temporaryNoteHours: 5 },
+      );
+      expect(payload.temporaryExpiresAt).toBeUndefined();
+      expect(db.selectFrom).not.toHaveBeenCalled();
+    });
+  });
 });

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

@@ -61,6 +61,7 @@ import {
   AuthProvenanceData,
   agentSourceFields,
 } from '../../../common/decorators/auth-provenance.decorator';
+import { DEFAULT_TEMPORARY_NOTE_HOURS } from '../constants/temporary-note.constants';
 
 // Hard upper bound on how deep the recursive page-tree CTEs (ancestor /
 // descendant traversals) may walk. Real page trees are only a handful of levels
@@ -140,6 +141,20 @@ export class PageService {
       parentPageId = parentPage.id;
     }
 
+    // Freeze the death timer here so later changes to the workspace setting
+    // never reschedule existing temporary notes. NULL => permanent page.
+    let temporaryExpiresAt: Date | undefined;
+    if (createPageDto.temporary) {
+      const workspace = await this.db
+        .selectFrom('workspaces')
+        .select(['temporaryNoteHours'])
+        .where('id', '=', workspaceId)
+        .executeTakeFirst();
+      const hours =
+        workspace?.temporaryNoteHours ?? DEFAULT_TEMPORARY_NOTE_HOURS;
+      temporaryExpiresAt = new Date(Date.now() + hours * 60 * 60 * 1000);
+    }
+
     let content = undefined;
     let textContent = undefined;
     let ydoc = undefined;
@@ -172,6 +187,7 @@ export class PageService {
       // (creatorId/lastUpdatedById); these only annotate the source. A normal
       // user request leaves the column default ('user').
       ...agentSourceFields(provenance, 'lastUpdatedSource', 'lastUpdatedAiChatId'),
+      temporaryExpiresAt,
       content,
       textContent,
       ydoc,
@@ -356,6 +372,7 @@ export class PageService {
         'spaceId',
         'creatorId',
         'isTemplate',
+        'temporaryExpiresAt',
         'deletedAt',
       ])
       .select((eb) => this.pageRepo.withHasChildren(eb))

apps/server/src/core/page/services/spec/temporary-note-cleanup.service.spec.ts

@@ -0,0 +1,154 @@
+import { TemporaryNoteCleanupService } from '../temporary-note-cleanup.service';
+
+/**
+ * Chainable Kysely stub that records every `.where(...)` call so the test can
+ * assert the sweep only selects armed, expired, not-yet-trashed notes. The
+ * terminal `.execute()` resolves the configured expired rows (the batch SELECT);
+ * `.executeTakeFirst()` resolves the per-row deadline re-read done just before
+ * each `removePage`. By default the re-read reports the note as still armed and
+ * still expired (epoch deadline < now), so the sweep proceeds to delete it;
+ * tests override `reReadFirst` to simulate a concurrent "Make permanent".
+ */
+function makeDbStub(expiredRows: any[]) {
+  const whereCalls: any[][] = [];
+  const reReadFirst = jest
+    .fn()
+    .mockResolvedValue({ temporaryExpiresAt: new Date(0), deletedAt: null });
+  const builder: any = {
+    selectFrom: jest.fn(() => builder),
+    select: jest.fn(() => builder),
+    where: jest.fn((...args: any[]) => {
+      whereCalls.push(args);
+      return builder;
+    }),
+    limit: jest.fn(() => builder),
+    execute: jest.fn().mockResolvedValue(expiredRows),
+    executeTakeFirst: reReadFirst,
+  };
+  return { builder, whereCalls, reReadFirst };
+}
+
+describe('TemporaryNoteCleanupService.sweepExpiredTemporaryNotes', () => {
+  it('selects only armed, expired, not-yet-trashed notes', async () => {
+    const { builder, whereCalls } = makeDbStub([]);
+    const pageRepo = { removePage: jest.fn() } as any;
+    const service = new TemporaryNoteCleanupService(builder, pageRepo);
+
+    await service.sweepExpiredTemporaryNotes();
+
+    // temporaryExpiresAt IS NOT NULL, temporaryExpiresAt < now, deletedAt IS NULL
+    const cols = whereCalls.map((c) => c[0]);
+    const ops = whereCalls.map((c) => c[1]);
+    expect(cols).toEqual([
+      'temporaryExpiresAt',
+      'temporaryExpiresAt',
+      'deletedAt',
+    ]);
+    expect(ops).toEqual(['is not', '<', 'is']);
+    // last operand is the trash filter -> null
+    expect(whereCalls[2][2]).toBeNull();
+    // The batch SELECT is capped so a large backlog is not pulled at once.
+    expect(builder.limit).toHaveBeenCalledTimes(1);
+    expect(builder.limit.mock.calls[0][0]).toBeGreaterThan(0);
+  });
+
+  it('soft-deletes each expired note via removePage, attributed to its creator', async () => {
+    const expired = [
+      { id: 'p1', creatorId: 'u1', workspaceId: 'w1' },
+      { id: 'p2', creatorId: 'u2', workspaceId: 'w1' },
+    ];
+    const { builder } = makeDbStub(expired);
+    const pageRepo = { removePage: jest.fn().mockResolvedValue(undefined) } as any;
+    const service = new TemporaryNoteCleanupService(builder, pageRepo);
+
+    await service.sweepExpiredTemporaryNotes();
+
+    expect(pageRepo.removePage).toHaveBeenCalledTimes(2);
+    expect(pageRepo.removePage).toHaveBeenNthCalledWith(1, 'p1', 'u1', 'w1');
+    expect(pageRepo.removePage).toHaveBeenNthCalledWith(2, 'p2', 'u2', 'w1');
+  });
+
+  it('continues past a failing note (one bad removePage does not abort the sweep)', async () => {
+    const expired = [
+      { id: 'bad', creatorId: 'u1', workspaceId: 'w1' },
+      { id: 'good', creatorId: 'u2', workspaceId: 'w1' },
+    ];
+    const { builder } = makeDbStub(expired);
+    const pageRepo = {
+      removePage: jest
+        .fn()
+        .mockRejectedValueOnce(new Error('boom'))
+        .mockResolvedValueOnce(undefined),
+    } as any;
+    const service = new TemporaryNoteCleanupService(builder, pageRepo);
+
+    await expect(
+      service.sweepExpiredTemporaryNotes(),
+    ).resolves.toBeUndefined();
+    expect(pageRepo.removePage).toHaveBeenCalledTimes(2);
+    expect(pageRepo.removePage).toHaveBeenNthCalledWith(2, 'good', 'u2', 'w1');
+  });
+
+  it('does NOT trash a note made permanent in the race window', async () => {
+    // The batch SELECT saw the note as expired, but before its turn in the loop
+    // the user clicked "Make permanent" (temporary_expires_at -> null). The
+    // deadline re-read must catch this and skip the delete so the keep wins.
+    const expired = [{ id: 'p1', creatorId: 'u1', workspaceId: 'w1' }];
+    const { builder, reReadFirst } = makeDbStub(expired);
+    reReadFirst.mockResolvedValueOnce({
+      temporaryExpiresAt: null,
+      deletedAt: null,
+    });
+    const pageRepo = { removePage: jest.fn() } as any;
+    const service = new TemporaryNoteCleanupService(builder, pageRepo);
+
+    await service.sweepExpiredTemporaryNotes();
+
+    expect(reReadFirst).toHaveBeenCalledTimes(1);
+    expect(pageRepo.removePage).not.toHaveBeenCalled();
+  });
+
+  it('skips a note already trashed since the batch SELECT', async () => {
+    const expired = [{ id: 'p1', creatorId: 'u1', workspaceId: 'w1' }];
+    const { builder, reReadFirst } = makeDbStub(expired);
+    reReadFirst.mockResolvedValueOnce({
+      temporaryExpiresAt: new Date(0),
+      deletedAt: new Date(),
+    });
+    const pageRepo = { removePage: jest.fn() } as any;
+    const service = new TemporaryNoteCleanupService(builder, pageRepo);
+
+    await service.sweepExpiredTemporaryNotes();
+
+    expect(pageRepo.removePage).not.toHaveBeenCalled();
+  });
+
+  it('does NOT trash a note re-armed to a future deadline in the race window', async () => {
+    // The batch SELECT saw the note as expired, but before its turn in the loop
+    // the user disarmed it and re-armed it to a fresh, still-future deadline
+    // (temporary_expires_at -> now + 1h). The deadline re-read must catch that
+    // the note is no longer expired and skip the delete so the keep wins.
+    const expired = [{ id: 'p1', creatorId: 'u1', workspaceId: 'w1' }];
+    const { builder, reReadFirst } = makeDbStub(expired);
+    reReadFirst.mockResolvedValueOnce({
+      temporaryExpiresAt: new Date(Date.now() + 60 * 60 * 1000),
+      deletedAt: null,
+    });
+    const pageRepo = { removePage: jest.fn() } as any;
+    const service = new TemporaryNoteCleanupService(builder, pageRepo);
+
+    await service.sweepExpiredTemporaryNotes();
+
+    expect(reReadFirst).toHaveBeenCalledTimes(1);
+    expect(pageRepo.removePage).not.toHaveBeenCalled();
+  });
+
+  it('does nothing when no notes are expired', async () => {
+    const { builder } = makeDbStub([]);
+    const pageRepo = { removePage: jest.fn() } as any;
+    const service = new TemporaryNoteCleanupService(builder, pageRepo);
+
+    await service.sweepExpiredTemporaryNotes();
+    expect(pageRepo.removePage).not.toHaveBeenCalled();
+  });
+});

apps/server/src/core/page/services/temporary-note-cleanup.service.ts

@@ -0,0 +1,105 @@
+import { Injectable, Logger } from '@nestjs/common';
+import { Interval } from '@nestjs/schedule';
+import { InjectKysely } from 'nestjs-kysely';
+import { KyselyDB } from '@docmost/db/types/kysely.types';
+import { PageRepo } from '@docmost/db/repos/page/page.repo';
+
+/**
+ * Background sweeper for temporary notes ("structure or die"). A note whose
+ * frozen deadline (`pages.temporary_expires_at`) has passed is auto-moved to
+ * trash via the exact same soft-delete path as a manual delete. Modelled on
+ * TrashCleanupService; `@nestjs/schedule` is already enabled globally.
+ */
+@Injectable()
+export class TemporaryNoteCleanupService {
+  private readonly logger = new Logger(TemporaryNoteCleanupService.name);
+
+  // Cap a single sweep so a large backlog (e.g. many notes created during
+  // downtime under a short lifetime) is not loaded into memory at once. The
+  // remainder is drained on the next hourly run; sub-hour overshoot is fine.
+  private static readonly SWEEP_BATCH_LIMIT = 500;
+
+  constructor(
+    @InjectKysely() private readonly db: KyselyDB,
+    private readonly pageRepo: PageRepo,
+  ) {}
+
+  // Hourly granularity: lifetimes are configured in hours, so a sub-hour
+  // overshoot past the deadline is acceptable.
+  @Interval('temporary-note-cleanup', 60 * 60 * 1000)
+  async sweepExpiredTemporaryNotes() {
+    try {
+      const now = new Date();
+
+      const expired = await this.db
+        .selectFrom('pages')
+        .select(['id', 'creatorId', 'workspaceId'])
+        .where('temporaryExpiresAt', 'is not', null)
+        .where('temporaryExpiresAt', '<', now)
+        .where('deletedAt', 'is', null) // not already in trash
+        .limit(TemporaryNoteCleanupService.SWEEP_BATCH_LIMIT)
+        .execute();
+
+      let trashed = 0;
+      for (const page of expired) {
+        try {
+          // Re-check the deadline at deletion time. The SELECT above is not
+          // transactional, so a user may click "Make permanent"
+          // (toggleTemporary sets temporary_expires_at = null) in the window
+          // between the SELECT and this per-row removePage. removePage deletes
+          // by id with only a `deletedAt IS NULL` filter and never re-reads the
+          // deadline, so without this guard a concurrently-kept note would
+          // still be trashed. Re-read the row and skip it unless it is still
+          // armed AND still expired, so a concurrent make-permanent wins.
+          const current = await this.db
+            .selectFrom('pages')
+            .select(['temporaryExpiresAt', 'deletedAt'])
+            .where('id', '=', page.id)
+            .executeTakeFirst();
+
+          if (
+            !current ||
+            current.deletedAt !== null ||
+            current.temporaryExpiresAt === null ||
+            new Date(current.temporaryExpiresAt) >= now
+          ) {
+            // Made permanent, already trashed, or no longer expired since the
+            // SELECT — leave it alone.
+            continue;
+          }
+
+          // Reuse the exact soft-delete path: recursive over children, removes
+          // shares in a transaction, and emits PAGE_SOFT_DELETED (tree
+          // invalidation + watcher notifications). Attribute the automatic
+          // deletion to the note's creator (no schema change). Both the SELECT
+          // above and removePage filter `deletedAt IS NULL`, so a double sweep
+          // is idempotent.
+          await this.pageRepo.removePage(
+            page.id,
+            // creatorId is set on every created page; a temporary note always
+            // has one. Cast to satisfy the non-null deletedById parameter.
+            page.creatorId as string,
+            page.workspaceId,
+          );
+          trashed++;
+        } catch (error) {
+          this.logger.error(
+            `Failed to trash expired temporary note ${page.id}`,
+            error instanceof Error ? error.stack : undefined,
+          );
+        }
+      }
+
+      if (trashed > 0) {
+        this.logger.debug(
+          `Temporary-note cleanup completed: ${trashed} notes trashed`,
+        );
+      }
+    } catch (error) {
+      this.logger.error(
+        'Temporary-note cleanup job failed',
+        error instanceof Error ? error.stack : undefined,
+      );
+    }
+  }
+}

apps/server/src/core/page/transclusion/dto/toggle-temporary.dto.ts

@@ -0,0 +1,15 @@
+import { IsBoolean, IsOptional, IsUUID } from 'class-validator';
+
+export class ToggleTemporaryDto {
+  @IsUUID()
+  pageId!: string;
+
+  /**
+   * When omitted, the temporary state is toggled relative to its current value.
+   * true  -> arm the timer (now + workspace temporaryNoteHours);
+   * false -> clear it (make permanent — "structure and survive").
+   */
+  @IsOptional()
+  @IsBoolean()
+  temporary?: boolean;
+}

apps/server/src/core/page/transclusion/page-template.controller.ts

@@ -16,8 +16,12 @@ import { TemplateLookupDto } from './dto/template-lookup.dto';
 import { PageRepo } from '@docmost/db/repos/page/page.repo';
 import { PageAccessService } from '../page-access/page-access.service';
 import { ToggleTemplateDto } from './dto/toggle-template.dto';
+import { ToggleTemporaryDto } from './dto/toggle-temporary.dto';
 import { UserThrottlerGuard } from '../../../integrations/throttle/user-throttler.guard';
 import { PAGE_TEMPLATE_THROTTLER } from '../../../integrations/throttle/throttler-names';
+import { InjectKysely } from 'nestjs-kysely';
+import { KyselyDB } from '@docmost/db/types/kysely.types';
+import { DEFAULT_TEMPORARY_NOTE_HOURS } from '../constants/temporary-note.constants';
 
 @UseGuards(JwtAuthGuard)
 @Controller('pages')
@@ -26,6 +30,7 @@ export class PageTemplateController {
     private readonly transclusionService: TransclusionService,
     private readonly pageRepo: PageRepo,
     private readonly pageAccessService: PageAccessService,
+    @InjectKysely() private readonly db: KyselyDB,
   ) {}
 
   /**
@@ -82,4 +87,54 @@ export class PageTemplateController {
 
     return { pageId: page.id, isTemplate };
   }
+
+  /**
+   * Arm or disarm the "death timer" on a page (`pages.temporary_expires_at`).
+   * Mirror of toggle-template: requires Edit on the page/space (CASL enforced in
+   * `validateCanEdit`). Arming freezes the deadline at now + the workspace's
+   * temporaryNoteHours; disarming ("Make permanent") clears it. Same workspace
+   * defense-in-depth as toggle-template (NotFound, never Forbidden, on mismatch).
+   */
+  @UseGuards(JwtAuthGuard, UserThrottlerGuard)
+  @Throttle({ [PAGE_TEMPLATE_THROTTLER]: { limit: 30, ttl: 60000 } })
+  @HttpCode(HttpStatus.OK)
+  @Post('toggle-temporary')
+  async toggleTemporary(
+    @Body() dto: ToggleTemporaryDto,
+    @AuthUser() user: User,
+  ) {
+    const page = await this.pageRepo.findById(dto.pageId);
+    if (!page || page.deletedAt) {
+      throw new NotFoundException('Page not found');
+    }
+
+    if (page.workspaceId !== user.workspaceId) {
+      // Defense-in-depth: never act on a page outside the caller's workspace.
+      // Use NotFound (not Forbidden) to avoid leaking cross-workspace existence.
+      throw new NotFoundException('Page not found');
+    }
+
+    await this.pageAccessService.validateCanEdit(page, user);
+
+    const makeTemporary =
+      typeof dto.temporary === 'boolean'
+        ? dto.temporary
+        : page.temporaryExpiresAt == null;
+
+    let temporaryExpiresAt: Date | null = null;
+    if (makeTemporary) {
+      const workspace = await this.db
+        .selectFrom('workspaces')
+        .select(['temporaryNoteHours'])
+        .where('id', '=', user.workspaceId)
+        .executeTakeFirst();
+      const hours =
+        workspace?.temporaryNoteHours ?? DEFAULT_TEMPORARY_NOTE_HOURS;
+      temporaryExpiresAt = new Date(Date.now() + hours * 60 * 60 * 1000);
+    }
+
+    await this.pageRepo.updatePage({ temporaryExpiresAt }, page.id);
+
+    return { pageId: page.id, temporaryExpiresAt };
+  }
 }

apps/server/src/core/page/transclusion/spec/page-template.controller.spec.ts

@@ -9,6 +9,7 @@ import { PageRepo } from '@docmost/db/repos/page/page.repo';
 import { PageAccessService } from '../../page-access/page-access.service';
 import { JwtAuthGuard } from '../../../../common/guards/jwt-auth.guard';
 import { UserThrottlerGuard } from '../../../../integrations/throttle/user-throttler.guard';
+import { KYSELY_MODULE_CONNECTION_TOKEN } from 'nestjs-kysely';
 
 describe('PageTemplateController.toggleTemplate', () => {
   let controller: PageTemplateController;
@@ -40,6 +41,8 @@ describe('PageTemplateController.toggleTemplate', () => {
         { provide: TransclusionService, useValue: transclusionService },
         { provide: PageRepo, useValue: pageRepo },
         { provide: PageAccessService, useValue: pageAccessService },
+        // toggleTemporary reads the workspace lifetime; toggleTemplate ignores it.
+        { provide: KYSELY_MODULE_CONNECTION_TOKEN(), useValue: {} },
       ],
     })
       .overrideGuard(JwtAuthGuard)

apps/server/src/core/page/transclusion/spec/page-temporary.controller.spec.ts

@@ -0,0 +1,220 @@
+import { Test } from '@nestjs/testing';
+import { ForbiddenException, NotFoundException } from '@nestjs/common';
+import { plainToInstance } from 'class-transformer';
+import { validate } from 'class-validator';
+import { KYSELY_MODULE_CONNECTION_TOKEN } from 'nestjs-kysely';
+import { PageTemplateController } from '../page-template.controller';
+import { TransclusionService } from '../transclusion.service';
+import { ToggleTemporaryDto } from '../dto/toggle-temporary.dto';
+import { PageRepo } from '@docmost/db/repos/page/page.repo';
+import { PageAccessService } from '../../page-access/page-access.service';
+import { JwtAuthGuard } from '../../../../common/guards/jwt-auth.guard';
+import { UserThrottlerGuard } from '../../../../integrations/throttle/user-throttler.guard';
+import { DEFAULT_TEMPORARY_NOTE_HOURS } from '../../constants/temporary-note.constants';
+
+/**
+ * Minimal chainable Kysely stub: every builder method returns `this`, and the
+ * terminal `executeTakeFirst` resolves the configured workspace row.
+ */
+function makeDbStub(workspaceRow: { temporaryNoteHours: number | null } | undefined) {
+  const builder: any = {
+    selectFrom: () => builder,
+    select: () => builder,
+    where: () => builder,
+    executeTakeFirst: jest.fn().mockResolvedValue(workspaceRow),
+  };
+  return builder;
+}
+
+describe('PageTemplateController.toggleTemporary', () => {
+  let controller: PageTemplateController;
+  let pageRepo: { findById: jest.Mock; updatePage: jest.Mock };
+  let pageAccessService: { validateCanEdit: jest.Mock };
+
+  const user = { id: 'u1', workspaceId: 'w1' } as any;
+
+  async function buildController(
+    page: any,
+    workspaceRow: { temporaryNoteHours: number | null } | undefined = {
+      temporaryNoteHours: null,
+    },
+  ) {
+    pageRepo = {
+      findById: jest.fn().mockResolvedValue(page),
+      updatePage: jest.fn().mockResolvedValue(undefined),
+    };
+    pageAccessService = {
+      validateCanEdit: jest.fn().mockResolvedValue(undefined),
+    };
+
+    const module = await Test.createTestingModule({
+      controllers: [PageTemplateController],
+      providers: [
+        { provide: TransclusionService, useValue: { lookupTemplate: jest.fn() } },
+        { provide: PageRepo, useValue: pageRepo },
+        { provide: PageAccessService, useValue: pageAccessService },
+        {
+          provide: KYSELY_MODULE_CONNECTION_TOKEN(),
+          useValue: makeDbStub(workspaceRow),
+        },
+      ],
+    })
+      .overrideGuard(JwtAuthGuard)
+      .useValue({ canActivate: () => true })
+      .overrideGuard(UserThrottlerGuard)
+      .useValue({ canActivate: () => true })
+      .compile();
+
+    controller = module.get(PageTemplateController);
+  }
+
+  beforeEach(() => {
+    jest.useFakeTimers().setSystemTime(new Date('2026-06-26T00:00:00.000Z'));
+  });
+
+  afterEach(() => {
+    jest.useRealTimers();
+  });
+
+  it('throws NotFound and does not touch the page when missing', async () => {
+    await buildController(null);
+    await expect(
+      controller.toggleTemporary({ pageId: 'p1' } as any, user),
+    ).rejects.toBeInstanceOf(NotFoundException);
+    expect(pageAccessService.validateCanEdit).not.toHaveBeenCalled();
+    expect(pageRepo.updatePage).not.toHaveBeenCalled();
+  });
+
+  it('throws NotFound (not Forbidden) for a cross-workspace page', async () => {
+    await buildController({
+      id: 'p1',
+      workspaceId: 'OTHER',
+      deletedAt: null,
+      temporaryExpiresAt: null,
+    });
+    await expect(
+      controller.toggleTemporary({ pageId: 'p1' } as any, user),
+    ).rejects.toBeInstanceOf(NotFoundException);
+    expect(pageRepo.updatePage).not.toHaveBeenCalled();
+  });
+
+  it('enforces CASL edit: when validateCanEdit throws, the timer is NOT changed', async () => {
+    await buildController({
+      id: 'p1',
+      workspaceId: 'w1',
+      deletedAt: null,
+      temporaryExpiresAt: null,
+    });
+    pageAccessService.validateCanEdit.mockRejectedValue(new ForbiddenException());
+    await expect(
+      controller.toggleTemporary({ pageId: 'p1' } as any, user),
+    ).rejects.toBeInstanceOf(ForbiddenException);
+    expect(pageRepo.updatePage).not.toHaveBeenCalled();
+  });
+
+  it('arms the timer (toggle) using the default hours when the page is permanent', async () => {
+    await buildController({
+      id: 'p1',
+      workspaceId: 'w1',
+      deletedAt: null,
+      temporaryExpiresAt: null,
+    });
+    const out = await controller.toggleTemporary({ pageId: 'p1' } as any, user);
+
+    const expected = new Date(
+      Date.now() + DEFAULT_TEMPORARY_NOTE_HOURS * 60 * 60 * 1000,
+    );
+    expect(pageAccessService.validateCanEdit).toHaveBeenCalled();
+    expect(pageRepo.updatePage).toHaveBeenCalledWith(
+      { temporaryExpiresAt: expected },
+      'p1',
+    );
+    expect(out).toEqual({ pageId: 'p1', temporaryExpiresAt: expected });
+  });
+
+  it('uses the workspace temporaryNoteHours override when set', async () => {
+    await buildController(
+      {
+        id: 'p1',
+        workspaceId: 'w1',
+        deletedAt: null,
+        temporaryExpiresAt: null,
+      },
+      { temporaryNoteHours: 3 },
+    );
+    const out = await controller.toggleTemporary({ pageId: 'p1' } as any, user);
+    const expected = new Date(Date.now() + 3 * 60 * 60 * 1000);
+    expect(pageRepo.updatePage).toHaveBeenCalledWith(
+      { temporaryExpiresAt: expected },
+      'p1',
+    );
+    expect(out.temporaryExpiresAt).toEqual(expected);
+  });
+
+  it('clears the timer (make permanent) when toggling an armed note', async () => {
+    await buildController({
+      id: 'p1',
+      workspaceId: 'w1',
+      deletedAt: null,
+      temporaryExpiresAt: new Date('2026-06-27T00:00:00.000Z'),
+    });
+    const out = await controller.toggleTemporary({ pageId: 'p1' } as any, user);
+    expect(pageRepo.updatePage).toHaveBeenCalledWith(
+      { temporaryExpiresAt: null },
+      'p1',
+    );
+    expect(out).toEqual({ pageId: 'p1', temporaryExpiresAt: null });
+  });
+
+  it('respects an explicit temporary:false instead of toggling', async () => {
+    await buildController({
+      id: 'p1',
+      workspaceId: 'w1',
+      deletedAt: null,
+      temporaryExpiresAt: null, // already permanent, but explicit false
+    });
+    const out = await controller.toggleTemporary(
+      { pageId: 'p1', temporary: false } as any,
+      user,
+    );
+    expect(pageRepo.updatePage).toHaveBeenCalledWith(
+      { temporaryExpiresAt: null },
+      'p1',
+    );
+    expect(out.temporaryExpiresAt).toBeNull();
+  });
+});
+
+describe('ToggleTemporaryDto validation (class-validator)', () => {
+  const uuid = '00000000-0000-4000-8000-000000000001';
+
+  it('accepts a valid UUID with no flag (toggle)', async () => {
+    const dto = plainToInstance(ToggleTemporaryDto, { pageId: uuid });
+    expect(await validate(dto)).toHaveLength(0);
+  });
+
+  it('accepts an explicit boolean temporary', async () => {
+    const dto = plainToInstance(ToggleTemporaryDto, {
+      pageId: uuid,
+      temporary: true,
+    });
+    expect(await validate(dto)).toHaveLength(0);
+  });
+
+  it('rejects a non-UUID pageId', async () => {
+    const dto = plainToInstance(ToggleTemporaryDto, { pageId: 'nope' });
+    const errors = await validate(dto);
+    expect(errors).toHaveLength(1);
+    expect(errors[0].constraints).toHaveProperty('isUuid');
+  });
+
+  it('rejects a non-boolean temporary', async () => {
+    const dto = plainToInstance(ToggleTemporaryDto, {
+      pageId: uuid,
+      temporary: 'yes',
+    });
+    const errors = await validate(dto);
+    expect(errors).toHaveLength(1);
+    expect(errors[0].constraints).toHaveProperty('isBoolean');
+  });
+});

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

@@ -84,6 +84,13 @@ export class UpdateWorkspaceDto extends PartialType(CreateWorkspaceDto) {
   @Min(1)
   trashRetentionDays: number;
 
+  // Default lifetime for new temporary notes, in HOURS. Frozen per-note at
+  // creation, so changing this never reschedules existing notes.
+  @IsOptional()
+  @IsInt()
+  @Min(1)
+  temporaryNoteHours: number;
+
   @IsOptional()
   @IsBoolean()
   allowMemberTemplates: boolean;

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

@@ -330,6 +330,7 @@ export class WorkspaceService {
     if (
       typeof updateWorkspaceDto.disablePublicSharing !== 'undefined' ||
       typeof updateWorkspaceDto.trashRetentionDays !== 'undefined' ||
+      typeof updateWorkspaceDto.temporaryNoteHours !== 'undefined' ||
       typeof updateWorkspaceDto.mcpEnabled !== 'undefined' ||
       typeof updateWorkspaceDto.restrictApiToAdmins !== 'undefined' ||
       typeof updateWorkspaceDto.allowMemberTemplates !== 'undefined' ||
@@ -337,7 +338,13 @@ export class WorkspaceService {
     ) {
       const ws = await this.db
         .selectFrom('workspaces')
-        .select(['id', 'licenseKey', 'plan', 'trashRetentionDays'])
+        .select([
+          'id',
+          'licenseKey',
+          'plan',
+          'trashRetentionDays',
+          'temporaryNoteHours',
+        ])
         .where('id', '=', workspaceId)
         .executeTakeFirst();
 
@@ -378,6 +385,14 @@ export class WorkspaceService {
         before.trashRetentionDays = ws.trashRetentionDays;
         after.trashRetentionDays = updateWorkspaceDto.trashRetentionDays;
       }
+
+      if (
+        typeof updateWorkspaceDto.temporaryNoteHours !== 'undefined' &&
+        updateWorkspaceDto.temporaryNoteHours !== ws.temporaryNoteHours
+      ) {
+        before.temporaryNoteHours = ws.temporaryNoteHours;
+        after.temporaryNoteHours = updateWorkspaceDto.temporaryNoteHours;
+      }
     }
 
     if (updateWorkspaceDto.aiSearch) {

apps/server/src/database/migrations/20260626T140000-page-temporary-notes.ts

@@ -0,0 +1,40 @@
+import { type Kysely, sql } from 'kysely';
+
+export async function up(db: Kysely<any>): Promise<void> {
+  // "Death timer" column. NULL = permanent page; non-NULL = temporary note,
+  // value is the exact moment the note auto-moves to trash. The deadline is
+  // frozen at creation, so changing the workspace setting never reschedules
+  // existing notes.
+  await db.schema
+    .alterTable('pages')
+    .addColumn('temporary_expires_at', 'timestamptz', (col) => col)
+    .execute();
+
+  // Partial index backing the cleanup sweep: only armed, not-yet-trashed notes.
+  await sql`
+    CREATE INDEX pages_temporary_expires_at_idx
+    ON pages (temporary_expires_at)
+    WHERE temporary_expires_at IS NOT NULL AND deleted_at IS NULL
+  `.execute(db);
+
+  // Default lifetime for new temporary notes, in HOURS. Frozen per-note at
+  // creation. NULL falls back to the in-code DEFAULT_TEMPORARY_NOTE_HOURS.
+  await db.schema
+    .alterTable('workspaces')
+    .addColumn('temporary_note_hours', 'int8', (col) => col)
+    .execute();
+}
+
+export async function down(db: Kysely<any>): Promise<void> {
+  await db.schema
+    .alterTable('workspaces')
+    .dropColumn('temporary_note_hours')
+    .execute();
+
+  await db.schema.dropIndex('pages_temporary_expires_at_idx').execute();
+
+  await db.schema
+    .alterTable('pages')
+    .dropColumn('temporary_expires_at')
+    .execute();
+}

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

@@ -18,7 +18,8 @@ import { executeWithCursorPagination } from '@docmost/db/pagination/cursor-pagin
 // (multi-instance deploy).
 const SWEEP_STREAMING_STALE_MS = 10 * 60 * 1000; // 10 minutes
 
-// Hard upper bound on the rows materialized by `findAllByChat` (export path).
+// Hard upper bound on the rows materialized by `findAllByChat`, which now feeds
+// BOTH the Markdown export and the per-turn model history.
 // A generous cap so a pathologically huge chat cannot load an unbounded result
 // into memory; far above any realistic transcript length.
 const FIND_ALL_BY_CHAT_LIMIT = 5000;
@@ -78,14 +79,17 @@ export class AiChatMessageRepo {
   }
 
   // Load ALL (non-deleted) messages of a chat in ascending chronological order
-  // (oldest -> newest), unpaginated. Used by the server-side Markdown export
-  // (#183), where the DB is the single source of truth and the whole transcript
-  // must be rendered in one pass (findByChat is cursor-paginated and would only
-  // return the first page).
+  // (oldest -> newest), unpaginated. Two callers, both treating the DB as the
+  // single source of truth and needing the whole transcript in one pass
+  // (findByChat is cursor-paginated and would only return the first page):
+  //   - the server-side Markdown export (#183);
+  //   - the per-turn model history, rebuilt fresh on every turn so the model
+  //     sees the full authoritative transcript.
   //
   // Hard-capped at FIND_ALL_BY_CHAT_LIMIT rows (a generous bound, far above any
-  // realistic transcript) so exporting a pathologically huge chat cannot
-  // materialize an unbounded result set in memory.
+  // realistic transcript) — a shared memory-safety backstop for BOTH paths so a
+  // pathologically huge chat cannot materialize an unbounded result set in
+  // memory. On overflow the NEWEST rows are kept and a warning is logged.
   async findAllByChat(
     chatId: string,
     workspaceId: string,
@@ -93,9 +97,9 @@ export class AiChatMessageRepo {
     limit: number = FIND_ALL_BY_CHAT_LIMIT,
   ): Promise<AiChatMessage[]> {
     // Fetch newest-first (+1 to DETECT truncation), so on overflow we keep the
-    // NEWEST `limit` messages — the recent conversation matters most for an
-    // export — rather than silently dropping the tail (#183 review). Reverse back
-    // to chronological for rendering, like findRecent.
+    // NEWEST `limit` messages — the recent conversation matters most — rather
+    // than silently dropping the tail (#183 review). Then reverse back to
+    // chronological order (oldest -> newest) for rendering / model replay.
     const rows = await this.db
       .selectFrom('aiChatMessages')
       .select(this.baseFields)
@@ -110,38 +114,13 @@ export class AiChatMessageRepo {
     if (rows.length > limit) {
       rows.length = limit; // keep the newest `limit` (rows are newest-first here)
       this.logger.warn(
-        `Chat ${chatId} export truncated to the newest ${limit} messages ` +
+        `Chat ${chatId} truncated to the newest ${limit} messages ` +
           `(older messages omitted).`,
       );
     }
     return rows.reverse();
   }
 
-  // Load the most RECENT `limit` messages for a chat and return them in
-  // ascending chronological order (oldest -> newest), as the model expects.
-  // `findByChat` returns the FIRST page ASC (the OLDEST messages), which loses
-  // recent turns once a chat grows beyond a page; this rebuilds the model
-  // history from the tail instead. Plain query (no cursor pagination).
-  async findRecent(
-    chatId: string,
-    workspaceId: string,
-    limit: number,
-  ): Promise<AiChatMessage[]> {
-    const rows = await this.db
-      .selectFrom('aiChatMessages')
-      .select(this.baseFields)
-      .where('chatId', '=', chatId)
-      .where('workspaceId', '=', workspaceId)
-      .where('deletedAt', 'is', null)
-      .orderBy('createdAt', 'desc')
-      .orderBy('id', 'desc')
-      .limit(limit)
-      .execute();
-
-    // Selected newest-first for the limit; reverse to oldest-first for the model.
-    return rows.reverse();
-  }
-
   async insert(
     insertable: InsertableAiChatMessage,
     trx?: KyselyTransaction,

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

@@ -0,0 +1,85 @@
+import { AiChatRepo } from './ai-chat.repo';
+import type { KyselyDB } from '../../types/kysely.types';
+
+/**
+ * Unit test for AiChatRepo.findLatestByPage — the "bound chat" resolver behind
+ * #191 (auto-open the last chat created on a document). It builds the scoping
+ * query, so we assert the EXACT predicates/ordering the spec mandates over a
+ * chainable builder mock (no live DB): user + workspace + page scope, the
+ * deletedAt filter, newest-by-createdAt with an id tiebreaker, limit 1. A
+ * live-Postgres ordering test is out of scope for this pure unit test.
+ */
+describe('AiChatRepo.findLatestByPage', () => {
+  type Recorded = {
+    table?: string;
+    wheres: Array<[string, string, unknown]>;
+    orderBys: Array<[string, string]>;
+    limit?: number;
+  };
+
+  function makeDb(result: unknown): { db: KyselyDB; rec: Recorded } {
+    const rec: Recorded = { wheres: [], orderBys: [] };
+    const builder: Record<string, unknown> = {};
+    const chain = () => builder;
+    builder.selectAll = chain;
+    builder.where = (col: string, op: string, val: unknown) => {
+      rec.wheres.push([col, op, val]);
+      return builder;
+    };
+    builder.orderBy = (col: string, dir: string) => {
+      rec.orderBys.push([col, dir]);
+      return builder;
+    };
+    builder.limit = (n: number) => {
+      rec.limit = n;
+      return builder;
+    };
+    builder.executeTakeFirst = () => Promise.resolve(result);
+    const db = {
+      selectFrom: (table: string) => {
+        rec.table = table;
+        return builder;
+      },
+    } as unknown as KyselyDB;
+    return { db, rec };
+  }
+
+  it('returns the matched chat and scopes by user + workspace + page (deletedAt null)', async () => {
+    const chat = { id: 'c1', creatorId: 'u1', workspaceId: 'ws1', pageId: 'p1' };
+    const { db, rec } = makeDb(chat);
+    const repo = new AiChatRepo(db);
+
+    const res = await repo.findLatestByPage('u1', 'ws1', 'p1');
+
+    expect(res).toBe(chat);
+    expect(rec.table).toBe('aiChats');
+    expect(rec.wheres).toEqual(
+      expect.arrayContaining([
+        ['creatorId', '=', 'u1'],
+        ['workspaceId', '=', 'ws1'],
+        ['pageId', '=', 'p1'],
+        ['deletedAt', 'is', null],
+      ]),
+    );
+  });
+
+  it('orders newest-first by createdAt then id, limit 1', async () => {
+    const { db, rec } = makeDb(undefined);
+    const repo = new AiChatRepo(db);
+
+    await repo.findLatestByPage('u1', 'ws1', 'p1');
+
+    expect(rec.orderBys).toEqual([
+      ['createdAt', 'desc'],
+      ['id', 'desc'],
+    ]);
+    expect(rec.limit).toBe(1);
+  });
+
+  it('returns undefined when the page has no owned chat', async () => {
+    const { db } = makeDb(undefined);
+    const repo = new AiChatRepo(db);
+
+    await expect(repo.findLatestByPage('u1', 'ws1', 'p1')).resolves.toBeUndefined();
+  });
+});

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

@@ -80,6 +80,32 @@ export class AiChatRepo {
     });
   }
 
+  /**
+   * The "bound chat" for a document: the requesting user's most recently
+   * created, non-deleted chat whose origin page is `pageId`. Auto-opened when
+   * the AI chat window is opened on that page. Newest-by-createdAt wins, so a
+   * chat created later on the same page supersedes earlier ones — exactly how
+   * "new chat -> becomes the bound one" falls out for free. Scoped to the user +
+   * workspace, so a foreign pageId can only ever match the caller's own chats.
+   */
+  async findLatestByPage(
+    creatorId: string,
+    workspaceId: string,
+    pageId: string,
+  ): Promise<AiChat | undefined> {
+    return this.db
+      .selectFrom('aiChats')
+      .selectAll('aiChats')
+      .where('creatorId', '=', creatorId)
+      .where('workspaceId', '=', workspaceId)
+      .where('pageId', '=', pageId)
+      .where('deletedAt', 'is', null)
+      .orderBy('createdAt', 'desc')
+      .orderBy('id', 'desc') // stable tiebreaker, mirrors findByCreator's cursor
+      .limit(1)
+      .executeTakeFirst();
+  }
+
   async insert(
     insertable: InsertableAiChat,
     trx?: KyselyTransaction,

apps/server/src/database/repos/page/page.repo.restore.spec.ts

@@ -0,0 +1,64 @@
+import { PageRepo } from './page.repo';
+
+/**
+ * Regression guard for #201: restorePage must disarm the temporary-note death
+ * timer by setting `temporaryExpiresAt = null` alongside the un-delete fields.
+ * Otherwise a restored note whose frozen deadline already passed would be
+ * re-trashed by the very next cleanup sweep. There is no real DB here — a
+ * chainable Kysely proxy records every `.set(...)` payload so we can assert the
+ * single restore UPDATE clears the deadline.
+ */
+function makeRestoreDbStub(opts: {
+  pageToRestore: any;
+  descendants: any[];
+}) {
+  const setCalls: any[] = [];
+  const proxy: any = new Proxy(function () {}, {
+    get(_t, prop) {
+      if (prop === 'then') return undefined;
+      if (prop === 'set')
+        return (payload: any) => {
+          setCalls.push(payload);
+          return proxy;
+        };
+      if (prop === 'executeTakeFirst')
+        return () => Promise.resolve(opts.pageToRestore);
+      if (prop === 'execute') return () => Promise.resolve(opts.descendants);
+      if (prop === 'withRecursive')
+        return (_name: string, cb: any) => {
+          // Exercise the recursive CTE builder against the proxy without a DB.
+          try {
+            cb(proxy);
+          } catch {
+            // builder shape only; ignore
+          }
+          return proxy;
+        };
+      return () => proxy;
+    },
+  });
+  return { proxy, setCalls };
+}
+
+describe('PageRepo.restorePage temporary-timer disarm (#201)', () => {
+  it('clears temporaryExpiresAt together with the un-delete fields', async () => {
+    const { proxy, setCalls } = makeRestoreDbStub({
+      // No parent => the deleted-parent lookup and detach branch are skipped, so
+      // the only UPDATE is the bulk restore we assert on.
+      pageToRestore: { id: 'p1', parentPageId: null, spaceId: 's1' },
+      descendants: [{ id: 'p1' }],
+    });
+    const eventEmitter = { emit: jest.fn() } as any;
+
+    const repo = new PageRepo(proxy, {} as any, eventEmitter);
+
+    await repo.restorePage('p1', 'w1');
+
+    expect(setCalls).toHaveLength(1);
+    expect(setCalls[0]).toEqual({
+      deletedById: null,
+      deletedAt: null,
+      temporaryExpiresAt: null,
+    });
+  });
+});

apps/server/src/database/repos/page/page.repo.ts

@@ -51,6 +51,7 @@ export class PageRepo {
     'workspaceId',
     'isLocked',
     'isTemplate',
+    'temporaryExpiresAt',
     'createdAt',
     'updatedAt',
     'deletedAt',
@@ -425,7 +426,10 @@ export class PageRepo {
     // Restore all pages, but only detach the root page if its parent is deleted
     await this.db
       .updateTable('pages')
-      .set({ deletedById: null, deletedAt: null })
+      // On restore, disarm the death timer: pulling a note out of trash means
+      // "keep it". Otherwise a deadline now in the past would re-trash it on the
+      // next cleanup sweep.
+      .set({ deletedById: null, deletedAt: null, temporaryExpiresAt: null })
       .where('id', 'in', pageIds)
       .execute();
 

apps/server/src/database/repos/workspace/workspace.repo.ts

@@ -58,6 +58,7 @@ export class WorkspaceRepo {
     'plan',
     'enforceMfa',
     'trashRetentionDays',
+    'temporaryNoteHours',
     'isScimEnabled',
   ];
   constructor(@InjectKysely() private readonly db: KyselyDB) {}

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

@@ -297,6 +297,7 @@ export interface Pages {
   position: string | null;
   slugId: string;
   spaceId: string;
+  temporaryExpiresAt: Timestamp | null;
   textContent: string | null;
   title: string | null;
   tsv: string | null;
@@ -419,6 +420,7 @@ export interface WorkspaceInvitations {
 export interface Workspaces {
   auditRetentionDays: Generated<number>;
   trashRetentionDays: Generated<number>;
+  temporaryNoteHours: Generated<number>;
   billingEmail: string | null;
   createdAt: Generated<Timestamp>;
   customDomain: string | null;

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

@@ -267,4 +267,36 @@ describe('AiChatMessageRepo.update + sweepStreaming [integration]', () => {
     const all = await repo.findAllByChat(cappedChat, workspaceId, 100);
     expect(all.map((r) => r.content)).toEqual(['m1-oldest', 'm2', 'm3-newest']);
   });
+
+  it('default findAllByChat returns the FULL transcript past 50 rows — no recent-tail window (#202)', async () => {
+    // PR #202 swapped the model-history rebuild in AiChatService.handle from
+    // findRecent(chatId, ws, 50) to findAllByChat(chatId, ws) WITHOUT a limit
+    // arg. This pins the behavioral guarantee that switch relies on: a chat
+    // longer than the old 50-msg window comes back in FULL (oldest -> newest),
+    // so no early turns are silently dropped from what the model sees. The old
+    // 50-cap would have returned only the last 50 of these 60 rows.
+    const longChat = (
+      await createChat(db, { workspaceId, creatorId: userId })
+    ).id;
+    const base = Date.now();
+    const total = 60;
+    for (let i = 0; i < total; i++) {
+      await createMessage(db, {
+        workspaceId,
+        chatId: longChat,
+        content: `msg-${i}`,
+        // Strictly increasing timestamps so ordering is deterministic.
+        createdAt: new Date(base + i * 1000),
+      });
+    }
+
+    // Default args == exactly how handle() calls it now.
+    const history = await repo.findAllByChat(longChat, workspaceId);
+    expect(history).toHaveLength(total);
+    expect(history.map((r) => r.content)).toEqual(
+      Array.from({ length: total }, (_, i) => `msg-${i}`),
+    );
+    // The very first turn (which the old 50-window would have dropped) is present.
+    expect(history[0]!.content).toBe('msg-0');
+  });
 });