From 57efb91bd3ad626bcbc360f344be796018c10572 Mon Sep 17 00:00:00 2001
From: Philip Okugbe <16838612+Philipinho@users.noreply.github.com>
Date: Fri, 10 Apr 2026 19:23:47 +0100
Subject: [PATCH] feat(ee): ai chat (#2098)

* feat: ai chat

* feat: ai chat

* sync

* cleanup

* view space button
---
 .../public/locales/en-US/translation.json     |  30 +-
 apps/client/src/App.tsx                       |   3 +
 apps/client/src/components/common/copy.tsx    |   7 +-
 .../layouts/global/app-header.module.css      |  16 +
 .../components/layouts/global/app-header.tsx  |  94 +++-
 .../src/components/layouts/global/aside.tsx   |  17 +-
 .../layouts/global/global-app-shell.tsx       |   5 +-
 .../components/ui/card-carousel.module.css    |  68 +++
 .../src/components/ui/card-carousel.tsx       |  77 ++++
 .../ee/ai-chat/components/ai-chat-layout.tsx  | 106 +++++
 .../components/ai-chat-sidebar-item.tsx       | 166 +++++++
 .../ee/ai-chat/components/ai-chat-sidebar.tsx | 224 ++++++++++
 .../ai-chat/components/aside-chat-history.tsx |  67 +++
 .../ai-chat/components/aside-chat-panel.tsx   | 258 +++++++++++
 .../ai-chat/components/chat-empty-state.tsx   |  91 ++++
 .../src/ee/ai-chat/components/chat-input.tsx  | 409 ++++++++++++++++++
 .../ai-chat/components/chat-message-list.tsx  | 174 ++++++++
 .../ee/ai-chat/components/chat-message.tsx    | 139 ++++++
 .../ee/ai-chat/components/chat-tool-group.tsx |  56 +++
 .../ai-chat/components/chat-tool-result.tsx   |  49 +++
 .../ee/ai-chat/components/enable-ai-chat.tsx  |  67 +++
 .../src/ee/ai-chat/hooks/use-chat-stream.ts   | 227 ++++++++++
 apps/client/src/ee/ai-chat/pages/ai-chat.tsx  |  39 ++
 .../src/ee/ai-chat/queries/ai-chat-query.ts   |  61 +++
 .../ee/ai-chat/services/ai-chat-service.ts    | 144 ++++++
 .../src/ee/ai-chat/styles/ai-chat.module.css  | 169 ++++++++
 .../styles/aside-chat-panel.module.css        | 139 ++++++
 .../ee/ai-chat/styles/chat-input.module.css   | 242 +++++++++++
 .../ee/ai-chat/styles/chat-message.module.css | 286 ++++++++++++
 .../ee/ai-chat/styles/chat-sidebar.module.css | 138 ++++++
 .../src/ee/ai-chat/types/ai-chat.types.ts     |  49 +++
 apps/client/src/ee/ai/pages/ai-settings.tsx   |   2 +
 .../components/mention/mention-list.tsx       |   2 +-
 .../components/mention/mention-suggestion.ts  |   4 +-
 .../home/components/home-ai-prompt.module.css |  28 ++
 .../home/components/home-ai-prompt.tsx        |  60 +++
 .../components/search-control.module.css      |   2 +
 .../components/space-carousel.module.css      |  22 +
 .../space/components/space-carousel.tsx       |  77 ++++
 .../workspace/types/workspace.types.ts        |   1 +
 apps/client/src/pages/dashboard/home.tsx      |   9 +-
 apps/server/package.json                      |   2 +
 .../core/attachment/attachment.constants.ts   |   1 +
 .../core/attachment/attachment.controller.ts  |  30 +-
 .../src/core/attachment/attachment.utils.ts   |   2 +
 .../processors/attachment.processor.ts        |   5 +
 .../attachment/services/attachment.service.ts |  25 ++
 apps/server/src/core/auth/auth.controller.ts  |  11 +-
 .../workspace/dto/update-workspace.dto.ts     |   4 +
 .../workspace/services/workspace.service.ts   |  17 +-
 .../migrations/20260409T132415-ai-chat.ts     | 118 +++++
 .../repos/attachment/attachment.repo.ts       |  51 +++
 apps/server/src/database/types/db.d.ts        |  28 ++
 .../server/src/database/types/entity.types.ts |  17 +
 apps/server/src/ee                            |   2 +-
 .../environment/environment.service.ts        |   7 +
 .../src/integrations/export/export.service.ts |   2 +-
 .../queue/constants/queue.constants.ts        |   1 +
 .../integrations/throttle/throttle.module.ts  |   6 +-
 .../integrations/throttle/throttler-names.ts  |   2 +
 .../throttle/user-throttler.guard.ts          |  13 +
 .../src/lib/markdown/utils/marked.utils.ts    |   7 +-
 pnpm-lock.yaml                                |  22 +
 63 files changed, 4149 insertions(+), 48 deletions(-)
 create mode 100644 apps/client/src/components/ui/card-carousel.module.css
 create mode 100644 apps/client/src/components/ui/card-carousel.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/ai-chat-layout.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/ai-chat-sidebar-item.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/ai-chat-sidebar.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/aside-chat-history.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/aside-chat-panel.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/chat-empty-state.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/chat-input.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/chat-message-list.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/chat-message.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/chat-tool-group.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/chat-tool-result.tsx
 create mode 100644 apps/client/src/ee/ai-chat/components/enable-ai-chat.tsx
 create mode 100644 apps/client/src/ee/ai-chat/hooks/use-chat-stream.ts
 create mode 100644 apps/client/src/ee/ai-chat/pages/ai-chat.tsx
 create mode 100644 apps/client/src/ee/ai-chat/queries/ai-chat-query.ts
 create mode 100644 apps/client/src/ee/ai-chat/services/ai-chat-service.ts
 create mode 100644 apps/client/src/ee/ai-chat/styles/ai-chat.module.css
 create mode 100644 apps/client/src/ee/ai-chat/styles/aside-chat-panel.module.css
 create mode 100644 apps/client/src/ee/ai-chat/styles/chat-input.module.css
 create mode 100644 apps/client/src/ee/ai-chat/styles/chat-message.module.css
 create mode 100644 apps/client/src/ee/ai-chat/styles/chat-sidebar.module.css
 create mode 100644 apps/client/src/ee/ai-chat/types/ai-chat.types.ts
 create mode 100644 apps/client/src/features/home/components/home-ai-prompt.module.css
 create mode 100644 apps/client/src/features/home/components/home-ai-prompt.tsx
 create mode 100644 apps/client/src/features/space/components/space-carousel.module.css
 create mode 100644 apps/client/src/features/space/components/space-carousel.tsx
 create mode 100644 apps/server/src/database/migrations/20260409T132415-ai-chat.ts
 create mode 100644 apps/server/src/integrations/throttle/throttler-names.ts
 create mode 100644 apps/server/src/integrations/throttle/user-throttler.guard.ts

diff --git a/apps/client/public/locales/en-US/translation.json b/apps/client/public/locales/en-US/translation.json
index 5db91598..b83b3548 100644
--- a/apps/client/public/locales/en-US/translation.json
+++ b/apps/client/public/locales/en-US/translation.json
@@ -627,6 +627,7 @@
   "AI Answer": "AI Answer",
   "Ask AI": "Ask AI",
   "AI is thinking...": "AI is thinking...",
+  "Thinking": "Thinking",
   "Ask a question...": "Ask a question...",
   "AI Answers": "AI Answers",
   "AI-powered search (AI Answers)": "AI-powered search (AI Answers)",
@@ -755,5 +756,32 @@
   "Publish": "Publish",
   "Security": "Security",
   "Enforce SSO": "Enforce SSO",
-  "Once enforced, members will not be able to login with email and password.": "Once enforced, members will not be able to login with email and password."
+  "Once enforced, members will not be able to login with email and password.": "Once enforced, members will not be able to login with email and password.",
+  "AI-generated content may not be accurate.": "AI-generated content may not be accurate.",
+  "AI Chat": "AI Chat",
+  "Analyze for insights": "Analyze for insights",
+  "Ask anything...": "Ask anything...",
+  "Chat history": "Chat history",
+  "Chat name": "Chat name",
+  "Close": "Close",
+  "Docmost AI": "Docmost AI",
+  "Failed to load chat. An error occurred.": "Failed to load chat. An error occurred.",
+  "Failed to render this message.": "Failed to render this message.",
+  "How can I help you today?": "How can I help you today?",
+  "New chat": "New chat",
+  "No chat history": "No chat history",
+  "No chats found": "No chats found",
+  "No conversations yet": "No conversations yet",
+  "Open full page": "Open full page",
+  "Previous 7 days": "Previous 7 days",
+  "Previous 30 days": "Previous 30 days",
+  "Search chats...": "Search chats...",
+  "Start a new chat to see it here.": "Start a new chat to see it here.",
+  "Summarize this page": "Summarize this page",
+  "Toggle AI Chat": "Toggle AI Chat",
+  "Translate this page": "Translate this page",
+  "Try a different search term.": "Try a different search term.",
+  "Try again": "Try again",
+  "Untitled chat": "Untitled chat",
+  "What can I help you with?": "What can I help you with?"
 }
diff --git a/apps/client/src/App.tsx b/apps/client/src/App.tsx
index b99e63b3..382660c7 100644
--- a/apps/client/src/App.tsx
+++ b/apps/client/src/App.tsx
@@ -38,6 +38,7 @@ import UserApiKeys from "@/ee/api-key/pages/user-api-keys";
 import WorkspaceApiKeys from "@/ee/api-key/pages/workspace-api-keys";
 import AiSettings from "@/ee/ai/pages/ai-settings.tsx";
 import AuditLogs from "@/ee/audit/pages/audit-logs.tsx";
+import AiChat from "@/ee/ai-chat/pages/ai-chat.tsx";
 import VerifyEmail from "@/ee/pages/verify-email.tsx";
 
 export default function App() {
@@ -81,6 +82,8 @@ export default function App() {
 
         <Route element={<Layout />}>
           <Route path={"/home"} element={<Home />} />
+          <Route path={"/ai"} element={<AiChat />} />
+          <Route path={"/ai/chat/:chatId"} element={<AiChat />} />
           <Route path={"/spaces"} element={<SpacesPage />} />
           <Route path={"/s/:spaceSlug"} element={<SpaceHome />} />
           <Route path={"/s/:spaceSlug/trash"} element={<SpaceTrash />} />
diff --git a/apps/client/src/components/common/copy.tsx b/apps/client/src/components/common/copy.tsx
index 81a70771..745fc4ba 100644
--- a/apps/client/src/components/common/copy.tsx
+++ b/apps/client/src/components/common/copy.tsx
@@ -1,4 +1,4 @@
-import { ActionIcon, Tooltip } from "@mantine/core";
+import { ActionIcon, MantineColor, MantineSize, Tooltip } from "@mantine/core";
 import { CopyButton } from "@/components/common/copy-button";
 import { IconCheck, IconCopy } from "@tabler/icons-react";
 import React from "react";
@@ -6,8 +6,10 @@ import { useTranslation } from "react-i18next";
 
 interface CopyProps {
   text: string;
+  size?: MantineSize;
+  color?: MantineColor;
 }
-export default function CopyTextButton({ text }: CopyProps) {
+export default function CopyTextButton({ text, size }: CopyProps) {
   const { t } = useTranslation();
 
   return (
@@ -22,6 +24,7 @@ export default function CopyTextButton({ text }: CopyProps) {
             color={copied ? "teal" : "gray"}
             variant="subtle"
             onClick={copy}
+            size={size}
           >
             {copied ? <IconCheck size={16} /> : <IconCopy size={16} />}
           </ActionIcon>
diff --git a/apps/client/src/components/layouts/global/app-header.module.css b/apps/client/src/components/layouts/global/app-header.module.css
index b2298f13..a70b57e7 100644
--- a/apps/client/src/components/layouts/global/app-header.module.css
+++ b/apps/client/src/components/layouts/global/app-header.module.css
@@ -7,6 +7,19 @@
     padding-right: var(--mantine-spacing-md);
 }
 
+.brand {
+    display: flex;
+    align-items: center;
+    text-decoration: none;
+    color: inherit;
+    cursor: pointer;
+}
+
+.brandIcon {
+    display: flex;
+    align-items: center;
+}
+
 .link {
     display: block;
     line-height: 1;
@@ -16,6 +29,9 @@
     color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-0));
     font-size: var(--mantine-font-size-sm);
     font-weight: 500;
+    user-select: none;
+    white-space: nowrap;
+    flex-shrink: 0;
 
     @mixin hover {
         background-color: light-dark(var(--mantine-color-gray-0), var(--mantine-color-dark-6));
diff --git a/apps/client/src/components/layouts/global/app-header.tsx b/apps/client/src/components/layouts/global/app-header.tsx
index 58b76b71..9add5d7a 100644
--- a/apps/client/src/components/layouts/global/app-header.tsx
+++ b/apps/client/src/components/layouts/global/app-header.tsx
@@ -1,8 +1,18 @@
-import { Badge, Group, Text, Tooltip } from "@mantine/core";
+import {
+  ActionIcon,
+  Badge,
+  Box,
+  Group,
+  Text,
+  Tooltip,
+  UnstyledButton,
+} from "@mantine/core";
 import classes from "./app-header.module.css";
 import React from "react";
 import TopMenu from "@/components/layouts/global/top-menu.tsx";
-import { Link } from "react-router-dom";
+import { Link, useLocation } from "react-router-dom";
+import { IconSparkles } from "@tabler/icons-react";
+import useToggleAside from "@/hooks/use-toggle-aside.tsx";
 import APP_ROUTE from "@/lib/app-route.ts";
 import { useAtom } from "jotai";
 import {
@@ -23,8 +33,11 @@ import {
   shareSearchSpotlight,
 } from "@/features/search/constants.ts";
 import { NotificationPopover } from "@/features/notification/components/notification-popover.tsx";
+import { workspaceAtom } from "@/features/user/atoms/current-user-atom.ts";
 
-const links = [{ link: APP_ROUTE.HOME, label: "Home" }];
+const links = [
+  { link: APP_ROUTE.HOME, label: "Home" },
+];
 
 export function AppHeader() {
   const { t } = useTranslation();
@@ -34,9 +47,14 @@ export function AppHeader() {
   const [desktopOpened] = useAtom(desktopSidebarAtom);
   const toggleDesktop = useToggleSidebar(desktopSidebarAtom);
   const { isTrial, trialDaysLeft } = useTrial();
+  const location = useLocation();
+  const toggleAside = useToggleAside();
+  const [workspace] = useAtom(workspaceAtom);
+  const aiChatEnabled = workspace?.settings?.ai?.chat === true;
 
   const isHomeRoute = location.pathname.startsWith("/home");
   const isSpacesRoute = location.pathname === "/spaces";
+  const isPageRoute = location.pathname.includes("/p/");
   const hideSidebar = isHomeRoute || isSpacesRoute;
 
   const items = links.map((link) => (
@@ -73,15 +91,24 @@ export function AppHeader() {
             </>
           )}
 
-          <Text
-            size="lg"
-            fw={600}
-            style={{ cursor: "pointer", userSelect: "none" }}
-            component={Link}
-            to="/home"
-          >
-            Docmost
-          </Text>
+          <Link to="/home" className={classes.brand} aria-label="Docmost">
+            <Box hiddenFrom="sm" className={classes.brandIcon}>
+              <img
+                src="/icons/favicon-32x32.png"
+                alt="Docmost"
+                width={22}
+                height={22}
+              />
+            </Box>
+            <Text
+              size="lg"
+              fw={600}
+              style={{ userSelect: "none" }}
+              visibleFrom="sm"
+            >
+              Docmost
+            </Text>
+          </Link>
 
           <Group ml={50} gap={5} className={classes.links} visibleFrom="sm">
             {items}
@@ -98,6 +125,49 @@ export function AppHeader() {
         </div>
 
         <Group px={"xl"} wrap="nowrap">
+          {aiChatEnabled && (
+            <>
+              <UnstyledButton
+                component={Link}
+                to="/ai"
+                className={classes.link}
+                visibleFrom="sm"
+                onClick={(e: React.MouseEvent) => {
+                  if (e.metaKey || e.ctrlKey || e.shiftKey || e.button === 1) {
+                    return;
+                  }
+                  if (isPageRoute) {
+                    e.preventDefault();
+                    toggleAside("chat");
+                  }
+                }}
+              >
+                {t("AI Chat")}
+              </UnstyledButton>
+              <Tooltip label={t("AI Chat")} openDelay={250} withArrow>
+                <ActionIcon
+                  component={Link}
+                  to="/ai"
+                  variant="subtle"
+                  color="dark"
+                  size="sm"
+                  hiddenFrom="sm"
+                  aria-label={t("AI Chat")}
+                  onClick={(e: React.MouseEvent) => {
+                    if (e.metaKey || e.ctrlKey || e.shiftKey || e.button === 1) {
+                      return;
+                    }
+                    if (isPageRoute) {
+                      e.preventDefault();
+                      toggleAside("chat");
+                    }
+                  }}
+                >
+                  <IconSparkles size={20} stroke={2} />
+                </ActionIcon>
+              </Tooltip>
+            </>
+          )}
           <NotificationPopover />
           {isCloud() && isTrial && trialDaysLeft !== 0 && (
             <Badge
diff --git a/apps/client/src/components/layouts/global/aside.tsx b/apps/client/src/components/layouts/global/aside.tsx
index 324bf3bf..4f2cf592 100644
--- a/apps/client/src/components/layouts/global/aside.tsx
+++ b/apps/client/src/components/layouts/global/aside.tsx
@@ -7,6 +7,7 @@ import { useTranslation } from "react-i18next";
 import { TableOfContents } from "@/features/editor/components/table-of-contents/table-of-contents.tsx";
 import { useAtomValue } from "jotai";
 import { pageEditorAtom } from "@/features/editor/atoms/editor-atoms.ts";
+import AsideChatPanel from "@/ee/ai-chat/components/aside-chat-panel";
 
 export default function Aside() {
   const [{ tab }] = useAtom(asideStateAtom);
@@ -25,6 +26,10 @@ export default function Aside() {
       component = <TableOfContents editor={pageEditor} />;
       title = "Table of contents";
       break;
+    case "chat":
+      component = <AsideChatPanel />;
+      title = "AI Chat";
+      break;
     default:
       component = null;
       title = null;
@@ -34,12 +39,14 @@ export default function Aside() {
     <Box p="md" style={{ height: "100%", display: "flex", flexDirection: "column" }}>
       {component && (
         <>
-          <Text mb="md" fw={500}>
-            {t(title)}
-          </Text>
+          {tab !== "chat" && (
+            <Text mb="md" fw={500}>
+              {t(title)}
+            </Text>
+          )}
 
-          {tab === "comments" ? (
-            <CommentListWithTabs />
+          {tab === "comments" || tab === "chat" ? (
+            component
           ) : (
             <ScrollArea
               style={{ height: "85vh" }}
diff --git a/apps/client/src/components/layouts/global/global-app-shell.tsx b/apps/client/src/components/layouts/global/global-app-shell.tsx
index 3e44b293..06629898 100644
--- a/apps/client/src/components/layouts/global/global-app-shell.tsx
+++ b/apps/client/src/components/layouts/global/global-app-shell.tsx
@@ -10,6 +10,7 @@ import {
   sidebarWidthAtom,
 } from "@/components/layouts/global/hooks/atoms/sidebar-atom.ts";
 import { SpaceSidebar } from "@/features/space/components/sidebar/space-sidebar.tsx";
+import AiChatSidebar from "@/ee/ai-chat/components/ai-chat-sidebar.tsx";
 import { AppHeader } from "@/components/layouts/global/app-header.tsx";
 import Aside from "@/components/layouts/global/aside.tsx";
 import classes from "./app-shell.module.css";
@@ -72,6 +73,7 @@ export default function GlobalAppShell({
   const location = useLocation();
   const isSettingsRoute = location.pathname.startsWith("/settings");
   const isSpaceRoute = location.pathname.startsWith("/s/");
+  const isAiRoute = location.pathname.startsWith("/ai");
   const isHomeRoute = location.pathname.startsWith("/home");
   const isSpacesRoute = location.pathname === "/spaces";
   const isPageRoute = location.pathname.includes("/p/");
@@ -108,9 +110,10 @@ export default function GlobalAppShell({
           withBorder={false}
           ref={sidebarRef}
         >
-          <div className={classes.resizeHandle} onMouseDown={startResizing} />
+          {!isAiRoute && <div className={classes.resizeHandle} onMouseDown={startResizing} />}
           {isSpaceRoute && <SpaceSidebar />}
           {isSettingsRoute && <SettingsSidebar />}
+          {isAiRoute && <AiChatSidebar />}
         </AppShell.Navbar>
       )}
       <AppShell.Main>
diff --git a/apps/client/src/components/ui/card-carousel.module.css b/apps/client/src/components/ui/card-carousel.module.css
new file mode 100644
index 00000000..4ec513f2
--- /dev/null
+++ b/apps/client/src/components/ui/card-carousel.module.css
@@ -0,0 +1,68 @@
+.root {
+  position: relative;
+}
+
+.track {
+  display: flex;
+  gap: var(--mantine-spacing-md);
+  overflow-x: auto;
+  scroll-snap-type: x mandatory;
+  scroll-behavior: smooth;
+  scrollbar-width: none;
+  -ms-overflow-style: none;
+  padding: 2px;
+  margin: -2px;
+}
+
+.track::-webkit-scrollbar {
+  display: none;
+}
+
+.track > * {
+  scroll-snap-align: start;
+  flex: 0 0 auto;
+}
+
+.arrow {
+  position: absolute;
+  top: 50%;
+  transform: translateY(-50%);
+  width: 32px;
+  height: 32px;
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  border-radius: 50%;
+  border: 1px solid light-dark(var(--mantine-color-gray-3), var(--mantine-color-dark-4));
+  background: light-dark(var(--mantine-color-white), var(--mantine-color-dark-6));
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+  cursor: pointer;
+  padding: 0;
+  box-shadow: 0 2px 8px rgba(0, 0, 0, 0.08);
+  opacity: 0;
+  pointer-events: none;
+  transition: opacity 120ms ease, background-color 120ms ease, transform 120ms ease;
+  z-index: 2;
+}
+
+.root:hover .arrow.visible,
+.arrow.visible:focus-visible {
+  opacity: 1;
+  pointer-events: auto;
+}
+
+.arrow:hover {
+  background: light-dark(var(--mantine-color-gray-0), var(--mantine-color-dark-5));
+}
+
+.arrow:active {
+  transform: translateY(-50%) scale(0.95);
+}
+
+.arrowLeft {
+  left: -14px;
+}
+
+.arrowRight {
+  right: -14px;
+}
diff --git a/apps/client/src/components/ui/card-carousel.tsx b/apps/client/src/components/ui/card-carousel.tsx
new file mode 100644
index 00000000..60d13aba
--- /dev/null
+++ b/apps/client/src/components/ui/card-carousel.tsx
@@ -0,0 +1,77 @@
+import { useCallback, useEffect, useRef, useState, type ReactNode } from "react";
+import { IconChevronLeft, IconChevronRight } from "@tabler/icons-react";
+import { useTranslation } from "react-i18next";
+import classes from "./card-carousel.module.css";
+
+type Props = {
+  children: ReactNode;
+  ariaLabel?: string;
+};
+
+export default function CardCarousel({ children, ariaLabel }: Props) {
+  const { t } = useTranslation();
+  const trackRef = useRef<HTMLDivElement>(null);
+  const [canScrollLeft, setCanScrollLeft] = useState(false);
+  const [canScrollRight, setCanScrollRight] = useState(false);
+
+  const updateScrollState = useCallback(() => {
+    const el = trackRef.current;
+    if (!el) return;
+    const maxScroll = el.scrollWidth - el.clientWidth;
+    setCanScrollLeft(el.scrollLeft > 1);
+    setCanScrollRight(el.scrollLeft < maxScroll - 1);
+  }, []);
+
+  useEffect(() => {
+    updateScrollState();
+    const el = trackRef.current;
+    if (!el) return;
+
+    const observer = new ResizeObserver(updateScrollState);
+    observer.observe(el);
+    for (const child of Array.from(el.children)) {
+      observer.observe(child);
+    }
+
+    return () => observer.disconnect();
+  }, [updateScrollState, children]);
+
+  const scrollBy = (direction: 1 | -1) => {
+    const el = trackRef.current;
+    if (!el) return;
+    el.scrollBy({ left: direction * el.clientWidth * 0.85, behavior: "smooth" });
+  };
+
+  return (
+    <div className={classes.root}>
+      <div
+        ref={trackRef}
+        className={classes.track}
+        onScroll={updateScrollState}
+        {...(ariaLabel ? { role: "region", "aria-label": ariaLabel } : {})}
+      >
+        {children}
+      </div>
+
+      <button
+        type="button"
+        className={`${classes.arrow} ${classes.arrowLeft} ${canScrollLeft ? classes.visible : ""}`}
+        onClick={() => scrollBy(-1)}
+        aria-label={t("Scroll left")}
+        tabIndex={canScrollLeft ? 0 : -1}
+      >
+        <IconChevronLeft size={18} />
+      </button>
+
+      <button
+        type="button"
+        className={`${classes.arrow} ${classes.arrowRight} ${canScrollRight ? classes.visible : ""}`}
+        onClick={() => scrollBy(1)}
+        aria-label={t("Scroll right")}
+        tabIndex={canScrollRight ? 0 : -1}
+      >
+        <IconChevronRight size={18} />
+      </button>
+    </div>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/ai-chat-layout.tsx b/apps/client/src/ee/ai-chat/components/ai-chat-layout.tsx
new file mode 100644
index 00000000..f0fe3035
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/ai-chat-layout.tsx
@@ -0,0 +1,106 @@
+import { useEffect, useRef } from "react";
+import { useLocation, useNavigate, useParams } from "react-router-dom";
+import { useChatInfoQuery } from "../queries/ai-chat-query";
+import { useChatStream } from "../hooks/use-chat-stream";
+import ChatMessageList from "./chat-message-list";
+import ChatEmptyState from "./chat-empty-state";
+import ChatInput from "./chat-input";
+import type { HomeAiPromptInitialState } from "@/features/home/components/home-ai-prompt";
+import classes from "../styles/ai-chat.module.css";
+
+export default function AiChatLayout() {
+  const { chatId } = useParams<{ chatId: string }>();
+  const location = useLocation();
+  const navigate = useNavigate();
+  const chatInfoQuery = useChatInfoQuery(chatId);
+
+  // If the URL points at a chat the user does not own, the info fetch 404s.
+  // Bounce them back to /ai so they cannot interact with any chat UI (including
+  // kicking off orphan uploads) tied to a chat they have no access to.
+  useEffect(() => {
+    if (chatId && chatInfoQuery.isError) {
+      navigate("/ai", { replace: true });
+    }
+  }, [chatId, chatInfoQuery.isError, navigate]);
+  const {
+    messages,
+    streamingContent,
+    streamingToolCalls,
+    isStreaming,
+    error,
+    sendMessage,
+    stopGeneration,
+    hydrateFromServer,
+  } = useChatStream(chatId);
+
+  const autoSentRef = useRef(false);
+
+  useEffect(() => {
+    if (chatInfoQuery.data?.messages) {
+      hydrateFromServer(chatInfoQuery.data.messages);
+    }
+  }, [chatInfoQuery.data, hydrateFromServer]);
+
+  useEffect(() => {
+    if (autoSentRef.current || chatId) return;
+    const state = location.state as HomeAiPromptInitialState | null;
+    if (!state?.initialContent && !state?.initialAttachments?.length) return;
+
+    autoSentRef.current = true;
+    sendMessage(
+      state.initialContent ?? "",
+      state.initialMentions ?? [],
+      state.initialAttachments ?? [],
+    );
+    navigate(location.pathname, { replace: true, state: null });
+  }, [chatId, location, navigate, sendMessage]);
+
+  const hasMessages = messages.length > 0 || isStreaming;
+
+  // While the redirect effect is running (or if the user is still on this
+  // component for any reason) never render the chat UI for a forbidden chat.
+  if (chatId && chatInfoQuery.isError) {
+    return null;
+  }
+
+  return (
+    <div className={classes.main}>
+      {error && (
+        <div
+          style={{
+            padding: "var(--mantine-spacing-sm) var(--mantine-spacing-lg)",
+            color: "var(--mantine-color-red-6)",
+            fontSize: "var(--mantine-font-size-sm)",
+          }}
+        >
+          {error}
+        </div>
+      )}
+
+      {hasMessages ? (
+        <>
+          <ChatMessageList
+            messages={messages}
+            isStreaming={isStreaming}
+            streamingContent={streamingContent}
+            streamingToolCalls={streamingToolCalls}
+          />
+          <div className={classes.inputArea}>
+            <ChatInput
+              isStreaming={isStreaming}
+              onSend={sendMessage}
+              onStop={stopGeneration}
+              chatId={chatId}
+            />
+          </div>
+        </>
+      ) : (
+        <ChatEmptyState
+          isStreaming={isStreaming}
+          onSend={sendMessage}
+          onStop={stopGeneration}
+        />
+      )}
+    </div>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/ai-chat-sidebar-item.tsx b/apps/client/src/ee/ai-chat/components/ai-chat-sidebar-item.tsx
new file mode 100644
index 00000000..f59b740e
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/ai-chat-sidebar-item.tsx
@@ -0,0 +1,166 @@
+import { useState, useRef, useEffect, useMemo, useCallback } from "react";
+import { ActionIcon, Menu, TextInput } from "@mantine/core";
+import { IconDots, IconTrash, IconEdit } from "@tabler/icons-react";
+import { Link } from "react-router-dom";
+import { useTranslation } from "react-i18next";
+import type { AiChat } from "../types/ai-chat.types";
+import classes from "../styles/chat-sidebar.module.css";
+
+type Props = {
+  chat: AiChat;
+  isActive: boolean;
+  onDelete: (chatId: string) => void;
+  onRename: (chatId: string, title: string) => void;
+};
+
+function formatChatDate(
+  isoString: string | Date,
+  locale: string | undefined,
+): string {
+  const date = new Date(isoString);
+  if (Number.isNaN(date.getTime())) return "";
+
+  const now = new Date();
+  const startOfToday = new Date(
+    now.getFullYear(),
+    now.getMonth(),
+    now.getDate(),
+  ).getTime();
+  const ts = date.getTime();
+  const sameYear = date.getFullYear() === now.getFullYear();
+
+  if (ts >= startOfToday) {
+    return date.toLocaleTimeString(locale, {
+      hour: "numeric",
+      minute: "2-digit",
+    });
+  }
+
+  if (sameYear) {
+    return date.toLocaleDateString(locale, {
+      month: "short",
+      day: "numeric",
+    });
+  }
+
+  return date.toLocaleDateString(locale, {
+    month: "short",
+    day: "numeric",
+    year: "numeric",
+  });
+}
+
+export default function AiChatSidebarItem({
+  chat,
+  isActive,
+  onDelete,
+  onRename,
+}: Props) {
+  const { t, i18n } = useTranslation();
+  const [renaming, setRenaming] = useState(false);
+  const [renameValue, setRenameValue] = useState("");
+  const inputRef = useRef<HTMLInputElement>(null);
+
+  const formattedDate = useMemo(
+    () => formatChatDate(chat.updatedAt, i18n.language),
+    [chat.updatedAt, i18n.language],
+  );
+
+  useEffect(() => {
+    if (renaming) {
+      // Wait for the input to be mounted before selecting.
+      const id = window.setTimeout(() => inputRef.current?.select(), 0);
+      return () => window.clearTimeout(id);
+    }
+  }, [renaming]);
+
+  const startRename = useCallback(() => {
+    setRenameValue(chat.title || "");
+    setRenaming(true);
+  }, [chat.title]);
+
+  const submitRename = useCallback(() => {
+    const trimmed = renameValue.trim();
+    if (trimmed && trimmed !== chat.title) {
+      onRename(chat.id, trimmed);
+    }
+    setRenaming(false);
+  }, [renameValue, chat.id, chat.title, onRename]);
+
+  if (renaming) {
+    return (
+      <div className={classes.chatItem} data-active={isActive || undefined}>
+        <TextInput
+          ref={inputRef}
+          size="xs"
+          variant="unstyled"
+          placeholder={t("Chat name")}
+          value={renameValue}
+          onChange={(e) => setRenameValue(e.currentTarget.value)}
+          onKeyDown={(e) => {
+            if (e.key === "Enter") {
+              e.preventDefault();
+              submitRename();
+            } else if (e.key === "Escape") {
+              e.preventDefault();
+              setRenaming(false);
+            }
+          }}
+          onBlur={submitRename}
+          classNames={{ input: classes.chatItemRenameInput }}
+          style={{ flex: 1 }}
+        />
+      </div>
+    );
+  }
+
+  return (
+    <Link
+      to={`/ai/chat/${chat.id}`}
+      className={classes.chatItem}
+      data-active={isActive || undefined}
+    >
+      <span className={classes.chatItemTitle}>
+        {chat.title || t("Untitled chat")}
+      </span>
+      <span className={classes.chatItemDate}>{formattedDate}</span>
+      <div className={classes.chatItemActions}>
+        <Menu position="bottom-end" withinPortal>
+          <Menu.Target>
+            <ActionIcon
+              variant="subtle"
+              size="xs"
+              color="gray"
+              onClick={(e) => e.preventDefault()}
+            >
+              <IconDots size={14} />
+            </ActionIcon>
+          </Menu.Target>
+          <Menu.Dropdown>
+            <Menu.Item
+              leftSection={<IconEdit size={14} />}
+              onClick={(e) => {
+                e.preventDefault();
+                e.stopPropagation();
+                startRename();
+              }}
+            >
+              {t("Rename")}
+            </Menu.Item>
+            <Menu.Item
+              leftSection={<IconTrash size={14} />}
+              color="red"
+              onClick={(e) => {
+                e.preventDefault();
+                e.stopPropagation();
+                onDelete(chat.id);
+              }}
+            >
+              {t("Delete")}
+            </Menu.Item>
+          </Menu.Dropdown>
+        </Menu>
+      </div>
+    </Link>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/ai-chat-sidebar.tsx b/apps/client/src/ee/ai-chat/components/ai-chat-sidebar.tsx
new file mode 100644
index 00000000..e3df3e52
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/ai-chat-sidebar.tsx
@@ -0,0 +1,224 @@
+import { useState, useCallback, useEffect, useMemo, useRef } from "react";
+import { Link, useNavigate, useParams } from "react-router-dom";
+import { ActionIcon, Center, TextInput, Loader, Tooltip } from "@mantine/core";
+import { useDebouncedValue } from "@mantine/hooks";
+import { IconPlus, IconSearch, IconMessageCircle2 } from "@tabler/icons-react";
+import { useTranslation } from "react-i18next";
+import {
+  useChatsQuery,
+  useDeleteChatMutation,
+  useUpdateChatTitleMutation,
+  useSearchChatsQuery,
+} from "../queries/ai-chat-query";
+import AiChatSidebarItem from "./ai-chat-sidebar-item";
+import type { AiChat } from "../types/ai-chat.types";
+import classes from "../styles/chat-sidebar.module.css";
+
+type ChatGroup = { key: string; label: string; chats: AiChat[] };
+
+function groupChatsByAge(
+  chats: AiChat[],
+  t: (key: string) => string,
+): ChatGroup[] {
+  if (chats.length === 0) return [];
+
+  const now = new Date();
+  const startOfToday = new Date(
+    now.getFullYear(),
+    now.getMonth(),
+    now.getDate(),
+  ).getTime();
+  const startOfYesterday = startOfToday - 24 * 60 * 60 * 1000;
+  const startOfLast7 = startOfToday - 7 * 24 * 60 * 60 * 1000;
+  const startOfLast30 = startOfToday - 30 * 24 * 60 * 60 * 1000;
+
+  const buckets: Record<string, ChatGroup> = {
+    today: { key: "today", label: t("Today"), chats: [] },
+    yesterday: { key: "yesterday", label: t("Yesterday"), chats: [] },
+    last7: { key: "last7", label: t("Previous 7 days"), chats: [] },
+    last30: { key: "last30", label: t("Previous 30 days"), chats: [] },
+    older: { key: "older", label: t("Older"), chats: [] },
+  };
+
+  for (const chat of chats) {
+    const ts = new Date(chat.updatedAt).getTime();
+    if (ts >= startOfToday) buckets.today.chats.push(chat);
+    else if (ts >= startOfYesterday) buckets.yesterday.chats.push(chat);
+    else if (ts >= startOfLast7) buckets.last7.chats.push(chat);
+    else if (ts >= startOfLast30) buckets.last30.chats.push(chat);
+    else buckets.older.chats.push(chat);
+  }
+
+  return [
+    buckets.today,
+    buckets.yesterday,
+    buckets.last7,
+    buckets.last30,
+    buckets.older,
+  ].filter((b) => b.chats.length > 0);
+}
+
+export default function AiChatSidebar() {
+  const { t } = useTranslation();
+  const navigate = useNavigate();
+  const { chatId } = useParams<{ chatId: string }>();
+  const [search, setSearch] = useState("");
+  const [debouncedSearch] = useDebouncedValue(search, 300);
+  const chatsQuery = useChatsQuery();
+  const searchQuery = useSearchChatsQuery(debouncedSearch);
+  const deleteMutation = useDeleteChatMutation();
+  const renameMutation = useUpdateChatTitleMutation();
+
+  const chats = useMemo(() => {
+    if (debouncedSearch) {
+      return searchQuery.data || [];
+    }
+    return chatsQuery.data?.pages.flatMap((p) => p.items) || [];
+  }, [debouncedSearch, searchQuery.data, chatsQuery.data]);
+
+  const groupedChats = useMemo(() => groupChatsByAge(chats, t), [chats, t]);
+
+  const sentinelRef = useRef<HTMLDivElement>(null);
+  const { hasNextPage, fetchNextPage, isFetchingNextPage } = chatsQuery;
+  const isSearching = Boolean(debouncedSearch);
+
+  useEffect(() => {
+    if (isSearching) return;
+    const sentinel = sentinelRef.current;
+    if (!sentinel) return;
+
+    const observer = new IntersectionObserver(
+      (entries) => {
+        if (entries[0].isIntersecting && hasNextPage && !isFetchingNextPage) {
+          fetchNextPage();
+        }
+      },
+      { threshold: 0.1 },
+    );
+
+    observer.observe(sentinel);
+    return () => observer.disconnect();
+  }, [isSearching, hasNextPage, isFetchingNextPage, fetchNextPage]);
+
+  const handleNewChat = useCallback(
+    (event: React.MouseEvent<HTMLAnchorElement>) => {
+      if (
+        event.button !== 0 ||
+        event.ctrlKey ||
+        event.metaKey ||
+        event.shiftKey
+      ) {
+        return;
+      }
+      event.preventDefault();
+      navigate("/ai");
+    },
+    [navigate],
+  );
+
+  const handleDelete = useCallback(
+    (id: string) => {
+      deleteMutation.mutate(id, {
+        onSuccess: () => {
+          if (chatId === id) {
+            navigate("/ai");
+          }
+        },
+      });
+    },
+    [deleteMutation, chatId, navigate],
+  );
+
+  const handleRename = useCallback(
+    (chatId: string, title: string) => {
+      renameMutation.mutate({ chatId, title });
+    },
+    [renameMutation],
+  );
+
+  const isLoading = chatsQuery.isLoading || searchQuery.isLoading;
+
+  return (
+    <div className={classes.sidebar}>
+      <div className={classes.header}>
+        <span className={classes.title}>{t("AI Chat")}</span>
+        <Tooltip label={t("New chat")} openDelay={250} withArrow>
+          <ActionIcon
+            component={Link}
+            to="/ai"
+            variant="subtle"
+            color="gray"
+            onClick={handleNewChat}
+            aria-label={t("New chat")}
+          >
+            <IconPlus size={18} />
+          </ActionIcon>
+        </Tooltip>
+      </div>
+
+      <TextInput
+        className={classes.searchInput}
+        placeholder="Search chats..."
+        leftSection={<IconSearch size={14} />}
+        size="xs"
+        value={search}
+        onChange={(e) => setSearch(e.currentTarget.value)}
+      />
+
+      <div className={classes.chatList}>
+        {isLoading && <Loader size="xs" mx="auto" mt="md" />}
+        {!isLoading && chats.length === 0 && (
+          <div className={classes.chatListEmpty}>
+            <IconMessageCircle2
+              size={28}
+              stroke={1.5}
+              className={classes.chatListEmptyIcon}
+            />
+            <div className={classes.chatListEmptyTitle}>
+              {isSearching ? t("No chats found") : t("No conversations yet")}
+            </div>
+            <div className={classes.chatListEmptyHint}>
+              {isSearching
+                ? t("Try a different search term.")
+                : t("Start a new chat to see it here.")}
+            </div>
+          </div>
+        )}
+        {isSearching
+          ? chats.map((chat) => (
+              <AiChatSidebarItem
+                key={chat.id}
+                chat={chat}
+                isActive={chat.id === chatId}
+                onDelete={handleDelete}
+                onRename={handleRename}
+              />
+            ))
+          : groupedChats.map((group) => (
+              <div key={group.key} className={classes.chatGroup}>
+                <div className={classes.chatGroupLabel}>{group.label}</div>
+                {group.chats.map((chat) => (
+                  <AiChatSidebarItem
+                    key={chat.id}
+                    chat={chat}
+                    isActive={chat.id === chatId}
+                    onDelete={handleDelete}
+                    onRename={handleRename}
+                  />
+                ))}
+              </div>
+            ))}
+        {!isSearching && (
+          <>
+            <div ref={sentinelRef} style={{ height: 1 }} />
+            {isFetchingNextPage && (
+              <Center py="xs">
+                <Loader size="xs" />
+              </Center>
+            )}
+          </>
+        )}
+      </div>
+    </div>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/aside-chat-history.tsx b/apps/client/src/ee/ai-chat/components/aside-chat-history.tsx
new file mode 100644
index 00000000..c31e5b10
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/aside-chat-history.tsx
@@ -0,0 +1,67 @@
+import { useState } from "react";
+import { TextInput, Loader, Text, ScrollArea } from "@mantine/core";
+import { IconSearch } from "@tabler/icons-react";
+import { useChatsQuery, useSearchChatsQuery } from "../queries/ai-chat-query";
+import { useDebouncedValue } from "@mantine/hooks";
+import { useTranslation } from "react-i18next";
+import classes from "../styles/aside-chat-panel.module.css";
+
+type Props = {
+  activeChatId: string | undefined;
+  onSelect: (chatId: string) => void;
+};
+
+export default function AsideChatHistory({ activeChatId, onSelect }: Props) {
+  const { t } = useTranslation();
+  const [searchValue, setSearchValue] = useState("");
+  const [debouncedSearch] = useDebouncedValue(searchValue, 300);
+
+  const chatsQuery = useChatsQuery();
+  const searchQuery = useSearchChatsQuery(debouncedSearch);
+
+  const isSearching = debouncedSearch.length > 0;
+  const chats = isSearching
+    ? (searchQuery.data ?? [])
+    : (chatsQuery.data?.pages.flatMap((p) => p.items) ?? []);
+  const isLoading = isSearching ? searchQuery.isLoading : chatsQuery.isLoading;
+
+  return (
+    <div>
+      <TextInput
+        placeholder={t("Search chats...")}
+        leftSection={<IconSearch size={14} />}
+        size="xs"
+        mb="xs"
+        value={searchValue}
+        onChange={(e) => setSearchValue(e.currentTarget.value)}
+      />
+
+      {isLoading ? (
+        <div style={{ display: "flex", justifyContent: "center", padding: 16 }}>
+          <Loader size="sm" />
+        </div>
+      ) : chats.length === 0 ? (
+        <Text size="sm" c="dimmed" ta="center" py="md">
+          {isSearching ? t("No chats found") : t("No chat history")}
+        </Text>
+      ) : (
+        <ScrollArea.Autosize mah={300} scrollbars="y">
+          <div className={classes.historyList}>
+            {chats.map((chat) => (
+              <div
+                key={chat.id}
+                className={classes.historyItem}
+                data-active={chat.id === activeChatId || undefined}
+                onClick={() => onSelect(chat.id)}
+              >
+                <span className={classes.historyItemTitle}>
+                  {chat.title || t("Untitled chat")}
+                </span>
+              </div>
+            ))}
+          </div>
+        </ScrollArea.Autosize>
+      )}
+    </div>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/aside-chat-panel.tsx b/apps/client/src/ee/ai-chat/components/aside-chat-panel.tsx
new file mode 100644
index 00000000..bd2b9569
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/aside-chat-panel.tsx
@@ -0,0 +1,258 @@
+import { useState, useEffect, useCallback } from "react";
+import { ActionIcon, Popover, Tooltip, UnstyledButton } from "@mantine/core";
+import {
+  IconPlus,
+  IconChevronDown,
+  IconArrowsDiagonal,
+  IconX,
+  IconSparkles,
+  IconFileText,
+  IconLanguage,
+  IconSearch,
+} from "@tabler/icons-react";
+import { useAtom } from "jotai";
+import { useNavigate, useParams } from "react-router-dom";
+import { useTranslation } from "react-i18next";
+import { asideStateAtom } from "@/components/layouts/global/hooks/atoms/sidebar-atom";
+import { usePageQuery } from "@/features/page/queries/page-query";
+import { extractPageSlugId } from "@/lib";
+import { useChatStream } from "../hooks/use-chat-stream";
+import { useChatInfoQuery } from "../queries/ai-chat-query";
+import ChatMessageList from "./chat-message-list";
+import ChatInput from "./chat-input";
+import AsideChatHistory from "./aside-chat-history";
+import type { ChatAttachment, PageMention } from "../types/ai-chat.types";
+import classes from "../styles/aside-chat-panel.module.css";
+
+type QuickAction = {
+  icon: React.ReactNode;
+  label: string;
+  prompt: string;
+};
+
+export default function AsideChatPanel() {
+  const { t } = useTranslation();
+  const navigate = useNavigate();
+  const [, setAsideState] = useAtom(asideStateAtom);
+  const [chatId, setChatId] = useState<string | undefined>(undefined);
+  const [historyOpen, setHistoryOpen] = useState(false);
+  const [contextPages, setContextPages] = useState<PageMention[]>([]);
+  const { pageSlug } = useParams();
+  const slugId = extractPageSlugId(pageSlug);
+  const { data: page } = usePageQuery({ pageId: slugId });
+
+  const chatInfoQuery = useChatInfoQuery(chatId);
+  const {
+    messages,
+    streamingContent,
+    streamingToolCalls,
+    isStreaming,
+    error,
+    sendMessage,
+    stopGeneration,
+    hydrateFromServer,
+  } = useChatStream(chatId, {
+    onChatCreated: (newChatId) => {
+      setChatId(newChatId);
+    },
+  });
+
+  useEffect(() => {
+    if (page && !chatId) {
+      setContextPages([{ id: page.id, title: page.title || "", slugId: page.slugId }]);
+    }
+  }, [page, chatId]);
+
+  const handleRemoveContextPage = useCallback((pageId: string) => {
+    setContextPages((prev) => prev.filter((p) => p.id !== pageId));
+  }, []);
+
+  useEffect(() => {
+    if (chatInfoQuery.data?.messages) {
+      hydrateFromServer(chatInfoQuery.data.messages);
+    }
+  }, [chatInfoQuery.data, hydrateFromServer]);
+
+  // Drop the open chatId if the current user lost access to it (404/403 on
+  // the info fetch). Reverts the panel to a fresh chat instead of presenting
+  // an input tied to a chat the user does not own.
+  useEffect(() => {
+    if (chatId && chatInfoQuery.isError) {
+      setChatId(undefined);
+    }
+  }, [chatId, chatInfoQuery.isError]);
+
+  const handleNewChat = useCallback(
+    (event: React.MouseEvent<HTMLAnchorElement>) => {
+      if (
+        event.button !== 0 ||
+        event.ctrlKey ||
+        event.metaKey ||
+        event.shiftKey
+      ) {
+        return;
+      }
+      event.preventDefault();
+      setChatId(undefined);
+      if (page) {
+        setContextPages([
+          { id: page.id, title: page.title || "", slugId: page.slugId },
+        ]);
+      }
+    },
+    [page],
+  );
+
+  const handleSelectChat = useCallback((selectedChatId: string) => {
+    setChatId(selectedChatId);
+    setHistoryOpen(false);
+  }, []);
+
+  const handleExpand = useCallback(() => {
+    if (chatId) {
+      navigate(`/ai/chat/${chatId}`);
+    } else {
+      navigate("/ai");
+    }
+    setAsideState({ tab: "", isAsideOpen: false });
+  }, [chatId, navigate, setAsideState]);
+
+  const handleClose = useCallback(() => {
+    setAsideState({ tab: "", isAsideOpen: false });
+  }, [setAsideState]);
+
+  const handleSend = useCallback(
+    (content: string, mentions: PageMention[], attachments: ChatAttachment[]) => {
+      const contextPageId = contextPages.length > 0 ? contextPages[0].id : undefined;
+      sendMessage(content, mentions, attachments, contextPageId);
+    },
+    [sendMessage, contextPages],
+  );
+
+  const handleQuickAction = useCallback(
+    (prompt: string) => {
+      handleSend(prompt, [], []);
+    },
+    [handleSend],
+  );
+
+  const hasMessages = messages.length > 0 || isStreaming;
+
+  const quickActions: QuickAction[] = [
+    { icon: <IconFileText size={16} />, label: t("Summarize this page"), prompt: "Summarize this page" },
+    { icon: <IconLanguage size={16} />, label: t("Translate this page"), prompt: "Translate this page" },
+    { icon: <IconSearch size={16} />, label: t("Analyze for insights"), prompt: "Analyze this page for insights" },
+  ];
+
+  return (
+    <div className={classes.panel}>
+      <div className={classes.toolbar}>
+        <Popover
+          opened={historyOpen}
+          onChange={setHistoryOpen}
+          position="bottom-start"
+          width={280}
+          shadow="md"
+        >
+          <Popover.Target>
+            <UnstyledButton
+              className={classes.titleButton}
+              onClick={() => setHistoryOpen((o) => !o)}
+            >
+              <span className={classes.titleText}>
+                {chatInfoQuery.data?.chat?.title || t("New chat")}
+              </span>
+              <IconChevronDown size={16} stroke={1.75} />
+            </UnstyledButton>
+          </Popover.Target>
+          <Popover.Dropdown>
+            <AsideChatHistory activeChatId={chatId} onSelect={handleSelectChat} />
+          </Popover.Dropdown>
+        </Popover>
+
+        <div className={classes.toolbarSpacer} />
+
+        <Tooltip label={t("New chat")} openDelay={250}>
+          <ActionIcon
+            component="a"
+            href="/ai"
+            variant="subtle"
+            color="dark"
+            onClick={handleNewChat}
+          >
+            <IconPlus size={20} stroke={1.75} />
+          </ActionIcon>
+        </Tooltip>
+
+        <Tooltip label={t("Open full page")} openDelay={250}>
+          <ActionIcon variant="subtle" color="dark" onClick={handleExpand}>
+            <IconArrowsDiagonal size={18} stroke={1.5} />
+          </ActionIcon>
+        </Tooltip>
+
+        <Tooltip label={t("Close")} openDelay={250}>
+          <ActionIcon variant="subtle" color="dark" onClick={handleClose}>
+            <IconX size={20} stroke={1.75} />
+          </ActionIcon>
+        </Tooltip>
+      </div>
+
+      {error && (
+        <div
+          style={{
+            padding: "var(--mantine-spacing-xs) var(--mantine-spacing-sm)",
+            color: "var(--mantine-color-red-6)",
+            fontSize: "var(--mantine-font-size-xs)",
+          }}
+        >
+          {error}
+        </div>
+      )}
+
+      {hasMessages ? (
+        <>
+          <div className={classes.messages} data-aside-chat>
+            <ChatMessageList
+              messages={messages}
+              isStreaming={isStreaming}
+              streamingContent={streamingContent}
+              streamingToolCalls={streamingToolCalls}
+            />
+          </div>
+        </>
+      ) : (
+        <div className={classes.emptyState}>
+          <IconSparkles size={36} stroke={1.5} className={classes.emptyStateIcon} />
+          <div className={classes.emptyStateTitle}>{t("How can I help you today?")}</div>
+          <div className={classes.quickActions}>
+            {quickActions.map((action) => (
+              <button
+                key={action.label}
+                type="button"
+                className={classes.quickAction}
+                onClick={() => handleQuickAction(action.prompt)}
+              >
+                <span className={classes.quickActionIcon}>{action.icon}</span>
+                {action.label}
+              </button>
+            ))}
+          </div>
+        </div>
+      )}
+
+      <div className={classes.inputArea}>
+        <ChatInput
+          isStreaming={isStreaming}
+          onSend={handleSend}
+          onStop={stopGeneration}
+          placeholder={t("Ask anything...")}
+          autofocus={false}
+          contextPages={contextPages}
+          onRemoveContextPage={handleRemoveContextPage}
+          variant="flat"
+          chatId={chatId}
+        />
+      </div>
+    </div>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/chat-empty-state.tsx b/apps/client/src/ee/ai-chat/components/chat-empty-state.tsx
new file mode 100644
index 00000000..d7bacf18
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/chat-empty-state.tsx
@@ -0,0 +1,91 @@
+import {
+  IconSparkles,
+  IconSearch,
+  IconFilePlus,
+  IconEdit,
+  IconFileText,
+} from "@tabler/icons-react";
+import { useTranslation } from "react-i18next";
+import ChatInput from "./chat-input";
+import type { ChatAttachment, PageMention } from "../types/ai-chat.types";
+import classes from "../styles/ai-chat.module.css";
+
+type Suggestion = {
+  icon: React.ReactNode;
+  text: string;
+  prompt: string;
+};
+
+const SUGGESTIONS: Suggestion[] = [
+  {
+    icon: <IconSearch size={16} />,
+    text: "Search across all pages",
+    prompt: "Search for pages about ",
+  },
+  {
+    icon: <IconFilePlus size={16} />,
+    text: "Create a new page",
+    prompt: "Create a new page titled ",
+  },
+  {
+    icon: <IconFileText size={16} />,
+    text: "Summarize a page",
+    prompt: "Summarize the page @",
+  },
+  {
+    icon: <IconEdit size={16} />,
+    text: "Update page content",
+    prompt: "Update the page @",
+  },
+];
+
+type Props = {
+  isStreaming: boolean;
+  onSend: (content: string, mentions: PageMention[], attachments: ChatAttachment[]) => void;
+  onStop: () => void;
+};
+
+export default function ChatEmptyState({ isStreaming, onSend, onStop }: Props) {
+  const { t } = useTranslation();
+
+  const handleSuggestionClick = (prompt: string) => {
+    onSend(prompt, [], []);
+  };
+
+  return (
+    <div className={classes.emptyState}>
+      <IconSparkles size={48} stroke={1.5} className={classes.emptyStateIcon} />
+      <div className={classes.emptyStateBrand}>{t("Docmost AI")}</div>
+      <div className={classes.emptyStateTitle}>
+        {t("What can I help you with?")}
+      </div>
+
+      <div className={classes.emptyStateInput}>
+        <ChatInput
+          isStreaming={isStreaming}
+          onSend={onSend}
+          onStop={onStop}
+          placeholder="Ask anything... Use @ to mention pages"
+          autofocus
+        />
+      </div>
+
+      <div className={classes.suggestionsSection}>
+        <div className={classes.suggestionsLabel}>Get started</div>
+        <div className={classes.suggestionsGrid}>
+          {SUGGESTIONS.map((s) => (
+            <button
+              key={s.text}
+              type="button"
+              className={classes.suggestionCard}
+              onClick={() => handleSuggestionClick(s.prompt)}
+            >
+              <span className={classes.suggestionIcon}>{s.icon}</span>
+              <span className={classes.suggestionText}>{s.text}</span>
+            </button>
+          ))}
+        </div>
+      </div>
+    </div>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/chat-input.tsx b/apps/client/src/ee/ai-chat/components/chat-input.tsx
new file mode 100644
index 00000000..d003adfb
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/chat-input.tsx
@@ -0,0 +1,409 @@
+import { useCallback, useRef, useEffect, useState } from "react";
+import { useTranslation } from "react-i18next";
+import { IconArrowUp, IconPaperclip, IconPlayerStopFilled, IconX, IconFile, IconPhoto, IconPlus, IconAt, IconFileText } from "@tabler/icons-react";
+import { Popover } from "@mantine/core";
+import { notifications } from "@mantine/notifications";
+import { EditorContent, ReactNodeViewRenderer, useEditor } from "@tiptap/react";
+import { Placeholder } from "@tiptap/extension-placeholder";
+import { CharacterCount } from "@tiptap/extensions";
+import { StarterKit } from "@tiptap/starter-kit";
+import { Mention, LinkExtension } from "@docmost/editor-ext";
+import EmojiCommand from "@/features/editor/extensions/emoji-command";
+import mentionRenderItems from "@/features/editor/components/mention/mention-suggestion";
+import MentionView from "@/features/editor/components/mention/mention-view";
+import { uploadChatFile } from "../services/ai-chat-service";
+import type { ChatAttachment, PageMention } from "../types/ai-chat.types";
+import classes from "../styles/chat-input.module.css";
+
+type PendingAttachment = ChatAttachment & { uploading: boolean };
+
+const IMAGE_EXTENSIONS = ["png", "jpg", "jpeg", "webp", "gif"];
+const ACCEPTED_FILE_TYPES = ".pdf,.docx,.txt,.csv,.md,.png,.jpg,.jpeg,.webp";
+// Kept in sync with MAX_ATTACHMENTS_PER_MESSAGE in apps/server/src/ee/ai-chat/ai-chat-limits.ts
+const MAX_ATTACHMENTS_PER_MESSAGE = 5;
+
+type Props = {
+  isStreaming: boolean;
+  onSend: (content: string, mentions: PageMention[], attachments: ChatAttachment[]) => void;
+  onStop: () => void;
+  placeholder?: string;
+  autofocus?: boolean;
+  contextPages?: PageMention[];
+  onRemoveContextPage?: (pageId: string) => void;
+  variant?: "card" | "flat";
+  showDisclaimer?: boolean;
+  chatId?: string;
+};
+
+function extractMentions(json: any): PageMention[] {
+  const mentions: PageMention[] = [];
+  const seen = new Set<string>();
+
+  function walk(node: any) {
+    if (node.type === "mention" && node.attrs?.entityType === "page" && node.attrs?.entityId) {
+      if (!seen.has(node.attrs.entityId)) {
+        seen.add(node.attrs.entityId);
+        mentions.push({
+          id: node.attrs.entityId,
+          title: node.attrs.label || "",
+          slugId: node.attrs.slugId || "",
+        });
+      }
+    }
+    if (node.content) {
+      for (const child of node.content) {
+        walk(child);
+      }
+    }
+  }
+
+  walk(json);
+  return mentions;
+}
+
+function editorJsonToText(json: any): string {
+  let text = "";
+
+  function walk(node: any) {
+    if (node.type === "text") {
+      text += node.text || "";
+    } else if (node.type === "mention") {
+      text += `@${node.attrs?.label || ""}`;
+    } else if (node.type === "paragraph") {
+      if (text.length > 0) text += "\n";
+      if (node.content) {
+        for (const child of node.content) {
+          walk(child);
+        }
+      }
+      return;
+    }
+    if (node.content) {
+      for (const child of node.content) {
+        walk(child);
+      }
+    }
+  }
+
+  walk(json);
+  return text;
+}
+
+export default function ChatInput({
+  isStreaming,
+  onSend,
+  onStop,
+  placeholder,
+  autofocus = true,
+  contextPages,
+  onRemoveContextPage,
+  variant = "card",
+  showDisclaimer = true,
+  chatId,
+}: Props) {
+  const chatIdRef = useRef(chatId);
+  chatIdRef.current = chatId;
+  const { t } = useTranslation();
+  const [isEmpty, setIsEmpty] = useState(true);
+  const [pendingAttachments, setPendingAttachments] = useState<PendingAttachment[]>([]);
+  const [plusMenuOpen, setPlusMenuOpen] = useState(false);
+  const fileInputRef = useRef<HTMLInputElement>(null);
+  const onSendRef = useRef(onSend);
+  onSendRef.current = onSend;
+
+  const handleFileSelect = useCallback(async (files: FileList | null) => {
+    if (!files?.length) return;
+
+    const room = MAX_ATTACHMENTS_PER_MESSAGE - pendingAttachments.length;
+    if (room <= 0) {
+      notifications.show({
+        color: "yellow",
+        message: t("You can attach up to {{max}} files per message.", {
+          max: MAX_ATTACHMENTS_PER_MESSAGE,
+        }),
+      });
+      if (fileInputRef.current) fileInputRef.current.value = "";
+      return;
+    }
+
+    const incoming = Array.from(files);
+    const accepted = incoming.slice(0, room);
+
+    if (incoming.length > accepted.length) {
+      notifications.show({
+        color: "yellow",
+        message: t(
+          "Only the first {{n}} file(s) were added (max {{max}} per message).",
+          { n: accepted.length, max: MAX_ATTACHMENTS_PER_MESSAGE },
+        ),
+      });
+    }
+
+    for (const file of accepted) {
+      const tempId = `uploading-${Date.now()}-${Math.random()}`;
+      const ext = file.name.split(".").pop()?.toLowerCase() || "";
+
+      const placeholder: PendingAttachment = {
+        id: tempId,
+        fileName: file.name,
+        fileExt: ext,
+        fileSize: file.size,
+        mimeType: file.type,
+        uploading: true,
+      };
+
+      setPendingAttachments((prev) => [...prev, placeholder]);
+
+      try {
+        const uploaded = await uploadChatFile(file, chatIdRef.current);
+        setPendingAttachments((prev) =>
+          prev.map((a) =>
+            a.id === tempId ? { ...uploaded, uploading: false } : a,
+          ),
+        );
+      } catch {
+        setPendingAttachments((prev) => prev.filter((a) => a.id !== tempId));
+      }
+    }
+
+    if (fileInputRef.current) {
+      fileInputRef.current.value = "";
+    }
+  }, [pendingAttachments.length, t]);
+
+  const removeAttachment = useCallback((id: string) => {
+    setPendingAttachments((prev) => prev.filter((a) => a.id !== id));
+  }, []);
+
+  const handleSubmit = useCallback(() => {
+    if (!editor || isStreaming) return;
+    const json = editor.getJSON();
+    const text = editorJsonToText(json).trim();
+    const readyAttachments = pendingAttachments.filter((a) => !a.uploading);
+    if (!text && readyAttachments.length === 0) return;
+
+    const mentions = extractMentions(json);
+    onSendRef.current(text, mentions, readyAttachments);
+    editor.commands.clearContent();
+    editor.commands.focus();
+    setPendingAttachments([]);
+  }, [isStreaming, pendingAttachments]);
+
+  const handleSubmitRef = useRef(handleSubmit);
+  handleSubmitRef.current = handleSubmit;
+
+  const editor = useEditor({
+    extensions: [
+      StarterKit.configure({
+        gapcursor: false,
+        dropcursor: false,
+        link: false,
+      }),
+      Placeholder.configure({
+        placeholder: placeholder || "Ask anything... Use @ to mention pages",
+      }),
+      CharacterCount.configure({
+        limit: 50000,
+      }),
+      LinkExtension,
+      EmojiCommand,
+      Mention.configure({
+        suggestion: {
+          allowSpaces: true,
+          items: () => [],
+          // @ts-ignore
+          render: mentionRenderItems,
+        },
+        HTMLAttributes: {
+          class: "mention",
+        },
+      }).extend({
+        addNodeView() {
+          this.editor.isInitialized = true;
+          return ReactNodeViewRenderer(MentionView);
+        },
+      }),
+    ],
+    editorProps: {
+      handleDOMEvents: {
+        keydown: (_view, event) => {
+          if (
+            ["ArrowUp", "ArrowDown", "ArrowLeft", "ArrowRight", "Enter"].includes(
+              event.key,
+            )
+          ) {
+            const emojiCommand = document.querySelector("#emoji-command");
+            const mentionPopup = document.querySelector("#mention");
+            if (emojiCommand || mentionPopup) {
+              return true;
+            }
+          }
+
+          if (event.key === "Enter" && !event.shiftKey) {
+            event.preventDefault();
+            handleSubmitRef.current();
+            return true;
+          }
+        },
+      },
+    },
+    content: "",
+    editable: true,
+    immediatelyRender: true,
+    shouldRerenderOnTransaction: false,
+    autofocus: autofocus ? "end" : false,
+    onUpdate: ({ editor: e }) => {
+      setIsEmpty(!e.getText().trim());
+    },
+  });
+
+  useEffect(() => {
+    if (editor && autofocus) {
+      editor.commands.focus();
+    }
+  }, [editor]);
+
+  const hasContent = !isEmpty || pendingAttachments.some((a) => !a.uploading) || (contextPages?.length ?? 0) > 0;
+
+  const wrapperClass = variant === "flat" ? classes.inputWrapperFlat : classes.inputWrapper;
+
+  return (
+    <>
+    <div className={wrapperClass} data-chat-input>
+      <input
+        ref={fileInputRef}
+        type="file"
+        accept={ACCEPTED_FILE_TYPES}
+        multiple
+        style={{ display: "none" }}
+        onChange={(e) => handleFileSelect(e.target.files)}
+      />
+
+      {((contextPages?.length ?? 0) > 0 || pendingAttachments.length > 0) && (
+        <div className={classes.attachmentChips}>
+          {contextPages?.map((page) => (
+            <div key={page.id} className={classes.attachmentChip}>
+              <IconFileText size={14} />
+              <span className={classes.attachmentChipName}>
+                {page.title || "Untitled"}
+              </span>
+              {onRemoveContextPage && (
+                <button
+                  type="button"
+                  className={classes.attachmentChipRemove}
+                  onClick={() => onRemoveContextPage(page.id)}
+                  aria-label={`Remove ${page.title}`}
+                >
+                  <IconX size={12} />
+                </button>
+              )}
+            </div>
+          ))}
+          {pendingAttachments.map((attachment) => (
+            <div
+              key={attachment.id}
+              className={`${classes.attachmentChip} ${attachment.uploading ? classes.attachmentChipUploading : ""}`}
+            >
+              {IMAGE_EXTENSIONS.includes(attachment.fileExt) ? (
+                <IconPhoto size={14} />
+              ) : (
+                <IconFile size={14} />
+              )}
+              <span className={classes.attachmentChipName}>
+                {attachment.fileName}
+              </span>
+              {!attachment.uploading && (
+                <button
+                  type="button"
+                  className={classes.attachmentChipRemove}
+                  onClick={() => removeAttachment(attachment.id)}
+                  aria-label={`Remove ${attachment.fileName}`}
+                >
+                  <IconX size={12} />
+                </button>
+              )}
+            </div>
+          ))}
+        </div>
+      )}
+
+      <EditorContent editor={editor} className={classes.editorContent} />
+      <div className={classes.actions}>
+        <Popover opened={plusMenuOpen} onChange={setPlusMenuOpen} position="top-start" width={220} shadow="md">
+          <Popover.Target>
+            <button
+              type="button"
+              className={classes.plusButton}
+              onClick={() => setPlusMenuOpen((o) => !o)}
+              aria-label="Add content"
+            >
+              <IconPlus size={14} />
+            </button>
+          </Popover.Target>
+          <Popover.Dropdown p={4}>
+            <button
+              type="button"
+              className={classes.plusMenuItem}
+              onClick={() => {
+                fileInputRef.current?.click();
+                setPlusMenuOpen(false);
+              }}
+              disabled={pendingAttachments.length >= MAX_ATTACHMENTS_PER_MESSAGE}
+              title={
+                pendingAttachments.length >= MAX_ATTACHMENTS_PER_MESSAGE
+                  ? t("Max {{max}} files per message", {
+                      max: MAX_ATTACHMENTS_PER_MESSAGE,
+                    })
+                  : undefined
+              }
+            >
+              <IconPaperclip size={16} className={classes.plusMenuIcon} />
+              {t("Add files")}
+            </button>
+            <button
+              type="button"
+              className={classes.plusMenuItem}
+              onClick={() => {
+                editor?.commands.insertContent("@");
+                editor?.commands.focus();
+                setPlusMenuOpen(false);
+              }}
+            >
+              <IconAt size={16} className={classes.plusMenuIcon} />
+              Mention a page
+            </button>
+          </Popover.Dropdown>
+        </Popover>
+
+        <div style={{ flex: 1 }} />
+
+        {isStreaming ? (
+          <button
+            type="button"
+            className={classes.stopButton}
+            onClick={onStop}
+            aria-label="Stop generation"
+          >
+            <IconPlayerStopFilled size={14} />
+          </button>
+        ) : (
+          <button
+            type="button"
+            className={classes.sendButton}
+            onClick={handleSubmit}
+            disabled={!hasContent}
+            aria-label="Send message"
+          >
+            <IconArrowUp size={16} stroke={2.5} />
+          </button>
+        )}
+      </div>
+    </div>
+    {showDisclaimer && (
+      <div className={classes.disclaimer}>
+        {t("AI-generated content may not be accurate.")}
+      </div>
+    )}
+    </>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/chat-message-list.tsx b/apps/client/src/ee/ai-chat/components/chat-message-list.tsx
new file mode 100644
index 00000000..3a6fffef
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/chat-message-list.tsx
@@ -0,0 +1,174 @@
+import { useEffect, useRef, useCallback, useState } from "react";
+import { ErrorBoundary } from "react-error-boundary";
+import { IconArrowDown, IconAlertTriangle } from "@tabler/icons-react";
+import { useTranslation } from "react-i18next";
+import type { AiChatMessage, AiChatToolCall } from "../types/ai-chat.types";
+import ChatMessage from "./chat-message";
+import classes from "../styles/ai-chat.module.css";
+
+function ChatMessageErrorFallback() {
+  const { t } = useTranslation();
+  return (
+    <div className={classes.messageErrorFallback}>
+      <IconAlertTriangle size={14} />
+      <span>{t("Failed to render this message.")}</span>
+    </div>
+  );
+}
+
+type Props = {
+  messages: AiChatMessage[];
+  isStreaming: boolean;
+  streamingContent: string;
+  streamingToolCalls: AiChatToolCall[];
+};
+
+const BOTTOM_THRESHOLD_PX = 32;
+const SCROLL_UP_THRESHOLD_PX = 5;
+const SMOOTH_SCROLL_SETTLE_MS = 600;
+
+export default function ChatMessageList({
+  messages,
+  isStreaming,
+  streamingContent,
+  streamingToolCalls,
+}: Props) {
+  const containerRef = useRef<HTMLDivElement>(null);
+  const bottomRef = useRef<HTMLDivElement>(null);
+  const isAtBottomRef = useRef(true);
+  const isAutoScrollingRef = useRef(false);
+  const prevScrollTopRef = useRef(0);
+  const [showScrollButton, setShowScrollButton] = useState(false);
+
+  const scrollToBottom = useCallback((behavior: ScrollBehavior = "smooth") => {
+    const container = containerRef.current;
+    if (!container) return;
+
+    isAutoScrollingRef.current = true;
+    const target = container.scrollHeight - container.clientHeight;
+    container.scrollTo({ top: target, behavior });
+    prevScrollTopRef.current = target;
+    isAtBottomRef.current = true;
+    setShowScrollButton(false);
+
+    if (behavior === "smooth") {
+      setTimeout(() => {
+        isAutoScrollingRef.current = false;
+        if (containerRef.current) {
+          prevScrollTopRef.current = containerRef.current.scrollTop;
+        }
+      }, SMOOTH_SCROLL_SETTLE_MS);
+    } else {
+      isAutoScrollingRef.current = false;
+    }
+  }, []);
+
+  const handleScroll = useCallback(() => {
+    if (isAutoScrollingRef.current) return;
+
+    const container = containerRef.current;
+    if (!container) return;
+
+    const currentScrollTop = container.scrollTop;
+    const scrolledUp =
+      currentScrollTop < prevScrollTopRef.current - SCROLL_UP_THRESHOLD_PX;
+    prevScrollTopRef.current = currentScrollTop;
+
+    const distanceFromBottom =
+      container.scrollHeight - currentScrollTop - container.clientHeight;
+    const atBottom = distanceFromBottom <= BOTTOM_THRESHOLD_PX;
+
+    if (scrolledUp) {
+      isAtBottomRef.current = atBottom;
+    } else if (atBottom) {
+      isAtBottomRef.current = true;
+    }
+
+    setShowScrollButton(!atBottom);
+  }, []);
+
+  useEffect(() => {
+    const container = containerRef.current;
+    if (!container) return;
+
+    container.addEventListener("scroll", handleScroll, { passive: true });
+    return () => container.removeEventListener("scroll", handleScroll);
+  }, [handleScroll]);
+
+  // Instant scroll during streaming to keep up with rapid updates
+  useEffect(() => {
+    if (isAtBottomRef.current) {
+      scrollToBottom("instant");
+    }
+  }, [streamingContent, streamingToolCalls.length, scrollToBottom]);
+
+  // Smooth scroll for new messages. Always force-scroll when the latest
+  // message is from the user (they just sent it), even if they were reading
+  // scrollback.
+  useEffect(() => {
+    const lastMessage = messages[messages.length - 1];
+    const lastIsUser = lastMessage?.role === "user";
+    if (lastIsUser || isAtBottomRef.current) {
+      scrollToBottom("smooth");
+      return;
+    }
+
+    // No auto-scroll: recompute from actual layout so that chat switches to
+    // content that doesn't overflow correctly hide the button even when no
+    // scroll event fires.
+    const container = containerRef.current;
+    if (!container) return;
+    const distanceFromBottom =
+      container.scrollHeight - container.scrollTop - container.clientHeight;
+    const atBottom = distanceFromBottom <= BOTTOM_THRESHOLD_PX;
+    isAtBottomRef.current = atBottom;
+    setShowScrollButton(!atBottom);
+  }, [messages, scrollToBottom]);
+
+  return (
+    <div className={classes.messageListWrapper}>
+      <div ref={containerRef} className={classes.messageList}>
+        {messages.map((msg) => (
+          <ErrorBoundary
+            key={msg.id}
+            fallback={<ChatMessageErrorFallback />}
+          >
+            <ChatMessage message={msg} />
+          </ErrorBoundary>
+        ))}
+        {isStreaming && (
+          <ErrorBoundary
+            resetKeys={[streamingContent, streamingToolCalls.length]}
+            fallback={<ChatMessageErrorFallback />}
+          >
+            <ChatMessage
+              message={{
+                id: "streaming",
+                chatId: "",
+                role: "assistant",
+                content: null,
+                toolCalls: null,
+                metadata: null,
+                createdAt: new Date().toISOString(),
+              }}
+              isStreaming
+              streamingContent={streamingContent}
+              streamingToolCalls={streamingToolCalls}
+            />
+          </ErrorBoundary>
+        )}
+        <div ref={bottomRef} />
+      </div>
+      {showScrollButton && (
+        <button
+          type="button"
+          aria-label="Scroll to bottom"
+          className={classes.scrollToBottomButton}
+          onClick={() => scrollToBottom("smooth")}
+        >
+          <IconArrowDown size={16} stroke={2} />
+        </button>
+      )}
+    </div>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/chat-message.tsx b/apps/client/src/ee/ai-chat/components/chat-message.tsx
new file mode 100644
index 00000000..d0e9443a
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/chat-message.tsx
@@ -0,0 +1,139 @@
+import { useCallback } from "react";
+import { useNavigate } from "react-router";
+import DOMPurify from "dompurify";
+import { ActionIcon, Tooltip } from "@mantine/core";
+import {
+  IconCheck,
+  IconCopy,
+  IconFile,
+  IconLoader2,
+  IconPhoto,
+} from "@tabler/icons-react";
+import { markdownToHtml } from "@docmost/editor-ext";
+import { CopyButton } from "@/components/common/copy-button";
+import type { AiChatMessage, AiChatToolCall } from "../types/ai-chat.types";
+import ChatToolGroup from "./chat-tool-group";
+import classes from "../styles/chat-message.module.css";
+import CopyTextButton from "@/components/common/copy.tsx";
+
+const chatSanitizer = DOMPurify();
+chatSanitizer.addHook("afterSanitizeAttributes", (node) => {
+  if (node.tagName === "A") {
+    const href = node.getAttribute("href") || "";
+    if (href.startsWith("http://") || href.startsWith("https://")) {
+      node.setAttribute("target", "_blank");
+      node.setAttribute("rel", "noopener noreferrer");
+    }
+  }
+});
+
+const IMAGE_EXTENSIONS = ["png", "jpg", "jpeg", "webp", "gif"];
+
+type Props = {
+  message: AiChatMessage;
+  isStreaming?: boolean;
+  streamingContent?: string;
+  streamingToolCalls?: AiChatToolCall[];
+};
+
+export default function ChatMessage({
+  message,
+  isStreaming,
+  streamingContent,
+  streamingToolCalls,
+}: Props) {
+  const navigate = useNavigate();
+
+  const handleContentClick = useCallback(
+    (e: React.MouseEvent<HTMLDivElement>) => {
+      const target = e.target as HTMLElement;
+      const anchor = target.closest("a");
+      if (!anchor) return;
+
+      const href = anchor.getAttribute("href");
+      if (href && (href.startsWith("/s/") || href.startsWith("/p/"))) {
+        e.preventDefault();
+        navigate(href);
+      }
+    },
+    [navigate],
+  );
+
+  if (message.role === "tool") return null;
+
+  const isUser = message.role === "user";
+  const content = isStreaming ? streamingContent : message.content;
+  const toolCalls = isStreaming ? streamingToolCalls : message.toolCalls;
+
+  if (isUser) {
+    const displayContent = (content || "").replace(
+      /\n\n<referenced_pages>[\s\S]*<\/referenced_pages>$/,
+      "",
+    );
+    const attachments =
+      (message.metadata?.attachments as {
+        id: string;
+        fileName: string;
+        fileExt: string;
+      }[]) || [];
+
+    return (
+      <div className={classes.userMessage}>
+        <div className={classes.userBubble}>
+          {attachments.length > 0 && (
+            <div className={classes.messageAttachments}>
+              {attachments.map((a) => (
+                <span key={a.id} className={classes.messageAttachmentChip}>
+                  {IMAGE_EXTENSIONS.includes(a.fileExt) ? (
+                    <IconPhoto size={13} />
+                  ) : (
+                    <IconFile size={13} />
+                  )}
+                  {a.fileName}
+                </span>
+              ))}
+            </div>
+          )}
+          {displayContent}
+        </div>
+      </div>
+    );
+  }
+
+  return (
+    <div className={classes.assistantMessage}>
+      <div className={classes.messageContent}>
+        {toolCalls && toolCalls.length > 0 && (
+          <ChatToolGroup toolCalls={toolCalls} isStreaming={isStreaming} />
+        )}
+        {content && (
+          <div
+            onClick={handleContentClick}
+            dangerouslySetInnerHTML={{
+              __html: chatSanitizer.sanitize(
+                markdownToHtml(content) as string,
+                { ADD_ATTR: ["target", "rel"] },
+              ),
+            }}
+          />
+        )}
+        {isStreaming && (
+          <>
+            {!content && (
+              <span className={classes.processingIndicator}>
+                <IconLoader2 size={16} className={classes.processingSpinner} />
+                Thinking
+              </span>
+            )}
+            <span className={classes.streamingCursor} />
+          </>
+        )}
+      </div>
+      {!isStreaming && message.content && (
+        <div className={classes.messageActions}>
+          <CopyTextButton text={message?.content} />
+        </div>
+      )}
+    </div>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/chat-tool-group.tsx b/apps/client/src/ee/ai-chat/components/chat-tool-group.tsx
new file mode 100644
index 00000000..b4e002f6
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/chat-tool-group.tsx
@@ -0,0 +1,56 @@
+import { useState } from "react";
+import {
+  IconChevronRight,
+  IconChevronDown,
+  IconLoader2,
+} from "@tabler/icons-react";
+import type { AiChatToolCall } from "../types/ai-chat.types";
+import ChatToolResult, { TOOL_LABELS } from "./chat-tool-result";
+import classes from "../styles/chat-message.module.css";
+
+type Props = {
+  toolCalls: AiChatToolCall[];
+  isStreaming?: boolean;
+};
+
+export default function ChatToolGroup({ toolCalls, isStreaming }: Props) {
+  const [expanded, setExpanded] = useState(false);
+
+  if (!toolCalls || toolCalls.length === 0) return null;
+
+  const activeCall =
+    isStreaming && toolCalls.length > 0
+      ? [...toolCalls].reverse().find((tc) => tc.result === undefined)
+      : undefined;
+
+  const activeLabel = activeCall
+    ? TOOL_LABELS[activeCall.name] || activeCall.name
+    : null;
+
+  return (
+    <div className={classes.toolGroup}>
+      <div
+        className={classes.toolGroupHeader}
+        onClick={() => setExpanded((prev) => !prev)}
+      >
+        {activeLabel ? (
+          <IconLoader2 size={12} className={classes.processingSpinner} />
+        ) : expanded ? (
+          <IconChevronDown size={12} />
+        ) : (
+          <IconChevronRight size={12} />
+        )}
+        <span className={classes.toolGroupLabel}>
+          {activeLabel ? `${activeLabel}…` : `Steps ${toolCalls.length}`}
+        </span>
+      </div>
+      {expanded && (
+        <div className={classes.toolGroupSteps}>
+          {toolCalls.map((tc) => (
+            <ChatToolResult key={tc.id} toolCall={tc} />
+          ))}
+        </div>
+      )}
+    </div>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/chat-tool-result.tsx b/apps/client/src/ee/ai-chat/components/chat-tool-result.tsx
new file mode 100644
index 00000000..55f20f91
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/chat-tool-result.tsx
@@ -0,0 +1,49 @@
+import { useState } from "react";
+import { IconChevronRight, IconChevronDown } from "@tabler/icons-react";
+import type { AiChatToolCall } from "../types/ai-chat.types";
+import classes from "../styles/chat-message.module.css";
+
+export const TOOL_LABELS: Record<string, string> = {
+  list_spaces: "Listed spaces",
+  search_pages: "Searched pages",
+  get_page: "Read page",
+  create_page: "Created page",
+  update_page: "Updated page",
+};
+
+type Props = {
+  toolCall: AiChatToolCall;
+};
+
+export default function ChatToolResult({ toolCall }: Props) {
+  const [expanded, setExpanded] = useState(false);
+  const label = TOOL_LABELS[toolCall.name] || toolCall.name;
+
+  return (
+    <div className={classes.toolStep}>
+      <div
+        className={classes.toolStepRow}
+        onClick={() => setExpanded((prev) => !prev)}
+      >
+        <span className={classes.toolStepBullet}>·</span>
+        {expanded ? (
+          <IconChevronDown size={12} />
+        ) : (
+          <IconChevronRight size={12} />
+        )}
+        <span>{label}</span>
+      </div>
+      {expanded && (
+        <div className={classes.toolStepDetails}>
+          <pre style={{ margin: 0, whiteSpace: "pre-wrap" }}>
+            {JSON.stringify(
+              { args: toolCall.args, result: toolCall.result },
+              null,
+              2,
+            )}
+          </pre>
+        </div>
+      )}
+    </div>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/components/enable-ai-chat.tsx b/apps/client/src/ee/ai-chat/components/enable-ai-chat.tsx
new file mode 100644
index 00000000..f4200e5b
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/components/enable-ai-chat.tsx
@@ -0,0 +1,67 @@
+import { Badge, Group, Text, Switch, Tooltip } from "@mantine/core";
+import { useAtom } from "jotai";
+import { workspaceAtom } from "@/features/user/atoms/current-user-atom.ts";
+import { useState } from "react";
+import { useTranslation } from "react-i18next";
+import { updateWorkspace } from "@/features/workspace/services/workspace-service.ts";
+import { notifications } from "@mantine/notifications";
+import { useHasFeature } from "@/ee/hooks/use-feature";
+import { Feature } from "@/ee/features";
+import { useUpgradeLabel } from "@/ee/hooks/use-upgrade-label";
+
+export default function EnableAiChat() {
+  const { t } = useTranslation();
+
+  return (
+    <Group justify="space-between" wrap="nowrap" gap="xl">
+      <div>
+        <Group gap="xs" align="center">
+          <Text size="md">{t("AI Chat")}</Text>
+          <Badge color="gray" variant="light" size="sm" radius="sm">
+            {t("Beta")}
+          </Badge>
+        </Group>
+        <Text size="sm" c="dimmed">
+          {t(
+            "Enable AI Chat to allow users to have multi-turn conversations with AI about your workspace content.",
+          )}
+        </Text>
+      </div>
+
+      <AiChatToggle />
+    </Group>
+  );
+}
+
+function AiChatToggle() {
+  const { t } = useTranslation();
+  const [workspace, setWorkspace] = useAtom(workspaceAtom);
+  const [checked, setChecked] = useState(workspace?.settings?.ai?.chat);
+  const hasAccess = useHasFeature(Feature.AI);
+  const upgradeLabel = useUpgradeLabel();
+
+  const handleChange = async (event: React.ChangeEvent<HTMLInputElement>) => {
+    const value = event.currentTarget.checked;
+    try {
+      const updatedWorkspace = await updateWorkspace({ aiChat: value } as any);
+      setChecked(value);
+      setWorkspace(updatedWorkspace);
+    } catch (err: any) {
+      notifications.show({
+        message: err?.response?.data?.message,
+        color: "red",
+      });
+    }
+  };
+
+  return (
+    <Tooltip label={upgradeLabel} disabled={hasAccess} refProp="rootRef">
+      <Switch
+        defaultChecked={checked}
+        onChange={handleChange}
+        disabled={!hasAccess}
+        aria-label={t("Toggle AI Chat")}
+      />
+    </Tooltip>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/hooks/use-chat-stream.ts b/apps/client/src/ee/ai-chat/hooks/use-chat-stream.ts
new file mode 100644
index 00000000..65a93a97
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/hooks/use-chat-stream.ts
@@ -0,0 +1,227 @@
+import { useState, useCallback, useEffect, useRef } from "react";
+import { useQueryClient } from "@tanstack/react-query";
+import { useNavigate } from "react-router-dom";
+import { sendChatMessage } from "../services/ai-chat-service";
+import type {
+  AiChatMessage,
+  AiChatStreamEvent,
+  AiChatToolCall,
+  ChatAttachment,
+  PageMention,
+} from "../types/ai-chat.types";
+
+type ChatStreamOptions = {
+  onChatCreated?: (chatId: string) => void;
+};
+
+export function useChatStream(
+  chatId: string | undefined,
+  options?: ChatStreamOptions,
+) {
+  const [messages, setMessages] = useState<AiChatMessage[]>([]);
+  const [streamingContent, setStreamingContent] = useState("");
+  const [streamingToolCalls, setStreamingToolCalls] = useState<AiChatToolCall[]>(
+    [],
+  );
+  const [isStreaming, setIsStreaming] = useState(false);
+  const [error, setError] = useState<string | null>(null);
+  const [errorCode, setErrorCode] = useState<string | null>(null);
+  const [isRetryable, setIsRetryable] = useState(false);
+  const abortRef = useRef<AbortController | null>(null);
+  const queryClient = useQueryClient();
+  const navigate = useNavigate();
+  const currentChatIdRef = useRef(chatId);
+  currentChatIdRef.current = chatId;
+  // Tracks which chatId the local `messages` state currently represents.
+  // Set when we seed from a server fetch AND when we optimistically own a
+  // freshly-created chat after `chat_created`. This is the single authority
+  // marker that keeps server-state effects from clobbering in-flight streams.
+  const hydratedChatIdRef = useRef<string | undefined>(undefined);
+
+  // Reset local state when the consumer switches to a different chat.
+  // Skip the reset if the new chatId is one the hook itself already claimed
+  // during a new-chat flow — in that case our optimistic state is the truth.
+  useEffect(() => {
+    if (chatId && chatId === hydratedChatIdRef.current) return;
+    hydratedChatIdRef.current = undefined;
+    setMessages([]);
+    setError(null);
+    setErrorCode(null);
+    setIsRetryable(false);
+  }, [chatId]);
+
+  const hydrateFromServer = useCallback((msgs: AiChatMessage[]) => {
+    const forId = currentChatIdRef.current;
+    if (!forId) return;
+    if (hydratedChatIdRef.current === forId) return;
+    hydratedChatIdRef.current = forId;
+    setMessages(msgs);
+  }, []);
+
+  const sendMessage = useCallback(
+    (content: string, mentions: PageMention[] = [], attachments: ChatAttachment[] = [], contextPageId?: string) => {
+      if (isStreaming || (!content.trim() && attachments.length === 0)) return;
+
+      setError(null);
+      setErrorCode(null);
+      setIsRetryable(false);
+      setIsStreaming(true);
+      setStreamingContent("");
+      setStreamingToolCalls([]);
+
+      const metadata: Record<string, unknown> = {};
+      if (mentions.length) {
+        metadata.mentionedPageIds = mentions.map((m) => m.id);
+      }
+      if (attachments.length) {
+        metadata.attachments = attachments.map((a) => ({
+          id: a.id,
+          fileName: a.fileName,
+          fileExt: a.fileExt,
+        }));
+      }
+
+      const userMessage: AiChatMessage = {
+        id: `temp-${Date.now()}`,
+        chatId: currentChatIdRef.current || "",
+        role: "user",
+        content,
+        toolCalls: null,
+        metadata: Object.keys(metadata).length ? metadata : null,
+        createdAt: new Date().toISOString(),
+      };
+
+      setMessages((prev) => [...prev, userMessage]);
+
+      const attachmentIds = attachments.map((a) => a.id);
+
+      const abortController = sendChatMessage(
+        {
+          chatId: currentChatIdRef.current,
+          content,
+          mentionedPageIds: mentions.map((m) => m.id),
+          ...(contextPageId && { contextPageId }),
+          ...(attachmentIds.length && { attachmentIds }),
+        },
+        (event: AiChatStreamEvent) => {
+          switch (event.type) {
+            case "chat_created":
+              currentChatIdRef.current = event.chatId;
+              // Claim authority over this new chatId so when the consumer's
+              // prop catches up via navigation/onChatCreated, the reset effect
+              // sees a match and preserves our optimistic messages.
+              hydratedChatIdRef.current = event.chatId;
+              if (options?.onChatCreated) {
+                options.onChatCreated(event.chatId);
+              } else {
+                navigate(`/ai/chat/${event.chatId}`, { replace: true });
+              }
+              queryClient.invalidateQueries({ queryKey: ["ai-chats"] });
+              break;
+            case "content":
+              setStreamingContent((prev) => prev + event.text);
+              break;
+            case "tool_call":
+              setStreamingToolCalls((prev) => [
+                ...prev,
+                {
+                  id: event.id,
+                  name: event.name,
+                  args: event.args,
+                },
+              ]);
+              break;
+            case "tool_result":
+              setStreamingToolCalls((prev) =>
+                prev.map((tc) =>
+                  tc.id === event.id ? { ...tc, result: event.result } : tc,
+                ),
+              );
+              break;
+            case "done": {
+              setStreamingContent((currentContent) => {
+                setStreamingToolCalls((currentToolCalls) => {
+                  const assistantMessage: AiChatMessage = {
+                    id: event.messageId,
+                    chatId: currentChatIdRef.current || "",
+                    role: "assistant",
+                    content: currentContent || null,
+                    toolCalls: currentToolCalls.length
+                      ? currentToolCalls
+                      : null,
+                    metadata: event.usage ? { tokenUsage: event.usage } : null,
+                    createdAt: new Date().toISOString(),
+                  };
+
+                  setMessages((prev) => [...prev, assistantMessage]);
+                  return [];
+                });
+                return "";
+              });
+              setIsStreaming(false);
+              queryClient.invalidateQueries({
+                queryKey: ["ai-chat", currentChatIdRef.current],
+              });
+              break;
+            }
+            case "error":
+              setError(event.message);
+              setErrorCode(event.code || null);
+              setIsRetryable(event.retryable || false);
+              setIsStreaming(false);
+              break;
+          }
+        },
+        (errorMsg) => {
+          setError(errorMsg);
+          setIsStreaming(false);
+        },
+        () => {
+          setIsStreaming(false);
+        },
+      );
+
+      abortRef.current = abortController;
+    },
+    [isStreaming, navigate, queryClient],
+  );
+
+  const stopGeneration = useCallback(() => {
+    abortRef.current?.abort();
+    abortRef.current = null;
+
+    setStreamingContent((currentContent) => {
+      setStreamingToolCalls((currentToolCalls) => {
+        if (currentContent || currentToolCalls.length > 0) {
+          const partialMessage: AiChatMessage = {
+            id: `stopped-${Date.now()}`,
+            chatId: currentChatIdRef.current || "",
+            role: "assistant",
+            content: currentContent || null,
+            toolCalls: currentToolCalls.length ? currentToolCalls : null,
+            metadata: null,
+            createdAt: new Date().toISOString(),
+          };
+          setMessages((prev) => [...prev, partialMessage]);
+        }
+        return [];
+      });
+      return "";
+    });
+
+    setIsStreaming(false);
+  }, []);
+
+  return {
+    messages,
+    streamingContent,
+    streamingToolCalls,
+    isStreaming,
+    error,
+    errorCode,
+    isRetryable,
+    sendMessage,
+    stopGeneration,
+    hydrateFromServer,
+  };
+}
diff --git a/apps/client/src/ee/ai-chat/pages/ai-chat.tsx b/apps/client/src/ee/ai-chat/pages/ai-chat.tsx
new file mode 100644
index 00000000..bb264b73
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/pages/ai-chat.tsx
@@ -0,0 +1,39 @@
+import { useParams } from "react-router-dom";
+import { ErrorBoundary } from "react-error-boundary";
+import { Button } from "@mantine/core";
+import { IconAlertTriangle } from "@tabler/icons-react";
+import { useTranslation } from "react-i18next";
+import AiChatLayout from "../components/ai-chat-layout";
+import { EmptyState } from "@/components/ui/empty-state.tsx";
+import classes from "../styles/ai-chat.module.css";
+
+export default function AiChat() {
+  const { t } = useTranslation();
+  const { chatId } = useParams<{ chatId: string }>();
+
+  return (
+    <div className={classes.layout}>
+      <ErrorBoundary
+        resetKeys={[chatId]}
+        fallbackRender={({ resetErrorBoundary }) => (
+          <EmptyState
+            icon={IconAlertTriangle}
+            title={t("Failed to load chat. An error occurred.")}
+            action={
+              <Button
+                variant="default"
+                size="sm"
+                mt="xs"
+                onClick={resetErrorBoundary}
+              >
+                {t("Try again")}
+              </Button>
+            }
+          />
+        )}
+      >
+        <AiChatLayout />
+      </ErrorBoundary>
+    </div>
+  );
+}
diff --git a/apps/client/src/ee/ai-chat/queries/ai-chat-query.ts b/apps/client/src/ee/ai-chat/queries/ai-chat-query.ts
new file mode 100644
index 00000000..8992a115
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/queries/ai-chat-query.ts
@@ -0,0 +1,61 @@
+import {
+  useQuery,
+  useMutation,
+  useQueryClient,
+  useInfiniteQuery,
+} from "@tanstack/react-query";
+import {
+  listChats,
+  getChatInfo,
+  deleteChat,
+  updateChatTitle,
+  searchChats,
+} from "../services/ai-chat-service";
+
+export function useChatsQuery() {
+  return useInfiniteQuery({
+    queryKey: ["ai-chats"],
+    queryFn: ({ pageParam }) =>
+      listChats({ cursor: pageParam, limit: 30 }),
+    initialPageParam: undefined as string | undefined,
+    getNextPageParam: (lastPage) =>
+      lastPage.meta.hasNextPage ? lastPage.meta.nextCursor : undefined,
+  });
+}
+
+export function useChatInfoQuery(chatId: string | undefined) {
+  return useQuery({
+    queryKey: ["ai-chat", chatId],
+    queryFn: () => getChatInfo(chatId!),
+    enabled: !!chatId,
+  });
+}
+
+export function useDeleteChatMutation() {
+  const queryClient = useQueryClient();
+  return useMutation({
+    mutationFn: (chatId: string) => deleteChat(chatId),
+    onSuccess: () => {
+      queryClient.invalidateQueries({ queryKey: ["ai-chats"] });
+    },
+  });
+}
+
+export function useUpdateChatTitleMutation() {
+  const queryClient = useQueryClient();
+  return useMutation({
+    mutationFn: ({ chatId, title }: { chatId: string; title: string }) =>
+      updateChatTitle(chatId, title),
+    onSuccess: () => {
+      queryClient.invalidateQueries({ queryKey: ["ai-chats"] });
+    },
+  });
+}
+
+export function useSearchChatsQuery(query: string) {
+  return useQuery({
+    queryKey: ["ai-chats-search", query],
+    queryFn: () => searchChats(query),
+    enabled: query.length > 0,
+  });
+}
diff --git a/apps/client/src/ee/ai-chat/services/ai-chat-service.ts b/apps/client/src/ee/ai-chat/services/ai-chat-service.ts
new file mode 100644
index 00000000..2932372e
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/services/ai-chat-service.ts
@@ -0,0 +1,144 @@
+import api from "@/lib/api-client.ts";
+import type {
+  AiChat,
+  AiChatMessage,
+  AiChatStreamEvent,
+  ChatAttachment,
+} from "../types/ai-chat.types";
+import { IPagination } from "@/lib/types.ts";
+
+export async function createChat(): Promise<AiChat> {
+  const req = await api.post<AiChat>("/ai/chats/create");
+  return req.data;
+}
+
+export async function listChats(params?: {
+  limit?: number;
+  cursor?: string;
+}): Promise<IPagination<AiChat>> {
+  const req = await api.post("/ai/chats", params);
+  return req.data;
+}
+
+export async function getChatInfo(
+  chatId: string,
+): Promise<{ chat: AiChat; messages: AiChatMessage[] }> {
+  const req = await api.post("/ai/chats/info", { chatId });
+  return req.data;
+}
+
+export async function deleteChat(chatId: string): Promise<void> {
+  await api.post("/ai/chats/delete", { chatId });
+}
+
+export async function updateChatTitle(
+  chatId: string,
+  title: string,
+): Promise<void> {
+  await api.post("/ai/chats/update", { chatId, title });
+}
+
+export async function searchChats(query: string): Promise<AiChat[]> {
+  const req = await api.post("/ai/chats/search", { query });
+  return req.data;
+}
+
+export async function uploadChatFile(
+  file: File,
+  chatId?: string,
+): Promise<ChatAttachment> {
+  const formData = new FormData();
+  formData.append("file", file);
+  if (chatId) {
+    formData.append("chatId", chatId);
+  }
+  return await api.post("/ai/chats/upload", formData, {
+    headers: { "Content-Type": "multipart/form-data" },
+  });
+}
+
+export function sendChatMessage(
+  params: {
+    chatId?: string;
+    content: string;
+    mentionedPageIds?: string[];
+    contextPageId?: string;
+    attachmentIds?: string[];
+  },
+  onEvent: (event: AiChatStreamEvent) => void,
+  onError?: (error: string) => void,
+  onComplete?: () => void,
+): AbortController {
+  const abortController = new AbortController();
+
+  (async () => {
+    try {
+      const response = await fetch("/api/ai/chats/send", {
+        method: "POST",
+        headers: { "Content-Type": "application/json" },
+        body: JSON.stringify(params),
+        signal: abortController.signal,
+        credentials: "include",
+      });
+
+      if (!response.ok) {
+        const errorBody = await response.text();
+        let errorMessage = `HTTP error ${response.status}`;
+        try {
+          const parsed = JSON.parse(errorBody);
+          errorMessage = parsed.message || errorMessage;
+        } catch {
+          // use default
+        }
+        onError?.(errorMessage);
+        return;
+      }
+
+      const reader = response.body?.getReader();
+      const decoder = new TextDecoder();
+
+      if (!reader) {
+        onError?.("Response body is not readable");
+        return;
+      }
+
+      let buffer = "";
+      try {
+        while (true) {
+          const { done, value } = await reader.read();
+          if (done) break;
+
+          buffer += decoder.decode(value, { stream: true });
+          const lines = buffer.split("\n");
+          buffer = lines.pop() || "";
+
+          for (const line of lines) {
+            if (line.startsWith("data: ")) {
+              const data = line.slice(6);
+              if (data === "[DONE]") {
+                onComplete?.();
+                return;
+              }
+              try {
+                const parsed = JSON.parse(data) as AiChatStreamEvent;
+                onEvent(parsed);
+              } catch {
+                // Skip invalid JSON
+              }
+            }
+          }
+        }
+      } finally {
+        reader.releaseLock();
+      }
+
+      onComplete?.();
+    } catch (error: any) {
+      if (error.name !== "AbortError") {
+        onError?.(error.message);
+      }
+    }
+  })();
+
+  return abortController;
+}
diff --git a/apps/client/src/ee/ai-chat/styles/ai-chat.module.css b/apps/client/src/ee/ai-chat/styles/ai-chat.module.css
new file mode 100644
index 00000000..27b0f0c0
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/styles/ai-chat.module.css
@@ -0,0 +1,169 @@
+.layout {
+  display: flex;
+  height: 100%;
+  width: 100%;
+}
+
+.main {
+  flex: 1;
+  display: flex;
+  flex-direction: column;
+  height: calc(100vh - 45px - 2 * var(--mantine-spacing-md));
+  max-width: 900px;
+  margin: 0 auto;
+  width: 100%;
+}
+
+.messageListWrapper {
+  flex: 1;
+  position: relative;
+  display: flex;
+  flex-direction: column;
+  min-height: 0;
+  height: 100%;
+  width: 100%;
+}
+
+.messageList {
+  flex: 1;
+  overflow-y: auto;
+  padding: var(--mantine-spacing-md) var(--mantine-spacing-lg);
+}
+
+.messageErrorFallback {
+  display: flex;
+  align-items: center;
+  gap: 6px;
+  padding: 8px 12px;
+  margin-bottom: var(--mantine-spacing-lg);
+  border-radius: var(--mantine-radius-sm);
+  background: light-dark(var(--mantine-color-gray-0), var(--mantine-color-dark-6));
+  color: light-dark(var(--mantine-color-gray-6), var(--mantine-color-dark-2));
+  font-size: var(--mantine-font-size-xs);
+}
+
+.scrollToBottomButton {
+  position: absolute;
+  bottom: 12px;
+  left: 50%;
+  transform: translateX(-50%);
+  width: 32px;
+  height: 32px;
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  border-radius: 50%;
+  border: 1px solid light-dark(var(--mantine-color-gray-3), var(--mantine-color-dark-4));
+  background: light-dark(var(--mantine-color-white), var(--mantine-color-dark-6));
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+  cursor: pointer;
+  padding: 0;
+  box-shadow: 0 2px 8px rgba(0, 0, 0, 0.08);
+  transition: background-color 120ms ease, border-color 120ms ease, transform 120ms ease;
+  z-index: 2;
+}
+
+.scrollToBottomButton:hover {
+  background: light-dark(var(--mantine-color-gray-0), var(--mantine-color-dark-5));
+  border-color: light-dark(var(--mantine-color-gray-4), var(--mantine-color-dark-3));
+}
+
+.scrollToBottomButton:active {
+  transform: translateX(-50%) scale(0.95);
+}
+
+.inputArea {
+  padding: var(--mantine-spacing-xs) var(--mantine-spacing-lg) var(--mantine-spacing-lg);
+}
+
+/* Empty state - Notion AI style centered layout */
+.emptyState {
+  flex: 1;
+  display: flex;
+  flex-direction: column;
+  align-items: center;
+  justify-content: center;
+  padding: var(--mantine-spacing-xl) var(--mantine-spacing-lg);
+}
+
+.emptyStateIcon {
+  width: 48px;
+  height: 48px;
+  margin-bottom: var(--mantine-spacing-sm);
+  color: light-dark(var(--mantine-color-gray-6), var(--mantine-color-dark-2));
+}
+
+.emptyStateBrand {
+  font-size: var(--mantine-font-size-xs);
+  font-weight: 600;
+  letter-spacing: 0.08em;
+  text-transform: uppercase;
+  color: light-dark(var(--mantine-color-gray-6), var(--mantine-color-dark-2));
+  margin-bottom: var(--mantine-spacing-xs);
+}
+
+.emptyStateTitle {
+  font-size: 1.5rem;
+  font-weight: 600;
+  color: light-dark(var(--mantine-color-gray-8), var(--mantine-color-dark-0));
+  margin-bottom: var(--mantine-spacing-xl);
+  text-align: center;
+}
+
+.emptyStateInput {
+  width: 100%;
+  max-width: 600px;
+  margin-bottom: var(--mantine-spacing-xl);
+  padding: 6px 0;
+}
+
+.suggestionsSection {
+  width: 100%;
+  max-width: 600px;
+}
+
+.suggestionsLabel {
+  font-size: var(--mantine-font-size-xs);
+  font-weight: 500;
+  color: light-dark(var(--mantine-color-gray-5), var(--mantine-color-dark-3));
+  text-transform: uppercase;
+  letter-spacing: 0.5px;
+  margin-bottom: var(--mantine-spacing-sm);
+}
+
+.suggestionsGrid {
+  display: grid;
+  grid-template-columns: repeat(2, 1fr);
+  gap: var(--mantine-spacing-sm);
+}
+
+.suggestionCard {
+  display: flex;
+  align-items: flex-start;
+  gap: var(--mantine-spacing-sm);
+  padding: var(--mantine-spacing-sm) var(--mantine-spacing-md);
+  border: 1px solid light-dark(var(--mantine-color-gray-2), var(--mantine-color-dark-5));
+  border-radius: var(--mantine-radius-md);
+  cursor: pointer;
+  background: transparent;
+  transition: background-color 150ms, border-color 150ms;
+  text-align: left;
+  width: 100%;
+
+  @mixin hover {
+    background: light-dark(var(--mantine-color-gray-0), var(--mantine-color-dark-6));
+    border-color: light-dark(var(--mantine-color-gray-3), var(--mantine-color-dark-4));
+  }
+}
+
+.suggestionIcon {
+  flex-shrink: 0;
+  color: light-dark(var(--mantine-color-gray-6), var(--mantine-color-dark-2));
+  margin-top: 1px;
+}
+
+.suggestionText {
+  font-size: var(--mantine-font-size-sm);
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+  line-height: 1.4;
+}
diff --git a/apps/client/src/ee/ai-chat/styles/aside-chat-panel.module.css b/apps/client/src/ee/ai-chat/styles/aside-chat-panel.module.css
new file mode 100644
index 00000000..f8958615
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/styles/aside-chat-panel.module.css
@@ -0,0 +1,139 @@
+.panel {
+  display: flex;
+  flex-direction: column;
+  height: 100%;
+  overflow: hidden;
+}
+
+.toolbar {
+  display: flex;
+  align-items: center;
+  gap: 4px;
+  padding: 0 0 var(--mantine-spacing-sm) 0;
+  border-bottom: 1px solid light-dark(var(--mantine-color-gray-2), var(--mantine-color-dark-5));
+}
+
+.toolbarSpacer {
+  flex: 1;
+}
+
+.titleButton {
+  display: flex;
+  align-items: center;
+  gap: 4px;
+  padding: 4px 8px;
+  border-radius: var(--mantine-radius-sm);
+  font-size: var(--mantine-font-size-sm);
+  font-weight: 500;
+  color: light-dark(var(--mantine-color-gray-8), var(--mantine-color-dark-0));
+  max-width: 60%;
+  min-width: 0;
+}
+
+.titleButton:hover {
+  background-color: light-dark(var(--mantine-color-gray-1), var(--mantine-color-dark-6));
+}
+
+.titleText {
+  overflow: hidden;
+  text-overflow: ellipsis;
+  white-space: nowrap;
+  min-width: 0;
+}
+
+.messages {
+  flex: 1;
+  overflow-y: auto;
+  padding: var(--mantine-spacing-sm) 0;
+  scroll-behavior: smooth;
+}
+
+.inputArea {
+  padding-top: var(--mantine-spacing-sm);
+}
+
+.emptyState {
+  flex: 1;
+  display: flex;
+  flex-direction: column;
+  align-items: center;
+  justify-content: center;
+  gap: var(--mantine-spacing-md);
+  padding: var(--mantine-spacing-xl) var(--mantine-spacing-sm);
+}
+
+.emptyStateIcon {
+  color: light-dark(var(--mantine-color-gray-5), var(--mantine-color-dark-3));
+}
+
+.emptyStateTitle {
+  font-size: var(--mantine-font-size-lg);
+  font-weight: 600;
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+  text-align: center;
+}
+
+.quickActions {
+  display: flex;
+  flex-direction: column;
+  gap: 6px;
+  width: 100%;
+}
+
+.quickAction {
+  display: flex;
+  align-items: center;
+  gap: var(--mantine-spacing-sm);
+  padding: var(--mantine-spacing-xs) var(--mantine-spacing-sm);
+  border: 1px solid light-dark(var(--mantine-color-gray-2), var(--mantine-color-dark-5));
+  border-radius: var(--mantine-radius-md);
+  cursor: pointer;
+  background: transparent;
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+  font-size: var(--mantine-font-size-sm);
+  text-align: left;
+  width: 100%;
+  transition: background-color 150ms, border-color 150ms;
+
+  @mixin hover {
+    background: light-dark(var(--mantine-color-gray-0), var(--mantine-color-dark-6));
+    border-color: light-dark(var(--mantine-color-gray-3), var(--mantine-color-dark-4));
+  }
+}
+
+.quickActionIcon {
+  flex-shrink: 0;
+  color: light-dark(var(--mantine-color-gray-5), var(--mantine-color-dark-3));
+}
+
+.historyList {
+  max-height: 300px;
+  overflow-y: auto;
+}
+
+.historyItem {
+  display: flex;
+  align-items: center;
+  padding: var(--mantine-spacing-xs) var(--mantine-spacing-sm);
+  cursor: pointer;
+  border-radius: var(--mantine-radius-sm);
+  font-size: var(--mantine-font-size-sm);
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+  transition: background-color 150ms;
+
+  @mixin hover {
+    background: light-dark(var(--mantine-color-gray-0), var(--mantine-color-dark-6));
+  }
+
+  &[data-active] {
+    background: light-dark(var(--mantine-color-gray-1), var(--mantine-color-dark-5));
+  }
+}
+
+.historyItemTitle {
+  flex: 1;
+  min-width: 0;
+  overflow: hidden;
+  text-overflow: ellipsis;
+  white-space: nowrap;
+}
diff --git a/apps/client/src/ee/ai-chat/styles/chat-input.module.css b/apps/client/src/ee/ai-chat/styles/chat-input.module.css
new file mode 100644
index 00000000..20b287c1
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/styles/chat-input.module.css
@@ -0,0 +1,242 @@
+.inputWrapper {
+  position: relative;
+  overflow: hidden;
+  border: 1px solid
+    light-dark(var(--mantine-color-gray-2), var(--mantine-color-dark-5));
+  border-radius: 16px;
+  background: light-dark(var(--mantine-color-white), var(--mantine-color-dark-7));
+  box-shadow: light-dark(
+    0 2px 40px 4px rgba(0, 0, 0, 0.07),
+    0 2px 40px 4px rgba(0, 0, 0, 0.5)
+  );
+  transition:
+    border-color 150ms,
+    box-shadow 150ms;
+
+  &:focus-within {
+    border-color: light-dark(
+      var(--mantine-color-gray-3),
+      var(--mantine-color-dark-4)
+    );
+    box-shadow: light-dark(
+      0 4px 48px 6px rgba(0, 0, 0, 0.09),
+      0 4px 48px 6px rgba(0, 0, 0, 0.6)
+    );
+  }
+}
+
+.inputWrapperFlat {
+  position: relative;
+  overflow: hidden;
+  border: 1px solid light-dark(var(--mantine-color-gray-2), var(--mantine-color-dark-5));
+  border-radius: 12px;
+  background: light-dark(var(--mantine-color-white), var(--mantine-color-dark-7));
+  box-shadow: none;
+  transition: border-color 150ms;
+
+  &:focus-within {
+    border-color: light-dark(var(--mantine-color-gray-3), var(--mantine-color-dark-4));
+  }
+}
+
+.disclaimer {
+  margin-top: 6px;
+  text-align: center;
+  font-size: var(--mantine-font-size-xs);
+  color: light-dark(var(--mantine-color-gray-5), var(--mantine-color-dark-3));
+}
+
+.attachmentChips {
+  display: flex;
+  flex-wrap: wrap;
+  gap: 6px;
+  padding: 10px 14px 0;
+}
+
+.attachmentChip {
+  display: inline-flex;
+  align-items: center;
+  gap: 5px;
+  padding: 4px 8px;
+  border-radius: 8px;
+  background: light-dark(var(--mantine-color-gray-1), var(--mantine-color-dark-6));
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+  font-size: var(--mantine-font-size-xs);
+  max-width: 200px;
+}
+
+.attachmentChipUploading {
+  opacity: 0.55;
+}
+
+.attachmentChipName {
+  overflow: hidden;
+  text-overflow: ellipsis;
+  white-space: nowrap;
+}
+
+.attachmentChipRemove {
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  border: none;
+  background: none;
+  cursor: pointer;
+  padding: 0;
+  margin-left: 2px;
+  color: light-dark(var(--mantine-color-gray-5), var(--mantine-color-dark-3));
+  border-radius: 50%;
+
+  @mixin hover {
+    color: light-dark(var(--mantine-color-gray-8), var(--mantine-color-dark-0));
+  }
+}
+
+.editorContent {
+  overflow: hidden;
+
+  :global(.ProseMirror) {
+    outline: none;
+    border: none;
+    background-color: transparent;
+    padding: 14px 18px 8px;
+    font-size: 15px;
+    line-height: 1.6;
+    max-height: 200px;
+    overflow-y: auto;
+    min-height: 24px;
+    color: light-dark(var(--mantine-color-gray-9), var(--mantine-color-dark-0));
+  }
+
+  :global(.ProseMirror p) {
+    margin-block-start: 0;
+    margin-block-end: 0;
+  }
+
+  :global(.ProseMirror p.is-editor-empty:first-child::before) {
+    color: light-dark(var(--mantine-color-gray-4), var(--mantine-color-dark-3));
+    content: attr(data-placeholder);
+    float: left;
+    height: 0;
+    pointer-events: none;
+  }
+}
+
+.actions {
+  display: flex;
+  align-items: center;
+  justify-content: flex-end;
+  padding: 4px 12px 10px;
+  gap: var(--mantine-spacing-xs);
+}
+
+.sendButton {
+  width: 28px;
+  height: 28px;
+  min-width: 28px;
+  min-height: 28px;
+  border-radius: 50%;
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  border: none;
+  cursor: pointer;
+  transition: background-color 150ms, opacity 150ms;
+  background: light-dark(var(--mantine-color-dark-9), var(--mantine-color-gray-0));
+  color: light-dark(var(--mantine-color-white), var(--mantine-color-dark-9));
+
+  &:disabled {
+    opacity: 0.25;
+    cursor: default;
+  }
+
+  @mixin hover {
+    &:not(:disabled) {
+      opacity: 0.85;
+    }
+  }
+}
+
+.attachButton {
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  border: none;
+  background: none;
+  cursor: pointer;
+  padding: 2px;
+  color: light-dark(var(--mantine-color-gray-5), var(--mantine-color-dark-3));
+  transition: color 150ms;
+
+  @mixin hover {
+    color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+  }
+}
+
+.plusButton {
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  width: 24px;
+  height: 24px;
+  border-radius: 50%;
+  border: 1px solid light-dark(var(--mantine-color-gray-3), var(--mantine-color-dark-4));
+  background: none;
+  cursor: pointer;
+  color: light-dark(var(--mantine-color-gray-5), var(--mantine-color-dark-3));
+  transition: color 150ms, background-color 150ms;
+
+  @mixin hover {
+    color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+    background: light-dark(var(--mantine-color-gray-0), var(--mantine-color-dark-6));
+  }
+}
+
+.plusMenuItem {
+  display: flex;
+  align-items: center;
+  gap: var(--mantine-spacing-sm);
+  padding: var(--mantine-spacing-xs) var(--mantine-spacing-sm);
+  border: none;
+  background: none;
+  cursor: pointer;
+  width: 100%;
+  font-size: var(--mantine-font-size-sm);
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+  border-radius: var(--mantine-radius-sm);
+  transition: background-color 150ms;
+
+  @mixin hover {
+    background: light-dark(var(--mantine-color-gray-0), var(--mantine-color-dark-6));
+  }
+
+  &:disabled {
+    opacity: 0.45;
+    cursor: not-allowed;
+    background: none;
+  }
+}
+
+.plusMenuIcon {
+  color: light-dark(var(--mantine-color-gray-5), var(--mantine-color-dark-3));
+}
+
+.stopButton {
+  width: 28px;
+  height: 28px;
+  min-width: 28px;
+  min-height: 28px;
+  border-radius: 50%;
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  border: 1px solid light-dark(var(--mantine-color-gray-3), var(--mantine-color-dark-4));
+  cursor: pointer;
+  transition: background-color 150ms;
+  background: light-dark(var(--mantine-color-white), var(--mantine-color-dark-6));
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+
+  @mixin hover {
+    background: light-dark(var(--mantine-color-gray-1), var(--mantine-color-dark-5));
+  }
+}
diff --git a/apps/client/src/ee/ai-chat/styles/chat-message.module.css b/apps/client/src/ee/ai-chat/styles/chat-message.module.css
new file mode 100644
index 00000000..33e39dd6
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/styles/chat-message.module.css
@@ -0,0 +1,286 @@
+.message {
+  margin-bottom: var(--mantine-spacing-lg);
+}
+
+.userMessage {
+  composes: message;
+  display: flex;
+  justify-content: flex-end;
+}
+
+.userBubble {
+  max-width: 75%;
+  padding: 10px 16px;
+  border-radius: 18px;
+  background: light-dark(var(--mantine-color-gray-1), var(--mantine-color-dark-6));
+  color: light-dark(var(--mantine-color-gray-9), var(--mantine-color-dark-0));
+  font-size: 15px;
+  line-height: 1.6;
+  word-wrap: break-word;
+  overflow-wrap: break-word;
+}
+
+[data-aside-chat] .userBubble {
+  background: light-dark(var(--mantine-color-white), var(--mantine-color-dark-7));
+  border: 1px solid light-dark(var(--mantine-color-gray-2), var(--mantine-color-dark-5));
+}
+
+.userBubble p {
+  margin: 0;
+}
+
+.messageAttachments {
+  display: flex;
+  flex-wrap: wrap;
+  gap: 4px;
+  margin-bottom: 6px;
+}
+
+.messageAttachmentChip {
+  display: inline-flex;
+  align-items: center;
+  gap: 4px;
+  padding: 2px 8px;
+  border-radius: 6px;
+  background: light-dark(var(--mantine-color-gray-2), var(--mantine-color-dark-5));
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-2));
+  font-size: var(--mantine-font-size-xs);
+  max-width: 180px;
+  overflow: hidden;
+  text-overflow: ellipsis;
+  white-space: nowrap;
+}
+
+.assistantMessage {
+  composes: message;
+}
+
+.messageContent {
+  font-size: 15px;
+  line-height: 1.7;
+  color: light-dark(var(--mantine-color-gray-8), var(--mantine-color-dark-1));
+  word-wrap: break-word;
+  overflow-wrap: break-word;
+}
+
+.messageContent p {
+  margin: 0 0 0.75em 0;
+}
+
+.messageContent p:last-child {
+  margin-bottom: 0;
+}
+
+.messageContent ul,
+.messageContent ol {
+  margin: 0.5em 0 0.75em 0;
+  padding-left: 1.5em;
+}
+
+.messageContent li {
+  margin-bottom: 0.3em;
+}
+
+.messageContent h1,
+.messageContent h2,
+.messageContent h3 {
+  margin: 1em 0 0.5em 0;
+  font-weight: 600;
+  color: light-dark(var(--mantine-color-gray-9), var(--mantine-color-dark-0));
+}
+
+.messageContent h1 {
+  font-size: 1.4em;
+}
+
+.messageContent h2 {
+  font-size: 1.2em;
+}
+
+.messageContent h3 {
+  font-size: 1.05em;
+}
+
+.messageContent pre {
+  background-color: light-dark(var(--mantine-color-gray-0), var(--mantine-color-dark-7));
+  padding: var(--mantine-spacing-sm) var(--mantine-spacing-md);
+  border-radius: var(--mantine-radius-md);
+  overflow-x: auto;
+  font-size: var(--mantine-font-size-sm);
+  margin: 0.75em 0;
+}
+
+.messageContent code {
+  background-color: light-dark(var(--mantine-color-gray-1), var(--mantine-color-dark-6));
+  padding: 2px 6px;
+  border-radius: 4px;
+  font-size: 0.88em;
+}
+
+.messageContent pre code {
+  background: none;
+  padding: 0;
+}
+
+.messageContent blockquote {
+  border-left: 3px solid light-dark(var(--mantine-color-gray-3), var(--mantine-color-dark-4));
+  padding-left: var(--mantine-spacing-md);
+  margin: 0.75em 0;
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-2));
+}
+
+.messageContent a {
+  color: light-dark(var(--mantine-color-blue-7), var(--mantine-color-blue-4));
+  text-decoration: none;
+
+  @mixin hover {
+    text-decoration: underline;
+  }
+}
+
+.messageContent a[href^="/s/"],
+.messageContent a[href^="/p/"] {
+  color: light-dark(var(--mantine-color-dark-4), var(--mantine-color-dark-1));
+  font-weight: 500;
+  text-decoration: none;
+  cursor: pointer;
+
+  @mixin light {
+    border-bottom: 0.05em solid var(--mantine-color-dark-0);
+  }
+
+  @mixin dark {
+    border-bottom: 0.05em solid var(--mantine-color-dark-2);
+  }
+
+  @mixin hover {
+    text-decoration: none;
+    @mixin light {
+      border-bottom-color: var(--mantine-color-dark-2);
+    }
+    @mixin dark {
+      border-bottom-color: var(--mantine-color-dark-0);
+    }
+  }
+}
+
+.messageContent hr {
+  border: none;
+  border-top: 1px solid light-dark(var(--mantine-color-gray-2), var(--mantine-color-dark-5));
+  margin: 1em 0;
+}
+
+.toolGroup {
+  margin: 6px 0;
+  font-size: var(--mantine-font-size-xs);
+}
+
+.toolGroupHeader {
+  display: inline-flex;
+  align-items: center;
+  gap: 6px;
+  cursor: pointer;
+  user-select: none;
+  color: light-dark(var(--mantine-color-gray-6), var(--mantine-color-dark-2));
+  line-height: 1.4;
+  transition: color 120ms ease;
+}
+
+.toolGroupHeader:hover {
+  color: light-dark(var(--mantine-color-gray-8), var(--mantine-color-dark-0));
+}
+
+.toolGroupLabel {
+  font-weight: 500;
+}
+
+.toolGroupSteps {
+  margin-top: 4px;
+  padding-left: 14px;
+  display: flex;
+  flex-direction: column;
+  gap: 2px;
+}
+
+.toolStep {
+  font-size: var(--mantine-font-size-xs);
+}
+
+.toolStepRow {
+  display: inline-flex;
+  align-items: center;
+  gap: 4px;
+  cursor: pointer;
+  user-select: none;
+  color: light-dark(var(--mantine-color-gray-6), var(--mantine-color-dark-2));
+  line-height: 1.5;
+  transition: color 120ms ease;
+}
+
+.toolStepRow:hover {
+  color: light-dark(var(--mantine-color-gray-8), var(--mantine-color-dark-0));
+}
+
+.toolStepBullet {
+  display: inline-block;
+  width: 8px;
+  text-align: center;
+  opacity: 0.6;
+}
+
+.toolStepDetails {
+  margin-top: 4px;
+  margin-left: 18px;
+  padding: 6px 10px;
+  border-radius: var(--mantine-radius-sm);
+  background: light-dark(var(--mantine-color-gray-0), var(--mantine-color-dark-7));
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+  font-size: 11px;
+  line-height: 1.5;
+  overflow-x: auto;
+}
+
+.messageActions {
+  display: flex;
+  align-items: center;
+  gap: 4px;
+  margin-top: 4px;
+  color: light-dark(var(--mantine-color-gray-6), var(--mantine-color-dark-2));
+}
+
+.processingIndicator {
+  display: inline-flex;
+  align-items: center;
+  gap: 6px;
+  color: light-dark(var(--mantine-color-gray-5), var(--mantine-color-dark-3));
+  font-size: var(--mantine-font-size-sm);
+}
+
+.processingSpinner {
+  animation: spin 1s linear infinite;
+}
+
+@keyframes spin {
+  from {
+    transform: rotate(0deg);
+  }
+  to {
+    transform: rotate(360deg);
+  }
+}
+
+.streamingCursor {
+  display: inline-block;
+  width: 2px;
+  height: 1em;
+  background: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-0));
+  animation: blink 1s step-end infinite;
+  vertical-align: text-bottom;
+  margin-left: 1px;
+}
+
+@keyframes blink {
+  50% {
+    opacity: 0;
+  }
+}
diff --git a/apps/client/src/ee/ai-chat/styles/chat-sidebar.module.css b/apps/client/src/ee/ai-chat/styles/chat-sidebar.module.css
new file mode 100644
index 00000000..c7991147
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/styles/chat-sidebar.module.css
@@ -0,0 +1,138 @@
+.sidebar {
+  height: 100%;
+  width: 100%;
+  padding: var(--mantine-spacing-md);
+  display: flex;
+  flex-direction: column;
+  gap: var(--mantine-spacing-xs);
+}
+
+.header {
+  display: flex;
+  align-items: center;
+  justify-content: space-between;
+  padding-bottom: var(--mantine-spacing-xs);
+}
+
+.title {
+  font-weight: 600;
+  font-size: var(--mantine-font-size-sm);
+}
+
+.searchInput {
+  margin-bottom: var(--mantine-spacing-xs);
+}
+
+.chatList {
+  flex: 1;
+  overflow-y: auto;
+}
+
+.chatGroup + .chatGroup {
+  margin-top: var(--mantine-spacing-sm);
+}
+
+.chatGroupLabel {
+  padding: 4px var(--mantine-spacing-xs);
+  font-size: var(--mantine-font-size-xs);
+  font-weight: 600;
+  color: light-dark(var(--mantine-color-gray-6), var(--mantine-color-dark-2));
+  user-select: none;
+}
+
+.chatListEmpty {
+  display: flex;
+  flex-direction: column;
+  align-items: center;
+  justify-content: center;
+  padding: var(--mantine-spacing-xl) var(--mantine-spacing-md);
+  text-align: center;
+  gap: 4px;
+  user-select: none;
+}
+
+.chatListEmptyIcon {
+  color: light-dark(var(--mantine-color-gray-5), var(--mantine-color-dark-3));
+  margin-bottom: var(--mantine-spacing-xs);
+}
+
+.chatListEmptyTitle {
+  font-size: var(--mantine-font-size-sm);
+  font-weight: 600;
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+}
+
+.chatListEmptyHint {
+  font-size: var(--mantine-font-size-xs);
+  color: light-dark(var(--mantine-color-gray-6), var(--mantine-color-dark-3));
+  line-height: 1.4;
+}
+
+.chatItem {
+  display: flex;
+  align-items: center;
+  padding: 8px var(--mantine-spacing-xs);
+  border-radius: var(--mantine-radius-sm);
+  cursor: pointer;
+  text-decoration: none;
+  color: light-dark(var(--mantine-color-gray-7), var(--mantine-color-dark-1));
+  font-size: var(--mantine-font-size-sm);
+  user-select: none;
+  gap: var(--mantine-spacing-xs);
+
+  @mixin hover {
+    background-color: light-dark(
+      var(--mantine-color-gray-1),
+      var(--mantine-color-dark-6)
+    );
+  }
+
+  &[data-active] {
+    background-color: light-dark(
+      var(--mantine-color-gray-2),
+      var(--mantine-color-dark-6)
+    );
+  }
+}
+
+.chatItemTitle {
+  flex: 1;
+  overflow: hidden;
+  text-overflow: ellipsis;
+  white-space: nowrap;
+}
+
+.chatItemDate {
+  font-size: var(--mantine-font-size-xs);
+  color: light-dark(var(--mantine-color-gray-5), var(--mantine-color-dark-3));
+  white-space: nowrap;
+  transition: opacity 150ms;
+}
+
+.chatItemRenameInput {
+  font-size: var(--mantine-font-size-sm);
+  padding: 0;
+  height: auto;
+  min-height: 0;
+  background: transparent;
+  color: inherit;
+}
+
+.chatItem:hover .chatItemDate {
+  opacity: 0;
+}
+
+.chatItemActions {
+  position: absolute;
+  right: var(--mantine-spacing-xs);
+  opacity: 0;
+  transition: opacity 150ms;
+}
+
+.chatItem {
+  position: relative;
+}
+
+.chatItem:hover .chatItemActions {
+  opacity: 1;
+}
diff --git a/apps/client/src/ee/ai-chat/types/ai-chat.types.ts b/apps/client/src/ee/ai-chat/types/ai-chat.types.ts
new file mode 100644
index 00000000..89754d26
--- /dev/null
+++ b/apps/client/src/ee/ai-chat/types/ai-chat.types.ts
@@ -0,0 +1,49 @@
+export type AiChat = {
+  id: string;
+  workspaceId: string;
+  creatorId: string;
+  title: string | null;
+  createdAt: string;
+  updatedAt: string;
+};
+
+export type AiChatToolCall = {
+  id: string;
+  name: string;
+  args: Record<string, unknown>;
+  result?: unknown;
+};
+
+export type AiChatMessage = {
+  id: string;
+  chatId: string;
+  role: 'user' | 'assistant' | 'tool';
+  content: string | null;
+  toolCalls: AiChatToolCall[] | null;
+  metadata: Record<string, unknown> | null;
+  createdAt: string;
+};
+
+export type AiChatStreamEvent =
+  | { type: 'chat_created'; chatId: string }
+  | { type: 'content'; text: string }
+  | { type: 'tool_call'; id: string; name: string; args: Record<string, unknown> }
+  | { type: 'tool_result'; id: string; result: unknown }
+  | { type: 'done'; messageId: string; usage?: Record<string, number> }
+  | { type: 'error'; message: string; code?: string; retryable?: boolean };
+
+export type PageMention = {
+  id: string;
+  title: string;
+  slugId: string;
+  spaceSlug?: string;
+  icon?: string;
+};
+
+export type ChatAttachment = {
+  id: string;
+  fileName: string;
+  fileExt: string;
+  fileSize: number;
+  mimeType: string;
+};
diff --git a/apps/client/src/ee/ai/pages/ai-settings.tsx b/apps/client/src/ee/ai/pages/ai-settings.tsx
index c3f93810..3a5a281e 100644
--- a/apps/client/src/ee/ai/pages/ai-settings.tsx
+++ b/apps/client/src/ee/ai/pages/ai-settings.tsx
@@ -6,6 +6,7 @@ import useUserRole from "@/hooks/use-user-role.tsx";
 import { useTranslation } from "react-i18next";
 import EnableAiSearch from "@/ee/ai/components/enable-ai-search.tsx";
 import EnableGenerativeAi from "@/ee/ai/components/enable-generative-ai.tsx";
+import EnableAiChat from "@/ee/ai-chat/components/enable-ai-chat.tsx";
 import McpSettings from "@/ee/ai/components/mcp-settings.tsx";
 import { Alert, Stack, Tabs } from "@mantine/core";
 import { IconInfoCircle } from "@tabler/icons-react";
@@ -71,6 +72,7 @@ export default function AiSettings() {
           <Stack gap="md">
             {!isCloud() && <EnableAiSearch />}
             <EnableGenerativeAi />
+            <EnableAiChat />
           </Stack>
         </Tabs.Panel>
 
diff --git a/apps/client/src/features/editor/components/mention/mention-list.tsx b/apps/client/src/features/editor/components/mention/mention-list.tsx
index af6f8a1d..3ddf3976 100644
--- a/apps/client/src/features/editor/components/mention/mention-list.tsx
+++ b/apps/client/src/features/editor/components/mention/mention-list.tsx
@@ -62,7 +62,7 @@ const MentionList = forwardRef<any, MentionListProps>((props, ref) => {
     query: props.query,
     includeUsers: true,
     includePages: true,
-    spaceId: space.id,
+    spaceId: space?.id,
     limit: props.query ? 10 : 5,
     preload: true,
   });
diff --git a/apps/client/src/features/editor/components/mention/mention-suggestion.ts b/apps/client/src/features/editor/components/mention/mention-suggestion.ts
index 658fd182..894e7204 100644
--- a/apps/client/src/features/editor/components/mention/mention-suggestion.ts
+++ b/apps/client/src/features/editor/components/mention/mention-suggestion.ts
@@ -53,8 +53,8 @@ const mentionRenderItems = () => {
       const editorDom = props.editor?.view?.dom;
       const asideEl = editorDom?.closest(".mantine-AppShell-aside");
       const dialogEl = editorDom?.closest("[data-comment-dialog]");
-      const isInCommentContext = !!(asideEl || dialogEl);
-     // const isInCommentContext = !!asideEl;
+      const chatInput = editorDom?.closest("[data-chat-input]");
+      const isInCommentContext = !!(asideEl || dialogEl || chatInput);
 
       component = new ReactRenderer(MentionList, {
         props: { ...props, isInCommentContext },
diff --git a/apps/client/src/features/home/components/home-ai-prompt.module.css b/apps/client/src/features/home/components/home-ai-prompt.module.css
new file mode 100644
index 00000000..e6d81606
--- /dev/null
+++ b/apps/client/src/features/home/components/home-ai-prompt.module.css
@@ -0,0 +1,28 @@
+.wrapper {
+  display: flex;
+  flex-direction: column;
+  align-items: center;
+  padding: var(--mantine-spacing-xl) var(--mantine-spacing-md) var(--mantine-spacing-lg);
+}
+
+.heading {
+  font-size: 1.75rem;
+  font-weight: 600;
+  color: light-dark(var(--mantine-color-gray-8), var(--mantine-color-dark-0));
+  text-align: center;
+  margin: 0;
+  line-height: 1.2;
+}
+
+.subtitle {
+  font-size: var(--mantine-font-size-sm);
+  color: light-dark(var(--mantine-color-gray-6), var(--mantine-color-dark-2));
+  text-align: center;
+  margin-top: 6px;
+  margin-bottom: var(--mantine-spacing-lg);
+}
+
+.inputContainer {
+  width: 100%;
+  max-width: 640px;
+}
diff --git a/apps/client/src/features/home/components/home-ai-prompt.tsx b/apps/client/src/features/home/components/home-ai-prompt.tsx
new file mode 100644
index 00000000..c3c69398
--- /dev/null
+++ b/apps/client/src/features/home/components/home-ai-prompt.tsx
@@ -0,0 +1,60 @@
+import { useAtomValue } from "jotai";
+import { useNavigate } from "react-router-dom";
+import { useTranslation } from "react-i18next";
+import { workspaceAtom } from "@/features/user/atoms/current-user-atom.ts";
+import ChatInput from "@/ee/ai-chat/components/chat-input";
+import type {
+  ChatAttachment,
+  PageMention,
+} from "@/ee/ai-chat/types/ai-chat.types";
+import classes from "./home-ai-prompt.module.css";
+
+export type HomeAiPromptInitialState = {
+  initialContent: string;
+  initialMentions: PageMention[];
+  initialAttachments: ChatAttachment[];
+};
+
+export default function HomeAiPrompt() {
+  const { t } = useTranslation();
+  const navigate = useNavigate();
+  const workspace = useAtomValue(workspaceAtom);
+
+  const aiChatEnabled = workspace?.settings?.ai?.chat === true;
+  if (!aiChatEnabled) return null;
+
+  const handleSend = (
+    content: string,
+    mentions: PageMention[],
+    attachments: ChatAttachment[],
+  ) => {
+    if (!content.trim() && attachments.length === 0) return;
+    const state: HomeAiPromptInitialState = {
+      initialContent: content,
+      initialMentions: mentions,
+      initialAttachments: attachments,
+    };
+    navigate("/ai", { state });
+  };
+
+  return (
+    <div className={classes.wrapper}>
+      <h1 className={classes.heading}>
+        {t("Welcome to {{name}}", { name: workspace?.name ?? "Docmost" })}
+      </h1>
+      <div className={classes.subtitle}>
+        {t("Ask anything or search your workspace")}
+      </div>
+
+      <div className={classes.inputContainer}>
+        <ChatInput
+          isStreaming={false}
+          onSend={handleSend}
+          onStop={() => {}}
+          placeholder={t("Ask anything... Use @ to mention pages")}
+          autofocus={false}
+        />
+      </div>
+    </div>
+  );
+}
diff --git a/apps/client/src/features/search/components/search-control.module.css b/apps/client/src/features/search/components/search-control.module.css
index 5e5a9c26..80be81d9 100644
--- a/apps/client/src/features/search/components/search-control.module.css
+++ b/apps/client/src/features/search/components/search-control.module.css
@@ -29,6 +29,8 @@
     border-radius: var(--mantine-radius-sm);
     border: 1px solid;
     font-weight: bold;
+    white-space: nowrap;
+    flex-shrink: 0;
 
     @mixin light {
         color: var(--mantine-color-gray-7);
diff --git a/apps/client/src/features/space/components/space-carousel.module.css b/apps/client/src/features/space/components/space-carousel.module.css
new file mode 100644
index 00000000..87b9f1de
--- /dev/null
+++ b/apps/client/src/features/space/components/space-carousel.module.css
@@ -0,0 +1,22 @@
+.card {
+  background-color: var(--mantine-color-body);
+  width: 220px;
+
+  @mixin hover {
+    box-shadow: var(--mantine-shadow-xs);
+    transform: scale(1.02);
+  }
+}
+
+.cardSection {
+  background: light-dark(var(--mantine-color-gray-1), var(--mantine-color-dark-6));
+}
+
+.title {
+  font-family:
+          Greycliff CF,
+          var(--mantine-font-family);
+  text-overflow: ellipsis;
+  overflow: hidden;
+  white-space: nowrap;
+}
diff --git a/apps/client/src/features/space/components/space-carousel.tsx b/apps/client/src/features/space/components/space-carousel.tsx
new file mode 100644
index 00000000..e8c4eada
--- /dev/null
+++ b/apps/client/src/features/space/components/space-carousel.tsx
@@ -0,0 +1,77 @@
+import { Text, Card, rem, Group, Button } from "@mantine/core";
+import {
+  prefetchSpace,
+  useGetSpacesQuery,
+} from "@/features/space/queries/space-query.ts";
+import { getSpaceUrl } from "@/lib/config.ts";
+import { Link } from "react-router-dom";
+import classes from "./space-carousel.module.css";
+import { formatMemberCount } from "@/lib";
+import { useTranslation } from "react-i18next";
+import { IconArrowRight } from "@tabler/icons-react";
+import { CustomAvatar } from "@/components/ui/custom-avatar.tsx";
+import { AvatarIconType } from "@/features/attachments/types/attachment.types.ts";
+import CardCarousel from "@/components/ui/card-carousel";
+
+export default function SpaceCarousel() {
+  const { t } = useTranslation();
+  const { data } = useGetSpacesQuery({ limit: 20 });
+
+  const cards = data?.items.map((space) => (
+    <Card
+      key={space.id}
+      p="xs"
+      radius="md"
+      component={Link}
+      to={getSpaceUrl(space.slug)}
+      onMouseEnter={() => prefetchSpace(space.slug, space.id)}
+      className={classes.card}
+      withBorder
+    >
+      <Card.Section className={classes.cardSection} h={40}></Card.Section>
+      <CustomAvatar
+        name={space.name}
+        avatarUrl={space.logo}
+        type={AvatarIconType.SPACE_ICON}
+        color="initials"
+        variant="filled"
+        size="md"
+        mt={rem(-20)}
+      />
+
+      <Text fz="md" fw={500} mt="xs" className={classes.title}>
+        {space.name}
+      </Text>
+
+      <Text c="dimmed" size="xs" fw={700} mt="md">
+        {formatMemberCount(space.memberCount, t)}
+      </Text>
+    </Card>
+  ));
+
+  return (
+    <>
+      <Group justify="space-between" align="center" mb="md">
+        <Text fz="sm" fw={500}>
+          {t("Spaces you belong to")}
+        </Text>
+      </Group>
+
+      <CardCarousel ariaLabel={t("Spaces you belong to")}>{cards}</CardCarousel>
+
+      {data?.items && data.items.length > 1 && (
+        <Group justify="flex-end" mt="lg">
+          <Button
+            component={Link}
+            to="/spaces"
+            variant="subtle"
+            rightSection={<IconArrowRight size={16} />}
+            size="sm"
+          >
+            {t("View all spaces")}
+          </Button>
+        </Group>
+      )}
+    </>
+  );
+}
diff --git a/apps/client/src/features/workspace/types/workspace.types.ts b/apps/client/src/features/workspace/types/workspace.types.ts
index 4d98a5ef..96df25b7 100644
--- a/apps/client/src/features/workspace/types/workspace.types.ts
+++ b/apps/client/src/features/workspace/types/workspace.types.ts
@@ -43,6 +43,7 @@ export interface IWorkspaceAiSettings {
   search?: boolean;
   generative?: boolean;
   mcp?: boolean;
+  chat?: boolean;
 }
 
 export interface IWorkspaceSharingSettings {
diff --git a/apps/client/src/pages/dashboard/home.tsx b/apps/client/src/pages/dashboard/home.tsx
index 900afa40..cefff053 100644
--- a/apps/client/src/pages/dashboard/home.tsx
+++ b/apps/client/src/pages/dashboard/home.tsx
@@ -1,6 +1,7 @@
 import { Container, Space } from "@mantine/core";
 import HomeTabs from "@/features/home/components/home-tabs";
-import SpaceGrid from "@/features/space/components/space-grid.tsx";
+import HomeAiPrompt from "@/features/home/components/home-ai-prompt";
+import SpaceCarousel from "@/features/space/components/space-carousel.tsx";
 import { getAppName } from "@/lib/config.ts";
 import { Helmet } from "react-helmet-async";
 import { useTranslation } from "react-i18next";
@@ -16,7 +17,11 @@ export default function Home() {
         </title>
       </Helmet>
       <Container size={"800"} pt="xl">
-        <SpaceGrid />
+        <HomeAiPrompt />
+
+        <Space h="xl" />
+
+        <SpaceCarousel />
 
         <Space h="xl" />
 
diff --git a/apps/server/package.json b/apps/server/package.json
index 9994ba43..a1a061db 100644
--- a/apps/server/package.json
+++ b/apps/server/package.json
@@ -75,10 +75,12 @@
     "class-transformer": "^0.5.1",
     "class-validator": "^0.15.1",
     "cookie": "^1.1.1",
+    "fast-bm25": "0.0.5",
     "fastify-ip": "^2.0.0",
     "fs-extra": "^11.3.4",
     "happy-dom": "20.8.9",
     "ioredis": "^5.10.1",
+    "js-tiktoken": "^1.0.21",
     "jsonwebtoken": "^9.0.3",
     "kysely": "^0.28.14",
     "kysely-migration-cli": "^0.4.2",
diff --git a/apps/server/src/core/attachment/attachment.constants.ts b/apps/server/src/core/attachment/attachment.constants.ts
index a9bce5c1..a5d90692 100644
--- a/apps/server/src/core/attachment/attachment.constants.ts
+++ b/apps/server/src/core/attachment/attachment.constants.ts
@@ -3,6 +3,7 @@ export enum AttachmentType {
   WorkspaceIcon = 'workspace-icon',
   SpaceIcon = 'space-icon',
   File = 'file',
+  Chat = 'chat',
 }
 
 export const validImageExtensions = ['.jpg', '.png', '.jpeg'];
diff --git a/apps/server/src/core/attachment/attachment.controller.ts b/apps/server/src/core/attachment/attachment.controller.ts
index 6382b34e..7b24cc35 100644
--- a/apps/server/src/core/attachment/attachment.controller.ts
+++ b/apps/server/src/core/attachment/attachment.controller.ts
@@ -178,21 +178,29 @@ export class AttachmentController {
     }
 
     const attachment = await this.attachmentRepo.findById(fileId);
-    if (
-      !attachment ||
-      attachment.workspaceId !== workspace.id ||
-      !attachment.pageId ||
-      !attachment.spaceId
-    ) {
+    if (!attachment || attachment.workspaceId !== workspace.id) {
       throw new NotFoundException();
     }
 
-    const page = await this.pageRepo.findById(attachment.pageId);
-    if (!page) {
-      throw new NotFoundException();
-    }
+    if (attachment.aiChatId) {
+      // Chat-owned attachment: only the user who uploaded (and therefore
+      // owns the chat, per AttachmentRepo.claimAttachmentsForChat) can
+      // read it back.
+      if (attachment.creatorId !== user.id) {
+        throw new NotFoundException();
+      }
+    } else {
+      if (!attachment.pageId || !attachment.spaceId) {
+        throw new NotFoundException();
+      }
 
-    await this.pageAccessService.validateCanView(page, user);
+      const page = await this.pageRepo.findById(attachment.pageId);
+      if (!page) {
+        throw new NotFoundException();
+      }
+
+      await this.pageAccessService.validateCanView(page, user);
+    }
 
     try {
       return await this.sendFileResponse(req, res, attachment, 'private');
diff --git a/apps/server/src/core/attachment/attachment.utils.ts b/apps/server/src/core/attachment/attachment.utils.ts
index 88edb2af..616fed53 100644
--- a/apps/server/src/core/attachment/attachment.utils.ts
+++ b/apps/server/src/core/attachment/attachment.utils.ts
@@ -71,6 +71,8 @@ export function getAttachmentFolderPath(
       return `${workspaceId}/space-logos`;
     case AttachmentType.File:
       return `${workspaceId}/files`;
+    case AttachmentType.Chat:
+      return `${workspaceId}/chat-files`;
     default:
       return `${workspaceId}/files`;
   }
diff --git a/apps/server/src/core/attachment/processors/attachment.processor.ts b/apps/server/src/core/attachment/processors/attachment.processor.ts
index bcf8a08a..7249a9fa 100644
--- a/apps/server/src/core/attachment/processors/attachment.processor.ts
+++ b/apps/server/src/core/attachment/processors/attachment.processor.ts
@@ -28,6 +28,11 @@ export class AttachmentProcessor extends WorkerHost implements OnModuleDestroy {
           job.data.pageId,
         );
       }
+      if (job.name === QueueJob.DELETE_AI_CHAT_ATTACHMENTS) {
+        await this.attachmentService.handleDeleteAiChatAttachments(
+          job.data.aiChatId,
+        );
+      }
       if (
         job.name === QueueJob.ATTACHMENT_INDEX_CONTENT ||
         job.name === QueueJob.ATTACHMENT_INDEXING
diff --git a/apps/server/src/core/attachment/services/attachment.service.ts b/apps/server/src/core/attachment/services/attachment.service.ts
index 6419ed58..766c9f65 100644
--- a/apps/server/src/core/attachment/services/attachment.service.ts
+++ b/apps/server/src/core/attachment/services/attachment.service.ts
@@ -289,6 +289,31 @@ export class AttachmentService {
     );
   }
 
+  async handleDeleteAiChatAttachments(aiChatId: string) {
+    try {
+      const attachments = await this.attachmentRepo.findByAiChatId(aiChatId);
+      if (!attachments || attachments.length === 0) {
+        return;
+      }
+
+      await Promise.all(
+        attachments.map(async (attachment) => {
+          try {
+            await this.storageService.delete(attachment.filePath);
+            await this.attachmentRepo.deleteAttachmentById(attachment.id);
+          } catch (err) {
+            this.logger.log(
+              `DeleteAiChatAttachments: failed to delete attachment ${attachment.id}:`,
+              err,
+            );
+          }
+        }),
+      );
+    } catch (err) {
+      throw err;
+    }
+  }
+
   async handleDeleteSpaceAttachments(spaceId: string) {
     try {
       const attachments = await this.attachmentRepo.findBySpaceId(spaceId);
diff --git a/apps/server/src/core/auth/auth.controller.ts b/apps/server/src/core/auth/auth.controller.ts
index 441bfc1c..89bb9e1b 100644
--- a/apps/server/src/core/auth/auth.controller.ts
+++ b/apps/server/src/core/auth/auth.controller.ts
@@ -11,6 +11,10 @@ import {
   Logger,
 } from '@nestjs/common';
 import { SkipThrottle, ThrottlerGuard } from '@nestjs/throttler';
+import {
+  AI_CHAT_THROTTLER,
+  AUTH_THROTTLER,
+} from '../../integrations/throttle/throttler-names';
 import { LoginDto } from './dto/login.dto';
 import { AuthService } from './services/auth.service';
 import { SessionService } from '../session/session.service';
@@ -34,6 +38,7 @@ import {
   IAuditService,
 } from '../../integrations/audit/audit.service';
 
+@SkipThrottle({ [AI_CHAT_THROTTLER]: true })
 @UseGuards(ThrottlerGuard)
 @Controller('auth')
 export class AuthController {
@@ -113,7 +118,7 @@ export class AuthController {
     return workspace;
   }
 
-  @SkipThrottle()
+  @SkipThrottle({ [AUTH_THROTTLER]: true })
   @UseGuards(JwtAuthGuard)
   @HttpCode(HttpStatus.OK)
   @Post('change-password')
@@ -176,7 +181,7 @@ export class AuthController {
     return this.authService.verifyUserToken(verifyUserTokenDto, workspace.id);
   }
 
-  @SkipThrottle()
+  @SkipThrottle({ [AUTH_THROTTLER]: true })
   @UseGuards(JwtAuthGuard)
   @HttpCode(HttpStatus.OK)
   @Post('collab-token')
@@ -187,7 +192,7 @@ export class AuthController {
     return this.authService.getCollabToken(user, workspace.id);
   }
 
-  @SkipThrottle()
+  @SkipThrottle({ [AUTH_THROTTLER]: true })
   @UseGuards(JwtAuthGuard)
   @HttpCode(HttpStatus.OK)
   @Post('logout')
diff --git a/apps/server/src/core/workspace/dto/update-workspace.dto.ts b/apps/server/src/core/workspace/dto/update-workspace.dto.ts
index 9b822f50..d3f029d4 100644
--- a/apps/server/src/core/workspace/dto/update-workspace.dto.ts
+++ b/apps/server/src/core/workspace/dto/update-workspace.dto.ts
@@ -46,6 +46,10 @@ export class UpdateWorkspaceDto extends PartialType(CreateWorkspaceDto) {
   @IsBoolean()
   mcpEnabled: boolean;
 
+  @IsOptional()
+  @IsBoolean()
+  aiChat: boolean;
+
   @IsOptional()
   @IsInt()
   @Min(1)
diff --git a/apps/server/src/core/workspace/services/workspace.service.ts b/apps/server/src/core/workspace/services/workspace.service.ts
index d0bd27c6..c6d822ff 100644
--- a/apps/server/src/core/workspace/services/workspace.service.ts
+++ b/apps/server/src/core/workspace/services/workspace.service.ts
@@ -142,7 +142,7 @@ export class WorkspaceService {
           status = WorkspaceStatus.Active;
           plan = 'standard';
           billingEmail = user.email;
-          settings = { ai: { generative: true } };
+          settings = { ai: { generative: true, chat: true } };
         }
 
         // create workspace
@@ -458,11 +458,26 @@ export class WorkspaceService {
         );
       }
 
+      if (typeof updateWorkspaceDto.aiChat !== 'undefined') {
+        const prev = settingsBefore?.ai?.chat ?? false;
+        if (prev !== updateWorkspaceDto.aiChat) {
+          before.aiChat = prev;
+          after.aiChat = updateWorkspaceDto.aiChat;
+        }
+        await this.workspaceRepo.updateAiSettings(
+          workspaceId,
+          'chat',
+          updateWorkspaceDto.aiChat,
+          trx,
+        );
+      }
+
       delete updateWorkspaceDto.restrictApiToAdmins;
       delete updateWorkspaceDto.aiSearch;
       delete updateWorkspaceDto.generativeAi;
       delete updateWorkspaceDto.disablePublicSharing;
       delete updateWorkspaceDto.mcpEnabled;
+      delete updateWorkspaceDto.aiChat;
 
       await this.workspaceRepo.updateWorkspace(
         updateWorkspaceDto,
diff --git a/apps/server/src/database/migrations/20260409T132415-ai-chat.ts b/apps/server/src/database/migrations/20260409T132415-ai-chat.ts
new file mode 100644
index 00000000..28b595f1
--- /dev/null
+++ b/apps/server/src/database/migrations/20260409T132415-ai-chat.ts
@@ -0,0 +1,118 @@
+import { type Kysely, sql } from 'kysely';
+
+export async function up(db: Kysely<any>): Promise<void> {
+  await db.schema
+    .createTable('ai_chats')
+    .ifNotExists()
+    .addColumn('id', 'uuid', (col) =>
+      col.primaryKey().defaultTo(sql`gen_uuid_v7()`),
+    )
+    .addColumn('workspace_id', 'uuid', (col) =>
+      col.references('workspaces.id').onDelete('cascade').notNull(),
+    )
+    .addColumn('creator_id', 'uuid', (col) =>
+      col.references('users.id').notNull(),
+    )
+    .addColumn('title', 'varchar', (col) => col)
+    .addColumn('created_at', 'timestamptz', (col) =>
+      col.notNull().defaultTo(sql`now()`),
+    )
+    .addColumn('updated_at', 'timestamptz', (col) =>
+      col.notNull().defaultTo(sql`now()`),
+    )
+    .addColumn('deleted_at', 'timestamptz', (col) => col)
+    .execute();
+
+  await db.schema
+    .createIndex('idx_ai_chats_workspace_creator')
+    .ifNotExists()
+    .on('ai_chats')
+    .columns(['workspace_id', 'creator_id', 'id'])
+    .execute();
+
+  await db.schema
+    .createTable('ai_chat_messages')
+    .ifNotExists()
+    .addColumn('id', 'uuid', (col) =>
+      col.primaryKey().defaultTo(sql`gen_uuid_v7()`),
+    )
+    .addColumn('chat_id', 'uuid', (col) =>
+      col.references('ai_chats.id').onDelete('cascade').notNull(),
+    )
+    .addColumn('workspace_id', 'uuid', (col) =>
+      col.references('workspaces.id').onDelete('cascade').notNull(),
+    )
+    .addColumn('user_id', 'uuid', (col) =>
+      col.references('users.id').onDelete('set null'),
+    )
+    .addColumn('role', 'varchar', (col) => col.notNull())
+    .addColumn('content', 'text', (col) => col)
+    .addColumn('tool_calls', 'jsonb', (col) => col)
+    .addColumn('metadata', 'jsonb', (col) => col)
+    .addColumn('tsv', sql`tsvector`, (col) => col)
+    .addColumn('created_at', 'timestamptz', (col) =>
+      col.notNull().defaultTo(sql`now()`),
+    )
+    .addColumn('updated_at', 'timestamptz', (col) =>
+      col.notNull().defaultTo(sql`now()`),
+    )
+    .addColumn('deleted_at', 'timestamptz', (col) => col)
+    .execute();
+
+  await db.schema
+    .createIndex('idx_ai_chat_messages_chat_id')
+    .ifNotExists()
+    .on('ai_chat_messages')
+    .columns(['chat_id', 'id'])
+    .execute();
+
+  await db.schema
+    .createIndex('idx_ai_chat_messages_tsv')
+    .ifNotExists()
+    .on('ai_chat_messages')
+    .using('GIN')
+    .column('tsv')
+    .execute();
+
+  //ts-vector
+  await sql`
+    CREATE OR REPLACE FUNCTION ai_chat_messages_tsvector_trigger() RETURNS trigger AS $$
+    BEGIN
+      NEW.tsv := to_tsvector('english', f_unaccent(substring(coalesce(NEW.content, ''), 1, 100000)));
+      RETURN NEW;
+    END;
+    $$ LANGUAGE plpgsql;
+  `.execute(db);
+
+  await sql`
+    CREATE OR REPLACE TRIGGER ai_chat_messages_tsvector_update
+      BEFORE INSERT OR UPDATE ON ai_chat_messages
+      FOR EACH ROW EXECUTE FUNCTION ai_chat_messages_tsvector_trigger();
+  `.execute(db);
+
+  await db.schema
+    .alterTable('attachments')
+    .addColumn('ai_chat_id', 'uuid', (col) => col)
+    .execute();
+
+  await db.schema
+    .createIndex('idx_attachments_ai_chat_id')
+    .ifNotExists()
+    .on('attachments')
+    .column('ai_chat_id')
+    .execute();
+}
+
+export async function down(db: Kysely<any>): Promise<void> {
+  await db.schema.dropIndex('idx_attachments_ai_chat_id').execute();
+  await db.schema.alterTable('attachments').dropColumn('ai_chat_id').execute();
+
+  await sql`DROP TRIGGER IF EXISTS ai_chat_messages_tsvector_update ON ai_chat_messages`.execute(
+    db,
+  );
+  await sql`DROP FUNCTION IF EXISTS ai_chat_messages_tsvector_trigger`.execute(
+    db,
+  );
+  await db.schema.dropTable('ai_chat_messages').execute();
+  await db.schema.dropTable('ai_chats').execute();
+}
diff --git a/apps/server/src/database/repos/attachment/attachment.repo.ts b/apps/server/src/database/repos/attachment/attachment.repo.ts
index 5824ce5f..bf2b5ecb 100644
--- a/apps/server/src/database/repos/attachment/attachment.repo.ts
+++ b/apps/server/src/database/repos/attachment/attachment.repo.ts
@@ -7,6 +7,7 @@ import {
   InsertableAttachment,
   UpdatableAttachment,
 } from '@docmost/db/types/entity.types';
+import { AttachmentType } from '../../../core/attachment/attachment.constants';
 
 @Injectable()
 export class AttachmentRepo {
@@ -23,6 +24,7 @@ export class AttachmentRepo {
     'creatorId',
     'pageId',
     'spaceId',
+    'aiChatId',
     'workspaceId',
     'createdAt',
     'updatedAt',
@@ -44,6 +46,21 @@ export class AttachmentRepo {
       .executeTakeFirst();
   }
 
+  async findByIdWithContent(
+    attachmentId: string,
+    opts?: {
+      trx?: KyselyTransaction;
+    },
+  ): Promise<Attachment> {
+    const db = dbOrTx(this.db, opts?.trx);
+
+    return db
+      .selectFrom('attachments')
+      .select([...this.baseFields, 'textContent'])
+      .where('id', '=', attachmentId)
+      .executeTakeFirst();
+  }
+
   async insertAttachment(
     insertableAttachment: InsertableAttachment,
     trx?: KyselyTransaction,
@@ -72,6 +89,21 @@ export class AttachmentRepo {
       .execute();
   }
 
+  async findByAiChatId(
+    aiChatId: string,
+    opts?: {
+      trx?: KyselyTransaction;
+    },
+  ): Promise<Attachment[]> {
+    const db = dbOrTx(this.db, opts?.trx);
+
+    return db
+      .selectFrom('attachments')
+      .select(this.baseFields)
+      .where('aiChatId', '=', aiChatId)
+      .execute();
+  }
+
   updateAttachmentsByPageId(
     updatableAttachment: UpdatableAttachment,
     pageIds: string[],
@@ -97,6 +129,25 @@ export class AttachmentRepo {
       .executeTakeFirst();
   }
 
+  async claimAttachmentsForChat(
+    attachmentIds: string[],
+    aiChatId: string,
+    creatorId: string,
+    workspaceId: string,
+  ): Promise<void> {
+    if (attachmentIds.length === 0) return;
+
+    await this.db
+      .updateTable('attachments')
+      .set({ aiChatId })
+      .where('id', 'in', attachmentIds)
+      .where('creatorId', '=', creatorId)
+      .where('workspaceId', '=', workspaceId)
+      .where('type', '=', AttachmentType.Chat)
+      .where('aiChatId', 'is', null)
+      .execute();
+  }
+
   async deleteAttachmentById(attachmentId: string): Promise<void> {
     await this.db
       .deleteFrom('attachments')
diff --git a/apps/server/src/database/types/db.d.ts b/apps/server/src/database/types/db.d.ts
index fe4d5a13..3f4081e1 100644
--- a/apps/server/src/database/types/db.d.ts
+++ b/apps/server/src/database/types/db.d.ts
@@ -43,6 +43,7 @@ export interface ApiKeys {
 }
 
 export interface Attachments {
+  aiChatId: string | null;
   createdAt: Generated<Timestamp>;
   creatorId: string;
   deletedAt: Timestamp | null;
@@ -429,6 +430,31 @@ export interface PagePermissions {
   updatedAt: Generated<Timestamp>;
 }
 
+export interface AiChats {
+  id: Generated<string>;
+  workspaceId: string;
+  creatorId: string;
+  title: string | null;
+  createdAt: Generated<Timestamp>;
+  updatedAt: Generated<Timestamp>;
+  deletedAt: Timestamp | null;
+}
+
+export interface AiChatMessages {
+  id: Generated<string>;
+  chatId: string;
+  workspaceId: string;
+  userId: string | null;
+  role: string;
+  content: string | null;
+  toolCalls: Json | null;
+  metadata: Json | null;
+  tsv: string | null;
+  createdAt: Generated<Timestamp>;
+  updatedAt: Generated<Timestamp>;
+  deletedAt: Timestamp | null;
+}
+
 export interface UserSessions {
   id: Generated<string>;
   userId: string;
@@ -445,6 +471,8 @@ export interface UserSessions {
 }
 
 export interface DB {
+  aiChats: AiChats;
+  aiChatMessages: AiChatMessages;
   apiKeys: ApiKeys;
   attachments: Attachments;
   audit: Audit;
diff --git a/apps/server/src/database/types/entity.types.ts b/apps/server/src/database/types/entity.types.ts
index d23e7475..8d4f482a 100644
--- a/apps/server/src/database/types/entity.types.ts
+++ b/apps/server/src/database/types/entity.types.ts
@@ -1,5 +1,7 @@
 import { Insertable, Selectable, Updateable } from 'kysely';
 import {
+  AiChats,
+  AiChatMessages,
   Attachments,
   Comments,
   Groups,
@@ -29,6 +31,21 @@ import {
 } from './db';
 import { PageEmbeddings } from '@docmost/db/types/embeddings.types';
 
+// AI Chat
+export type AiChat = Selectable<AiChats>;
+export type InsertableAiChat = Insertable<AiChats>;
+export type UpdatableAiChat = Updateable<Omit<AiChats, 'id'>>;
+
+// AI Chat Message
+// `tsv` is an internal tsvector column maintained by a trigger for
+// full-text search. It is omitted from the public type so it never leaks
+// into HTTP responses or the chat history fed to the language model.
+export type AiChatMessage = Omit<Selectable<AiChatMessages>, 'tsv'>;
+export type InsertableAiChatMessage = Omit<
+  Insertable<AiChatMessages>,
+  'tsv'
+>;
+
 // Workspace
 export type Workspace = Selectable<Workspaces>;
 export type InsertableWorkspace = Insertable<Workspaces>;
diff --git a/apps/server/src/ee b/apps/server/src/ee
index dc7ae0e3..d3bc4c51 160000
--- a/apps/server/src/ee
+++ b/apps/server/src/ee
@@ -1 +1 @@
-Subproject commit dc7ae0e3b066df842248b2295ccfad190a0c5a93
+Subproject commit d3bc4c5160fec9c4fabf769180f0ff00ef12042b
diff --git a/apps/server/src/integrations/environment/environment.service.ts b/apps/server/src/integrations/environment/environment.service.ts
index b1b27d40..ceb2eae7 100644
--- a/apps/server/src/integrations/environment/environment.service.ts
+++ b/apps/server/src/integrations/environment/environment.service.ts
@@ -252,6 +252,13 @@ export class EnvironmentService {
     return this.configService.get<string>('AI_COMPLETION_MODEL');
   }
 
+  getAiChatModel(): string {
+    return (
+      this.configService.get<string>('AI_CHAT_MODEL') ||
+      this.configService.get<string>('AI_COMPLETION_MODEL')
+    );
+  }
+
   getAiEmbeddingDimension(): number {
     return parseInt(
       this.configService.get<string>('AI_EMBEDDING_DIMENSION'),
diff --git a/apps/server/src/integrations/export/export.service.ts b/apps/server/src/integrations/export/export.service.ts
index d93f9ba0..3f8da1bf 100644
--- a/apps/server/src/integrations/export/export.service.ts
+++ b/apps/server/src/integrations/export/export.service.ts
@@ -353,7 +353,7 @@ export class ExportService {
     if (attachmentIds.length > 0) {
       const attachments = await this.db
         .selectFrom('attachments')
-        .selectAll()
+        .select(['id', 'fileName', 'filePath'])
         .where('id', 'in', attachmentIds)
         .where('spaceId', '=', spaceId)
         .execute();
diff --git a/apps/server/src/integrations/queue/constants/queue.constants.ts b/apps/server/src/integrations/queue/constants/queue.constants.ts
index 92d15426..6d92f09c 100644
--- a/apps/server/src/integrations/queue/constants/queue.constants.ts
+++ b/apps/server/src/integrations/queue/constants/queue.constants.ts
@@ -17,6 +17,7 @@ export enum QueueJob {
   ATTACHMENT_INDEX_CONTENT = 'attachment-index-content',
   ATTACHMENT_INDEXING = 'attachment-indexing',
   DELETE_PAGE_ATTACHMENTS = 'delete-page-attachments',
+  DELETE_AI_CHAT_ATTACHMENTS = 'delete-ai-chat-attachments',
 
   DELETE_USER_AVATARS = 'delete-user-avatars',
 
diff --git a/apps/server/src/integrations/throttle/throttle.module.ts b/apps/server/src/integrations/throttle/throttle.module.ts
index 8f080e1d..42dd0ec4 100644
--- a/apps/server/src/integrations/throttle/throttle.module.ts
+++ b/apps/server/src/integrations/throttle/throttle.module.ts
@@ -4,6 +4,7 @@ import { ThrottlerStorageRedisService } from '@nest-lab/throttler-storage-redis'
 import { EnvironmentService } from '../environment/environment.service';
 import { EnvironmentModule } from '../environment/environment.module';
 import { parseRedisUrl } from '../../common/helpers';
+import { AUTH_THROTTLER, AI_CHAT_THROTTLER } from './throttler-names';
 import Redis from 'ioredis';
 
 @Module({
@@ -14,7 +15,10 @@ import Redis from 'ioredis';
         const redisConfig = parseRedisUrl(environmentService.getRedisUrl());
 
         return {
-          throttlers: [{ name: 'auth', ttl: 60_000, limit: 10 }],
+          throttlers: [
+            { name: AUTH_THROTTLER, ttl: 60_000, limit: 10 },
+            { name: AI_CHAT_THROTTLER, ttl: 60_000, limit: 25 },
+          ],
           errorMessage: 'Too many requests',
           storage: new ThrottlerStorageRedisService(
             new Redis({
diff --git a/apps/server/src/integrations/throttle/throttler-names.ts b/apps/server/src/integrations/throttle/throttler-names.ts
new file mode 100644
index 00000000..388ba29d
--- /dev/null
+++ b/apps/server/src/integrations/throttle/throttler-names.ts
@@ -0,0 +1,2 @@
+export const AUTH_THROTTLER = 'auth';
+export const AI_CHAT_THROTTLER = 'ai-chat';
diff --git a/apps/server/src/integrations/throttle/user-throttler.guard.ts b/apps/server/src/integrations/throttle/user-throttler.guard.ts
new file mode 100644
index 00000000..35744c09
--- /dev/null
+++ b/apps/server/src/integrations/throttle/user-throttler.guard.ts
@@ -0,0 +1,13 @@
+import { Injectable } from '@nestjs/common';
+import { ThrottlerGuard } from '@nestjs/throttler';
+
+type AuthedRequest = { user?: { id?: string } };
+
+@Injectable()
+export class UserThrottlerGuard extends ThrottlerGuard {
+  protected async getTracker(req: AuthedRequest): Promise<string> {
+    const userId = req.user?.id;
+    if (userId) return `user:${userId}`;
+    return super.getTracker(req as Parameters<ThrottlerGuard['getTracker']>[0]);
+  }
+}
diff --git a/packages/editor-ext/src/lib/markdown/utils/marked.utils.ts b/packages/editor-ext/src/lib/markdown/utils/marked.utils.ts
index 04dc1978..7556aa4f 100644
--- a/packages/editor-ext/src/lib/markdown/utils/marked.utils.ts
+++ b/packages/editor-ext/src/lib/markdown/utils/marked.utils.ts
@@ -37,6 +37,8 @@ marked.use({
   extensions: [calloutExtension, mathBlockExtension, mathInlineExtension],
 });
 
+marked.setOptions({ breaks: true });
+
 export function markdownToHtml(
   markdownInput: string,
 ): string | Promise<string> {
@@ -46,8 +48,5 @@ export function markdownToHtml(
     .replace(YAML_FONT_MATTER_REGEX, "")
     .trimStart();
 
-  return marked
-    .options({ breaks: true })
-    .parse(markdown)
-    .toString();
+  return marked.parse(markdown).toString();
 }
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index ff37ec78..cfdfcdcb 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -589,6 +589,9 @@ importers:
       cookie:
         specifier: ^1.1.1
         version: 1.1.1
+      fast-bm25:
+        specifier: 0.0.5
+        version: 0.0.5(typescript@5.9.3)
       fastify-ip:
         specifier: ^2.0.0
         version: 2.0.0
@@ -601,6 +604,9 @@ importers:
       ioredis:
         specifier: ^5.10.1
         version: 5.10.1
+      js-tiktoken:
+        specifier: ^1.0.21
+        version: 1.0.21
       jsonwebtoken:
         specifier: ^9.0.3
         version: 9.0.3
@@ -6874,6 +6880,12 @@ packages:
   exsolve@1.0.7:
     resolution: {integrity: sha512-VO5fQUzZtI6C+vx4w/4BWJpg3s/5l+6pRQEHzFRM8WFi4XffSP1Z+4qi7GbjWbvRQEbdIco5mIMq+zX4rPuLrw==}
 
+  fast-bm25@0.0.5:
+    resolution: {integrity: sha512-6HTiLmPkgeqcPJHccN0pXdqnA7OzhaEQZTFzWnfjIyPoX5sGVKUUpfRc2K2o6zMwK+g009miRhADYn/f2Ax0Mg==}
+    engines: {node: '>=14.0.0'}
+    peerDependencies:
+      typescript: ^5.6.3
+
   fast-copy@4.0.2:
     resolution: {integrity: sha512-ybA6PDXIXOXivLJK/z9e+Otk7ve13I4ckBvGO5I2RRmBU1gMHLVDJYEuJYhGwez7YNlYji2M2DvVU+a9mSFDlw==}
 
@@ -8966,6 +8978,9 @@ packages:
   points-on-path@0.2.1:
     resolution: {integrity: sha512-25ClnWWuw7JbWZcgqY/gJ4FQWadKxGWk+3kR/7kD0tCaDtPPMj7oHu2ToLaVhfpnHrZzYby2w6tUA0eOIuUg8g==}
 
+  porter2@1.1.0:
+    resolution: {integrity: sha512-Io2cLEdZn0O1dH60pRsjmr/cH/qJJ/j6Cjubz8wQWi0b6vPdQIUxSBQKyx9d+8CN7fSnY+5uOU3rErMFjNqcLw==}
+
   possible-typed-array-names@1.0.0:
     resolution: {integrity: sha512-d7Uw+eZoloe0EHDIYoe+bQ5WXnGMOpmiZFTuMWCwpjzzkL2nTjcKiAk4hh8TjnGye2TwWOk3UXucZ+3rbmBa8Q==}
     engines: {node: '>= 0.4'}
@@ -17795,6 +17810,11 @@ snapshots:
 
   exsolve@1.0.7: {}
 
+  fast-bm25@0.0.5(typescript@5.9.3):
+    dependencies:
+      porter2: 1.1.0
+      typescript: 5.9.3
+
   fast-copy@4.0.2: {}
 
   fast-decode-uri-component@1.0.1: {}
@@ -20144,6 +20164,8 @@ snapshots:
       path-data-parser: 0.1.0
       points-on-curve: 0.2.0
 
+  porter2@1.1.0: {}
+
   possible-typed-array-names@1.0.0: {}
 
   postcss-js@4.0.1(postcss@8.5.8):