diff --git a/packages/frontend/core/src/components/root-app-sidebar/index.tsx b/packages/frontend/core/src/components/root-app-sidebar/index.tsx
index 46b3a1e67..c97a17853 100644
--- a/packages/frontend/core/src/components/root-app-sidebar/index.tsx
+++ b/packages/frontend/core/src/components/root-app-sidebar/index.tsx
@@ -18,7 +18,7 @@ import { useI18n } from '@affine/i18n';
 import { track } from '@affine/track';
 import type { Store } from '@blocksuite/affine/store';
 import {
-  AiIcon,
+  AiOutlineIcon,
   AllDocsIcon,
   ImportIcon,
   JournalIcon,
@@ -97,8 +97,8 @@ const AIChatButton = () => {
   );
 
   return (
-    <MenuLinkItem icon={<AiIcon />} active={aiChatActive} to={'/chat'}>
-      <span data-testid="ai-chat">Intelligent</span>
+    <MenuLinkItem icon={<AiOutlineIcon />} active={aiChatActive} to={'/chat'}>
+      <span data-testid="ai-chat">AFFiNE Intelligence</span>
     </MenuLinkItem>
   );
 };
@@ -198,10 +198,10 @@ export const RootAppSidebar = memo((): ReactElement => {
           />
           <AddPageButton />
         </div>
-        <AIChatButton />
         <AllDocsButton />
         <AppSidebarJournalButton />
         {sessionStatus === 'authenticated' && <NotificationButton />}
+        <AIChatButton />
         <MenuItem
           data-testid="slider-bar-workspace-setting-button"
           icon={<SettingsIcon />}
diff --git a/packages/frontend/core/src/desktop/components/ai-island/index.tsx b/packages/frontend/core/src/desktop/components/ai-island/index.tsx
index a40c10658..61e56847c 100644
--- a/packages/frontend/core/src/desktop/components/ai-island/index.tsx
+++ b/packages/frontend/core/src/desktop/components/ai-island/index.tsx
@@ -1,12 +1,17 @@
 import { WorkbenchService } from '@affine/core/modules/workbench';
 import { useLiveData, useService } from '@toeverything/infra';
 import clsx from 'clsx';
-import { useEffect, useState } from 'react';
+import { useCallback, useEffect, useState } from 'react';
 
 import { IslandContainer } from './container';
 import { AIIcon } from './icons';
 import { aiIslandBtn, aiIslandWrapper, toolStyle } from './styles.css';
 
+const hideChat: Array<string | ((path: string) => boolean)> = [
+  '/chat',
+  path => path.includes('attachments'),
+];
+
 export const AIIsland = () => {
   // to make sure ai island is hidden first and animate in
   const [hide, setHide] = useState(true);
@@ -16,12 +21,33 @@ export const AIIsland = () => {
   const haveChatTab = useLiveData(
     activeView.sidebarTabs$.map(tabs => tabs.some(t => t.id === 'chat'))
   );
+  const activeLocation = useLiveData(activeView.location$);
   const activeTab = useLiveData(activeView.activeSidebarTab$);
   const sidebarOpen = useLiveData(workbench.sidebarOpen$);
 
   useEffect(() => {
-    setHide((sidebarOpen && activeTab?.id === 'chat') || !haveChatTab);
-  }, [activeTab, haveChatTab, sidebarOpen]);
+    let hide = true;
+    if (haveChatTab) {
+      hide = !!sidebarOpen && activeTab?.id === 'chat';
+    } else {
+      const path = activeLocation.pathname;
+      hide = hideChat.some(item =>
+        typeof item === 'string' ? path === item : item(path)
+      );
+    }
+    setHide(hide);
+  }, [activeLocation.pathname, activeTab, haveChatTab, sidebarOpen]);
+
+  const onOpenChat = useCallback(() => {
+    if (hide) return;
+    if (haveChatTab) {
+      workbench.openSidebar();
+      activeView.activeSidebarTab('chat');
+    } else {
+      workbench.open('/chat');
+      workbench.closeSidebar();
+    }
+  }, [activeView, haveChatTab, hide, workbench]);
 
   return (
     <IslandContainer className={clsx(toolStyle, { hide })}>
@@ -29,11 +55,7 @@ export const AIIsland = () => {
         <button
           className={aiIslandBtn}
           data-testid="ai-island"
-          onClick={() => {
-            if (hide) return;
-            workbench.openSidebar();
-            activeView.activeSidebarTab('chat');
-          }}
+          onClick={onOpenChat}
         >
           <AIIcon />
         </button>
diff --git a/packages/frontend/core/src/modules/workbench/view/route-container.css.ts b/packages/frontend/core/src/modules/workbench/view/route-container.css.ts
index 7a5b44db0..09cb5f8f9 100644
--- a/packages/frontend/core/src/modules/workbench/view/route-container.css.ts
+++ b/packages/frontend/core/src/modules/workbench/view/route-container.css.ts
@@ -57,6 +57,8 @@ export const rightSidebarButton = style({
       opacity: 0,
       maxWidth: 0,
       marginLeft: 0,
+      // prevent click event from being triggered
+      pointerEvents: 'none',
     },
   },
 });