diff --git a/frontend/appflowy_flutter/integration_test/desktop/document/document_with_inline_math_equation_test.dart b/frontend/appflowy_flutter/integration_test/desktop/document/document_with_inline_math_equation_test.dart
index 27f02f17cd..c4a8e71a02 100644
--- a/frontend/appflowy_flutter/integration_test/desktop/document/document_with_inline_math_equation_test.dart
+++ b/frontend/appflowy_flutter/integration_test/desktop/document/document_with_inline_math_equation_test.dart
@@ -33,7 +33,7 @@ void main() {
       );
 
       // tap the inline math equation button
-      final inlineMathEquationButton = find.byTooltip(
+      final inlineMathEquationButton = find.findFlowyTooltip(
         LocaleKeys.document_plugins_createInlineMathEquation.tr(),
       );
       await tester.tapButton(inlineMathEquationButton);
@@ -78,7 +78,7 @@ void main() {
       );
 
       // tap the inline math equation button
-      var inlineMathEquationButton = find.byTooltip(
+      var inlineMathEquationButton = find.findFlowyTooltip(
         LocaleKeys.document_plugins_createInlineMathEquation.tr(),
       );
       await tester.tapButton(inlineMathEquationButton);
@@ -93,11 +93,11 @@ void main() {
       );
 
       // expect to the see the inline math equation button is highlighted
-      inlineMathEquationButton = find.byWidgetPredicate(
-        (widget) =>
-            widget is SVGIconItemWidget &&
-            widget.tooltip ==
-                LocaleKeys.document_plugins_createInlineMathEquation.tr(),
+      inlineMathEquationButton = find.descendant(
+        of: find.findFlowyTooltip(
+          LocaleKeys.document_plugins_createInlineMathEquation.tr(),
+        ),
+        matching: find.byType(SVGIconItemWidget),
       );
       expect(
         tester.widget<SVGIconItemWidget>(inlineMathEquationButton).isHighlight,
diff --git a/frontend/appflowy_flutter/integration_test/desktop/uncategorized/open_ai_smart_menu_test.dart b/frontend/appflowy_flutter/integration_test/desktop/uncategorized/open_ai_smart_menu_test.dart
deleted file mode 100644
index 1d42cd8d28..0000000000
--- a/frontend/appflowy_flutter/integration_test/desktop/uncategorized/open_ai_smart_menu_test.dart
+++ /dev/null
@@ -1,113 +0,0 @@
-import 'package:appflowy/plugins/document/presentation/editor_plugins/openai/service/ai_client.dart';
-import 'package:appflowy/startup/startup.dart';
-import 'package:appflowy_editor/appflowy_editor.dart';
-import 'package:appflowy_editor/src/render/toolbar/toolbar_widget.dart';
-import 'package:flowy_infra_ui/flowy_infra_ui.dart';
-import 'package:flutter/services.dart';
-import 'package:flutter_test/flutter_test.dart';
-import 'package:integration_test/integration_test.dart';
-
-import '../../shared/mock/mock_openai_repository.dart';
-import '../../shared/util.dart';
-
-void main() {
-  IntegrationTestWidgetsFlutterBinding.ensureInitialized();
-  const service = TestWorkspaceService(TestWorkspace.aiWorkSpace);
-
-  group('integration tests for open-ai smart menu', () {
-    setUpAll(() async => service.setUpAll());
-    setUp(() async => service.setUp());
-
-    testWidgets('testing selection on open-ai smart menu replace',
-        (tester) async {
-      final appFlowyEditor = await setUpOpenAITesting(tester);
-      final editorState = appFlowyEditor.editorState;
-
-      editorState.service.selectionService.updateSelection(
-        Selection(
-          start: Position(path: [1], offset: 4),
-          end: Position(path: [1], offset: 10),
-        ),
-      );
-      await tester.pumpAndSettle(const Duration(milliseconds: 500));
-      await tester.pumpAndSettle();
-
-      expect(find.byType(ToolbarWidget), findsAtLeastNWidgets(1));
-
-      await tester.tap(find.byTooltip('AI Assistants'));
-      await tester.pumpAndSettle(const Duration(milliseconds: 500));
-
-      await tester.tap(find.text('Summarize'));
-      await tester.pumpAndSettle();
-
-      await tester
-          .tap(find.byType(FlowyRichTextButton, skipOffstage: false).first);
-      await tester.pumpAndSettle();
-
-      expect(
-        editorState.service.selectionService.currentSelection.value,
-        Selection(
-          start: Position(path: [1], offset: 4),
-          end: Position(path: [1], offset: 84),
-        ),
-      );
-    });
-    testWidgets('testing selection on open-ai smart menu insert',
-        (tester) async {
-      final appFlowyEditor = await setUpOpenAITesting(tester);
-      final editorState = appFlowyEditor.editorState;
-
-      editorState.service.selectionService.updateSelection(
-        Selection(
-          start: Position(path: [1]),
-          end: Position(path: [1], offset: 5),
-        ),
-      );
-      await tester.pumpAndSettle(const Duration(milliseconds: 500));
-      await tester.pumpAndSettle();
-      expect(find.byType(ToolbarWidget), findsAtLeastNWidgets(1));
-
-      await tester.tap(find.byTooltip('AI Assistants'));
-      await tester.pumpAndSettle(const Duration(milliseconds: 500));
-
-      await tester.tap(find.text('Summarize'));
-      await tester.pumpAndSettle();
-
-      await tester
-          .tap(find.byType(FlowyRichTextButton, skipOffstage: false).at(1));
-      await tester.pumpAndSettle();
-
-      expect(
-        editorState.service.selectionService.currentSelection.value,
-        Selection(
-          start: Position(path: [2]),
-          end: Position(path: [3]),
-        ),
-      );
-    });
-  });
-}
-
-Future<AppFlowyEditor> setUpOpenAITesting(WidgetTester tester) async {
-  await tester.initializeAppFlowy();
-  await mockOpenAIRepository();
-
-  await simulateKeyDownEvent(LogicalKeyboardKey.controlLeft);
-  await simulateKeyDownEvent(LogicalKeyboardKey.backslash);
-  await tester.pumpAndSettle();
-
-  final Finder editor = find.byType(AppFlowyEditor);
-  await tester.tap(editor);
-  await tester.pumpAndSettle();
-  return tester.state(editor).widget as AppFlowyEditor;
-}
-
-Future<void> mockOpenAIRepository() async {
-  await getIt.unregister<AIRepository>();
-  getIt.registerFactoryAsync<AIRepository>(
-    () => Future.value(
-      MockOpenAIRepository(),
-    ),
-  );
-  return;
-}
diff --git a/frontend/appflowy_flutter/integration_test/shared/base.dart b/frontend/appflowy_flutter/integration_test/shared/base.dart
index ab72247c24..16a576154f 100644
--- a/frontend/appflowy_flutter/integration_test/shared/base.dart
+++ b/frontend/appflowy_flutter/integration_test/shared/base.dart
@@ -1,9 +1,6 @@
 import 'dart:async';
 import 'dart:io';
 
-import 'package:flutter/gestures.dart';
-import 'package:flutter/services.dart';
-
 import 'package:appflowy/env/cloud_env.dart';
 import 'package:appflowy/env/cloud_env_test.dart';
 import 'package:appflowy/startup/entry_point.dart';
@@ -16,6 +13,8 @@ import 'package:appflowy/user/presentation/screens/sign_in_screen/widgets/widget
 import 'package:appflowy/workspace/application/settings/prelude.dart';
 import 'package:flowy_infra/uuid.dart';
 import 'package:flowy_infra_ui/flowy_infra_ui.dart';
+import 'package:flutter/gestures.dart';
+import 'package:flutter/services.dart';
 import 'package:flutter_test/flutter_test.dart';
 import 'package:path/path.dart' as p;
 import 'package:path_provider/path_provider.dart';
@@ -231,6 +230,16 @@ extension AppFlowyFinderTestBase on CommonFinders {
       (widget) => widget is FlowyText && widget.text == text,
     );
   }
+
+  Finder findFlowyTooltip(String richMessage, {bool skipOffstage = true}) {
+    return byWidgetPredicate(
+      (widget) =>
+          widget is FlowyTooltip &&
+          widget.richMessage != null &&
+          widget.richMessage!.toPlainText().contains(richMessage),
+      skipOffstage: skipOffstage,
+    );
+  }
 }
 
 Future<void> useTestSupabaseCloud() async {
diff --git a/frontend/appflowy_flutter/integration_test/shared/editor_test_operations.dart b/frontend/appflowy_flutter/integration_test/shared/editor_test_operations.dart
index a92f6548bb..0c712f8e24 100644
--- a/frontend/appflowy_flutter/integration_test/shared/editor_test_operations.dart
+++ b/frontend/appflowy_flutter/integration_test/shared/editor_test_operations.dart
@@ -3,7 +3,7 @@ import 'dart:ui';
 
 import 'package:appflowy/generated/locale_keys.g.dart';
 import 'package:appflowy/plugins/base/emoji/emoji_picker.dart';
-import 'package:appflowy/plugins/base/emoji/emoji_skin_tone.dart';
+import 'package:appflowy/shared/icon_emoji_picker/emoji_skin_tone.dart';
 import 'package:appflowy/plugins/document/presentation/editor_plugins/actions/block_action_add_button.dart';
 import 'package:appflowy/plugins/document/presentation/editor_plugins/actions/block_action_option_button.dart';
 import 'package:appflowy/plugins/document/presentation/editor_plugins/header/cover_editor.dart';
diff --git a/frontend/appflowy_flutter/lib/plugins/base/emoji/emoji_picker.dart b/frontend/appflowy_flutter/lib/plugins/base/emoji/emoji_picker.dart
index f2c9f53551..43e7035e38 100644
--- a/frontend/appflowy_flutter/lib/plugins/base/emoji/emoji_picker.dart
+++ b/frontend/appflowy_flutter/lib/plugins/base/emoji/emoji_picker.dart
@@ -1,5 +1,5 @@
 import 'package:appflowy/plugins/base/emoji/emoji_picker_header.dart';
-import 'package:appflowy/plugins/base/emoji/emoji_skin_tone.dart';
+import 'package:appflowy/shared/icon_emoji_picker/emoji_skin_tone.dart';
 import 'package:appflowy/shared/icon_emoji_picker/emoji_search_bar.dart';
 import 'package:flowy_infra/size.dart';
 import 'package:flowy_infra_ui/flowy_infra_ui.dart';
diff --git a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_page.dart b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_page.dart
index c7f8643b68..54b45d0397 100644
--- a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_page.dart
+++ b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_page.dart
@@ -387,6 +387,8 @@ class _AppFlowyEditorPageState extends State<AppFlowyEditorPage> {
         editorState: editorState,
         editorScrollController: editorScrollController,
         textDirection: textDirection,
+        tooltipBuilder: (context, id, message, child) => widget.styleCustomizer
+            .buildToolbarItemTooltip(context, id, message, child,),
         child: editor,
       ),
     );
diff --git a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/align_toolbar_item/align_toolbar_item.dart b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/align_toolbar_item/align_toolbar_item.dart
index 9723158be5..4fd81395e9 100644
--- a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/align_toolbar_item/align_toolbar_item.dart
+++ b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/align_toolbar_item/align_toolbar_item.dart
@@ -9,12 +9,13 @@ import 'package:flutter/material.dart';
 const String leftAlignmentKey = 'left';
 const String centerAlignmentKey = 'center';
 const String rightAlignmentKey = 'right';
+const String kAlignToolbarItemId = 'editor.align';
 
 final alignToolbarItem = ToolbarItem(
-  id: 'editor.align',
+  id: kAlignToolbarItemId,
   group: 4,
   isActive: onlyShowInTextType,
-  builder: (context, editorState, highlightColor, _) {
+  builder: (context, editorState, highlightColor, _, tooltipBuilder) {
     final selection = editorState.selection!;
     final nodes = editorState.getNodesInSelection(selection);
 
@@ -37,35 +38,37 @@ final alignToolbarItem = ToolbarItem(
       data = FlowySvgs.toolbar_align_right_s;
     }
 
-    final child = FlowySvg(
+    Widget child = FlowySvg(
       data,
       size: const Size.square(16),
       color: isHighlight ? highlightColor : Colors.white,
     );
 
-    return MouseRegion(
-      cursor: SystemMouseCursors.click,
-      child: FlowyTooltip(
-        message: LocaleKeys.document_plugins_optionAction_align.tr(),
-        child: Padding(
-          padding: const EdgeInsets.symmetric(horizontal: 4.0),
-          child: _AlignmentButtons(
-            child: child,
-            onAlignChanged: (align) async {
-              await editorState.updateNode(
-                selection,
-                (node) => node.copyWith(
-                  attributes: {
-                    ...node.attributes,
-                    blockComponentAlign: align,
-                  },
-                ),
-              );
+    child = _AlignmentButtons(
+      child: child,
+      onAlignChanged: (align) async {
+        await editorState.updateNode(
+          selection,
+          (node) => node.copyWith(
+            attributes: {
+              ...node.attributes,
+              blockComponentAlign: align,
             },
           ),
-        ),
-      ),
+        );
+      },
     );
+
+    if (tooltipBuilder != null) {
+      child = tooltipBuilder(
+        context,
+        kAlignToolbarItemId,
+        LocaleKeys.document_plugins_optionAction_align.tr(),
+        child,
+      );
+    }
+
+    return child;
   },
 );
 
@@ -83,13 +86,15 @@ class _AlignmentButtons extends StatefulWidget {
 }
 
 class _AlignmentButtonsState extends State<_AlignmentButtons> {
+  final controller = PopoverController();
+
   @override
   Widget build(BuildContext context) {
     return AppFlowyPopover(
       windowPadding: const EdgeInsets.all(0),
-      margin: const EdgeInsets.all(4),
+      margin: const EdgeInsets.symmetric(vertical: 2.0),
       direction: PopoverDirection.bottomWithCenterAligned,
-      offset: const Offset(0, 10),
+      offset: const Offset(0, 12),
       decorationColor: Theme.of(context).colorScheme.onTertiary,
       borderRadius: const BorderRadius.all(Radius.circular(4)),
       popupBuilder: (_) {
@@ -99,7 +104,12 @@ class _AlignmentButtonsState extends State<_AlignmentButtons> {
       onClose: () {
         keepEditorFocusNotifier.decrease();
       },
-      child: widget.child,
+      child: FlowyButton(
+        useIntrinsicWidth: true,
+        text: widget.child,
+        hoverColor: Colors.grey.withOpacity(0.3),
+        onTap: () => controller.show(),
+      ),
     );
   }
 }
@@ -114,7 +124,7 @@ class _AlignButtons extends StatelessWidget {
   @override
   Widget build(BuildContext context) {
     return SizedBox(
-      height: 32,
+      height: 28,
       child: Row(
         mainAxisSize: MainAxisSize.min,
         children: [
@@ -156,17 +166,16 @@ class _AlignButton extends StatelessWidget {
 
   @override
   Widget build(BuildContext context) {
-    return MouseRegion(
-      cursor: SystemMouseCursors.click,
-      child: GestureDetector(
-        onTap: onTap,
-        child: FlowyTooltip(
-          message: tooltips,
-          child: FlowySvg(
-            icon,
-            size: const Size.square(16),
-            color: Colors.white,
-          ),
+    return FlowyButton(
+      useIntrinsicWidth: true,
+      hoverColor: Colors.grey.withOpacity(0.3),
+      onTap: onTap,
+      text: FlowyTooltip(
+        message: tooltips,
+        child: FlowySvg(
+          icon,
+          size: const Size.square(16),
+          color: Colors.white,
         ),
       ),
     );
@@ -179,7 +188,7 @@ class _Divider extends StatelessWidget {
   @override
   Widget build(BuildContext context) {
     return Padding(
-      padding: const EdgeInsets.all(8),
+      padding: const EdgeInsets.all(4),
       child: Container(
         width: 1,
         color: Colors.grey,
diff --git a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/font/customize_font_toolbar_item.dart b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/font/customize_font_toolbar_item.dart
index c610be4dbf..da4e0f2546 100644
--- a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/font/customize_font_toolbar_item.dart
+++ b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/font/customize_font_toolbar_item.dart
@@ -1,6 +1,3 @@
-import 'package:appflowy/workspace/application/settings/appearance/base_appearance.dart';
-import 'package:flutter/material.dart';
-
 import 'package:appflowy/generated/flowy_svgs.g.dart';
 import 'package:appflowy/generated/locale_keys.g.dart';
 import 'package:appflowy/plugins/document/application/document_appearance_cubit.dart';
@@ -9,6 +6,7 @@ import 'package:appflowy/util/font_family_extension.dart';
 import 'package:appflowy/util/levenshtein.dart';
 import 'package:appflowy/workspace/application/appearance_defaults.dart';
 import 'package:appflowy/workspace/application/settings/appearance/appearance_cubit.dart';
+import 'package:appflowy/workspace/application/settings/appearance/base_appearance.dart';
 import 'package:appflowy/workspace/presentation/settings/shared/setting_list_tile.dart';
 import 'package:appflowy/workspace/presentation/settings/shared/setting_value_dropdown.dart';
 import 'package:appflowy_backend/log.dart';
@@ -20,56 +18,66 @@ import 'package:flowy_infra/theme_extension.dart';
 import 'package:flowy_infra_ui/style_widget/button.dart';
 import 'package:flowy_infra_ui/style_widget/text.dart';
 import 'package:flowy_infra_ui/style_widget/text_field.dart';
-import 'package:flowy_infra_ui/widget/flowy_tooltip.dart';
+import 'package:flutter/material.dart';
 import 'package:flutter_bloc/flutter_bloc.dart';
 import 'package:google_fonts/google_fonts.dart';
 
+const kFontToolbarItemId = 'editor.font';
+
 final customizeFontToolbarItem = ToolbarItem(
-  id: 'editor.font',
+  id: kFontToolbarItemId,
   group: 4,
   isActive: onlyShowInTextType,
-  builder: (context, editorState, highlightColor, _) {
+  builder: (context, editorState, highlightColor, _, tooltipBuilder) {
     final selection = editorState.selection!;
     final popoverController = PopoverController();
     final String? currentFontFamily = editorState
         .getDeltaAttributeValueInSelection(AppFlowyRichTextKeys.fontFamily);
-    return MouseRegion(
-      cursor: SystemMouseCursors.click,
-      child: FontFamilyDropDown(
-        currentFontFamily: currentFontFamily ?? '',
-        offset: const Offset(0, 12),
-        popoverController: popoverController,
-        onOpen: () => keepEditorFocusNotifier.increase(),
-        onClose: () => keepEditorFocusNotifier.decrease(),
-        showResetButton: true,
-        onFontFamilyChanged: (fontFamily) async {
-          popoverController.close();
-          try {
-            await editorState.formatDelta(selection, {
-              AppFlowyRichTextKeys.fontFamily: fontFamily,
-            });
-          } catch (e) {
-            Log.error('Failed to set font family: $e');
-          }
-        },
-        onResetFont: () async {
-          popoverController.close();
-          await editorState
-              .formatDelta(selection, {AppFlowyRichTextKeys.fontFamily: null});
-        },
-        child: Padding(
-          padding: const EdgeInsets.symmetric(horizontal: 4.0),
-          child: FlowyTooltip(
-            message: LocaleKeys.document_plugins_fonts.tr(),
-            child: const FlowySvg(
-              FlowySvgs.font_family_s,
-              size: Size.square(16.0),
-              color: Colors.white,
-            ),
-          ),
+
+    Widget child = FontFamilyDropDown(
+      currentFontFamily: currentFontFamily ?? '',
+      offset: const Offset(0, 12),
+      popoverController: popoverController,
+      onOpen: () => keepEditorFocusNotifier.increase(),
+      onClose: () => keepEditorFocusNotifier.decrease(),
+      showResetButton: true,
+      onFontFamilyChanged: (fontFamily) async {
+        popoverController.close();
+        try {
+          await editorState.formatDelta(selection, {
+            AppFlowyRichTextKeys.fontFamily: fontFamily,
+          });
+        } catch (e) {
+          Log.error('Failed to set font family: $e');
+        }
+      },
+      onResetFont: () async {
+        popoverController.close();
+        await editorState
+            .formatDelta(selection, {AppFlowyRichTextKeys.fontFamily: null});
+      },
+      child: FlowyButton(
+        useIntrinsicWidth: true,
+        hoverColor: Colors.grey.withOpacity(0.3),
+        onTap: () => popoverController.show(),
+        text: const FlowySvg(
+          FlowySvgs.font_family_s,
+          size: Size.square(16.0),
+          color: Colors.white,
         ),
       ),
     );
+
+    if (tooltipBuilder != null) {
+      child = tooltipBuilder(
+        context,
+        kFontToolbarItemId,
+        LocaleKeys.document_plugins_fonts.tr(),
+        child,
+      );
+    }
+
+    return child;
   },
 );
 
diff --git a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/inline_math_equation/inline_math_equation_toolbar_item.dart b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/inline_math_equation/inline_math_equation_toolbar_item.dart
index 08c23df05b..a66a9ee317 100644
--- a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/inline_math_equation/inline_math_equation_toolbar_item.dart
+++ b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/inline_math_equation/inline_math_equation_toolbar_item.dart
@@ -5,11 +5,13 @@ import 'package:appflowy_editor/appflowy_editor.dart';
 import 'package:easy_localization/easy_localization.dart';
 import 'package:flutter/material.dart';
 
+const _kInlineMathEquationToolbarItemId = 'editor.inline_math_equation';
+
 final ToolbarItem inlineMathEquationItem = ToolbarItem(
-  id: 'editor.inline_math_equation',
+  id: _kInlineMathEquationToolbarItemId,
   group: 2,
   isActive: onlyShowInSingleSelectionAndTextType,
-  builder: (context, editorState, highlightColor, _) {
+  builder: (context, editorState, highlightColor, _, tooltipBuilder) {
     final selection = editorState.selection!;
     final nodes = editorState.getNodesInSelection(selection);
     final isHighlight = nodes.allSatisfyInSelection(selection, (delta) {
@@ -17,7 +19,7 @@ final ToolbarItem inlineMathEquationItem = ToolbarItem(
         (attributes) => attributes[InlineMathEquationKeys.formula] != null,
       );
     });
-    return SVGIconItemWidget(
+    final child = SVGIconItemWidget(
       iconBuilder: (_) => FlowySvg(
         FlowySvgs.math_lg,
         size: const Size.square(16),
@@ -25,7 +27,6 @@ final ToolbarItem inlineMathEquationItem = ToolbarItem(
       ),
       isHighlight: isHighlight,
       highlightColor: highlightColor,
-      tooltip: LocaleKeys.document_plugins_createInlineMathEquation.tr(),
       onPressed: () async {
         final selection = editorState.selection;
         if (selection == null || selection.isCollapsed) {
@@ -71,5 +72,16 @@ final ToolbarItem inlineMathEquationItem = ToolbarItem(
         await editorState.apply(transaction);
       },
     );
+
+    if (tooltipBuilder != null) {
+      return tooltipBuilder(
+        context,
+        _kInlineMathEquationToolbarItemId,
+        LocaleKeys.document_plugins_createInlineMathEquation.tr(),
+        child,
+      );
+    }
+
+    return child;
   },
 );
diff --git a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/openai/widgets/smart_edit_toolbar_item.dart b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/openai/widgets/smart_edit_toolbar_item.dart
index 84d122cf18..434857891e 100644
--- a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/openai/widgets/smart_edit_toolbar_item.dart
+++ b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_plugins/openai/widgets/smart_edit_toolbar_item.dart
@@ -11,12 +11,15 @@ import 'package:easy_localization/easy_localization.dart';
 import 'package:flowy_infra_ui/style_widget/icon_button.dart';
 import 'package:flutter/material.dart';
 
+const _kSmartEditToolbarItemId = 'appflowy.editor.smart_edit';
+
 final ToolbarItem smartEditItem = ToolbarItem(
-  id: 'appflowy.editor.smart_edit',
+  id: _kSmartEditToolbarItemId,
   group: 0,
   isActive: onlyShowInSingleSelectionAndTextType,
-  builder: (context, editorState, _, __) => SmartEditActionList(
+  builder: (context, editorState, _, __, tooltipBuilder) => SmartEditActionList(
     editorState: editorState,
+    tooltipBuilder: tooltipBuilder,
   ),
 );
 
@@ -24,9 +27,11 @@ class SmartEditActionList extends StatefulWidget {
   const SmartEditActionList({
     super.key,
     required this.editorState,
+    this.tooltipBuilder,
   });
 
   final EditorState editorState;
+  final ToolbarTooltipBuilder? tooltipBuilder;
 
   @override
   State<SmartEditActionList> createState() => _SmartEditActionListState();
@@ -60,11 +65,8 @@ class _SmartEditActionListState extends State<SmartEditActionList> {
       onClosed: () => keepEditorFocusNotifier.decrease(),
       buildChild: (controller) {
         keepEditorFocusNotifier.increase();
-        return FlowyIconButton(
+        final child = FlowyIconButton(
           hoverColor: Colors.transparent,
-          tooltipText: isAIEnabled
-              ? LocaleKeys.document_plugins_smartEdit.tr()
-              : LocaleKeys.document_plugins_appflowyAIEditDisabled.tr(),
           preferBelow: false,
           icon: const Icon(
             Icons.lightbulb_outline,
@@ -83,6 +85,19 @@ class _SmartEditActionListState extends State<SmartEditActionList> {
             }
           },
         );
+
+        if (widget.tooltipBuilder != null) {
+          return widget.tooltipBuilder!(
+            context,
+            _kSmartEditToolbarItemId,
+            isAIEnabled
+                ? LocaleKeys.document_plugins_smartEdit.tr()
+                : LocaleKeys.document_plugins_appflowyAIEditDisabled.tr(),
+            child,
+          );
+        }
+
+        return child;
       },
       onSelected: (action, controller) {
         controller.close();
diff --git a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_style.dart b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_style.dart
index 529c2a549c..7464b81a81 100644
--- a/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_style.dart
+++ b/frontend/appflowy_flutter/lib/plugins/document/presentation/editor_style.dart
@@ -1,4 +1,7 @@
+import 'dart:io';
+
 import 'package:appflowy/core/helpers/url_launcher.dart';
+import 'package:appflowy/generated/locale_keys.g.dart';
 import 'package:appflowy/mobile/application/page_style/document_page_style_bloc.dart';
 import 'package:appflowy/plugins/document/application/document_appearance_cubit.dart';
 import 'package:appflowy/plugins/document/presentation/editor_plugins/base/font_colors.dart';
@@ -13,7 +16,10 @@ import 'package:appflowy/workspace/application/settings/appearance/appearance_cu
 import 'package:appflowy/workspace/application/settings/appearance/base_appearance.dart';
 import 'package:appflowy_editor/appflowy_editor.dart' hide Log;
 import 'package:collection/collection.dart';
+import 'package:easy_localization/easy_localization.dart';
 import 'package:flowy_infra/theme_extension.dart';
+import 'package:flowy_infra_ui/style_widget/hover.dart';
+import 'package:flowy_infra_ui/widget/flowy_tooltip.dart';
 import 'package:flutter/gestures.dart';
 import 'package:flutter/material.dart';
 import 'package:flutter_bloc/flutter_bloc.dart';
@@ -394,4 +400,83 @@ class EditorStyleCustomizer {
       after,
     );
   }
+
+  Widget buildToolbarItemTooltip(
+    BuildContext context,
+    String id,
+    String message,
+    Widget child,
+  ) {
+    final tooltipMessage = _buildTooltipMessage(id, message);
+    child = FlowyTooltip(
+      richMessage: tooltipMessage,
+      preferBelow: false,
+      verticalOffset: 20,
+      child: child,
+    );
+
+    // the align/font toolbar item doesn't need the hover effect
+    final toolbarItemsWithoutHover = {
+      kFontToolbarItemId,
+      kAlignToolbarItemId,
+    };
+
+    if (!toolbarItemsWithoutHover.contains(id)) {
+      child = Padding(
+        padding: const EdgeInsets.symmetric(vertical: 4.0),
+        child: FlowyHover(
+          style: HoverStyle(
+            hoverColor: Colors.grey.withOpacity(0.3),
+          ),
+          child: child,
+        ),
+      );
+    }
+
+    return child;
+  }
+
+  TextSpan _buildTooltipMessage(String id, String message) {
+    final markdownItemTooltips = {
+      'underline': (LocaleKeys.toolbar_underline.tr(), 'U'),
+      'bold': (LocaleKeys.toolbar_bold.tr(), 'B'),
+      'italic': (LocaleKeys.toolbar_italic.tr(), 'I'),
+      'strikethrough': (LocaleKeys.toolbar_strike.tr(), 'Shift+S'),
+      'code': (LocaleKeys.toolbar_inlineCode.tr(), 'E'),
+    };
+
+    final markdownItemIds = markdownItemTooltips.keys.toSet();
+    // the items without shortcuts
+    if (!markdownItemIds.contains(id)) {
+      return TextSpan(
+        text: message,
+        style: context.tooltipTextStyle(),
+      );
+    }
+
+    final tooltip = markdownItemTooltips[id];
+    if (tooltip == null) {
+      return TextSpan(
+        text: message,
+        style: context.tooltipTextStyle(),
+      );
+    }
+
+    final textSpan = TextSpan(
+      children: [
+        TextSpan(
+          text: '${tooltip.$1}\n',
+          style: context.tooltipTextStyle(),
+        ),
+        TextSpan(
+          text: (Platform.isMacOS ? '⌘+' : 'Ctrl+\\') + tooltip.$2,
+          style: context
+              .tooltipTextStyle()
+              ?.copyWith(color: Theme.of(context).hintColor),
+        ),
+      ],
+    );
+
+    return textSpan;
+  }
 }
diff --git a/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/colors.dart b/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/colors.dart
new file mode 100644
index 0000000000..8728c3be4a
--- /dev/null
+++ b/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/colors.dart
@@ -0,0 +1,26 @@
+import 'package:appflowy/util/theme_extension.dart';
+import 'package:flutter/material.dart';
+
+extension PickerColors on BuildContext {
+  Color get pickerTextColor {
+    return Theme.of(this).isLightMode
+        ? const Color(0x80171717)
+        : Colors.white.withOpacity(0.5);
+  }
+
+  Color get pickerIconColor {
+    return Theme.of(this).isLightMode ? const Color(0xFF171717) : Colors.white;
+  }
+
+  Color get pickerSearchBarBorderColor {
+    return Theme.of(this).isLightMode
+        ? const Color(0x1E171717)
+        : Colors.white.withOpacity(0.12);
+  }
+
+  Color get pickerButtonBoarderColor {
+    return Theme.of(this).isLightMode
+        ? const Color(0x1E171717)
+        : Colors.white.withOpacity(0.12);
+  }
+}
diff --git a/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/emoji_search_bar.dart b/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/emoji_search_bar.dart
index 57dba3c93e..8dbee9ec29 100644
--- a/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/emoji_search_bar.dart
+++ b/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/emoji_search_bar.dart
@@ -1,12 +1,14 @@
 import 'package:appflowy/generated/flowy_svgs.g.dart';
 import 'package:appflowy/generated/locale_keys.g.dart';
-import 'package:appflowy/plugins/base/emoji/emoji_skin_tone.dart';
+import 'package:appflowy/shared/icon_emoji_picker/emoji_skin_tone.dart';
 import 'package:appflowy_editor/appflowy_editor.dart';
 import 'package:easy_localization/easy_localization.dart';
 import 'package:flowy_infra_ui/flowy_infra_ui.dart';
 import 'package:flutter/material.dart';
 import 'package:flutter_emoji_mart/flutter_emoji_mart.dart';
 
+import 'colors.dart';
+
 typedef EmojiKeywordChangedCallback = void Function(String keyword);
 typedef EmojiSkinToneChanged = void Function(EmojiSkinTone skinTone);
 
@@ -82,7 +84,7 @@ class _RandomEmojiButton extends StatelessWidget {
       height: 36,
       decoration: ShapeDecoration(
         shape: RoundedRectangleBorder(
-          side: const BorderSide(color: Color(0x1E171717)),
+          side: BorderSide(color: context.pickerButtonBoarderColor),
           borderRadius: BorderRadius.circular(8),
         ),
       ),
@@ -141,7 +143,7 @@ class _SearchTextFieldState extends State<_SearchTextField> {
               fontWeight: FontWeight.w400,
               color: Theme.of(context).hintColor,
             ),
-        enableBorderColor: const Color(0x1E171717),
+        enableBorderColor: context.pickerSearchBarBorderColor,
         controller: controller,
         onChanged: widget.onKeywordChanged,
         prefixIcon: const Padding(
diff --git a/frontend/appflowy_flutter/lib/plugins/base/emoji/emoji_skin_tone.dart b/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/emoji_skin_tone.dart
similarity index 96%
rename from frontend/appflowy_flutter/lib/plugins/base/emoji/emoji_skin_tone.dart
rename to frontend/appflowy_flutter/lib/shared/icon_emoji_picker/emoji_skin_tone.dart
index 5206075769..e802e0dba0 100644
--- a/frontend/appflowy_flutter/lib/plugins/base/emoji/emoji_skin_tone.dart
+++ b/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/emoji_skin_tone.dart
@@ -5,6 +5,8 @@ import 'package:flowy_infra_ui/flowy_infra_ui.dart';
 import 'package:flutter/material.dart';
 import 'package:flutter_emoji_mart/flutter_emoji_mart.dart';
 
+import 'colors.dart';
+
 // use a temporary global value to store last selected skin tone
 EmojiSkinTone? lastSelectedEmojiSkinTone;
 
@@ -68,7 +70,7 @@ class _FlowyEmojiSkinToneSelectorState
       width: 36,
       height: 36,
       decoration: BoxDecoration(
-        border: Border.all(color: const Color(0x1E171717)),
+        border: Border.all(color: context.pickerButtonBoarderColor),
         borderRadius: BorderRadius.circular(8),
       ),
       child: FlowyButton(
diff --git a/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/icon_picker.dart b/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/icon_picker.dart
index f9d5cbf9b5..707e2ffe79 100644
--- a/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/icon_picker.dart
+++ b/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/icon_picker.dart
@@ -13,6 +13,7 @@ import 'package:flowy_infra_ui/flowy_infra_ui.dart';
 import 'package:flutter/material.dart' hide Icon;
 import 'package:flutter/services.dart';
 
+import 'colors.dart';
 import 'icon_color_picker.dart';
 
 // cache the icon groups to avoid loading them multiple times
@@ -200,7 +201,7 @@ class _IconPickerState extends State<IconPicker> {
               iconGroup.displayName,
               fontSize: 12,
               figmaLineHeight: 18.0,
-              color: const Color(0x80171717),
+              color: context.pickerTextColor,
             ),
             const VSpace(4.0),
             Wrap(
@@ -252,7 +253,7 @@ class _Icon extends StatelessWidget {
             child: FlowySvg.string(
               icon.content,
               size: const Size.square(20),
-              color: const Color(0xFF171717),
+              color: context.pickerIconColor,
               opacity: 0.7,
             ),
           ),
diff --git a/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/icon_search_bar.dart b/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/icon_search_bar.dart
index 06a3566d21..31e1e285c0 100644
--- a/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/icon_search_bar.dart
+++ b/frontend/appflowy_flutter/lib/shared/icon_emoji_picker/icon_search_bar.dart
@@ -6,6 +6,8 @@ import 'package:flowy_infra_ui/flowy_infra_ui.dart';
 import 'package:flutter/material.dart';
 import 'package:flutter_emoji_mart/flutter_emoji_mart.dart';
 
+import 'colors.dart';
+
 typedef IconKeywordChangedCallback = void Function(String keyword);
 typedef EmojiSkinToneChanged = void Function(EmojiSkinTone skinTone);
 
@@ -70,7 +72,7 @@ class _RandomIconButton extends StatelessWidget {
       height: 36,
       decoration: ShapeDecoration(
         shape: RoundedRectangleBorder(
-          side: const BorderSide(color: Color(0x1E171717)),
+          side: BorderSide(color: context.pickerButtonBoarderColor),
           borderRadius: BorderRadius.circular(8),
         ),
       ),
@@ -123,7 +125,7 @@ class _SearchTextFieldState extends State<_SearchTextField> {
               fontWeight: FontWeight.w400,
               color: Theme.of(context).hintColor,
             ),
-        enableBorderColor: const Color(0x1E171717),
+        enableBorderColor: context.pickerSearchBarBorderColor,
         controller: controller,
         onChanged: widget.onKeywordChanged,
         prefixIcon: const Padding(
diff --git a/frontend/appflowy_flutter/packages/flowy_infra_ui/lib/widget/flowy_tooltip.dart b/frontend/appflowy_flutter/packages/flowy_infra_ui/lib/widget/flowy_tooltip.dart
index 960b8b3ad4..d723a67a3f 100644
--- a/frontend/appflowy_flutter/packages/flowy_infra_ui/lib/widget/flowy_tooltip.dart
+++ b/frontend/appflowy_flutter/packages/flowy_infra_ui/lib/widget/flowy_tooltip.dart
@@ -10,6 +10,7 @@ class FlowyTooltip extends StatelessWidget {
     this.preferBelow,
     this.showDuration,
     this.margin,
+    this.verticalOffset,
     this.child,
   });
 
@@ -19,6 +20,7 @@ class FlowyTooltip extends StatelessWidget {
   final Duration? showDuration;
   final EdgeInsetsGeometry? margin;
   final Widget? child;
+  final double? verticalOffset;
 
   @override
   Widget build(BuildContext context) {
@@ -28,16 +30,14 @@ class FlowyTooltip extends StatelessWidget {
 
     return Tooltip(
       margin: margin,
-      verticalOffset: 16.0,
-      padding: const EdgeInsets.only(
-        left: 12.0,
-        right: 12.0,
-        top: 5.0,
-        bottom: 8.0,
+      verticalOffset: verticalOffset ?? 16.0,
+      padding: const EdgeInsets.symmetric(
+        horizontal: 12.0,
+        vertical: 8.0,
       ),
       decoration: BoxDecoration(
         color: context.tooltipBackgroundColor(),
-        borderRadius: BorderRadius.circular(12.0),
+        borderRadius: BorderRadius.circular(10.0),
       ),
       waitDuration: _tooltipWaitDuration,
       message: message,
@@ -50,7 +50,7 @@ class FlowyTooltip extends StatelessWidget {
 }
 
 extension FlowyToolTipExtension on BuildContext {
-  double tooltipFontSize() => 13.0;
+  double tooltipFontSize() => 14.0;
   double tooltipHeight() => 18.0 / tooltipFontSize();
   Color tooltipFontColor() => Theme.of(this).brightness == Brightness.light
       ? Colors.white
diff --git a/frontend/appflowy_flutter/pubspec.lock b/frontend/appflowy_flutter/pubspec.lock
index 4827c94bbc..10f14ba563 100644
--- a/frontend/appflowy_flutter/pubspec.lock
+++ b/frontend/appflowy_flutter/pubspec.lock
@@ -53,8 +53,8 @@ packages:
     dependency: "direct main"
     description:
       path: "."
-      ref: c064543
-      resolved-ref: c064543e0e40f862f1db2db36725d48465a8aea5
+      ref: "4536488faf458ab45e304c1715850d4d1ae517ee"
+      resolved-ref: "4536488faf458ab45e304c1715850d4d1ae517ee"
       url: "https://github.com/AppFlowy-IO/appflowy-editor.git"
     source: git
     version: "3.1.0"
diff --git a/frontend/appflowy_flutter/pubspec.yaml b/frontend/appflowy_flutter/pubspec.yaml
index 17c37f3287..928766a845 100644
--- a/frontend/appflowy_flutter/pubspec.yaml
+++ b/frontend/appflowy_flutter/pubspec.yaml
@@ -199,7 +199,7 @@ dependency_overrides:
   appflowy_editor:
     git:
       url: https://github.com/AppFlowy-IO/appflowy-editor.git
-      ref: "c064543"
+      ref: "4536488faf458ab45e304c1715850d4d1ae517ee"
 
   appflowy_editor_plugins:
     git: