diff --git a/apps/web/src/app/test/report-playground/ReportPlayground.tsx b/apps/web/src/app/test/report-playground/ReportPlayground.tsx
index 8ebd2bb2b..6c8f26e6a 100644
--- a/apps/web/src/app/test/report-playground/ReportPlayground.tsx
+++ b/apps/web/src/app/test/report-playground/ReportPlayground.tsx
@@ -207,7 +207,7 @@ const value: ReportElements = [
     children: [
       {
         text: 'This is a todo list',
-        subscript: true
+        subscript: false
       }
     ],
     indent: 1,
diff --git a/apps/web/src/components/ui/report/config/icons.tsx b/apps/web/src/components/ui/report/config/icons.tsx
index 6d648f74b..86d0289a2 100644
--- a/apps/web/src/components/ui/report/config/icons.tsx
+++ b/apps/web/src/components/ui/report/config/icons.tsx
@@ -203,6 +203,7 @@ export const NodeTypeIcons = {
   indent: IndentIncrease,
   outdent: IndentDecrease,
   download: Download,
+  turnInto: Pilcrow,
 
   // Tools
   equation: Equation,
diff --git a/apps/web/src/components/ui/report/config/labels.tsx b/apps/web/src/components/ui/report/config/labels.tsx
index 873b72b2e..5f3507bc9 100644
--- a/apps/web/src/components/ui/report/config/labels.tsx
+++ b/apps/web/src/components/ui/report/config/labels.tsx
@@ -124,6 +124,21 @@ export const NodeTypeLabels = {
     keyboard: '⌘+⇧+Z',
     keywords: []
   },
+  delete: {
+    label: 'Delete',
+    keyboard: '⌘+⌫',
+    keywords: []
+  },
+  duplicate: {
+    label: 'Duplicate',
+    keyboard: undefined,
+    keywords: []
+  },
+  askAI: {
+    label: 'Ask AI',
+    keyboard: undefined,
+    keywords: []
+  },
   link: {
     label: 'Link',
     keyboard: '⌘+K',
@@ -161,13 +176,18 @@ export const NodeTypeLabels = {
     keyboard: undefined,
     keywords: []
   },
-  insert: {
-    label: 'Insert',
+  align: {
+    label: 'Align',
     keyboard: undefined,
     keywords: []
   },
-  align: {
-    label: 'Align',
+  indentation: {
+    label: 'Indentation',
+    keyboard: undefined,
+    keywords: ['indent', 'outdent']
+  },
+  insert: {
+    label: 'Insert',
     keyboard: undefined,
     keywords: []
   },
diff --git a/apps/web/src/components/ui/report/elements/AlignToolbarButton.tsx b/apps/web/src/components/ui/report/elements/AlignToolbarButton.tsx
index 6fa89c76e..bada71c62 100644
--- a/apps/web/src/components/ui/report/elements/AlignToolbarButton.tsx
+++ b/apps/web/src/components/ui/report/elements/AlignToolbarButton.tsx
@@ -19,6 +19,7 @@ import {
 } from '@/components/ui/dropdown-menu';
 
 import { ToolbarButton } from '@/components/ui/toolbar/Toolbar';
+import { Tooltip } from '../../tooltip';
 
 const items = [
   {
@@ -69,13 +70,15 @@ export function AlignToolbarButton(props: DropdownMenuProps) {
             tf.textAlign.setNodes(value as Alignment);
             editor.tf.focus();
           }}>
-          {items.map(({ icon: Icon, value: itemValue }) => (
-            <DropdownMenuRadioItem
-              key={itemValue}
-              className="data-[state=checked]:bg-accent pl-2 *:first:[span]:hidden"
-              value={itemValue}>
-              <Icon />
-            </DropdownMenuRadioItem>
+          {items.map(({ icon: Icon, label, value: itemValue }) => (
+            <Tooltip key={itemValue} title={label} side="left">
+              <DropdownMenuRadioItem
+                key={itemValue}
+                className="data-[state=checked]:bg-accent pl-2 *:first:[span]:hidden"
+                value={itemValue}>
+                <Icon />
+              </DropdownMenuRadioItem>
+            </Tooltip>
           ))}
         </DropdownMenuRadioGroup>
       </DropdownMenuContent>
diff --git a/apps/web/src/components/ui/report/elements/BlockContextMenu.tsx b/apps/web/src/components/ui/report/elements/BlockContextMenu.tsx
index 1c723c025..4a57410de 100644
--- a/apps/web/src/components/ui/report/elements/BlockContextMenu.tsx
+++ b/apps/web/src/components/ui/report/elements/BlockContextMenu.tsx
@@ -16,6 +16,7 @@ import {
   ContextMenuContent,
   ContextMenuGroup,
   ContextMenuItem,
+  ContextMenuShortcut,
   ContextMenuSub,
   ContextMenuSubContent,
   ContextMenuSubTrigger,
@@ -23,10 +24,33 @@ import {
 } from '@/components/ui/context-menu';
 import { useIsTouchDevice } from '@/hooks/useIsTouchDevice';
 import { THEME_RESET_STYLE } from '@/styles/theme-reset';
+import { NodeTypeIcons } from '../config/icons';
+import { NodeTypeLabels } from '../config/labels';
+
+// Helper function to render menu item content
+const MenuItemContent = ({
+  icon,
+  labelKey
+}: {
+  icon: React.ComponentType;
+  labelKey: keyof typeof NodeTypeLabels;
+}) => {
+  const label = NodeTypeLabels[labelKey];
+  const Icon = icon;
+  return (
+    <>
+      <div className="text-icon-color text-md size-4">
+        <Icon />
+      </div>
+      {label.label}
+      {label.keyboard && <ContextMenuShortcut>{label.keyboard}</ContextMenuShortcut>}
+    </>
+  );
+};
 
 type Value = 'askAI' | null;
 
-export function BlockContextMenu({ children }: { children: React.ReactNode }) {
+function BlockContextMenuComponent({ children }: { children: React.ReactNode }) {
   const { api, editor } = useEditorPlugin(BlockMenuPlugin);
   const [value, setValue] = React.useState<Value>(null);
   const isTouch = useIsTouchDevice();
@@ -88,7 +112,7 @@ export function BlockContextMenu({ children }: { children: React.ReactNode }) {
             y: event.clientY
           });
         }}>
-        <div className="w-full">{children}</div>
+        <div className="block-context-menu-trigger">{children}</div>
       </ContextMenuTrigger>
       <ContextMenuContent
         className="w-64"
@@ -104,56 +128,84 @@ export function BlockContextMenu({ children }: { children: React.ReactNode }) {
           setValue(null);
         }}>
         <ContextMenuGroup>
-          <ContextMenuItem
+          {/* <ContextMenuItem
             onClick={() => {
               setValue('askAI');
             }}>
-            Ask AI
-          </ContextMenuItem>
+            <MenuItemContent icon={NodeTypeIcons.ai} labelKey="askAI" />
+          </ContextMenuItem> */}
           <ContextMenuItem
             onClick={() => {
               editor.getTransforms(BlockSelectionPlugin).blockSelection.removeNodes();
               editor.tf.focus();
             }}>
-            Delete
+            <MenuItemContent icon={NodeTypeIcons.trash} labelKey="delete" />
           </ContextMenuItem>
           <ContextMenuItem
             onClick={() => {
               editor.getTransforms(BlockSelectionPlugin).blockSelection.duplicate();
             }}>
-            Duplicate
-            {/* <ContextMenuShortcut>⌘ + D</ContextMenuShortcut> */}
+            <MenuItemContent icon={NodeTypeIcons.copy} labelKey="duplicate" />
           </ContextMenuItem>
           <ContextMenuSub>
-            <ContextMenuSubTrigger>Turn into</ContextMenuSubTrigger>
+            <ContextMenuSubTrigger>
+              <MenuItemContent icon={NodeTypeIcons.turnInto} labelKey="turnInto" />
+            </ContextMenuSubTrigger>
             <ContextMenuSubContent className="w-48">
-              <ContextMenuItem onClick={() => handleTurnInto(KEYS.p)}>Paragraph</ContextMenuItem>
+              <ContextMenuItem onClick={() => handleTurnInto(KEYS.p)}>
+                <MenuItemContent icon={NodeTypeIcons.paragraph} labelKey="paragraph" />
+              </ContextMenuItem>
 
-              <ContextMenuItem onClick={() => handleTurnInto(KEYS.h1)}>Heading 1</ContextMenuItem>
-              <ContextMenuItem onClick={() => handleTurnInto(KEYS.h2)}>Heading 2</ContextMenuItem>
-              <ContextMenuItem onClick={() => handleTurnInto(KEYS.h3)}>Heading 3</ContextMenuItem>
+              <ContextMenuItem onClick={() => handleTurnInto(KEYS.h1)}>
+                <MenuItemContent icon={NodeTypeIcons.h1} labelKey="h1" />
+              </ContextMenuItem>
+              <ContextMenuItem onClick={() => handleTurnInto(KEYS.h2)}>
+                <MenuItemContent icon={NodeTypeIcons.h2} labelKey="h2" />
+              </ContextMenuItem>
+              <ContextMenuItem onClick={() => handleTurnInto(KEYS.h3)}>
+                <MenuItemContent icon={NodeTypeIcons.h3} labelKey="h3" />
+              </ContextMenuItem>
               <ContextMenuItem onClick={() => handleTurnInto(KEYS.blockquote)}>
-                Blockquote
+                <MenuItemContent icon={NodeTypeIcons.quote} labelKey="blockquote" />
               </ContextMenuItem>
             </ContextMenuSubContent>
           </ContextMenuSub>
         </ContextMenuGroup>
 
         <ContextMenuGroup>
-          <ContextMenuItem
-            onClick={() => editor.getTransforms(BlockSelectionPlugin).blockSelection.setIndent(1)}>
-            Indent
-          </ContextMenuItem>
-          <ContextMenuItem
-            onClick={() => editor.getTransforms(BlockSelectionPlugin).blockSelection.setIndent(-1)}>
-            Outdent
-          </ContextMenuItem>
           <ContextMenuSub>
-            <ContextMenuSubTrigger>Align</ContextMenuSubTrigger>
+            <ContextMenuSubTrigger>
+              <MenuItemContent icon={NodeTypeIcons.indent} labelKey="indentation" />
+            </ContextMenuSubTrigger>
             <ContextMenuSubContent className="w-48">
-              <ContextMenuItem onClick={() => handleAlign('left')}>Left</ContextMenuItem>
-              <ContextMenuItem onClick={() => handleAlign('center')}>Center</ContextMenuItem>
-              <ContextMenuItem onClick={() => handleAlign('right')}>Right</ContextMenuItem>
+              <ContextMenuItem
+                onClick={() =>
+                  editor.getTransforms(BlockSelectionPlugin).blockSelection.setIndent(1)
+                }>
+                <MenuItemContent icon={NodeTypeIcons.indent} labelKey="indent" />
+              </ContextMenuItem>
+              <ContextMenuItem
+                onClick={() =>
+                  editor.getTransforms(BlockSelectionPlugin).blockSelection.setIndent(-1)
+                }>
+                <MenuItemContent icon={NodeTypeIcons.outdent} labelKey="outdent" />
+              </ContextMenuItem>
+            </ContextMenuSubContent>
+          </ContextMenuSub>
+          <ContextMenuSub>
+            <ContextMenuSubTrigger>
+              <MenuItemContent icon={NodeTypeIcons.alignLeft} labelKey="align" />
+            </ContextMenuSubTrigger>
+            <ContextMenuSubContent className="w-48">
+              <ContextMenuItem onClick={() => handleAlign('left')}>
+                <MenuItemContent icon={NodeTypeIcons.alignLeft} labelKey="alignLeft" />
+              </ContextMenuItem>
+              <ContextMenuItem onClick={() => handleAlign('center')}>
+                <MenuItemContent icon={NodeTypeIcons.alignCenter} labelKey="alignCenter" />
+              </ContextMenuItem>
+              <ContextMenuItem onClick={() => handleAlign('right')}>
+                <MenuItemContent icon={NodeTypeIcons.alignRight} labelKey="alignRight" />
+              </ContextMenuItem>
             </ContextMenuSubContent>
           </ContextMenuSub>
         </ContextMenuGroup>
@@ -161,3 +213,5 @@ export function BlockContextMenu({ children }: { children: React.ReactNode }) {
     </ContextMenu>
   );
 }
+
+export const BlockContextMenu = React.memo(BlockContextMenuComponent);