diff --git a/packages/twenty-ui/src/navigation/menu/menu-item/components/MenuItem.tsx b/packages/twenty-ui/src/navigation/menu/menu-item/components/MenuItem.tsx
index dd6153fd5c..da1d0ce009 100644
--- a/packages/twenty-ui/src/navigation/menu/menu-item/components/MenuItem.tsx
+++ b/packages/twenty-ui/src/navigation/menu/menu-item/components/MenuItem.tsx
@@ -1,9 +1,5 @@
 import { useTheme } from '@emotion/react';
-import {
-  IconChevronRight,
-  OverflowingTextWithTooltip,
-  type IconComponent,
-} from '@ui/display';
+import { IconChevronRight, type IconComponent } from '@ui/display';
 import { type LightIconButtonProps } from '@ui/input/button/components/LightIconButton';
 import { LightIconButtonGroup } from '@ui/input/button/components/LightIconButtonGroup';
 import {
@@ -14,16 +10,12 @@ import {
 } from 'react';
 
 import styled from '@emotion/styled';
-import { isString } from '@sniptt/guards';
 import { MenuItemHotKeys } from '@ui/navigation/menu/menu-item/components/MenuItemHotKeys';
 import { motion } from 'framer-motion';
 import { MenuItemLeftContent } from '../internals/components/MenuItemLeftContent';
 import {
   StyledHoverableMenuItemBase,
-  StyledMenuItemLabel,
-  StyledMenuItemLeftContent,
   StyledMenuItemRightContent,
-  StyledRightMenuItemContextualText,
 } from '../internals/components/StyledMenuItemBase';
 import { type MenuItemAccent } from '../types/MenuItemAccent';
 
@@ -111,30 +103,17 @@ export const MenuItem = ({
       onMouseLeave={onMouseLeave}
       focused={focused}
     >
-      <StyledMenuItemLeftContent>
-        <MenuItemLeftContent
-          LeftIcon={LeftIcon ?? undefined}
-          LeftComponent={LeftComponent}
-          withIconContainer={withIconContainer}
-          text={text}
-          contextualText={
-            contextualTextPosition === 'left' ? contextualText : null
-          }
-          disabled={disabled}
-        />
-      </StyledMenuItemLeftContent>
+      <MenuItemLeftContent
+        LeftIcon={LeftIcon ?? undefined}
+        LeftComponent={LeftComponent}
+        withIconContainer={withIconContainer}
+        text={text}
+        contextualText={contextualText}
+        contextualTextPosition={contextualTextPosition}
+        disabled={disabled}
+      />
+
       <StyledMenuItemRightContent>
-        {contextualTextPosition === 'right' && (
-          <StyledMenuItemLabel>
-            {isString(contextualText) ? (
-              <StyledRightMenuItemContextualText>
-                <OverflowingTextWithTooltip text={contextualText} />
-              </StyledRightMenuItemContextualText>
-            ) : (
-              contextualText
-            )}
-          </StyledMenuItemLabel>
-        )}
         {iconButtons && (
           <div className="hoverable-buttons">
             {showIconButtons && (
diff --git a/packages/twenty-ui/src/navigation/menu/menu-item/components/__stories__/MenuItem.stories.tsx b/packages/twenty-ui/src/navigation/menu/menu-item/components/__stories__/MenuItem.stories.tsx
index 188691071f..37cd76bf9b 100644
--- a/packages/twenty-ui/src/navigation/menu/menu-item/components/__stories__/MenuItem.stories.tsx
+++ b/packages/twenty-ui/src/navigation/menu/menu-item/components/__stories__/MenuItem.stories.tsx
@@ -198,6 +198,7 @@ export const ContextualTextCatalog: CatalogStory<Story, typeof MenuItem> = {
   },
   decorators: [CatalogDecorator],
   parameters: {
+    pseudo: { hover: ['.hover'], active: ['.pressed'], focus: ['.focus'] },
     catalog: {
       dimensions: [
         {
@@ -227,6 +228,55 @@ export const ContextualTextCatalog: CatalogStory<Story, typeof MenuItem> = {
             }
           },
         },
+        {
+          name: 'iconButtons',
+          values: ['no icon button', 'one icon button'],
+          props: (choice: string) => {
+            switch (choice) {
+              case 'no icon button': {
+                return {
+                  iconButtons: [],
+                };
+              }
+              case 'one icon button': {
+                return {
+                  iconButtons: [
+                    {
+                      Icon: IconBell,
+                      onClick: action('Clicked on icon button'),
+                    },
+                  ],
+                };
+              }
+              default:
+                return {};
+            }
+          },
+          labels: (choice: string) => {
+            switch (choice) {
+              case 'no icon button':
+                return 'No icon button';
+              case 'one icon button':
+                return 'One icon button';
+              default:
+                return choice;
+            }
+          },
+        },
+        {
+          name: 'states',
+          values: ['default', 'hover'],
+          props: (state: string) => {
+            switch (state) {
+              case 'default':
+                return {};
+              case 'hover':
+                return { className: 'hover' };
+              default:
+                return {};
+            }
+          },
+        },
       ],
       options: {
         elementContainer: {
diff --git a/packages/twenty-ui/src/navigation/menu/menu-item/internals/components/MenuItemLeftContent.tsx b/packages/twenty-ui/src/navigation/menu/menu-item/internals/components/MenuItemLeftContent.tsx
index 88fa9a978f..1f5a84c154 100644
--- a/packages/twenty-ui/src/navigation/menu/menu-item/internals/components/MenuItemLeftContent.tsx
+++ b/packages/twenty-ui/src/navigation/menu/menu-item/internals/components/MenuItemLeftContent.tsx
@@ -13,6 +13,7 @@ import {
   StyledMenuItemContextualText,
   StyledMenuItemLabel,
   StyledMenuItemLeftContent,
+  StyledRightMenuItemContextualText,
 } from './StyledMenuItemBase';
 
 const StyledMainText = styled.div`
@@ -32,6 +33,10 @@ const StyledIconContainer = styled.div`
   padding: ${({ theme }) => theme.spacing(1)};
 `;
 
+const StyledMenuItemLabelRight = styled(StyledMenuItemLabel)`
+  margin-left: auto;
+`;
+
 type MenuItemLeftContentProps = {
   className?: string;
   LeftComponent?: ReactNode;
@@ -41,6 +46,7 @@ type MenuItemLeftContentProps = {
   disabled?: boolean;
   text: ReactNode;
   contextualText?: ReactNode;
+  contextualTextPosition?: 'left' | 'right';
 };
 
 export const MenuItemLeftContent = ({
@@ -50,6 +56,7 @@ export const MenuItemLeftContent = ({
   withIconContainer = false,
   text,
   contextualText,
+  contextualTextPosition = 'left',
   showGrip = false,
   disabled = false,
 }: MenuItemLeftContentProps) => {
@@ -89,18 +96,29 @@ export const MenuItemLeftContent = ({
         ) : (
           text
         )}
-        {isString(contextualText) ? (
+        {contextualTextPosition === 'left' && (
           <>
-            {isNonEmptyString(contextualText) && (
-              <StyledMenuItemContextualText>
-                <OverflowingTextWithTooltip text={`· ${contextualText}`} />
-              </StyledMenuItemContextualText>
-            )}
+            {isString(contextualText)
+              ? isNonEmptyString(contextualText) && (
+                  <StyledMenuItemContextualText>
+                    <OverflowingTextWithTooltip text={`· ${contextualText}`} />
+                  </StyledMenuItemContextualText>
+                )
+              : contextualText}
           </>
-        ) : (
-          contextualText
         )}
       </StyledMenuItemLabel>
+      {contextualTextPosition === 'right' && (
+        <StyledMenuItemLabelRight>
+          <StyledRightMenuItemContextualText>
+            {isString(contextualText) ? (
+              <OverflowingTextWithTooltip text={contextualText} />
+            ) : (
+              contextualText
+            )}
+          </StyledRightMenuItemContextualText>
+        </StyledMenuItemLabelRight>
+      )}
     </StyledMenuItemLeftContent>
   );
 };
diff --git a/packages/twenty-ui/src/navigation/menu/menu-item/internals/components/StyledMenuItemBase.tsx b/packages/twenty-ui/src/navigation/menu/menu-item/internals/components/StyledMenuItemBase.tsx
index 36df7e3163..a474a927c3 100644
--- a/packages/twenty-ui/src/navigation/menu/menu-item/internals/components/StyledMenuItemBase.tsx
+++ b/packages/twenty-ui/src/navigation/menu/menu-item/internals/components/StyledMenuItemBase.tsx
@@ -112,16 +112,22 @@ export const StyledMenuItemLeftContent = styled.div`
 
   gap: ${({ theme }) => theme.spacing(2)};
   min-width: 0;
-  max-width: 100%;
+  width: 100%;
 
-  flex-shrink: 0;
+  & svg {
+    flex-shrink: 0;
+  }
 `;
 
 export const StyledMenuItemRightContent = styled.div`
   align-items: center;
   display: flex;
   flex-direction: row;
-  overflow: hidden;
+  gap: ${({ theme }) => theme.spacing(2)};
+
+  & svg {
+    flex-shrink: 0;
+  }
 `;
 
 export const StyledDraggableItem = styled.div`
@@ -187,7 +193,5 @@ export const StyledMenuItemContextualText = styled.div`
 export const StyledRightMenuItemContextualText = styled(
   StyledMenuItemContextualText,
 )`
-  display: flex;
   text-align: right;
-  padding-right: ${({ theme }) => theme.spacing(1)};
 `;