diff --git a/packages/twenty-front/src/modules/navigation/components/AppNavigationDrawer.tsx b/packages/twenty-front/src/modules/navigation/components/AppNavigationDrawer.tsx
index 310aadc735ef..522f76f3e33c 100644
--- a/packages/twenty-front/src/modules/navigation/components/AppNavigationDrawer.tsx
+++ b/packages/twenty-front/src/modules/navigation/components/AppNavigationDrawer.tsx
@@ -3,7 +3,7 @@ import { useRecoilValue, useSetRecoilState } from 'recoil';
 
 import { currentWorkspaceState } from '@/auth/states/currentWorkspaceState';
 import { SettingsNavigationDrawerItems } from '@/settings/components/SettingsNavigationDrawerItems';
-import { SupportChat } from '@/support/components/SupportChat';
+import { SupportDropdown } from '@/support/components/SupportDropdown';
 import { GithubVersionLink } from '@/ui/navigation/link/components/GithubVersionLink';
 import {
   NavigationDrawer,
@@ -53,7 +53,7 @@ export const AppNavigationDrawer = ({
           undefined,
         title: currentWorkspace?.displayName ?? undefined,
         children: <MainNavigationDrawerItems />,
-        footer: <SupportChat />,
+        footer: <SupportDropdown />,
       };
 
   useEffect(() => {
diff --git a/packages/twenty-front/src/modules/support/components/SupportChat.tsx b/packages/twenty-front/src/modules/support/components/SupportButton.tsx
similarity index 95%
rename from packages/twenty-front/src/modules/support/components/SupportChat.tsx
rename to packages/twenty-front/src/modules/support/components/SupportButton.tsx
index 05da707b6128..11ea7684cb23 100644
--- a/packages/twenty-front/src/modules/support/components/SupportChat.tsx
+++ b/packages/twenty-front/src/modules/support/components/SupportButton.tsx
@@ -1,6 +1,6 @@
-import { useCallback, useEffect, useState } from 'react';
 import styled from '@emotion/styled';
 import { isNonEmptyString } from '@sniptt/guards';
+import { useCallback, useEffect, useState } from 'react';
 import { useRecoilValue } from 'recoil';
 import { IconHelpCircle } from 'twenty-ui';
 
@@ -8,7 +8,7 @@ import { currentUserState } from '@/auth/states/currentUserState';
 import { currentWorkspaceMemberState } from '@/auth/states/currentWorkspaceMemberState';
 import { supportChatState } from '@/client-config/states/supportChatState';
 import { useIsPrefetchLoading } from '@/prefetch/hooks/useIsPrefetchLoading';
-import { SupportChatSkeletonLoader } from '@/support/components/SupportChatSkeletonLoader';
+import { SupportButtonSkeletonLoader } from '@/support/components/SupportButtonSkeletonLoader';
 import { Button } from '@/ui/input/button/components/Button';
 import { WorkspaceMember } from '@/workspace-member/types/WorkspaceMember';
 import { User } from '~/generated/graphql';
@@ -34,7 +34,7 @@ const insertScript = ({
   document.body.appendChild(script);
 };
 
-export const SupportChat = () => {
+export const SupportButton = () => {
   const currentUser = useRecoilValue(currentUserState);
   const currentWorkspaceMember = useRecoilValue(currentWorkspaceMemberState);
   const supportChat = useRecoilValue(supportChatState);
@@ -102,7 +102,7 @@ export const SupportChat = () => {
   ]);
 
   if (loading) {
-    return <SupportChatSkeletonLoader />;
+    return <SupportButtonSkeletonLoader />;
   }
 
   return isFrontChatLoaded ? (
diff --git a/packages/twenty-front/src/modules/support/components/SupportChatSkeletonLoader.tsx b/packages/twenty-front/src/modules/support/components/SupportButtonSkeletonLoader.tsx
similarity index 87%
rename from packages/twenty-front/src/modules/support/components/SupportChatSkeletonLoader.tsx
rename to packages/twenty-front/src/modules/support/components/SupportButtonSkeletonLoader.tsx
index 08d5fc380696..86d4d1b93231 100644
--- a/packages/twenty-front/src/modules/support/components/SupportChatSkeletonLoader.tsx
+++ b/packages/twenty-front/src/modules/support/components/SupportButtonSkeletonLoader.tsx
@@ -1,7 +1,7 @@
 import Skeleton, { SkeletonTheme } from 'react-loading-skeleton';
 import { useTheme } from '@emotion/react';
 
-export const SupportChatSkeletonLoader = () => {
+export const SupportButtonSkeletonLoader = () => {
   const theme = useTheme();
   return (
     <SkeletonTheme
diff --git a/packages/twenty-front/src/modules/support/components/SupportDropdown.tsx b/packages/twenty-front/src/modules/support/components/SupportDropdown.tsx
new file mode 100644
index 000000000000..ff2399678f08
--- /dev/null
+++ b/packages/twenty-front/src/modules/support/components/SupportDropdown.tsx
@@ -0,0 +1,51 @@
+import { SupportButton } from '@/support/components/SupportButton';
+import { Dropdown } from '@/ui/layout/dropdown/components/Dropdown';
+import { DropdownMenu } from '@/ui/layout/dropdown/components/DropdownMenu';
+import { DropdownMenuItemsContainer } from '@/ui/layout/dropdown/components/DropdownMenuItemsContainer';
+import { useDropdown } from '@/ui/layout/dropdown/hooks/useDropdown';
+import { MenuItem } from '@/ui/navigation/menu-item/components/MenuItem';
+import { IconHelpCircle, IconMessage } from 'twenty-ui';
+
+export const SupportDropdown = () => {
+  const dropdownId = `support-field-active-action-dropdown`;
+
+  const { closeDropdown } = useDropdown(dropdownId);
+
+  const handleTalkToUs = () => {
+    window.FrontChat?.('show');
+    closeDropdown();
+  };
+
+  const handleUserGuide = () => {
+    window.open('https://twenty.com/user-guide', '_blank');
+    closeDropdown();
+  };
+
+  return (
+    <Dropdown
+      dropdownId={dropdownId}
+      dropdownPlacement="top-start"
+      dropdownOffset={{ x: 0, y: -28 }}
+      clickableComponent={<SupportButton />}
+      dropdownComponents={
+        <DropdownMenu width="160px">
+          <DropdownMenuItemsContainer>
+            <MenuItem
+              text="Talk to us"
+              LeftIcon={IconMessage}
+              onClick={handleTalkToUs}
+            />
+            <MenuItem
+              text="Documentation"
+              LeftIcon={IconHelpCircle}
+              onClick={handleUserGuide}
+            />
+          </DropdownMenuItemsContainer>
+        </DropdownMenu>
+      }
+      dropdownHotkeyScope={{
+        scope: dropdownId,
+      }}
+    />
+  );
+};
diff --git a/packages/twenty-front/src/modules/support/components/__stories__/SupportChat.stories.tsx b/packages/twenty-front/src/modules/support/components/__stories__/SupportButton.stories.tsx
similarity index 74%
rename from packages/twenty-front/src/modules/support/components/__stories__/SupportChat.stories.tsx
rename to packages/twenty-front/src/modules/support/components/__stories__/SupportButton.stories.tsx
index da0c12334d18..06cb0fe3d9ea 100644
--- a/packages/twenty-front/src/modules/support/components/__stories__/SupportChat.stories.tsx
+++ b/packages/twenty-front/src/modules/support/components/__stories__/SupportButton.stories.tsx
@@ -1,6 +1,6 @@
 import { expect } from '@storybook/jest';
 import { Meta, StoryObj } from '@storybook/react';
-import { within } from '@storybook/test';
+import { within, userEvent } from '@storybook/test';
 import { useSetRecoilState } from 'recoil';
 
 import { currentUserState } from '@/auth/states/currentUserState';
@@ -14,11 +14,11 @@ import {
   mockedWorkspaceMemberData,
 } from '~/testing/mock-data/users';
 
-import { SupportChat } from '../SupportChat';
+import { SupportDropdown } from '@/support/components/SupportDropdown';
 
-const meta: Meta<typeof SupportChat> = {
-  title: 'Modules/Support/SupportChat',
-  component: SupportChat,
+const meta: Meta<typeof SupportDropdown> = {
+  title: 'Modules/Support/SupportDropdown',
+  component: SupportDropdown,
   decorators: [
     (Story) => {
       const setCurrentUser = useSetRecoilState(currentUserState);
@@ -42,11 +42,16 @@ const meta: Meta<typeof SupportChat> = {
 };
 
 export default meta;
-type Story = StoryObj<typeof SupportChat>;
+type Story = StoryObj<typeof SupportDropdown>;
 
 export const Default: Story = {
   play: async () => {
     const canvas = within(document.body);
+
     expect(await canvas.findByText('Support')).toBeInTheDocument();
+    await userEvent.click(canvas.getByText('Support'));
+
+    expect(await canvas.findByText('Documentation')).toBeInTheDocument();
+    expect(await canvas.findByText('Talk to us')).toBeInTheDocument();
   },
 };
diff --git a/packages/twenty-front/src/pages/settings/SettingsBilling.tsx b/packages/twenty-front/src/pages/settings/SettingsBilling.tsx
index fd128ecb2f7c..f348e345522c 100644
--- a/packages/twenty-front/src/pages/settings/SettingsBilling.tsx
+++ b/packages/twenty-front/src/pages/settings/SettingsBilling.tsx
@@ -14,7 +14,7 @@ import { currentWorkspaceState } from '@/auth/states/currentWorkspaceState';
 import { SettingsBillingCoverImage } from '@/billing/components/SettingsBillingCoverImage';
 import { useOnboardingStatus } from '@/onboarding/hooks/useOnboardingStatus';
 import { SettingsPageContainer } from '@/settings/components/SettingsPageContainer';
-import { SupportChat } from '@/support/components/SupportChat';
+import { SupportButton } from '@/support/components/SupportButton';
 import { AppPath } from '@/types/AppPath';
 import { Info } from '@/ui/display/info/components/Info';
 import { SnackBarVariant } from '@/ui/feedback/snack-bar-manager/components/SnackBar';
@@ -218,7 +218,7 @@ export const SettingsBilling = () => {
         )}
       </SettingsPageContainer>
       <StyledInvisibleChat>
-        <SupportChat />
+        <SupportButton />
       </StyledInvisibleChat>
       <ConfirmationModal
         isOpen={isSwitchingIntervalModalOpen}
diff --git a/packages/twenty-ui/src/display/icon/components/TablerIcons.ts b/packages/twenty-ui/src/display/icon/components/TablerIcons.ts
index 5c38e5250d37..8c1b94e40066 100644
--- a/packages/twenty-ui/src/display/icon/components/TablerIcons.ts
+++ b/packages/twenty-ui/src/display/icon/components/TablerIcons.ts
@@ -116,6 +116,7 @@ export {
   IconMailCog,
   IconMap,
   IconMaximize,
+  IconMessage,
   IconMinus,
   IconMoneybag,
   IconMouse2,