diff --git a/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.test.tsx b/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.test.tsx
index 97218602f..d63a15553 100644
--- a/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.test.tsx
+++ b/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.test.tsx
@@ -10,7 +10,7 @@ const mocks = vi.hoisted(() => ({
   appRestart: vi.fn(),
   updaterCheck: vi.fn(),
   shellOpenUrl: vi.fn(),
-  useShortcutLabel: vi.fn(),
+  useShortcutKeys: vi.fn(),
   setupProgress: {
     ready: true,
     coreDoneCount: 2,
@@ -32,7 +32,7 @@ vi.mock('@/store', () => ({
 }))
 
 vi.mock('@/hooks/useShortcutLabel', () => ({
-  useShortcutLabel: mocks.useShortcutLabel
+  useShortcutKeys: mocks.useShortcutKeys
 }))
 
 vi.mock('@/hooks/useMountedRef', () => ({
@@ -72,12 +72,14 @@ vi.mock('@/components/ui/tooltip', () => ({
 vi.mock('@/components/ui/button', () => ({
   Button: ({
     children,
-    onClick
+    onClick,
+    'aria-label': ariaLabel
   }: {
     children: ReactNode
     onClick?: (event: React.MouseEvent) => void
+    'aria-label'?: string
   }) => (
-    <button data-testid="trigger-button" onClick={onClick}>
+    <button data-testid="trigger-button" aria-label={ariaLabel} onClick={onClick}>
       {children}
     </button>
   )
@@ -97,7 +99,7 @@ vi.mock('./SidebarFeedbackDialog', () => ({
 describe('SidebarSettingsHelpMenu', () => {
   beforeEach(() => {
     vi.clearAllMocks()
-    mocks.useShortcutLabel.mockReturnValue('⌘,')
+    mocks.useShortcutKeys.mockReturnValue(['⌘', ','])
     updateStatus = { state: 'idle' }
     mocks.setupProgress = {
       ready: true,
@@ -112,9 +114,17 @@ describe('SidebarSettingsHelpMenu', () => {
     expect(html).toContain('Help')
   })
 
-  it('renders Settings menu item', () => {
+  it('renders the settings button with correct aria-label', () => {
     const html = renderToStaticMarkup(<SidebarSettingsHelpMenu />)
-    expect(html).toContain('Settings')
+    expect(html).toContain('aria-label="Settings"')
+  })
+
+  it('renders the settings button before the help button', () => {
+    const html = renderToStaticMarkup(<SidebarSettingsHelpMenu />)
+    const settingsIndex = html.indexOf('lucide-settings')
+    const helpIndex = html.indexOf('lucide-circle-question-mark')
+    expect(settingsIndex).toBeGreaterThanOrEqual(0)
+    expect(helpIndex).toBeGreaterThan(settingsIndex)
   })
 
   it('renders Send Feedback menu item', () => {
@@ -179,8 +189,9 @@ describe('SidebarSettingsHelpMenu', () => {
     expect(html).toContain('Check for Updates')
   })
 
-  it('renders shortcut label next to Settings', () => {
+  it('renders shortcut keys in the settings tooltip', () => {
     const html = renderToStaticMarkup(<SidebarSettingsHelpMenu />)
-    expect(html).toContain('⌘,')
+    expect(html).toContain('⌘')
+    expect(html).toContain('>,</span>')
   })
 })
diff --git a/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.tsx b/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.tsx
index a56c8ba70..0da82554d 100644
--- a/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.tsx
+++ b/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.tsx
@@ -26,7 +26,8 @@ import {
   DropdownMenuTrigger
 } from '@/components/ui/dropdown-menu'
 import { useMountedRef } from '@/hooks/useMountedRef'
-import { useShortcutLabel } from '@/hooks/useShortcutLabel'
+import { useShortcutKeys } from '@/hooks/useShortcutLabel'
+import { ShortcutKeyCombo } from '@/components/ShortcutKeyCombo'
 import { showOnboardingFromRenderer } from '../onboarding/show-onboarding-event'
 import { SetupGuideProgressRing } from '../setup-guide/SetupGuideProgressRing'
 import { useSetupGuideProgress } from '../setup-guide/use-setup-guide-progress'
@@ -84,7 +85,7 @@ export function SidebarSettingsHelpMenu(): React.JSX.Element {
   const updateStatus = useAppStore((s) => s.updateStatus)
   const setupProgress = useSetupGuideProgress(true, false, false)
 
-  const settingsShortcut = useShortcutLabel('app.settings')
+  const settingsShortcutKeys = useShortcutKeys('app.settings')
   const [menuOpen, setMenuOpen] = useState(false)
   const [feedbackOpen, setFeedbackOpen] = useState(false)
   const [showAdminOptions, setShowAdminOptions] = useState(false)
@@ -157,145 +158,173 @@ export function SidebarSettingsHelpMenu(): React.JSX.Element {
 
   return (
     <>
-      <DropdownMenu modal={false} open={menuOpen} onOpenChange={handleMenuOpenChange}>
+      <div className="flex items-center gap-1">
         <Tooltip>
           <TooltipTrigger asChild>
-            <DropdownMenuTrigger asChild>
-              <Button
-                variant="ghost"
-                size="icon-xs"
-                type="button"
-                aria-label={translate(
-                  'auto.components.sidebar.SidebarSettingsHelpMenu.2991a0106c',
-                  'Help'
-                )}
-                className="text-muted-foreground"
-                onPointerDown={(event) => revealAdminOptions(event.altKey)}
-                onClick={(event) => revealAdminOptions(event.altKey)}
-              >
-                <CircleHelp className="size-3.5" />
-              </Button>
-            </DropdownMenuTrigger>
+            <Button
+              variant="ghost"
+              size="icon-xs"
+              type="button"
+              aria-label={translate(
+                'auto.components.sidebar.SidebarSettingsHelpMenu.a428c25998',
+                'Settings'
+              )}
+              className="text-muted-foreground"
+              onClick={openSettingsPage}
+            >
+              <Settings className="size-3.5" />
+            </Button>
           </TooltipTrigger>
-          <TooltipContent side="top" sideOffset={4}>
-            {translate('auto.components.sidebar.SidebarSettingsHelpMenu.2991a0106c', 'Help')}
+          <TooltipContent side="top" sideOffset={4} className="flex items-center gap-1.5">
+            {translate('auto.components.sidebar.SidebarSettingsHelpMenu.a428c25998', 'Settings')}
+            {settingsShortcutKeys.length > 0 ? (
+              <ShortcutKeyCombo
+                keys={settingsShortcutKeys}
+                className="gap-0.5"
+                keyCapClassName="min-w-0 border-background/20 bg-background/10 px-1 py-0 text-[10px] text-background shadow-none"
+                separatorClassName="text-[10px] text-background/70"
+              />
+            ) : null}
           </TooltipContent>
         </Tooltip>
-        <DropdownMenuContent side="top" align="start" sideOffset={8} className="w-52">
-          <DropdownMenuItem onSelect={openSettingsPage}>
-            <Settings className="size-3.5" />
-            {translate('auto.components.sidebar.SidebarSettingsHelpMenu.a428c25998', 'Settings')}
-            <span className="ml-auto text-xs tracking-wide opacity-60">{settingsShortcut}</span>
-          </DropdownMenuItem>
-          <DropdownMenuItem onSelect={openShortcutsSettings}>
-            <Keyboard className="size-3.5" />
-            {translate(
-              'auto.components.sidebar.SidebarSettingsHelpMenu.e565171a7c',
-              'Keyboard Shortcuts'
-            )}
-          </DropdownMenuItem>
-          <DropdownMenuSeparator />
-          <DropdownMenuItem onSelect={() => setFeedbackOpen(true)}>
-            <MessageSquareText className="size-3.5" />
-            {translate(
-              'auto.components.sidebar.SidebarSettingsHelpMenu.4cf5b868d7',
-              'Send Feedback'
-            )}
-          </DropdownMenuItem>
-          {showMilestones ? (
-            <DropdownMenuItem onSelect={openMilestones}>
-              <img
-                src={logo}
-                alt=""
-                aria-hidden="true"
-                className="size-3.5 object-contain invert opacity-55 dark:invert-0"
-              />
+        <DropdownMenu modal={false} open={menuOpen} onOpenChange={handleMenuOpenChange}>
+          <Tooltip>
+            <TooltipTrigger asChild>
+              <DropdownMenuTrigger asChild>
+                <Button
+                  variant="ghost"
+                  size="icon-xs"
+                  type="button"
+                  aria-label={translate(
+                    'auto.components.sidebar.SidebarSettingsHelpMenu.2991a0106c',
+                    'Help'
+                  )}
+                  className="text-muted-foreground"
+                  onPointerDown={(event) => revealAdminOptions(event.altKey)}
+                  onClick={(event) => revealAdminOptions(event.altKey)}
+                >
+                  <CircleHelp className="size-3.5" />
+                </Button>
+              </DropdownMenuTrigger>
+            </TooltipTrigger>
+            <TooltipContent side="top" sideOffset={4}>
+              {translate('auto.components.sidebar.SidebarSettingsHelpMenu.2991a0106c', 'Help')}
+            </TooltipContent>
+          </Tooltip>
+          <DropdownMenuContent side="top" align="start" sideOffset={8} className="w-52">
+            <DropdownMenuItem onSelect={openShortcutsSettings}>
+              <Keyboard className="size-3.5" />
               {translate(
-                'auto.components.sidebar.SidebarSettingsHelpMenu.f8a2c91d4e',
-                'Milestones'
-              )}
-              <SetupGuideProgressRing
-                done={setupProgress.coreDoneCount}
-                total={setupProgress.coreTotal}
-                sizeClassName="size-4"
-                className="ml-auto"
-              />
-            </DropdownMenuItem>
-          ) : null}
-          {showAdminOptions ? (
-            <DropdownMenuItem
-              className="whitespace-nowrap"
-              onClick={handleShowOnboarding}
-              onSelect={handleShowOnboarding}
-            >
-              <School className="size-3.5" />
-              {translate(
-                'auto.components.sidebar.SidebarSettingsHelpMenu.b7e4d2a19c',
-                'Onboarding'
+                'auto.components.sidebar.SidebarSettingsHelpMenu.e565171a7c',
+                'Keyboard Shortcuts'
               )}
             </DropdownMenuItem>
-          ) : null}
-          <ExternalMenuItem
-            label={translate('auto.components.sidebar.SidebarSettingsHelpMenu.cdc87f897e', 'Docs')}
-            url={DOCS_URL}
-            icon={<BookOpen className="size-3.5" />}
-          />
-          <ExternalMenuItem
-            label={translate(
-              'auto.components.sidebar.SidebarSettingsHelpMenu.5f83d86d92',
-              'Changelog'
-            )}
-            url={CHANGELOG_URL}
-            icon={<ScrollText className="size-3.5" />}
-          />
-          <DropdownMenuSeparator />
-          <ExternalMenuItem
-            label={translate(
-              'auto.components.sidebar.SidebarSettingsHelpMenu.5687ab246a',
-              'GitHub'
-            )}
-            url={GITHUB_URL}
-            icon={<Github className="size-3.5" />}
-          />
-          <DropdownMenuItem onSelect={() => openExternalUrl(DISCORD_URL)}>
-            <DiscordIcon />
-            {translate('auto.components.sidebar.SidebarSettingsHelpMenu.eb9884e55b', 'Discord')}
-            <ExternalLink className="ml-auto size-3 text-muted-foreground" />
-          </DropdownMenuItem>
-          <DropdownMenuItem onSelect={() => openExternalUrl(X_URL)}>
-            <XIcon />
-            {translate('auto.components.sidebar.SidebarSettingsHelpMenu.c4f8e1b72a', 'X')}
-            <ExternalLink className="ml-auto size-3 text-muted-foreground" />
-          </DropdownMenuItem>
-          <DropdownMenuSeparator />
-          <DropdownMenuItem
-            disabled={updateStatus.state === 'checking' || updateStatus.state === 'downloading'}
-            onSelect={handleCheckForUpdates}
-          >
-            {updateStatus.state === 'checking' ? (
-              <Loader2 className="size-3.5 animate-spin" />
-            ) : (
-              <RefreshCw className="size-3.5" />
-            )}
-            {translate(
-              'auto.components.sidebar.SidebarSettingsHelpMenu.29c56f30ee',
-              'Check for Updates'
-            )}
-          </DropdownMenuItem>
-          {showAdminOptions ? (
-            <>
-              <DropdownMenuSeparator />
-              <DropdownMenuItem onSelect={handleRestartOrca} disabled={isRestartingOrca}>
-                <RotateCw className="size-3.5" />
+            <DropdownMenuSeparator />
+            <DropdownMenuItem onSelect={() => setFeedbackOpen(true)}>
+              <MessageSquareText className="size-3.5" />
+              {translate(
+                'auto.components.sidebar.SidebarSettingsHelpMenu.4cf5b868d7',
+                'Send Feedback'
+              )}
+            </DropdownMenuItem>
+            {showMilestones ? (
+              <DropdownMenuItem onSelect={openMilestones}>
+                <img
+                  src={logo}
+                  alt=""
+                  aria-hidden="true"
+                  className="size-3.5 object-contain invert opacity-55 dark:invert-0"
+                />
                 {translate(
-                  'auto.components.sidebar.SidebarSettingsHelpMenu.ad3d3ed7f1',
-                  'Restart Orca'
+                  'auto.components.sidebar.SidebarSettingsHelpMenu.f8a2c91d4e',
+                  'Milestones'
+                )}
+                <SetupGuideProgressRing
+                  done={setupProgress.coreDoneCount}
+                  total={setupProgress.coreTotal}
+                  sizeClassName="size-4"
+                  className="ml-auto"
+                />
+              </DropdownMenuItem>
+            ) : null}
+            {showAdminOptions ? (
+              <DropdownMenuItem
+                className="whitespace-nowrap"
+                onClick={handleShowOnboarding}
+                onSelect={handleShowOnboarding}
+              >
+                <School className="size-3.5" />
+                {translate(
+                  'auto.components.sidebar.SidebarSettingsHelpMenu.b7e4d2a19c',
+                  'Onboarding'
                 )}
               </DropdownMenuItem>
-            </>
-          ) : null}
-        </DropdownMenuContent>
-      </DropdownMenu>
+            ) : null}
+            <ExternalMenuItem
+              label={translate(
+                'auto.components.sidebar.SidebarSettingsHelpMenu.cdc87f897e',
+                'Docs'
+              )}
+              url={DOCS_URL}
+              icon={<BookOpen className="size-3.5" />}
+            />
+            <ExternalMenuItem
+              label={translate(
+                'auto.components.sidebar.SidebarSettingsHelpMenu.5f83d86d92',
+                'Changelog'
+              )}
+              url={CHANGELOG_URL}
+              icon={<ScrollText className="size-3.5" />}
+            />
+            <DropdownMenuSeparator />
+            <ExternalMenuItem
+              label={translate(
+                'auto.components.sidebar.SidebarSettingsHelpMenu.5687ab246a',
+                'GitHub'
+              )}
+              url={GITHUB_URL}
+              icon={<Github className="size-3.5" />}
+            />
+            <DropdownMenuItem onSelect={() => openExternalUrl(DISCORD_URL)}>
+              <DiscordIcon />
+              {translate('auto.components.sidebar.SidebarSettingsHelpMenu.eb9884e55b', 'Discord')}
+              <ExternalLink className="ml-auto size-3 text-muted-foreground" />
+            </DropdownMenuItem>
+            <DropdownMenuItem onSelect={() => openExternalUrl(X_URL)}>
+              <XIcon />
+              {translate('auto.components.sidebar.SidebarSettingsHelpMenu.c4f8e1b72a', 'X')}
+              <ExternalLink className="ml-auto size-3 text-muted-foreground" />
+            </DropdownMenuItem>
+            <DropdownMenuSeparator />
+            <DropdownMenuItem
+              disabled={updateStatus.state === 'checking' || updateStatus.state === 'downloading'}
+              onSelect={handleCheckForUpdates}
+            >
+              {updateStatus.state === 'checking' ? (
+                <Loader2 className="size-3.5 animate-spin" />
+              ) : (
+                <RefreshCw className="size-3.5" />
+              )}
+              {translate(
+                'auto.components.sidebar.SidebarSettingsHelpMenu.29c56f30ee',
+                'Check for Updates'
+              )}
+            </DropdownMenuItem>
+            {showAdminOptions ? (
+              <>
+                <DropdownMenuSeparator />
+                <DropdownMenuItem onSelect={handleRestartOrca} disabled={isRestartingOrca}>
+                  <RotateCw className="size-3.5" />
+                  {translate(
+                    'auto.components.sidebar.SidebarSettingsHelpMenu.ad3d3ed7f1',
+                    'Restart Orca'
+                  )}
+                </DropdownMenuItem>
+              </>
+            ) : null}
+          </DropdownMenuContent>
+        </DropdownMenu>
+      </div>
       <SidebarFeedbackDialog open={feedbackOpen} onOpenChange={setFeedbackOpen} />
     </>
   )