diff --git a/src/renderer/src/components/sidebar/SidebarNav.test.tsx b/src/renderer/src/components/sidebar/SidebarNav.test.tsx
index 6ccf6da2251..5558a512055 100644
--- a/src/renderer/src/components/sidebar/SidebarNav.test.tsx
+++ b/src/renderer/src/components/sidebar/SidebarNav.test.tsx
@@ -273,6 +273,17 @@ describe('SidebarNav', () => {
     expect(mocks.updateSettings).toHaveBeenCalledWith({ showMobileButton: false })
   })
 
+  it('hides task source shortcuts until the Tasks row is hovered or focused', async () => {
+    const container = await renderSidebarNav()
+
+    const tasksButton = getButtonByText(container, 'Tasks')
+    const shortcuts = tasksButton.querySelector('[aria-label="Open GitHub tasks"]')?.parentElement
+
+    expect(shortcuts?.className).toContain('hidden')
+    expect(shortcuts?.className).toContain('group-hover:flex')
+    expect(shortcuts?.className).toContain('group-focus-within:flex')
+  })
+
   it('hides available Tasks from its sidebar context menu', async () => {
     const container = await renderSidebarNav()
 
diff --git a/src/renderer/src/components/sidebar/SidebarNav.tsx b/src/renderer/src/components/sidebar/SidebarNav.tsx
index 8071ae40f86..d6da2029835 100644
--- a/src/renderer/src/components/sidebar/SidebarNav.tsx
+++ b/src/renderer/src/components/sidebar/SidebarNav.tsx
@@ -51,7 +51,8 @@ function HideSidebarMenu({ onHide }: { onHide: () => void }): React.JSX.Element
     <ContextMenuContent>
       <ContextMenuItem onSelect={onHide}>
         <EyeOff className="size-3.5" />
-        {translate("auto.components.sidebar.SidebarNav.d599269755", "Hide from sidebar")}</ContextMenuItem>
+        {translate('auto.components.sidebar.SidebarNav.d599269755', 'Hide from sidebar')}
+      </ContextMenuItem>
     </ContextMenuContent>
   )
 }
@@ -237,7 +238,7 @@ const SidebarNav = React.memo(function SidebarNav() {
               aria-current={tasksActive ? 'page' : undefined}
               data-contextual-tour-target="sidebar-tasks"
               className={cn(
-                'flex w-full items-center gap-2 rounded-md px-2 py-1.5 text-left text-[13px] font-medium tracking-tight transition-colors',
+                'group flex w-full items-center gap-2 rounded-md px-2 py-1.5 text-left text-[13px] font-medium tracking-tight transition-colors',
                 tasksActive
                   ? 'bg-worktree-sidebar-accent text-worktree-sidebar-accent-foreground'
                   : 'text-worktree-sidebar-foreground/60 hover:bg-worktree-sidebar-foreground/8',
@@ -251,12 +252,17 @@ const SidebarNav = React.memo(function SidebarNav() {
                 )}
                 strokeWidth={tasksActive ? 2.25 : 1.75}
               />
-              <span className="flex-1">{translate("auto.components.sidebar.SidebarNav.fee535205b", "Tasks")}</span>
-              <span className="flex items-center gap-1">
+              <span className="flex-1">
+                {translate('auto.components.sidebar.SidebarNav.fee535205b', 'Tasks')}
+              </span>
+              <span className="hidden items-center gap-1 group-hover:flex group-focus-within:flex">
                 {visibleTaskProviders.includes('github') ? (
                   <TaskProviderShortcut
                     canBrowseTasks={canBrowseTasks}
-                    label={translate("auto.components.sidebar.SidebarNav.0ccba862b8", "Open GitHub tasks")}
+                    label={translate(
+                      'auto.components.sidebar.SidebarNav.0ccba862b8',
+                      'Open GitHub tasks'
+                    )}
                     onOpen={() => {
                       openTaskPage({ taskSource: 'github' })
                     }}
@@ -267,7 +273,10 @@ const SidebarNav = React.memo(function SidebarNav() {
                 {visibleTaskProviders.includes('gitlab') ? (
                   <TaskProviderShortcut
                     canBrowseTasks={canBrowseTasks}
-                    label={translate("auto.components.sidebar.SidebarNav.196c1b5362", "Open GitLab tasks")}
+                    label={translate(
+                      'auto.components.sidebar.SidebarNav.196c1b5362',
+                      'Open GitLab tasks'
+                    )}
                     onOpen={() => {
                       openTaskPage({ taskSource: 'gitlab' })
                     }}
@@ -278,7 +287,10 @@ const SidebarNav = React.memo(function SidebarNav() {
                 {visibleTaskProviders.includes('linear') ? (
                   <TaskProviderShortcut
                     canBrowseTasks={canBrowseTasks}
-                    label={translate("auto.components.sidebar.SidebarNav.c39ab10000", "Open Linear tasks")}
+                    label={translate(
+                      'auto.components.sidebar.SidebarNav.c39ab10000',
+                      'Open Linear tasks'
+                    )}
                     onOpen={() => {
                       openTaskPage({ taskSource: 'linear' })
                     }}
@@ -289,7 +301,10 @@ const SidebarNav = React.memo(function SidebarNav() {
                 {visibleTaskProviders.includes('jira') ? (
                   <TaskProviderShortcut
                     canBrowseTasks={canBrowseTasks}
-                    label={translate("auto.components.sidebar.SidebarNav.e7ad3c540d", "Open Jira tasks")}
+                    label={translate(
+                      'auto.components.sidebar.SidebarNav.e7ad3c540d',
+                      'Open Jira tasks'
+                    )}
                     onOpen={() => {
                       openTaskPage({ taskSource: 'jira' })
                     }}
@@ -324,7 +339,9 @@ const SidebarNav = React.memo(function SidebarNav() {
                 )}
                 strokeWidth={automationsActive ? 2.25 : 1.75}
               />
-              <span className="flex-1">{translate("auto.components.sidebar.SidebarNav.f323383e9a", "Automations")}</span>
+              <span className="flex-1">
+                {translate('auto.components.sidebar.SidebarNav.f323383e9a', 'Automations')}
+              </span>
             </button>
           </ContextMenuTrigger>
           <HideSidebarMenu onHide={hideAutomationsButton} />
@@ -349,7 +366,9 @@ const SidebarNav = React.memo(function SidebarNav() {
             )}
             strokeWidth={activityActive ? 2.25 : 1.75}
           />
-          <span className="flex-1">{translate("auto.components.sidebar.SidebarNav.9c95e1ce91", "Agents")}</span>
+          <span className="flex-1">
+            {translate('auto.components.sidebar.SidebarNav.9c95e1ce91', 'Agents')}
+          </span>
           {activityUnreadCount > 0 ? (
             <span className="rounded-full bg-primary px-1.5 py-px text-[10px] font-semibold text-primary-foreground">
               {activityUnreadCount}
@@ -381,10 +400,13 @@ const SidebarNav = React.memo(function SidebarNav() {
                 )}
                 strokeWidth={mobileActive ? 2.25 : 1.75}
               />
-              <span className="flex-1">{translate("auto.components.sidebar.SidebarNav.1b5c41caee", "Orca Mobile")}</span>
+              <span className="flex-1">
+                {translate('auto.components.sidebar.SidebarNav.1b5c41caee', 'Orca Mobile')}
+              </span>
               {mobileOnboardingBadge.visible ? (
                 <span className="rounded-full bg-primary px-1.5 py-px text-[10px] font-semibold text-primary-foreground">
-                  {translate("auto.components.sidebar.SidebarNav.c86d83b5c3", "New")}</span>
+                  {translate('auto.components.sidebar.SidebarNav.c86d83b5c3', 'New')}
+                </span>
               ) : null}
             </button>
           </ContextMenuTrigger>
@@ -394,14 +416,19 @@ const SidebarNav = React.memo(function SidebarNav() {
       <button
         type="button"
         onClick={() => openModal('worktree-palette')}
-        aria-label={translate("auto.components.sidebar.SidebarNav.0c3395fd32", "Search worktrees and browser tabs")}
+        aria-label={translate(
+          'auto.components.sidebar.SidebarNav.0c3395fd32',
+          'Search worktrees and browser tabs'
+        )}
         className="group flex w-full items-center gap-2 rounded-md px-2 py-1.5 text-left text-[13px] font-medium tracking-tight text-worktree-sidebar-foreground/60 transition-colors hover:bg-worktree-sidebar-foreground/8"
       >
         <Search
           className="size-4 shrink-0 text-worktree-sidebar-foreground/30"
           strokeWidth={1.75}
         />
-        <span className="flex-1">{translate("auto.components.sidebar.SidebarNav.80611a8b10", "Search")}</span>
+        <span className="flex-1">
+          {translate('auto.components.sidebar.SidebarNav.80611a8b10', 'Search')}
+        </span>
         <kbd className="hidden rounded border border-border/60 bg-background/40 px-1.5 py-px font-mono text-[10px] font-medium text-muted-foreground group-hover:inline-flex items-center">
           {worktreePaletteShortcut}
         </kbd>
diff --git a/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.test.tsx b/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.test.tsx
index 2715a9dad32..97218602f21 100644
--- a/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.test.tsx
+++ b/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.test.tsx
@@ -4,12 +4,19 @@ import { beforeEach, describe, expect, it, vi } from 'vitest'
 import { SidebarSettingsHelpMenu } from './SidebarSettingsHelpMenu'
 
 const mocks = vi.hoisted(() => ({
+  openModal: vi.fn(),
   openSettingsPage: vi.fn(),
   openSettingsTarget: vi.fn(),
   appRestart: vi.fn(),
   updaterCheck: vi.fn(),
   shellOpenUrl: vi.fn(),
-  useShortcutLabel: vi.fn()
+  useShortcutLabel: vi.fn(),
+  setupProgress: {
+    ready: true,
+    coreDoneCount: 2,
+    coreTotal: 5,
+    stepDone: {}
+  }
 }))
 
 let updateStatus = { state: 'idle' } as const
@@ -17,6 +24,7 @@ let updateStatus = { state: 'idle' } as const
 vi.mock('@/store', () => ({
   useAppStore: (selector: (state: unknown) => unknown) =>
     selector({
+      openModal: mocks.openModal,
       openSettingsPage: mocks.openSettingsPage,
       openSettingsTarget: mocks.openSettingsTarget,
       updateStatus
@@ -31,6 +39,18 @@ vi.mock('@/hooks/useMountedRef', () => ({
   useMountedRef: () => ({ current: true })
 }))
 
+vi.mock('../onboarding/show-onboarding-event', () => ({
+  showOnboardingFromRenderer: vi.fn()
+}))
+
+vi.mock('../setup-guide/use-setup-guide-progress', () => ({
+  useSetupGuideProgress: () => mocks.setupProgress
+}))
+
+vi.mock('../setup-guide/SetupGuideProgressRing', () => ({
+  SetupGuideProgressRing: () => <span data-testid="setup-guide-progress-ring" />
+}))
+
 vi.mock('@/components/ui/dropdown-menu', () => ({
   DropdownMenu: ({ children }: { children: ReactNode }) => <>{children}</>,
   DropdownMenuContent: ({ children }: { children: ReactNode }) => <>{children}</>,
@@ -79,10 +99,15 @@ describe('SidebarSettingsHelpMenu', () => {
     vi.clearAllMocks()
     mocks.useShortcutLabel.mockReturnValue('⌘,')
     updateStatus = { state: 'idle' }
+    mocks.setupProgress = {
+      ready: true,
+      coreDoneCount: 2,
+      coreTotal: 5,
+      stepDone: {}
+    }
   })
 
   it('renders the help button with correct aria-label', () => {
-    updateStatus = { state: 'idle' }
     const html = renderToStaticMarkup(<SidebarSettingsHelpMenu />)
     expect(html).toContain('Help')
   })
@@ -102,6 +127,28 @@ describe('SidebarSettingsHelpMenu', () => {
     expect(html).toContain('Keyboard Shortcuts')
   })
 
+  it('renders Milestones with progress when setup is incomplete', () => {
+    const html = renderToStaticMarkup(<SidebarSettingsHelpMenu />)
+    expect(html).toContain('Milestones')
+    expect(html).toContain('data-testid="setup-guide-progress-ring"')
+  })
+
+  it('hides Milestones when setup is complete', () => {
+    mocks.setupProgress = {
+      ready: true,
+      coreDoneCount: 5,
+      coreTotal: 5,
+      stepDone: {}
+    }
+    const html = renderToStaticMarkup(<SidebarSettingsHelpMenu />)
+    expect(html).not.toContain('Milestones')
+  })
+
+  it('hides the Onboarding admin entry by default', () => {
+    const html = renderToStaticMarkup(<SidebarSettingsHelpMenu />)
+    expect(html).not.toContain('Onboarding')
+  })
+
   it('renders Docs link', () => {
     const html = renderToStaticMarkup(<SidebarSettingsHelpMenu />)
     expect(html).toContain('Docs')
@@ -122,6 +169,11 @@ describe('SidebarSettingsHelpMenu', () => {
     expect(html).toContain('Discord')
   })
 
+  it('renders X link', () => {
+    const html = renderToStaticMarkup(<SidebarSettingsHelpMenu />)
+    expect(html).toContain('>X<')
+  })
+
   it('renders Check for Updates menu item', () => {
     const html = renderToStaticMarkup(<SidebarSettingsHelpMenu />)
     expect(html).toContain('Check for Updates')
diff --git a/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.tsx b/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.tsx
index 54654aaf3bd..a56c8ba7092 100644
--- a/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.tsx
+++ b/src/renderer/src/components/sidebar/SidebarSettingsHelpMenu.tsx
@@ -1,14 +1,20 @@
 import React, { useState } from 'react'
 import {
+  BookOpen,
   CircleHelp,
   ExternalLink,
+  Github,
+  Keyboard,
   Loader2,
   MessageSquareText,
   RefreshCw,
   RotateCw,
+  School,
+  ScrollText,
   Settings
 } from 'lucide-react'
 import { toast } from 'sonner'
+import logo from '../../../../../resources/logo.svg'
 import { useAppStore } from '@/store'
 import { Button } from '@/components/ui/button'
 import { Tooltip, TooltipContent, TooltipTrigger } from '@/components/ui/tooltip'
@@ -21,6 +27,9 @@ import {
 } from '@/components/ui/dropdown-menu'
 import { useMountedRef } from '@/hooks/useMountedRef'
 import { useShortcutLabel } from '@/hooks/useShortcutLabel'
+import { showOnboardingFromRenderer } from '../onboarding/show-onboarding-event'
+import { SetupGuideProgressRing } from '../setup-guide/SetupGuideProgressRing'
+import { useSetupGuideProgress } from '../setup-guide/use-setup-guide-progress'
 import { SidebarFeedbackDialog } from './SidebarFeedbackDialog'
 import { translate } from '@/i18n/i18n'
 
@@ -28,6 +37,7 @@ const DOCS_URL = 'https://www.onorca.dev/docs'
 const CHANGELOG_URL = 'https://onorca.dev/changelog'
 const GITHUB_URL = 'https://github.com/stablyai/orca'
 const DISCORD_URL = 'https://discord.gg/fzjDKHxv8Q'
+const X_URL = 'https://x.com/orca_build'
 
 function openExternalUrl(url: string): void {
   void window.api.shell.openUrl(url)
@@ -41,9 +51,26 @@ function DiscordIcon(): React.JSX.Element {
   )
 }
 
-function ExternalMenuItem({ label, url }: { label: string; url: string }): React.JSX.Element {
+function XIcon(): React.JSX.Element {
+  return (
+    <svg viewBox="0 0 24 24" aria-hidden="true" className="size-3.5 fill-current">
+      <path d="M18.244 2.25h3.308l-7.227 8.26 8.502 11.24H16.17l-5.214-6.817L4.99 21.75H1.68l7.73-8.835L1.254 2.25H8.08l4.713 6.231zm-1.161 17.52h1.833L7.084 4.126H5.117z" />
+    </svg>
+  )
+}
+
+function ExternalMenuItem({
+  label,
+  url,
+  icon
+}: {
+  label: string
+  url: string
+  icon: React.ReactNode
+}): React.JSX.Element {
   return (
     <DropdownMenuItem onSelect={() => openExternalUrl(url)}>
+      {icon}
       {label}
       <ExternalLink className="ml-auto size-3 text-muted-foreground" />
     </DropdownMenuItem>
@@ -51,17 +78,23 @@ function ExternalMenuItem({ label, url }: { label: string; url: string }): React
 }
 
 export function SidebarSettingsHelpMenu(): React.JSX.Element {
+  const openModal = useAppStore((s) => s.openModal)
   const openSettingsPage = useAppStore((s) => s.openSettingsPage)
   const openSettingsTarget = useAppStore((s) => s.openSettingsTarget)
   const updateStatus = useAppStore((s) => s.updateStatus)
+  const setupProgress = useSetupGuideProgress(true, false, false)
 
   const settingsShortcut = useShortcutLabel('app.settings')
   const [menuOpen, setMenuOpen] = useState(false)
   const [feedbackOpen, setFeedbackOpen] = useState(false)
   const [showAdminOptions, setShowAdminOptions] = useState(false)
   const [isRestartingOrca, setIsRestartingOrca] = useState(false)
+  const lastShowOnboardingAtRef = React.useRef(0)
   const mountedRef = useMountedRef()
 
+  const showMilestones =
+    setupProgress.ready && setupProgress.coreDoneCount < setupProgress.coreTotal
+
   const handleMenuOpenChange = (open: boolean): void => {
     setMenuOpen(open)
     if (!open) {
@@ -70,9 +103,20 @@ export function SidebarSettingsHelpMenu(): React.JSX.Element {
   }
 
   const revealAdminOptions = (altKey: boolean): void => {
+    // Why: onboarding replay and restart stay off the default Help menu; holding
+    // Option/Alt before opening is an intentional power-user affordance.
     setShowAdminOptions(altKey)
   }
 
+  const handleShowOnboarding = (): void => {
+    const now = Date.now()
+    if (now - lastShowOnboardingAtRef.current < 500) {
+      return
+    }
+    lastShowOnboardingAtRef.current = now
+    void showOnboardingFromRenderer()
+  }
+
   const handleRestartOrca = (): void => {
     if (isRestartingOrca) {
       return
@@ -107,6 +151,10 @@ export function SidebarSettingsHelpMenu(): React.JSX.Element {
     void window.api.updater.check({ includePrerelease: shiftKey })
   }
 
+  const openMilestones = (): void => {
+    openModal('setup-guide', { telemetrySource: 'help_menu' })
+  }
+
   return (
     <>
       <DropdownMenu modal={false} open={menuOpen} onOpenChange={handleMenuOpenChange}>
@@ -133,12 +181,20 @@ export function SidebarSettingsHelpMenu(): React.JSX.Element {
             {translate('auto.components.sidebar.SidebarSettingsHelpMenu.2991a0106c', 'Help')}
           </TooltipContent>
         </Tooltip>
-        <DropdownMenuContent side="top" align="start" sideOffset={8} className="w-48">
+        <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(
@@ -146,17 +202,43 @@ export function SidebarSettingsHelpMenu(): React.JSX.Element {
               'Send Feedback'
             )}
           </DropdownMenuItem>
-          <DropdownMenuItem onSelect={openShortcutsSettings}>
-            <ExternalLink className="size-3.5" />
-            {translate(
-              'auto.components.sidebar.SidebarSettingsHelpMenu.e565171a7c',
-              'Keyboard Shortcuts'
-            )}
-          </DropdownMenuItem>
-          <DropdownMenuSeparator />
+          {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.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}
           <ExternalMenuItem
             label={translate('auto.components.sidebar.SidebarSettingsHelpMenu.cdc87f897e', 'Docs')}
             url={DOCS_URL}
+            icon={<BookOpen className="size-3.5" />}
           />
           <ExternalMenuItem
             label={translate(
@@ -164,19 +246,27 @@ export function SidebarSettingsHelpMenu(): React.JSX.Element {
               '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'}