diff --git a/src/main/index.ts b/src/main/index.ts
index 41fa5436492..676fa2308c5 100644
--- a/src/main/index.ts
+++ b/src/main/index.ts
@@ -5,7 +5,7 @@
 import { existsSync, statSync } from 'node:fs'
 import { isAbsolute, join } from 'node:path'
 import os from 'node:os'
-import { app, BrowserWindow, dialog, ipcMain, nativeTheme } from 'electron'
+import { app, BrowserWindow, dialog, ipcMain, nativeTheme, type Tray } from 'electron'
 import { electronApp, is } from '@electron-toolkit/utils'
 import * as QRCode from 'qrcode'
 import {
@@ -54,6 +54,7 @@ import {
   rebuildAppMenu
 } from './menu/register-app-menu'
 import { checkForUpdatesFromMenu, isQuittingForUpdate } from './updater'
+import type { UpdateCheckOptions } from '../shared/types'
 import { recordUpdaterLifecycle } from './updater-lifecycle-diagnostics'
 import {
   configureElectronNetworkCompatibility,
@@ -246,9 +247,8 @@ let keybindings: KeybindingService | null = null
 // sweep spare live sessions across that one reload (#5787).
 const expectedRendererReload = createWebContentsTimedFlag()
 const recoveryReloadInFlight = createWebContentsTimedFlag()
-// Why: the tray/menu-bar "Settings…" item can fire before a freshly created
-// renderer has attached its ui:openSettings listener, so leave a one-shot
-// intent the renderer pulls on mount instead of racing a time-based push.
+// Why: a tray/menu-bar "Settings…" click can precede the renderer attaching
+// its ui:openSettings listener; the renderer pulls this one-shot on mount.
 const pendingOpenSettings = createWebContentsTimedFlag()
 let firstWindowStartupServicesReady: Promise<void> = Promise.resolve()
 let managedWslCliReconciliationReady: Promise<void> = Promise.resolve()
@@ -806,7 +806,6 @@ function showMainWindowFromTray(): void {
 }
 
 function openSettingsFromSystemMenu(): void {
-  const existingWindow = mainWindow && !mainWindow.isDestroyed() ? mainWindow : null
   showMainWindowFromTray()
   const targetWindow = mainWindow && !mainWindow.isDestroyed() ? mainWindow : null
   if (!targetWindow) {
@@ -814,16 +813,13 @@ function openSettingsFromSystemMenu(): void {
   }
   recordCrashBreadcrumb('settings_opened')
 
-  // Why: an already-mounted renderer has its ui:openSettings listener attached,
-  // so a direct push lands. A freshly recreated or still-loading renderer has
-  // not subscribed yet — a time-based push would race its useEffect and could
-  // be dropped (with no fallback if the load fails), so leave a one-shot intent
-  // it consumes on mount instead.
-  if (existingWindow === targetWindow && !targetWindow.webContents.isLoadingMainFrame()) {
-    targetWindow.webContents.send('ui:openSettings')
-    return
-  }
-  pendingOpenSettings.mark(targetWindow.webContents.id)
+  // Why: no main-side signal proves the renderer listener is attached, so push
+  // and leave a one-shot intent — a mounted renderer acts on the push, an
+  // unmounted one pulls the intent at mount; only one fires per renderer life.
+  targetWindow.webContents.send('ui:openSettings')
+  // Why: 60s outlives the default flag TTL, which a cold renderer start can
+  // exceed — an expired flag silently drops the Settings click.
+  pendingOpenSettings.mark(targetWindow.webContents.id, 60_000)
 }
 
 function quitFromSystemTray(): void {
@@ -838,6 +834,13 @@ function quitFromSystemTray(): void {
   app.quit()
 }
 
+// Why: a manual check must run against a configured updater; the menu and
+// tray are both clickable before anything else configures it.
+function runUserInitiatedUpdateCheck(options?: UpdateCheckOptions): void {
+  ensureAutoUpdaterConfigured()
+  checkForUpdatesFromMenu(options)
+}
+
 function getSystemTrayOptions(): SystemTrayOptions | null {
   if (!store) {
     return null
@@ -847,21 +850,21 @@ function getSystemTrayOptions(): SystemTrayOptions | null {
     onOpen: showMainWindowFromTray,
     onOpenSettings: openSettingsFromSystemMenu,
     onCheckForUpdates: () => {
-      ensureAutoUpdaterConfigured()
-      checkForUpdatesFromMenu()
+      // Why: updater status renders in the main window; with every window
+      // closed a bare check would complete invisibly.
+      showMainWindowFromTray()
+      runUserInitiatedUpdateCheck()
     },
     onQuit: quitFromSystemTray
   }
 }
 
-function syncMacMenuBarIcon(showMenuBarIcon: boolean): void {
+function syncMacMenuBarIcon(showMenuBarIcon: boolean): Tray | null {
   if (process.platform !== 'darwin' || isServeMode) {
-    return
+    return null
   }
   const options = getSystemTrayOptions()
-  if (options) {
-    setMacMenuBarIconVisible(showMenuBarIcon, options)
-  }
+  return options ? setMacMenuBarIconVisible(showMenuBarIcon, options) : null
 }
 
 function openMainWindow(): BrowserWindow {
@@ -976,26 +979,21 @@ function openMainWindow(): BrowserWindow {
   recordCrashBreadcrumb('main_window_created')
   logStartupMilestone('window-created')
   // Why: Windows Tray construction can synchronously block on Shell_NotifyIcon,
-  // so both desktop status-item platforms share post-paint creation. The timer
-  // fallback also covers windows revealed without ready-to-show ever firing;
-  // Windows still needs its close target and macOS still needs its entry point.
+  // so both desktop status-item platforms defer creation to after first paint.
   let trayCreated = false
   const createSystemTrayDeferred = (): void => {
     if (trayCreated || window.isDestroyed() || isQuitting || !store) {
       return
     }
     trayCreated = true
-    // Why: keep the two macOS visibility paths in agreement — syncMacMenuBarIcon
-    // refuses serve mode, so the deferred creator must too, or an activated
-    // headless host would show an icon the live toggle can't manage.
-    if (
-      process.platform === 'darwin' &&
-      (isServeMode || store.getSettings().showMenuBarIcon === false)
-    ) {
+    if (process.platform === 'darwin') {
+      // Why: route through syncMacMenuBarIcon so startup and the live toggle
+      // share one serve-mode/visibility policy.
+      if (syncMacMenuBarIcon(store.getSettings().showMenuBarIcon !== false)) {
+        logStartupMilestone('tray-created')
+      }
       return
     }
-    // Why: Windows notification-area creation can block before first paint;
-    // macOS shares the deferred path to keep startup ordering identical.
     const options = getSystemTrayOptions()
     if (options && createSystemTray(options)) {
       logStartupMilestone('tray-created')
@@ -2077,12 +2075,7 @@ app.whenReady().then(async () => {
   logStartupMilestone('i18n-ready')
 
   registerAppMenu({
-    onCheckForUpdates: (options) => {
-      // Why: the menu is clickable before first paint; a manual check must
-      // run against a configured updater (see attach-main-window-services).
-      ensureAutoUpdaterConfigured()
-      return checkForUpdatesFromMenu(options)
-    },
+    onCheckForUpdates: (options) => runUserInitiatedUpdateCheck(options),
     onBeforeReload: ({ ignoreCache, webContentsId }) => {
       if (mainWindow?.webContents.id === webContentsId) {
         markExpectedRendererReload(webContentsId)
diff --git a/src/main/tray/system-tray.test.ts b/src/main/tray/system-tray.test.ts
index b85526f0273..71c94f84e74 100644
--- a/src/main/tray/system-tray.test.ts
+++ b/src/main/tray/system-tray.test.ts
@@ -19,6 +19,7 @@ const {
   const makeImage = (name: string) => ({
     name,
     addRepresentation: vi.fn(),
+    getScaleFactors: vi.fn(() => [1, 2]),
     getSize: vi.fn(() => ({ width: 16, height: 16 })),
     setTemplateImage: vi.fn(),
     toBitmap: vi.fn(() => Buffer.alloc(16 * 16 * 4)),
@@ -135,6 +136,7 @@ beforeEach(() => {
   )
   for (const image of [baseMacImage, retinaMacImage, tintedMacImage, attentionImage]) {
     image.addRepresentation.mockClear()
+    image.getScaleFactors.mockReset().mockReturnValue([1, 2])
     image.getSize.mockReset().mockReturnValue({ width: 16, height: 16 })
     image.setTemplateImage.mockClear()
     image.toBitmap.mockClear()
@@ -190,7 +192,7 @@ describe('createSystemTray', () => {
     expect(builtMenuItems().map((item) => item.label)).toEqual([
       'Open Orca',
       undefined,
-      'Settings...',
+      'Settings',
       'Check for Updates...',
       undefined,
       'Quit'
@@ -200,7 +202,7 @@ describe('createSystemTray', () => {
 
     for (const [label, callback] of [
       ['Open Orca', options.onOpen],
-      ['Settings...', options.onOpenSettings],
+      ['Settings', options.onOpenSettings],
       ['Check for Updates...', options.onCheckForUpdates],
       ['Quit', options.onQuit]
     ] as const) {
@@ -278,6 +280,13 @@ describe('setTrayAttention', () => {
     setTrayAttention(true)
     expect(tintTemplateMock).toHaveBeenCalledWith(baseMacImage, false)
     expect(composeAttentionMock).toHaveBeenCalledWith(tintedMacImage)
+    // Why: the attention image is rebuilt from 1x pixels, so the @2x
+    // representation must be re-added or the glyph blurs on Retina.
+    expect(tintTemplateMock).toHaveBeenCalledWith(baseMacImage, false, 2)
+    expect(attentionImage.addRepresentation).toHaveBeenCalledWith({
+      scaleFactor: 2,
+      dataURL: 'data:image/png;base64,attention'
+    })
     expect(attentionImage.setTemplateImage).toHaveBeenCalledWith(false)
     expect(created.setImage).toHaveBeenCalledWith(attentionImage)
     expect(created.setToolTip).toHaveBeenCalledWith('Orca - activity waiting')
@@ -309,6 +318,33 @@ describe('setTrayAttention', () => {
 
     expect(trayInstances[0].setImage).toHaveBeenCalledWith(attentionImage)
   })
+
+  it('ignores repeated same-state attention calls', async () => {
+    setPlatform('win32')
+    const { createSystemTray, setTrayAttention } = await loadModule()
+    createSystemTray(createOptions())
+    const created = trayInstances[0]
+    created.setImage.mockClear()
+
+    setTrayAttention(true)
+    setTrayAttention(true)
+
+    expect(created.setImage).toHaveBeenCalledTimes(1)
+  })
+
+  it('keeps a pending attention dot across a macOS hide/show toggle', async () => {
+    setPlatform('darwin')
+    const { setMacMenuBarIconVisible, setTrayAttention } = await loadModule()
+    const options = createOptions()
+    setMacMenuBarIconVisible(true, options)
+    setTrayAttention(true)
+
+    setMacMenuBarIconVisible(false, options)
+    setMacMenuBarIconVisible(true, options)
+
+    expect(trayInstances).toHaveLength(2)
+    expect(trayInstances[1].setImage).toHaveBeenCalledWith(attentionImage)
+  })
 })
 
 describe('destroySystemTray', () => {
@@ -372,7 +408,7 @@ describe('macOS hardening', () => {
     })
     createSystemTray(options)
 
-    const settingsItem = builtMenuItems().find((item) => item.label === 'Settings...')
+    const settingsItem = builtMenuItems().find((item) => item.label === 'Settings')
     expect(() => settingsItem?.click?.()).not.toThrow()
     expect(error).toHaveBeenCalledWith('[system-tray] menu action failed', expect.any(Error))
   })
diff --git a/src/main/tray/system-tray.ts b/src/main/tray/system-tray.ts
index 3cda04cac7f..27d2487a3c5 100644
--- a/src/main/tray/system-tray.ts
+++ b/src/main/tray/system-tray.ts
@@ -49,11 +49,21 @@ function applyTrayImage(): void {
       try {
         // Why: disabling template tinting makes the amber dot possible, but the
         // glyph then needs literal pixels chosen for the current menu-bar theme.
-        const tintedGlyph = tintTrayTemplateForAttention(
-          baseTrayImage,
-          nativeTheme.shouldUseDarkColors
+        const useLightGlyph = nativeTheme.shouldUseDarkColors
+        const attentionImage = composeTrayAttentionIcon(
+          tintTrayTemplateForAttention(baseTrayImage, useLightGlyph)
         )
-        const attentionImage = composeTrayAttentionIcon(tintedGlyph)
+        if (baseTrayImage.getScaleFactors().includes(2)) {
+          // Why: toBitmap reads only the 1x pixels, so rebuild the @2x
+          // representation or the glyph blurs on Retina during attention.
+          const retinaAttentionImage = composeTrayAttentionIcon(
+            tintTrayTemplateForAttention(baseTrayImage, useLightGlyph, 2)
+          )
+          attentionImage.addRepresentation({
+            scaleFactor: 2,
+            dataURL: retinaAttentionImage.toDataURL()
+          })
+        }
         attentionImage.setTemplateImage(false)
         tray.setImage(attentionImage)
         tray.setToolTip(translateMain('tray.activityWaiting', 'Orca - activity waiting'))
@@ -168,34 +178,28 @@ export function createSystemTray(opts: SystemTrayOptions): Tray | null {
   // Why: reflect any attention event that fired before the tray existed.
   applyTrayImage()
 
-  const menu = Menu.buildFromTemplate(
-    process.platform === 'darwin'
-      ? [
+  const menu = Menu.buildFromTemplate([
+    {
+      label: translateMain('tray.openOrca', 'Open Orca'),
+      click: safeMenuAction(() => opts.onOpen())
+    },
+    { type: 'separator' },
+    // Why: reuse the app menu's keys so the two entry points never drift.
+    ...(process.platform === 'darwin'
+      ? ([
           {
-            label: translateMain('tray.openOrca', 'Open Orca'),
-            click: safeMenuAction(() => opts.onOpen())
-          },
-          { type: 'separator' },
-          {
-            label: translateMain('tray.settings', 'Settings...'),
+            label: translateMain('menu.settings', 'Settings'),
             click: safeMenuAction(() => opts.onOpenSettings())
           },
           {
-            label: translateMain('tray.checkForUpdates', 'Check for Updates...'),
+            label: translateMain('menu.checkForUpdates', 'Check for Updates...'),
             click: safeMenuAction(() => opts.onCheckForUpdates())
           },
-          { type: 'separator' },
-          { label: translateMain('tray.quit', 'Quit'), click: safeMenuAction(() => opts.onQuit()) }
-        ]
-      : [
-          {
-            label: translateMain('tray.openOrca', 'Open Orca'),
-            click: safeMenuAction(() => opts.onOpen())
-          },
-          { type: 'separator' },
-          { label: translateMain('tray.quit', 'Quit'), click: safeMenuAction(() => opts.onQuit()) }
-        ]
-  )
+          { type: 'separator' }
+        ] as Electron.MenuItemConstructorOptions[])
+      : []),
+    { label: translateMain('tray.quit', 'Quit'), click: safeMenuAction(() => opts.onQuit()) }
+  ])
   tray.setContextMenu(menu)
   if (process.platform === 'win32') {
     tray.setToolTip('Orca')
@@ -245,5 +249,6 @@ export function destroySystemTray(): void {
   }
   tray = null
   baseTrayImage = null
-  attentionActive = false
+  // Why: attention is owned by the notification/visibility flow, and must
+  // survive the macOS hide/show toggle so a re-shown icon keeps its dot.
 }
diff --git a/src/main/tray/tray-attention-icon.test.ts b/src/main/tray/tray-attention-icon.test.ts
index 1bc00daa77c..090847e284e 100644
--- a/src/main/tray/tray-attention-icon.test.ts
+++ b/src/main/tray/tray-attention-icon.test.ts
@@ -114,4 +114,31 @@ describe('tintTrayTemplateForAttention', () => {
 
     expect(createFromBitmapMock.mock.calls[0][0]).toEqual(Buffer.from([0xff, 0xff, 0xff, 0xff]))
   })
+
+  it('keeps white edge pixels premultiplied-valid at partial alpha', () => {
+    createFromBitmapMock.mockClear()
+    const base = {
+      getSize: () => ({ width: 1, height: 1 }),
+      toBitmap: () => Buffer.from([0x00, 0x00, 0x00, 0x80])
+    }
+
+    tintTrayTemplateForAttention(base as never, true)
+
+    // Why: the bitmap is premultiplied — white at 50% coverage is 0x80, not 0xff.
+    expect(createFromBitmapMock.mock.calls[0][0]).toEqual(Buffer.from([0x80, 0x80, 0x80, 0x80]))
+  })
+
+  it('reads and sizes the requested scale factor', () => {
+    createFromBitmapMock.mockClear()
+    const toBitmap = vi.fn(() => Buffer.from([0x00, 0x00, 0x00, 0xff]))
+    const base = {
+      getSize: () => ({ width: 1, height: 1 }),
+      toBitmap
+    }
+
+    tintTrayTemplateForAttention(base as never, true, 2)
+
+    expect(toBitmap).toHaveBeenCalledWith({ scaleFactor: 2 })
+    expect(createFromBitmapMock.mock.calls[0][1]).toEqual({ width: 2, height: 2 })
+  })
 })
diff --git a/src/main/tray/tray-attention-icon.ts b/src/main/tray/tray-attention-icon.ts
index 5a7041f111e..ffdf4528d47 100644
--- a/src/main/tray/tray-attention-icon.ts
+++ b/src/main/tray/tray-attention-icon.ts
@@ -13,22 +13,28 @@ const RING_RGB = { r: 0xff, g: 0xff, b: 0xff }
  */
 export function tintTrayTemplateForAttention(
   base: NativeImage,
-  useLightGlyph: boolean
+  useLightGlyph: boolean,
+  scaleFactor = 1
 ): NativeImage {
   const { width, height } = base.getSize()
   if (width <= 0 || height <= 0) {
     return base
   }
 
-  const bitmap = Buffer.from(base.toBitmap())
-  const channel = useLightGlyph ? 0xff : 0x00
+  const bitmap = Buffer.from(base.toBitmap({ scaleFactor }))
   for (let offset = 0; offset < bitmap.length; offset += 4) {
+    // Why: the bitmap is premultiplied, so a light glyph must write the pixel's
+    // alpha (not 0xff) or antialiased edges become invalid over-bright pixels.
+    const channel = useLightGlyph ? bitmap[offset + 3] : 0x00
     bitmap[offset] = channel
     bitmap[offset + 1] = channel
     bitmap[offset + 2] = channel
   }
 
-  return nativeImage.createFromBitmap(bitmap, { width, height })
+  return nativeImage.createFromBitmap(bitmap, {
+    width: width * scaleFactor,
+    height: height * scaleFactor
+  })
 }
 
 /**
diff --git a/src/renderer/src/hooks/useIpcEvents.ts b/src/renderer/src/hooks/useIpcEvents.ts
index 1f64369bc88..159926a9993 100644
--- a/src/renderer/src/hooks/useIpcEvents.ts
+++ b/src/renderer/src/hooks/useIpcEvents.ts
@@ -1214,14 +1214,17 @@ export function useIpcEvents(): void {
       })
     )
 
-    // Why: the tray/menu-bar "Settings…" item can fire before this listener
-    // attaches on a freshly created window; pull any one-shot intent left for
-    // us so the request is not lost to that race.
-    void window.api.ui.consumePendingOpenSettings().then((open) => {
-      if (open) {
-        useAppStore.getState().openSettingsPage()
-      }
-    })
+    // Why: a tray/menu-bar "Settings…" click can fire before this listener
+    // attaches on a fresh window; consume any intent queued for us. Guarded
+    // with `?.` so a stale preload bundle doesn't crash the listener set.
+    void window.api.ui
+      .consumePendingOpenSettings?.()
+      .then((open) => {
+        if (open) {
+          useAppStore.getState().openSettingsPage()
+        }
+      })
+      .catch(() => {})
 
     unsubs.push(
       window.api.ui.onOpenSetupGuide?.(() => {
diff --git a/src/renderer/src/i18n/locales/en.json b/src/renderer/src/i18n/locales/en.json
index 3bd44870cf3..8a9ed738a87 100644
--- a/src/renderer/src/i18n/locales/en.json
+++ b/src/renderer/src/i18n/locales/en.json
@@ -72,9 +72,7 @@
     "minimizeNotice": {
       "body": "Orca is still running in the system tray"
     },
-    "activityWaiting": "Orca - activity waiting",
-    "settings": "Settings...",
-    "checkForUpdates": "Check for Updates..."
+    "activityWaiting": "Orca - activity waiting"
   },
   "worktreeJumpPalette": {
     "matchLabel": {
diff --git a/src/renderer/src/i18n/locales/es.json b/src/renderer/src/i18n/locales/es.json
index 3ce19041a4f..4bf70ef388e 100644
--- a/src/renderer/src/i18n/locales/es.json
+++ b/src/renderer/src/i18n/locales/es.json
@@ -34,7 +34,7 @@
       },
       "menuBarIcon": {
         "title": "Mostrar icono en la barra de menús",
-        "description": "Manten un acceso directo de Orca e indicador de actividad en la barra de menús de macOS."
+        "description": "Mantén un acceso directo de Orca e indicador de actividad en la barra de menús de macOS."
       }
     }
   },
@@ -72,9 +72,7 @@
     "minimizeNotice": {
       "body": "Orca sigue ejecutándose en la bandeja del sistema"
     },
-    "activityWaiting": "Orca: actividad en espera",
-    "settings": "Ajustes...",
-    "checkForUpdates": "Buscar actualizaciones..."
+    "activityWaiting": "Orca: actividad en espera"
   },
   "worktreeJumpPalette": {
     "matchLabel": {
diff --git a/src/renderer/src/i18n/locales/ja.json b/src/renderer/src/i18n/locales/ja.json
index 36e001bfc42..05f995d671d 100644
--- a/src/renderer/src/i18n/locales/ja.json
+++ b/src/renderer/src/i18n/locales/ja.json
@@ -72,9 +72,7 @@
     "minimizeNotice": {
       "body": "Orcaはシステムトレイで実行中です"
     },
-    "activityWaiting": "Orca - アクティビティ待機中",
-    "settings": "設定...",
-    "checkForUpdates": "アップデートを確認..."
+    "activityWaiting": "Orca - アクティビティ待機中"
   },
   "worktreeJumpPalette": {
     "matchLabel": {
diff --git a/src/renderer/src/i18n/locales/ko.json b/src/renderer/src/i18n/locales/ko.json
index 2a8d947cb8f..e0d9b4c1e9d 100644
--- a/src/renderer/src/i18n/locales/ko.json
+++ b/src/renderer/src/i18n/locales/ko.json
@@ -72,9 +72,7 @@
     "minimizeNotice": {
       "body": "Orca가 시스템 트레이에서 계속 실행 중입니다"
     },
-    "activityWaiting": "Orca - 활동 대기 중",
-    "settings": "설정...",
-    "checkForUpdates": "업데이트 확인..."
+    "activityWaiting": "Orca - 활동 대기 중"
   },
   "worktreeJumpPalette": {
     "matchLabel": {
diff --git a/src/renderer/src/i18n/locales/zh.json b/src/renderer/src/i18n/locales/zh.json
index 0e72c1d4808..05a7617ccc2 100644
--- a/src/renderer/src/i18n/locales/zh.json
+++ b/src/renderer/src/i18n/locales/zh.json
@@ -72,9 +72,7 @@
     "minimizeNotice": {
       "body": "Orca 仍在系统托盘中运行"
     },
-    "activityWaiting": "Orca - 活动等待中",
-    "settings": "设置...",
-    "checkForUpdates": "检查更新..."
+    "activityWaiting": "Orca - 活动等待中"
   },
   "worktreeJumpPalette": {
     "matchLabel": {