diff --git a/src/main/index.ts b/src/main/index.ts
index 8d432d5f281..bca05a3b85c 100644
--- a/src/main/index.ts
+++ b/src/main/index.ts
@@ -14,7 +14,13 @@ import { registerShellHandlers } from './ipc/shell'
 import { registerSessionHandlers } from './ipc/session'
 import { registerUIHandlers } from './ipc/ui'
 import { warmSystemFontFamilies } from './system-fonts'
-import { setupAutoUpdater, checkForUpdates, getUpdateStatus, quitAndInstall } from './updater'
+import {
+  setupAutoUpdater,
+  checkForUpdates,
+  checkForUpdatesFromMenu,
+  getUpdateStatus,
+  quitAndInstall
+} from './updater'
 
 let mainWindow: BrowserWindow | null = null
 let store: Store | null = null
@@ -113,7 +119,7 @@ app.whenReady().then(() => {
         { role: 'about' },
         {
           label: 'Check for Updates...',
-          click: () => checkForUpdates()
+          click: () => checkForUpdatesFromMenu()
         },
         {
           label: 'Settings',
diff --git a/src/main/updater.ts b/src/main/updater.ts
index 8cf25c7c614..5b6674ad9f1 100644
--- a/src/main/updater.ts
+++ b/src/main/updater.ts
@@ -26,6 +26,54 @@ export function checkForUpdates(): void {
   })
 }
 
+/** Menu-triggered check that shows native dialogs for feedback */
+export function checkForUpdatesFromMenu(): void {
+  if (!app.isPackaged || is.dev) {
+    dialog.showMessageBox({ type: 'info', message: 'You\u2019re on the latest version.' })
+    return
+  }
+
+  sendStatus({ state: 'checking' })
+
+  const onAvailable = (): void => {
+    cleanup()
+  }
+  const onNotAvailable = (): void => {
+    cleanup()
+    dialog.showMessageBox({ type: 'info', message: 'You\u2019re on the latest version.' })
+  }
+  const onError = (err: Error): void => {
+    cleanup()
+    dialog.showMessageBox({
+      type: 'error',
+      title: 'Update Error',
+      message: 'Could not check for updates.',
+      detail: err?.message
+    })
+  }
+
+  function cleanup(): void {
+    autoUpdater.off('update-available', onAvailable)
+    autoUpdater.off('update-not-available', onNotAvailable)
+    autoUpdater.off('error', onError)
+  }
+
+  autoUpdater.once('update-available', onAvailable)
+  autoUpdater.once('update-not-available', onNotAvailable)
+  autoUpdater.once('error', onError)
+
+  autoUpdater.checkForUpdates().catch((err) => {
+    sendStatus({ state: 'error', message: String(err?.message ?? err) })
+    cleanup()
+    dialog.showMessageBox({
+      type: 'error',
+      title: 'Update Error',
+      message: 'Could not check for updates.',
+      detail: String(err?.message ?? err)
+    })
+  })
+}
+
 export function quitAndInstall(): void {
   autoUpdater.quitAndInstall()
 }
@@ -38,6 +86,10 @@ export function setupAutoUpdater(mainWindow: BrowserWindow): void {
 
   autoUpdater.autoDownload = true
   autoUpdater.autoInstallOnAppQuit = true
+  // Use allowPrerelease to bypass broken /releases/latest endpoint (returns 406)
+  // and instead parse the version directly from the atom feed which works reliably.
+  // This is safe since we don't publish prerelease versions.
+  autoUpdater.allowPrerelease = true
 
   autoUpdater.on('checking-for-update', () => {
     sendStatus({ state: 'checking' })