diff --git a/AudioType/App/AudioTypeApp.swift b/AudioType/App/AudioTypeApp.swift
index 3054019..dbe8f6d 100644
--- a/AudioType/App/AudioTypeApp.swift
+++ b/AudioType/App/AudioTypeApp.swift
@@ -14,6 +14,8 @@ struct AudioTypeApp: App {
 
 @MainActor
 class AppDelegate: NSObject, NSApplicationDelegate {
+  static let onboardingCompletedKey = "onboardingCompleted"
+
   private var statusItem: NSStatusItem!
   private var menuBarController: MenuBarController!
   private var transcriptionManager: TranscriptionManager!
@@ -47,15 +49,47 @@ class AppDelegate: NSObject, NSApplicationDelegate {
   private func checkPermissions() async {
     let micPermission = await Permissions.checkMicrophone()
     let accessibilityPermission = Permissions.checkAccessibility()
+    let engineAvailable = EngineResolver.anyEngineAvailable
+    let allGood = micPermission && accessibilityPermission && engineAvailable
+
+    if allGood {
+      markOnboardingCompleted()
+      await transcriptionManager.initialize()
+      return
+    }
 
-    // Show onboarding if permissions are missing or no engine is usable
-    if !micPermission || !accessibilityPermission || !EngineResolver.anyEngineAvailable {
+    // If the user already completed onboarding before but accessibility is
+    // now failing, it's almost always a cdhash mismatch after a fresh release
+    // (TCC.db still says granted, but AXIsProcessTrusted returns false because
+    // the saved cdhash no longer matches the ad-hoc-signed binary). Show a
+    // narrow re-approval prompt instead of the full first-run onboarding.
+    let onboardingDone = UserDefaults.standard.bool(forKey: Self.onboardingCompletedKey)
+    if onboardingDone && micPermission && engineAvailable && !accessibilityPermission {
       await MainActor.run {
-        showOnboarding()
+        showReapprovePrompt()
       }
-    } else {
-      // All set — start listening for hotkey
-      await transcriptionManager.initialize()
+      return
+    }
+
+    await MainActor.run {
+      showOnboarding()
+    }
+  }
+
+  fileprivate func markOnboardingCompleted() {
+    UserDefaults.standard.set(true, forKey: Self.onboardingCompletedKey)
+  }
+
+  fileprivate func startTranscriptionIfNeeded() {
+    Task {
+      await self.transcriptionManager.initialize()
+    }
+  }
+
+  fileprivate func dismissOnboarding() {
+    DispatchQueue.main.asyncAfter(deadline: .now() + 0.5) {
+      self.onboardingWindow?.orderOut(nil)
+      self.onboardingWindow = nil
     }
   }
 
@@ -75,14 +109,32 @@ class AppDelegate: NSObject, NSApplicationDelegate {
 
     window.contentView = NSHostingView(
       rootView: OnboardingView { [weak self] in
-        // Delay to let animations complete before releasing
-        DispatchQueue.main.asyncAfter(deadline: .now() + 0.5) {
-          self?.onboardingWindow?.orderOut(nil)
-          self?.onboardingWindow = nil
-        }
-        Task {
-          await self?.transcriptionManager.initialize()
-        }
+        guard let self = self else { return }
+        self.markOnboardingCompleted()
+        self.dismissOnboarding()
+        self.startTranscriptionIfNeeded()
+      })
+    window.makeKeyAndOrderFront(nil)
+    NSApp.activate(ignoringOtherApps: true)
+  }
+
+  private func showReapprovePrompt() {
+    let window = NSWindow(
+      contentRect: NSRect(x: 0, y: 0, width: 420, height: 280),
+      styleMask: [.titled],
+      backing: .buffered,
+      defer: false
+    )
+    window.title = "AudioType needs re-approval"
+    window.center()
+    window.isReleasedWhenClosed = false
+    self.onboardingWindow = window
+
+    window.contentView = NSHostingView(
+      rootView: ReapproveAccessibilityView { [weak self] in
+        guard let self = self else { return }
+        self.dismissOnboarding()
+        self.startTranscriptionIfNeeded()
       })
     window.makeKeyAndOrderFront(nil)
     NSApp.activate(ignoringOtherApps: true)
diff --git a/AudioType/App/MenuBarController.swift b/AudioType/App/MenuBarController.swift
index 57f99f4..87bb45e 100644
--- a/AudioType/App/MenuBarController.swift
+++ b/AudioType/App/MenuBarController.swift
@@ -75,6 +75,23 @@ class MenuBarController: NSObject, NSWindowDelegate {
       name: .audioLevelChanged,
       object: nil
     )
+
+    // Refresh the hotkey menu item when the binding changes from Settings.
+    NotificationCenter.default.addObserver(
+      self,
+      selector: #selector(hotKeyBindingDidChange),
+      name: HotKeyBindingStore.didChangeNotification,
+      object: nil
+    )
+
+    // Surface a clear error in the menu bar when the event tap can't be
+    // created — almost always an Accessibility permission problem.
+    NotificationCenter.default.addObserver(
+      self,
+      selector: #selector(hotKeyTapFailed),
+      name: .hotKeyTapCreationFailed,
+      object: nil
+    )
   }
 
   deinit {
@@ -96,8 +113,13 @@ class MenuBarController: NSObject, NSWindowDelegate {
     statusMenuItem.tag = 100  // Tag to identify status item
     menu.addItem(statusMenuItem)
 
-    // Hotkey info
-    let hotkeyItem = NSMenuItem(title: "Hotkey: Hold fn", action: nil, keyEquivalent: "")
+    // Hotkey info (live-updated when the binding changes in Settings)
+    let hotkeyItem = NSMenuItem(
+      title: hotkeyMenuTitle(),
+      action: nil,
+      keyEquivalent: ""
+    )
+    hotkeyItem.tag = 101
     hotkeyItem.isEnabled = false
     menu.addItem(hotkeyItem)
 
@@ -167,6 +189,41 @@ class MenuBarController: NSObject, NSWindowDelegate {
     }
   }
 
+  private func hotkeyMenuTitle() -> String {
+    "Hotkey: Hold \(HotKeyBindingStore.current.displayName)"
+  }
+
+  @objc private func hotKeyBindingDidChange() {
+    DispatchQueue.main.async { [weak self] in
+      guard let self = self,
+        let menu = self.statusItem?.menu,
+        let item = menu.item(withTag: 101)
+      else { return }
+      item.title = self.hotkeyMenuTitle()
+    }
+  }
+
+  @objc private func hotKeyTapFailed() {
+    DispatchQueue.main.async { [weak self] in
+      guard let self = self, let button = self.statusItem?.button else { return }
+      button.image = self.errorIcon
+      self.updateStatusMenuItem("Accessibility permission required")
+      self.replaceHotkeyItemWithAccessibilityFix()
+    }
+  }
+
+  private func replaceHotkeyItemWithAccessibilityFix() {
+    guard let menu = statusItem?.menu, let item = menu.item(withTag: 101) else { return }
+    item.title = "Open Accessibility Settings…"
+    item.action = #selector(openAccessibilitySettingsFromMenu)
+    item.target = self
+    item.isEnabled = true
+  }
+
+  @objc private func openAccessibilitySettingsFromMenu() {
+    Permissions.openAccessibilitySettings()
+  }
+
   private func showRecordingIndicator() {
     if recordingWindow == nil {
       let window = NSWindow(
diff --git a/AudioType/Core/HotKeyManager.swift b/AudioType/Core/HotKeyManager.swift
index 1a2564c..210283d 100644
--- a/AudioType/Core/HotKeyManager.swift
+++ b/AudioType/Core/HotKeyManager.swift
@@ -8,6 +8,12 @@ enum HotKeyEvent {
   case keyUp
 }
 
+extension Notification.Name {
+  /// Posted when `CGEvent.tapCreate` fails, almost always because Accessibility
+  /// permission isn't actually trusted for the running binary.
+  static let hotKeyTapCreationFailed = Notification.Name("hotKeyTapCreationFailed")
+}
+
 class HotKeyManager {
   private var eventTap: CFMachPort?
   private var runLoopSource: CFRunLoopSource?
@@ -79,6 +85,9 @@ class HotKeyManager {
       retained.release()
       refconRetained = nil
       logger.error("Failed to create event tap. Accessibility permission may be required.")
+      // Surface the failure so the menu bar can show an error state and the
+      // user understands the hotkey isn't going to work.
+      NotificationCenter.default.post(name: .hotKeyTapCreationFailed, object: nil)
       return
     }
 
diff --git a/AudioType/UI/OnboardingView.swift b/AudioType/UI/OnboardingView.swift
index 8155343..1d39300 100644
--- a/AudioType/UI/OnboardingView.swift
+++ b/AudioType/UI/OnboardingView.swift
@@ -9,8 +9,12 @@ struct OnboardingView: View {
   @State private var anyCloudKeyConfigured = GroqEngine.isConfigured || OpenAIEngine.isConfigured
   @State private var apiKeyText = ""
   @State private var apiKeySaveError: String?
+  @State private var didAutoComplete = false
 
-  let timer = Timer.publish(every: 0.5, on: .main, in: .common).autoconnect()
+  // Poll every 2 seconds to pick up permission changes the user made in
+  // System Settings. Cheaper than the previous 0.5s cadence and we stop
+  // polling entirely once everything's ready (see onReceive below).
+  let timer = Timer.publish(every: 2.0, on: .main, in: .common).autoconnect()
 
   let onComplete: () -> Void
 
@@ -164,16 +168,26 @@ struct OnboardingView: View {
       checkPermissions()
     }
     .onReceive(timer) { _ in
-      // Continuously refresh permission state so the UI reflects changes made
-      // in System Settings. The user closes the window themselves via the
-      // "Get Started" button once everything is ready.
-      microphoneGranted = AVCaptureDevice.authorizationStatus(for: .audio) == .authorized
-      accessibilityGranted = Permissions.checkAccessibility()
-      speechRecognitionGranted = Permissions.isSpeechRecognitionAuthorized
-      anyCloudKeyConfigured = GroqEngine.isConfigured || OpenAIEngine.isConfigured
+      refreshPermissionState()
+
+      // Once every required permission lands, finish onboarding automatically.
+      // This avoids the trap where the user grants AX in System Settings,
+      // returns to AudioType, but the hotkey listener never starts because
+      // they haven't clicked "Get Started" yet.
+      if canContinue && !didAutoComplete {
+        didAutoComplete = true
+        onComplete()
+      }
     }
   }
 
+  private func refreshPermissionState() {
+    microphoneGranted = AVCaptureDevice.authorizationStatus(for: .audio) == .authorized
+    accessibilityGranted = Permissions.checkAccessibility()
+    speechRecognitionGranted = Permissions.isSpeechRecognitionAuthorized
+    anyCloudKeyConfigured = GroqEngine.isConfigured || OpenAIEngine.isConfigured
+  }
+
   /// The user can proceed once mic + accessibility are granted AND at least one engine is usable.
   private var canContinue: Bool {
     microphoneGranted && accessibilityGranted
@@ -257,3 +271,56 @@ struct PermissionRow: View {
     .padding(.vertical, 8)
   }
 }
+
+/// Slim follow-up shown after a re-install/update when the user has already
+/// granted Accessibility before, but the new binary's cdhash doesn't match
+/// the saved TCC entry so `AXIsProcessTrusted` returns false. Recovering
+/// only requires removing + re-adding AudioType in Accessibility settings.
+struct ReapproveAccessibilityView: View {
+  let onApproved: () -> Void
+
+  // Poll every 2 seconds and dismiss as soon as AX trust comes back.
+  let timer = Timer.publish(every: 2.0, on: .main, in: .common).autoconnect()
+  @State private var didFinish = false
+
+  var body: some View {
+    VStack(spacing: 20) {
+      Image(systemName: "lock.shield")
+        .font(.system(size: 40))
+        .foregroundColor(AudioTypeTheme.coral)
+
+      Text("AudioType needs re-approval")
+        .font(.title3)
+        .fontWeight(.semibold)
+
+      Text(
+        "After updating AudioType, macOS needs you to re-approve "
+          + "Accessibility access. In System Settings, remove AudioType from "
+          + "the Accessibility list and add it back from /Applications."
+      )
+      .font(.callout)
+      .multilineTextAlignment(.center)
+      .foregroundColor(.secondary)
+      .padding(.horizontal)
+      .fixedSize(horizontal: false, vertical: true)
+
+      Button("Open Accessibility Settings") {
+        Permissions.openAccessibilitySettings()
+      }
+      .buttonStyle(.borderedProminent)
+      .tint(AudioTypeTheme.coral)
+
+      Text("This window closes itself when access is restored.")
+        .font(.caption)
+        .foregroundColor(.secondary)
+    }
+    .padding(24)
+    .frame(width: 420)
+    .onReceive(timer) { _ in
+      if Permissions.checkAccessibility() && !didFinish {
+        didFinish = true
+        onApproved()
+      }
+    }
+  }
+}
diff --git a/AudioType/UI/SettingsView.swift b/AudioType/UI/SettingsView.swift
index 3ca2c5c..0f5e812 100644
--- a/AudioType/UI/SettingsView.swift
+++ b/AudioType/UI/SettingsView.swift
@@ -238,7 +238,7 @@ struct SettingsView: View {
         HStack {
           Text("Version")
           Spacer()
-          Text("2.4.0")
+          Text("2.4.1")
             .foregroundColor(.secondary)
         }
 
diff --git a/Resources/Info.plist b/Resources/Info.plist
index 09701e6..afb86a3 100644
--- a/Resources/Info.plist
+++ b/Resources/Info.plist
@@ -11,9 +11,9 @@
     <key>CFBundleDisplayName</key>
     <string>AudioType</string>
 	<key>CFBundleVersion</key>
-	<string>2.4.0</string>
+	<string>2.4.1</string>
 	<key>CFBundleShortVersionString</key>
-	<string>2.4.0</string>
+	<string>2.4.1</string>
     <key>CFBundlePackageType</key>
     <string>APPL</string>
     <key>LSMinimumSystemVersion</key>