diff --git a/src/logic/SystemPermissions.swift b/src/logic/SystemPermissions.swift
index d3dd8bc9..a0086623 100644
--- a/src/logic/SystemPermissions.swift
+++ b/src/logic/SystemPermissions.swift
@@ -59,9 +59,7 @@ class SystemPermissions {
         let accessibility = accessibilityIsGranted()
         let screenRecording = screenRecordingIsGranted()
         logger.d(accessibility, screenRecording, preStartupPermissionsPassed)
-        Menubar.permissionCalloutMenuItems?.forEach {
-            $0.isHidden = screenRecording != .skipped
-        }
+        Menubar.togglePermissionCallout(screenRecording == .skipped)
         if accessibility == .notGranted {
             App.app.restart()
         }
@@ -82,9 +80,7 @@ class SystemPermissions {
         let accessibility = accessibilityIsGranted()
         let screenRecording = screenRecordingIsGranted()
         logger.d(accessibility, screenRecording, preStartupPermissionsPassed)
-        Menubar.permissionCalloutMenuItems?.forEach {
-            $0.isHidden = screenRecording != .skipped
-        }
+        Menubar.togglePermissionCallout(screenRecording == .skipped)
         if accessibility != App.app.permissionsWindow?.accessibilityView?.permissionStatus {
             App.app.permissionsWindow?.accessibilityView.updatePermissionStatus(accessibility)
         }
diff --git a/src/ui/Menubar.swift b/src/ui/Menubar.swift
index c67a6df7..7eec8f86 100644
--- a/src/ui/Menubar.swift
+++ b/src/ui/Menubar.swift
@@ -12,8 +12,6 @@ class Menubar {
         permissionCalloutMenuItem.view = PermissionCallout()
         let calloutSeparator = NSMenuItem.separator()
         permissionCalloutMenuItems = [permissionCalloutMenuItem, calloutSeparator]
-        menu.addItem(permissionCalloutMenuItem)
-        menu.addItem(calloutSeparator)
         menu.addItem(
                 withTitle: String(format: NSLocalizedString("About %@", comment: "Menubar option. %@ is AltTab"), App.name),
             action: #selector(App.app.showAboutTab),
@@ -55,6 +53,18 @@ class Menubar {
         menubarIconCallback(nil)
     }
 
+    // NSMenuItem.isHidden isn't reliable with custom views. We add/remove to hide/show these items
+    static func togglePermissionCallout(_ show: Bool) {
+        permissionCalloutMenuItems?.enumerated().forEach { offset, element in
+            if show && !menu.items.contains(element) {
+                menu.insertItem(element, at: offset)
+            }
+            if !show && menu.items.contains(element) {
+                menu.removeItem(element)
+            }
+        }
+    }
+
     @objc static func statusItemOnClick() {
         // NSApp.currentEvent == nil if the icon is "clicked" through VoiceOver
         if let type = NSApp.currentEvent?.type, type != .leftMouseDown {