diff --git a/apps/macos/LauncherApp/look-app/Support/Launcher/PermissionPrompt.swift b/apps/macos/LauncherApp/look-app/Support/Launcher/PermissionPrompt.swift
index 1a9ed26d..8d3e40a5 100644
--- a/apps/macos/LauncherApp/look-app/Support/Launcher/PermissionPrompt.swift
+++ b/apps/macos/LauncherApp/look-app/Support/Launcher/PermissionPrompt.swift
@@ -1,23 +1,52 @@
 import AppKit
 
-/// Runs a TCC request with the launcher pinned open.
+/// Runs a TCC request so its dialog is visible and a sequence of them can
+/// finish.
 ///
-/// The system dialog takes focus, which fires `didResignActive` and hides the
-/// window. The app is then in the background, where macOS will not present the
-/// next prompt, so a sequence of requests dies after the first one.
+/// Two things get in the way. The system draws the dialog at normal window
+/// level, and the launcher floats above that, so it opens behind the launcher.
+/// And hiding on `didResignActive` backgrounds the app, where macOS will not
+/// present the next prompt at all.
 @MainActor
 enum PermissionPrompt {
+    /// The launcher's own minimum frame. Smaller windows are the status item
+    /// and popover anchors, whose levels must stay as they are.
+    private static let launcherMinimumSide: CGFloat = 400
+
     /// Counted, not a flag: `await` inside `run` is a suspension point, so a
     /// second request can start before the first returns, and the first to
-    /// finish would otherwise unpin the window while a dialog is still up.
+    /// finish would otherwise restore the level while a dialog is still up.
     private static var active = 0
+    private static var restoreLevels: [(window: NSWindow, level: NSWindow.Level)] = []
 
     static var isPresenting: Bool { active > 0 }
 
     static func run(_ request: () async -> Void) async {
+        beginPresenting()
+        defer { endPresenting() }
+        await request()
+    }
+
+    private static func beginPresenting() {
         active += 1
-        defer { active -= 1 }
+        guard active == 1 else { return }
         NSApplication.shared.activate(ignoringOtherApps: true)
-        await request()
+        restoreLevels = launcherWindows().map { ($0, $0.level) }
+        for entry in restoreLevels { entry.window.level = .normal }
+    }
+
+    private static func endPresenting() {
+        active -= 1
+        guard active == 0 else { return }
+        for entry in restoreLevels { entry.window.level = entry.level }
+        restoreLevels = []
+    }
+
+    private static func launcherWindows() -> [NSWindow] {
+        NSApplication.shared.windows.filter {
+            $0.isVisible
+                && $0.frame.width >= launcherMinimumSide
+                && $0.frame.height >= launcherMinimumSide
+        }
     }
 }