diff --git a/apps/macos/LauncherApp/look-app/Support/Actions/ActionController+Links.swift b/apps/macos/LauncherApp/look-app/Support/Actions/ActionController+Links.swift
index 5842a640..a7b3dc78 100644
--- a/apps/macos/LauncherApp/look-app/Support/Actions/ActionController+Links.swift
+++ b/apps/macos/LauncherApp/look-app/Support/Actions/ActionController+Links.swift
@@ -21,7 +21,7 @@ extension ActionController {
             // retrying on that loops.
             guard !didAsk else { return Self.noCalendarAccess }
             Task {
-                await EventKitService.shared.requestCalendarAccess()
+                await PermissionPrompt.run { await EventKitService.shared.requestCalendarAccess() }
                 setFeedback(presentJoinChoices(named: name, didAsk: true))
             }
             return ""
@@ -68,7 +68,7 @@ extension ActionController {
             // Once only: see the calendar branch.
             guard !didAsk else { return Self.noContactsAccess }
             Task {
-                await ContactsService.shared.requestAccess()
+                await PermissionPrompt.run { await ContactsService.shared.requestAccess() }
                 setFeedback(presentCallChoices(named: name, modality: modality, didAsk: true))
             }
             return ""
diff --git a/apps/macos/LauncherApp/look-app/Support/Launcher/PermissionPrompt.swift b/apps/macos/LauncherApp/look-app/Support/Launcher/PermissionPrompt.swift
new file mode 100644
index 00000000..1918ab5d
--- /dev/null
+++ b/apps/macos/LauncherApp/look-app/Support/Launcher/PermissionPrompt.swift
@@ -0,0 +1,18 @@
+import AppKit
+
+/// Runs a TCC request with the launcher pinned open.
+///
+/// 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.
+@MainActor
+enum PermissionPrompt {
+    private(set) static var isPresenting = false
+
+    static func run(_ request: () async -> Void) async {
+        isPresenting = true
+        NSApplication.shared.activate(ignoringOtherApps: true)
+        await request()
+        isPresenting = false
+    }
+}
diff --git a/apps/macos/LauncherApp/look-app/Views/Launcher/LauncherView.swift b/apps/macos/LauncherApp/look-app/Views/Launcher/LauncherView.swift
index 0d755fd6..9e455b49 100644
--- a/apps/macos/LauncherApp/look-app/Views/Launcher/LauncherView.swift
+++ b/apps/macos/LauncherApp/look-app/Views/Launcher/LauncherView.swift
@@ -929,7 +929,9 @@ struct LauncherView: View {
         .onReceive(
             NotificationCenter.default.publisher(for: NSApplication.didResignActiveNotification)
         ) { _ in
-            if launcherWindow()?.isVisible == true {
+            // Not while a TCC dialog is up: it steals focus, and hiding here
+            // backgrounds the app so the next prompt never appears.
+            if !PermissionPrompt.isPresenting, launcherWindow()?.isVisible == true {
                 Logger(subsystem: "noah-code.Look", category: "window-resize")
                     .debug("didResignActiveNotification -> hideLauncherWindow(restorePreviousApp: false)")
                 hideLauncherWindow(restorePreviousApp: false)
diff --git a/apps/macos/LauncherApp/look-app/Views/Settings/PermissionsRow.swift b/apps/macos/LauncherApp/look-app/Views/Settings/PermissionsRow.swift
index f3e23e4f..b7a195b5 100644
--- a/apps/macos/LauncherApp/look-app/Views/Settings/PermissionsRow.swift
+++ b/apps/macos/LauncherApp/look-app/Views/Settings/PermissionsRow.swift
@@ -157,10 +157,12 @@ struct PermissionsRow: View {
     }
 
     private func request(_ capability: PermissionItem.Capability) async {
-        switch capability {
-        case .calendar: await EventKitService.shared.requestCalendarAccess()
-        case .reminders: await EventKitService.shared.requestReminderAccess()
-        case .contacts: await ContactsService.shared.requestAccess()
+        await PermissionPrompt.run {
+            switch capability {
+            case .calendar: await EventKitService.shared.requestCalendarAccess()
+            case .reminders: await EventKitService.shared.requestReminderAccess()
+            case .contacts: await ContactsService.shared.requestAccess()
+            }
         }
     }