Fall back to System Settings when the Mail consent prompt is the known beta bug

Confirmed via multiple live rounds with Rune this is a macOS 27 beta issue,
not a Confab bug — matches an already-documented pattern in this project
(Calendar/Contacts requestAccess failing identically). Every failure
returns in single-digit milliseconds, ruled out threading, wrong API,
build/signing, and notarization; even a fresh notarized build fails
identically, while Terminal->Mail (first-party) works with no prompt at
all, and the same-style bug already has a drafted Apple Feedback report
for a different permission category.

Kept the real Apple Event attempt as the primary path (the way this
should work once the OS bug is fixed), but now time it: a failure faster
than any human could plausibly answer a real dialog (default 300ms) is
classified as the platform bug rather than a genuine denial, and the UI
falls back to opening System Settings' Automation pane directly with an
explanatory note, instead of the button silently doing nothing.

oAI/Services/AppleMailService.swift

@@ -76,34 +76,63 @@ final class AppleMailService {
         }
     }
 
+    /// Outcome of `requestAccess()`. `.suspectedPlatformBug` is distinct from `.denied` because a
+    /// genuine user denial requires the system dialog to actually be shown and answered, which
+    /// takes real human time — see `classifyRequestOutcome` for the timing heuristic that tells
+    /// the two apart.
+    enum MailAccessOutcome: Equatable {
+        case granted
+        case denied
+        case suspectedPlatformBug
+    }
+
+    /// Below this, a failure almost certainly means no dialog was ever shown — no human reads,
+    /// decides, and clicks a permission dialog in under this long. Generous on purpose: the goal
+    /// is zero false positives (never mistake a real, if fast, denial for the platform bug), not a
+    /// tight bound.
+    nonisolated static let suspectedBugThreseholdSeconds: TimeInterval = 0.3
+
+    /// Pure classification, kept separate from the live call for testability.
+    nonisolated static func classifyRequestOutcome(succeeded: Bool, elapsedSeconds: TimeInterval) -> MailAccessOutcome {
+        if succeeded { return .granted }
+        return elapsedSeconds < suspectedBugThreseholdSeconds ? .suspectedPlatformBug : .denied
+    }
+
     /// Triggers the real macOS "Confab wants to control Mail" Automation permission prompt if
     /// the user hasn't been asked yet (a no-op if already granted or denied).
     ///
-    /// Two earlier attempts used `AEDeterminePermissionToAutomateTarget(askUserIfNeeded: true)` —
-    /// first called directly (relying on implicit MainActor isolation), then wrapped in
-    /// `DispatchQueue.main.async`. Neither worked live: logs showed it returning -1743 in ~9ms,
-    /// far too fast for any real human response, immediately followed by the passive status check
-    /// (`askUserIfNeeded: false`) still reporting -1744 ("would need to ask") — i.e. the OS never
-    /// actually recorded a decision despite the "denied" return. That points at
-    /// `AEDeterminePermissionToAutomateTarget` itself misbehaving in this context (possibly a
-    /// macOS 27 beta issue — this project has hit other real TCC/permission regressions on this
-    /// beta before, see CLAUDE.md's Personal Data Tools Apple Feedback note), not a threading bug.
+    /// Live-verified (2026-08-19, several rounds with Rune): the prompt never appears on this
+    /// machine (macOS 27 beta) for Confab specifically — not a threading bug (tried direct call,
+    /// `DispatchQueue.main.async`), not the wrong API (tried `AEDeterminePermissionToAutomateTarget`
+    /// AND a real Apple Event via `runHandler`, both fail identically), not a build/signing issue
+    /// (verified the installed app's signature, team ID, Info.plist key, and even a notarized
+    /// build — all correct), and not an OS-wide Automation outage (Terminal → Mail works fine).
+    /// Every failure returns in single-digit milliseconds — far too fast for a real dialog to have
+    /// been shown and answered. This matches an already-documented macOS 27 beta bug in this same
+    /// project (`EKEventStore.requestFullAccessToEvents()`/`CNContactStore.requestAccess()` failing
+    /// identically for Calendar/Contacts while Reminders/Location work fine) — a category of
+    /// TCC-gated permission requests that this OS beta just never prompts for from third-party
+    /// apps, regardless of what the app does.
     ///
-    /// Switched strategy entirely: attempt a real, harmless Apple Event via the same `runHandler`
-    /// path `mail_list_accounts`/`testConnection()` already use — sending an actual Apple Event is
-    /// the standard, well-proven way macOS shows the first-time "X wants to control Y" Automation
-    /// prompt, and this exact path is already confirmed working (it's what correctly reported
-    /// "not authorized" in the very first live test).
+    /// Given that, this still attempts the real thing first (the way it *should* work, and will
+    /// once the OS bug is fixed) via the same `runHandler` path `mail_list_accounts`/
+    /// `testConnection()` use, but times the attempt and treats an implausibly-fast failure as the
+    /// known platform bug rather than a real denial — callers can then fall back to sending the
+    /// user straight to System Settings' Automation pane instead of a dead-end "nothing happened."
     @discardableResult
-    func requestAccess() async -> Bool {
+    func requestAccess() async -> MailAccessOutcome {
         Log.mail.info("requestAccess: called — attempting a real Apple Event (listAccounts) to trigger the OS consent prompt")
-        switch await runHandler("listAccounts", arguments: []) {
+        let start = Date()
+        let result = await runHandler("listAccounts", arguments: [])
+        let elapsed = Date().timeIntervalSince(start)
+        switch result {
         case .success:
-            Log.mail.info("requestAccess: real Apple Event succeeded — access granted")
-            return true
+            Log.mail.info("requestAccess: real Apple Event succeeded after \(String(format: "%.3f", elapsed))s — access granted")
+            return .granted
         case .failure(let error):
-            Log.mail.info("requestAccess: real Apple Event failed — \(String(describing: error))")
-            return false
+            let outcome = Self.classifyRequestOutcome(succeeded: false, elapsedSeconds: elapsed)
+            Log.mail.info("requestAccess: real Apple Event failed after \(String(format: "%.3f", elapsed))s — \(String(describing: error)) — classified as \(String(describing: outcome))")
+            return outcome
         }
     }
 

oAI/Views/Screens/SettingsView.swift

@@ -134,6 +134,7 @@ struct SettingsView: View {
     @State private var isTestingMail = false
     @State private var mailTestResult: String?
     @State private var mailAccessState: PersonalDataAccessState = AppleMailService.shared.accessState
+    @State private var mailAccessNote: String?
 
     private let labelWidth: CGFloat = 160
 
@@ -1060,8 +1061,34 @@ It's better to admit "I need more information" or "I cannot do that" than to fak
                     isEnabled: $settingsService.mailEnabled,
                     state: mailAccessState,
                     systemSettingsAnchor: "Privacy_Automation",
-                    requestAccess: { mailAccessState = await AppleMailService.shared.requestAccess() ? .granted : AppleMailService.shared.accessState }
+                    requestAccess: {
+                        switch await AppleMailService.shared.requestAccess() {
+                        case .granted:
+                            mailAccessState = .granted
+                            mailAccessNote = nil
+                        case .denied:
+                            mailAccessState = .denied
+                            mailAccessNote = nil
+                        case .suspectedPlatformBug:
+                            // Known macOS 27 beta issue (see AppleMailService.requestAccess doc
+                            // comment) — the OS never shows the consent dialog for this app, so
+                            // there's nothing more to try in-app. Send the user to System Settings
+                            // directly rather than leaving the button looking like it did nothing.
+                            mailAccessState = .denied
+                            mailAccessNote = "macOS isn't showing the permission prompt (a known macOS 27 beta issue) — opened System Settings instead. If Confab isn't listed there under Automation, this can't be granted until Apple fixes it."
+                            openPrivacySettings(anchor: "Privacy_Automation")
+                        }
+                    }
                 )
+                if let mailAccessNote {
+                    rowDivider()
+                    Text(mailAccessNote)
+                        .font(.system(size: 12))
+                        .foregroundStyle(.orange)
+                        .fixedSize(horizontal: false, vertical: true)
+                        .padding(.horizontal, 16)
+                        .padding(.vertical, 8)
+                }
                 if settingsService.mailEnabled {
                     rowDivider()
                     row("Require Approval for Every Action") {

oAITests/AppleMailServiceTests.swift

@@ -188,4 +188,29 @@ struct AppleMailServiceTests {
         #expect(AppleMailService.mapAutomationPermissionStatus(-1744) == .notDetermined)
         #expect(AppleMailService.mapAutomationPermissionStatus(-9999) == .notDetermined)
     }
+
+    // MARK: - classifyRequestOutcome
+
+    @Test("classifyRequestOutcome maps success to granted regardless of elapsed time")
+    func classifiesSuccessAsGranted() {
+        #expect(AppleMailService.classifyRequestOutcome(succeeded: true, elapsedSeconds: 0.001) == .granted)
+        #expect(AppleMailService.classifyRequestOutcome(succeeded: true, elapsedSeconds: 5.0) == .granted)
+    }
+
+    @Test("classifyRequestOutcome treats an implausibly fast failure as the suspected platform bug")
+    func classifiesFastFailureAsSuspectedBug() {
+        #expect(AppleMailService.classifyRequestOutcome(succeeded: false, elapsedSeconds: 0.009) == .suspectedPlatformBug)
+        #expect(AppleMailService.classifyRequestOutcome(succeeded: false, elapsedSeconds: 0.0) == .suspectedPlatformBug)
+    }
+
+    @Test("classifyRequestOutcome treats a slower failure as a real denial")
+    func classifiesSlowFailureAsDenied() {
+        #expect(AppleMailService.classifyRequestOutcome(succeeded: false, elapsedSeconds: 1.5) == .denied)
+    }
+
+    @Test("classifyRequestOutcome threshold is right at the boundary")
+    func classifiesThresholdBoundary() {
+        #expect(AppleMailService.classifyRequestOutcome(succeeded: false, elapsedSeconds: AppleMailService.suspectedBugThreseholdSeconds) == .denied)
+        #expect(AppleMailService.classifyRequestOutcome(succeeded: false, elapsedSeconds: AppleMailService.suspectedBugThreseholdSeconds - 0.001) == .suspectedPlatformBug)
+    }
 }