Sources/Shotdeck/AppModel.swift

@@ -139,6 +139,14 @@ public final class AppModel {
     /// lets the LAST choice win instead of applying stale, superseded work. Not
     /// `@Observable`-relevant state — pure internal bookkeeping, never read by a View.
     var reconcileGeneration = 0
+    /// The MOST RECENT watcher-reconcile Task spawned by chooseTransport/
+    /// chooseOneDriveFolder, if one is still (or was just) in flight. send() awaits
+    /// this BEFORE snapshotting transport/folder, so a toggle immediately followed by
+    /// Send can never race ahead of the reconcile it depends on (the watcher's
+    /// recordUncommented flag briefly lagging the just-chosen transport, for example).
+    /// `Task<Void, Never>` never throws; awaiting an already-completed task's `.value`
+    /// returns immediately. Not `@Observable`-relevant — pure internal bookkeeping.
+    var pendingReconcileTask: Task<Void, Never>?
     func rememberLastComposedPDF(_ url: URL) { lastComposedPDFURL = url }
 
     /// True when a last-composed PDF path is known this run, or the newest
@@ -241,19 +249,29 @@ public final class AppModel {
             setStatus((error as? ShotdeckError)?.errorDescription ?? "Could not watch the return folder.")
         }
 
-        let pref = HotkeyPreference.load()
-        captureHotkey = pref
-        if !bindCaptureHotkey(pref) {
-            setStatus("\(pref.displayString) is already used by another app — capture only works from the menu.")
-        }
-
-        let skipSchedule =
+        // Env-var-flagged self-test/headless runs (PickerSelfTest's phases, PanelSnapshot,
+        // and the new ShotdeckTests launch-wiring regression test) skip two real-world
+        // side effects that are unsafe or meaningless in that context: the update-check
+        // schedule (a real network call), and binding the REAL, process-wide Carbon
+        // global hotkey — which is not safe to exercise in an automated/parallel test
+        // process (it can collide with ShotdeckCoreTests' own HotkeyCenterCarbonTests
+        // running in the same test binary) and was never meaningfully exercised by any
+        // self-test anyway. A real user launch never sets these env vars, so production
+        // behavior is unchanged.
+        let isSelfTestRun =
             ProcessInfo.processInfo.environment["SHOTDECK_PICKER_SELFTEST"] != nil
             || ProcessInfo.processInfo.environment["SHOTDECK_SNAPSHOT_DIR"] != nil
             || ProcessInfo.processInfo.environment["SHOTDECK_UPDATE_SELFTEST"] != nil
             || ProcessInfo.processInfo.environment["SHOTDECK_ONEDRIVE_SELFTEST"] != nil
             || ProcessInfo.processInfo.environment["REDLINE_SELFTEST_PHASE"] != nil
-        if !skipSchedule {
+
+        let pref = HotkeyPreference.load()
+        captureHotkey = pref
+        if !isSelfTestRun, !bindCaptureHotkey(pref) {
+            setStatus("\(pref.displayString) is already used by another app — capture only works from the menu.")
+        }
+
+        if !isSelfTestRun {
             updateChecker.startSchedule()
         }
     }

Sources/Shotdeck/SettingsView.swift

@@ -255,6 +255,9 @@ extension AppModel: SettingsWindowPresenting {
     /// the live value before every mutating step, so rapid toggling (this function or
     /// chooseOneDriveFolder, in any order) always lets the LAST choice win instead of an
     /// earlier, superseded call applying its stale folder/flag after a later one already won.
+    /// The Task's handle is stored in `pendingReconcileTask` so send() can await its
+    /// completion before snapshotting transport/folder — closing the OTHER race, where a
+    /// toggle is immediately followed by Send before this reconcile has settled.
     func chooseTransport(_ value: SendTransport) {
         guard !isSending else {
             setStatus("Finish the current send first.")
@@ -274,7 +277,7 @@ extension AppModel: SettingsWindowPresenting {
 
         reconcileGeneration += 1
         let generation = reconcileGeneration
-        Task {
+        pendingReconcileTask = Task {
             guard generation == self.reconcileGeneration else { return }
             await watcher.setRecordUncommented(value == .airDrop)
             guard generation == self.reconcileGeneration else { return }
@@ -306,7 +309,7 @@ extension AppModel: SettingsWindowPresenting {
 
         reconcileGeneration += 1
         let generation = reconcileGeneration
-        Task {
+        pendingReconcileTask = Task {
             guard generation == self.reconcileGeneration else { return }
             do {
                 try await watcher.updateWatchFolder(url)