Tests/ShotdeckCoreTests/ReturnWatcherTests.swift

@@ -282,3 +282,110 @@ func recordUncommentedFalseSkipsUnmarkedThenRecordsAfterInPlaceMarkup() async th
     #expect(commented.count == 1)
     #expect(commented.first?.fileURL.resolvingSymlinksInPath().path == pdfURL.resolvingSymlinksInPath().path)
 }
+
+// MARK: - Launch-paths BLOCKER regression (adversarial review, 20260905)
+//
+// The bug: AppDelegate.makeLaunchModel() built `paths` via the AirDrop-only
+// FolderSettings.resolvedAppSupportPaths(), so ReturnWatcher's internal watchFolder
+// (seeded from paths.watchFolder in its own init) was the AirDrop folder even when
+// OneDrive was the persisted transport, and bootstrap() never reconciled it before
+// starting. Net effect: PDFs went to OneDrive but FSEvents kept watching the stale
+// AirDrop folder for the whole session — marked-up returns were never detected.
+// The fix: launch paths now come from TransportSettings.resolvedAppSupportPaths()
+// (transport-aware), and AppModel.bootstrap() unconditionally reconciles the watcher's
+// folder via updateWatchFolder() before it starts. These two tests characterize the
+// bug (still reproducible via the old AirDrop-only construction) and prove the fix
+// (the real launch-construction path, end to end).
+
+@Test("Launch regression (fix): OneDrive persisted -> transport-aware launch paths -> bootstrap-style reconcile -> a marked PDF is detected")
+func launchStyleConstructionWithOneDriveTransportDetectsAMarkedReturn() async throws {
+    let suite = try makeTransportDefaultsSuite()
+    defer { tearDownTransportSuite(suite) }
+    let oneDriveFolder = try makeTransportTemporaryDirectory(prefix: "shotdeck-launch-onedrive")
+    defer { try? FileManager.default.removeItem(at: oneDriveFolder) }
+    let appSupportRoot = try makeTransportTemporaryDirectory(prefix: "shotdeck-launch-approot")
+    defer { try? FileManager.default.removeItem(at: appSupportRoot) }
+
+    TransportSettings.setTransport(.oneDrive, defaults: suite.defaults)
+    TransportSettings.setOneDriveFolder(oneDriveFolder, defaults: suite.defaults)
+
+    // Exactly what AppDelegate.makeLaunchModel() now does: build launch paths from the
+    // transport-aware resolver — the fix, NOT FolderSettings.resolvedAppSupportPaths(),
+    // which is AirDrop-only and is the root cause the next test characterizes.
+    let paths = try TransportSettings.resolvedAppSupportPaths(
+        root: appSupportRoot, defaults: suite.defaults, fileManager: .default
+    )
+    #expect(paths.outbox.path == oneDriveFolder.path)
+    #expect(paths.watchFolder.path == oneDriveFolder.path)
+
+    let ledger = try ReturnLedger(paths: paths)
+    let watcher = ReturnWatcher(paths: paths, ledger: ledger)
+
+    // What AppModel.bootstrap() now does, unconditionally, before watcher.start():
+    await watcher.setRecordUncommented(false)   // transport == .oneDrive
+    try await watcher.updateWatchFolder(paths.watchFolder)
+
+    let pdfURL = oneDriveFolder.appendingPathComponent("Redline-20260905-100000.pdf")
+    try makePDF(
+        at: pdfURL, pageCount: 1, creator: "Redline",
+        annotations: [(page: 0, annotation: makeAnnotation(
+            .ink, bounds: CGRect(x: 100, y: 100, width: 120, height: 50)
+        ))]
+    )
+
+    let found = try await watcher.scanNow()
+    #expect(found.contains(where: {
+        $0.fileURL.resolvingSymlinksInPath().path == pdfURL.resolvingSymlinksInPath().path && $0.isCommented
+    }))
+
+    let commented = try await ledger.commented()
+    #expect(commented.contains(where: {
+        $0.fileURL.resolvingSymlinksInPath().path == pdfURL.resolvingSymlinksInPath().path
+    }))
+}
+
+@Test("Launch regression (characterizes the bug): AirDrop-only launch paths with no reconcile miss an OneDrive-mode return")
+func airDropOnlyLaunchPathsWithoutReconcileMissesAMarkedOneDriveReturn() async throws {
+    let suite = try makeTransportDefaultsSuite()
+    defer { tearDownTransportSuite(suite) }
+    let oneDriveFolder = try makeTransportTemporaryDirectory(prefix: "shotdeck-buggy-onedrive")
+    defer { try? FileManager.default.removeItem(at: oneDriveFolder) }
+    // A configured AirDrop watch-folder override, isolated to a temp dir — NOT the real
+    // ~/Downloads, which may already hold real marked-up Redline PDFs from actual use
+    // and would make this test's "found.isEmpty" assertion depend on the state of
+    // Ben's real Downloads folder instead of the isolated fixture under test.
+    let staleAirDropFolder = try makeTransportTemporaryDirectory(prefix: "shotdeck-buggy-airdrop-stale")
+    defer { try? FileManager.default.removeItem(at: staleAirDropFolder) }
+    let appSupportRoot = try makeTransportTemporaryDirectory(prefix: "shotdeck-buggy-approot")
+    defer { try? FileManager.default.removeItem(at: appSupportRoot) }
+
+    TransportSettings.setTransport(.oneDrive, defaults: suite.defaults)
+    TransportSettings.setOneDriveFolder(oneDriveFolder, defaults: suite.defaults)
+    FolderSettings.setWatchFolder(staleAirDropFolder, defaults: suite.defaults)
+
+    // The BUG's exact construction: FolderSettings.resolvedAppSupportPaths() ignores
+    // the persisted transport entirely and always resolves the AirDrop folders.
+    let buggyPaths = try FolderSettings.resolvedAppSupportPaths(root: appSupportRoot, defaults: suite.defaults)
+    #expect(buggyPaths.watchFolder.path == staleAirDropFolder.path)
+    #expect(buggyPaths.watchFolder.path != oneDriveFolder.path)
+
+    let ledger = try ReturnLedger(paths: buggyPaths)
+    let watcher = ReturnWatcher(paths: buggyPaths, ledger: ledger)
+    // The old bootstrap(): recordUncommented was set, but there was NO
+    // updateWatchFolder() call before start() to reconcile the folder.
+    await watcher.setRecordUncommented(false)
+
+    let pdfURL = oneDriveFolder.appendingPathComponent("Redline-20260905-100100.pdf")
+    try makePDF(
+        at: pdfURL, pageCount: 1, creator: "Redline",
+        annotations: [(page: 0, annotation: makeAnnotation(
+            .ink, bounds: CGRect(x: 100, y: 100, width: 120, height: 50)
+        ))]
+    )
+
+    // The watcher is still pointed at the stale (configured-AirDrop) watch folder, so
+    // scanning it — NOT the OneDrive folder the PDF actually landed in — finds nothing.
+    // This is the exact BLOCKER the fix above closes.
+    let found = try await watcher.scanNow()
+    #expect(found.isEmpty)
+}

Tests/ShotdeckCoreTests/TransportSettingsTests.swift

@@ -90,6 +90,38 @@ func oneDriveFolderUnavailableErrorDescriptionContainsThePath() throws {
     #expect(description.contains(path))
 }
 
+@Test
+func isWritableDirectoryTrueForAnOrdinaryWritableDirectory() throws {
+    let dir = try makeTransportTemporaryDirectory(prefix: "shotdeck-writable")
+    defer { try? FileManager.default.removeItem(at: dir) }
+    #expect(OneDriveLocator.isWritableDirectory(at: dir))
+}
+
+@Test
+func isWritableDirectoryFalseForAnExistingButUnwritableDirectory() throws {
+    let dir = try makeTransportTemporaryDirectory(prefix: "shotdeck-unwritable")
+    defer {
+        // Restore perms BEFORE removal — an unwritable dir can't otherwise be cleaned up.
+        try? FileManager.default.setAttributes([.posixPermissions: 0o755], ofItemAtPath: dir.path)
+        try? FileManager.default.removeItem(at: dir)
+    }
+    #expect(OneDriveLocator.isWritableDirectory(at: dir))   // sanity check before chmod
+
+    try FileManager.default.setAttributes([.posixPermissions: 0o500], ofItemAtPath: dir.path)
+    #expect(!OneDriveLocator.isWritableDirectory(at: dir))
+}
+
+@Test
+func isWritableDirectoryFalseForAPlainFileAndForANonexistentPath() throws {
+    let dir = try makeTransportTemporaryDirectory(prefix: "shotdeck-writable-check-parent")
+    defer { try? FileManager.default.removeItem(at: dir) }
+    let filePath = dir.appendingPathComponent("plain-file.txt")
+    FileManager.default.createFile(atPath: filePath.path, contents: Data("x".utf8))
+
+    #expect(!OneDriveLocator.isWritableDirectory(at: filePath))
+    #expect(!OneDriveLocator.isWritableDirectory(at: dir.appendingPathComponent("does-not-exist")))
+}
+
 struct TransportDefaultsSuite {
     let name: String
     let defaults: UserDefaults