release: v0.2.0

# Conflicts:
#	Sources/Shotdeck/PickerSelfTest.swift

Info.plist

@@ -2,28 +2,24 @@
 <!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
 <plist version="1.0">
 <dict>
-	<!-- Identity invariants: CFBundleIdentifier stays ai.flowmaster.shotdeck and
-	     CFBundleExecutable stays Shotdeck. Changing either one invalidates the
-	     user's existing Screen Recording grant. CFBundleName is the user-facing
-	     product name only. -->
+	<key>CFBundleExecutable</key>
+	<string>Shotdeck</string>
+	<key>CFBundleIconFile</key>
+	<string>AppIcon</string>
 	<key>CFBundleIdentifier</key>
 	<string>ai.flowmaster.shotdeck</string>
 	<key>CFBundleName</key>
 	<string>Redline</string>
-	<key>CFBundleExecutable</key>
-	<string>Shotdeck</string>
 	<key>CFBundlePackageType</key>
 	<string>APPL</string>
 	<key>CFBundleShortVersionString</key>
-	<string>0.1.0</string>
+	<string>0.2.0</string>
 	<key>CFBundleVersion</key>
-	<string>1</string>
-	<key>CFBundleIconFile</key>
-	<string>AppIcon</string>
-	<key>LSUIElement</key>
-	<true/>
+	<string>2</string>
 	<key>LSMinimumSystemVersion</key>
 	<string>14.0</string>
+	<key>LSUIElement</key>
+	<true/>
 	<key>NSHumanReadableCopyright</key>
 	<string>Copyright © 2026 Flowmaster FZC LLC. All rights reserved.</string>
 </dict>

Sources/Shotdeck/AppModel.swift

@@ -36,9 +36,13 @@ public final class AppModel {
     public private(set) var outboxURL: URL
     /// Live watch folder; WP-4c updates this alongside `ReturnWatcher.updateWatchFolder`.
     public private(set) var watchFolderURL: URL
+    /// Absolute URL of the PDF composed this run, if any. Used by "Reveal last PDF".
+    public private(set) var lastComposedPDFURL: URL?
     /// Currently bound capture combo (the last one Carbon accepted, or the preferred load).
     private(set) var captureHotkey: HotkeyPreference
     var hotkeyDisplayString: String { captureHotkey.displayString }
+    /// Staged update offered in the menu. Set only after checksum + payload validation.
+    public private(set) var updateAvailable: (version: String, notes: String)?
 
     let paths: AppSupportPaths
     let spool: SpoolStore
@@ -48,6 +52,7 @@ public final class AppModel {
     let picker: RegionPickerController
     let ledger: ReturnLedger
     let watcher: ReturnWatcher
+    let updateChecker: UpdateChecker
 
     public init(
         paths: AppSupportPaths,
@@ -83,6 +88,14 @@ public final class AppModel {
         self.outboxDisplayName = folders.outbox.lastPathComponent
         self.watchFolderDisplayName = folders.watch.lastPathComponent
         self.captureHotkey = HotkeyPreference.load()
+        self.updateChecker = UpdateChecker()
+        self.updateChecker.onChecked = { [weak self] in
+            guard let self else { return }
+            self.updateAvailable = self.updateChecker.availableUpdate
+            if let message = self.updateChecker.statusMessage {
+                self.setStatus(message)
+            }
+        }
     }
 
     // MARK: Seam mutators — the only way a WP-4b/4c extension changes state.
@@ -105,6 +118,42 @@ public final class AppModel {
         watchFolderURL = watch
         setFolderDisplayNames(outbox: outbox.lastPathComponent, watch: watch.lastPathComponent)
     }
+    func rememberLastComposedPDF(_ url: URL) { lastComposedPDFURL = url }
+
+    /// True when a last-composed PDF path is known this run, or the newest
+    /// `Redline-*.pdf` in the outbox exists on disk.
+    var canRevealLastPDF: Bool { revealablePDFURL() != nil }
+
+    public func revealLastPDF() {
+        guard let url = revealablePDFURL() else { return }
+        NSWorkspace.shared.activateFileViewerSelecting([url])
+    }
+
+    func revealablePDFURL() -> URL? {
+        if let last = lastComposedPDFURL, FileManager.default.fileExists(atPath: last.path) {
+            return last
+        }
+        return newestOutboxRedlinePDF()
+    }
+
+    func newestOutboxRedlinePDF() -> URL? {
+        let fm = FileManager.default
+        let items = (try? fm.contentsOfDirectory(
+            at: outboxURL,
+            includingPropertiesForKeys: [.contentModificationDateKey],
+            options: [.skipsHiddenFiles]
+        )) ?? []
+        let matches = items.filter {
+            $0.lastPathComponent.hasPrefix("Redline-") && $0.pathExtension.lowercased() == "pdf"
+        }
+        return matches.max { a, b in
+            let da = (try? a.resourceValues(forKeys: [.contentModificationDateKey])
+                .contentModificationDate) ?? .distantPast
+            let db = (try? b.resourceValues(forKeys: [.contentModificationDateKey])
+                .contentModificationDate) ?? .distantPast
+            return da < db
+        }
+    }
 
     public var iconState: MenuIconState {
         if !screenRecordingGranted { return .recordingMissing }
@@ -154,6 +203,20 @@ public final class AppModel {
         if !bindCaptureHotkey(pref) {
             setStatus("\(pref.displayString) is already used by another app — capture only works from the menu.")
         }
+
+        let skipSchedule =
+            ProcessInfo.processInfo.environment["SHOTDECK_PICKER_SELFTEST"] != nil
+            || ProcessInfo.processInfo.environment["SHOTDECK_SNAPSHOT_DIR"] != nil
+            || ProcessInfo.processInfo.environment["SHOTDECK_UPDATE_SELFTEST"] != nil
+        if !skipSchedule {
+            updateChecker.startSchedule()
+        }
+    }
+
+    /// Installs the staged update over `/Applications/Redline.app` and relaunches.
+    /// Does nothing unless the user clicked the menu row.
+    public func installUpdate() {
+        updateChecker.installStaged()
     }
 
     /// Unregisters `capture` and binds `HotkeyPreference.load()`. If Carbon rejects the new

Sources/Shotdeck/MenuBarView.swift

@@ -74,6 +74,15 @@ struct MenuBarView: View {
 
     private var actionsList: some View {
         VStack(alignment: .leading, spacing: 2) {
+            if let update = model.updateAvailable {
+                Button {
+                    model.installUpdate()
+                } label: {
+                    actionLabel("Update to \(update.version)")
+                        .foregroundStyle(Color.accentColor)
+                }
+            }
+
             Button {
                 let anchor = NSApp.keyWindow?.contentView
                 if let sender = model as? SendCapable {
@@ -86,6 +95,13 @@ struct MenuBarView: View {
             }
             .disabled(model.session.isEmpty || model.isSending)
 
+            Button {
+                model.revealLastPDF()
+            } label: {
+                actionLabel("Reveal last PDF")
+            }
+            .disabled(!model.canRevealLastPDF)
+
             Button {
                 Task { await model.captureNow() }
             } label: {

Sources/Shotdeck/PickerSelfTest.swift

@@ -1,6 +1,8 @@
 import AppKit
+import CoreGraphics
 import Darwin
 import Foundation
+import ImageIO
 import ShotdeckCore
 
 /// In-process self-test for the region picker, driven by `SHOTDECK_PICKER_SELFTEST`.
@@ -113,7 +115,10 @@ enum PickerSelfTest {
         fflush(stdout)
 
         runRegionPersistPhase()
-        exit(0)
+        // Hop off this MainActor job so the SEND-TRUTH Task can run; do not
+        // exit(0) here — runSendTruthPhase prints its own PASS/FAIL, then
+        // chains to UPDATE-SELFTEST (or exits if that phase is not requested).
+        runSendTruthPhase()
     }
 
     /// Phase 2: writes a known region under `CaptureRegion.defaultsKey`, reloads it through
@@ -157,6 +162,317 @@ enum PickerSelfTest {
         fflush(stdout)
     }
 
+    /// Phase 3: drive SendController's share-outcome seams with no AirDrop sheet.
+    /// Fail path must leave the session open in the temp spool; success path archives
+    /// and mints a fresh empty session. Scheduled as a new MainActor job because this
+    /// function is called from inside `execute()` — a nested run-loop wait would never
+    /// let the Task start. On success, chains to UPDATE-SELFTEST instead of exiting.
+    private static func runSendTruthPhase() {
+        Task { @MainActor in
+            do {
+                try await executeSendTruth()
+                print("SEND-TRUTH PASS")
+                fflush(stdout)
+                if !startUpdateSelfTestIfRequested() {
+                    exit(0)
+                }
+            } catch {
+                print("SEND-TRUTH FAIL \(error)")
+                fflush(stdout)
+                exit(1)
+            }
+        }
+    }
+
+    private static func executeSendTruth() async throws {
+        let fm = FileManager.default
+        let root = fm.temporaryDirectory
+            .appendingPathComponent("shotdeck-send-truth-\(UUID().uuidString)", isDirectory: true)
+        defer { try? fm.removeItem(at: root) }
+
+        let paths = try AppSupportPaths(
+            root: root,
+            outbox: root.appendingPathComponent("outbox", isDirectory: true),
+            watchFolder: root.appendingPathComponent("watch", isDirectory: true)
+        )
+        let ledger = try ReturnLedger(paths: paths)
+        let model = AppModel(
+            paths: paths,
+            spool: try SpoolStore(paths: paths),
+            composer: PDFComposer(),
+            capturer: ScreenCapturer(),
+            hotkeys: HotkeyCenter(),
+            picker: RegionPickerController(),
+            ledger: ledger,
+            watcher: ReturnWatcher(paths: paths, ledger: ledger)
+        )
+        model.setFolderURLs(outbox: paths.outbox, watch: paths.watchFolder)
+
+        let png = try makeTinyPNGData()
+        _ = try await model.spool.append(
+            pngData: png,
+            pixelWidth: 64,
+            pixelHeight: 48,
+            scale: 1,
+            capturedAt: Date()
+        )
+        model.replaceSession(try await model.spool.currentSession())
+        let openID = model.session.id
+        guard !model.session.isEmpty else {
+            sendTruthFail("seeded session was empty")
+        }
+
+        let pending = try await model.composePDFForSend()
+        guard fm.fileExists(atPath: pending.fileURL.path) else {
+            sendTruthFail("PDF was not written")
+        }
+
+        model.handleDidFailToShareItems(fileName: pending.fileName)
+        let still = try await model.spool.currentSession()
+        guard still.id == openID, !still.isEmpty, still.state == .open else {
+            sendTruthFail("fail path archived or replaced the session")
+        }
+        let spoolDir = paths.sessionDirectory(openID)
+        guard fm.fileExists(atPath: spoolDir.path) else {
+            sendTruthFail("fail path: session missing from temp spool")
+        }
+        guard let status = model.statusLine, status.contains("nothing was sent") else {
+            sendTruthFail("fail path status missing 'nothing was sent': \(model.statusLine ?? "nil")")
+        }
+
+        await model.handleDidShareItems(fileName: pending.fileName, pageCount: pending.pageCount)
+        let fresh = try await model.spool.currentSession()
+        guard fresh.isEmpty, fresh.id != openID, fresh.state == .open else {
+            sendTruthFail("success path did not mint a fresh empty session")
+        }
+        let archived = try await model.spool.archivedSessions()
+        guard archived.contains(where: { $0.id == openID && $0.state == .archived }) else {
+            sendTruthFail("success path did not archive the session")
+        }
+        let archiveDir = paths.archiveDirectory(openID)
+        guard fm.fileExists(atPath: archiveDir.path) else {
+            sendTruthFail("success path: archive dir missing")
+        }
+        guard !fm.fileExists(atPath: spoolDir.path) else {
+            sendTruthFail("success path: session still in spool")
+        }
+    }
+
+    private static func makeTinyPNGData() throws -> Data {
+        let width = 64
+        let height = 48
+        let colorSpace = CGColorSpaceCreateDeviceRGB()
+        guard let context = CGContext(
+            data: nil,
+            width: width,
+            height: height,
+            bitsPerComponent: 8,
+            bytesPerRow: width * 4,
+            space: colorSpace,
+            bitmapInfo: CGImageAlphaInfo.premultipliedLast.rawValue
+        ) else {
+            sendTruthFail("could not create PNG context")
+        }
+        context.setFillColor(red: 0.2, green: 0.4, blue: 0.8, alpha: 1)
+        context.fill(CGRect(x: 0, y: 0, width: width, height: height))
+        guard let image = context.makeImage() else {
+            sendTruthFail("could not make CGImage")
+        }
+        let buffer = NSMutableData()
+        guard let destination = CGImageDestinationCreateWithData(
+            buffer,
+            "public.png" as CFString,
+            1,
+            nil
+        ) else {
+            sendTruthFail("could not create PNG destination")
+        }
+        CGImageDestinationAddImage(destination, image, nil)
+        guard CGImageDestinationFinalize(destination) else {
+            sendTruthFail("could not finalize PNG")
+        }
+        return buffer as Data
+    }
+
+    private static func sendTruthFail(_ reason: String) -> Never {
+        print("SEND-TRUTH FAIL \(reason)")
+        fflush(stdout)
+        exit(1)
+    }
+
+    /// Phase 4: builds a fake 99.0.0 bundle, serves a local appcast, stages via
+    /// `checkNow`, then `installStaged` into the env dir — never `/Applications`.
+    /// Returns true when the async phase was scheduled (it calls `exit` itself).
+    @discardableResult
+    private static func startUpdateSelfTestIfRequested() -> Bool {
+        guard let raw = ProcessInfo.processInfo.environment["SHOTDECK_UPDATE_SELFTEST"],
+              !raw.isEmpty
+        else { return false }
+
+        let output = URL(fileURLWithPath: raw, isDirectory: true)
+        Task { @MainActor in
+            do {
+                try await runUpdateSelfTest(outputDirectory: output)
+                print("UPDATE-SELFTEST PASS version=99.0.0")
+                fflush(stdout)
+                exit(0)
+            } catch let error as UpdateSelfTestError {
+                updateFail(error.description)
+            } catch {
+                updateFail(String(describing: error))
+            }
+        }
+        return true
+    }
+
+    private static func runUpdateSelfTest(outputDirectory: URL) async throws {
+        let fm = FileManager.default
+        try fm.createDirectory(at: outputDirectory, withIntermediateDirectories: true)
+
+        guard let sourceApp = ownAppBundleURL() else {
+            throw UpdateSelfTestError.detail("own bundle is not a .app (\(Bundle.main.bundleURL.path))")
+        }
+
+        let payload = outputDirectory.appendingPathComponent("payload", isDirectory: true)
+        if fm.fileExists(atPath: payload.path) {
+            try fm.removeItem(at: payload)
+        }
+        try fm.createDirectory(at: payload, withIntermediateDirectories: true)
+        let fakeApp = payload.appendingPathComponent("Redline.app")
+        try fm.copyItem(at: sourceApp, to: fakeApp)
+
+        let plistURL = fakeApp.appendingPathComponent("Contents/Info.plist")
+        let plistData = try Data(contentsOf: plistURL)
+        guard var plist = try PropertyListSerialization.propertyList(from: plistData, format: nil) as? [String: Any] else {
+            throw UpdateSelfTestError.detail("could not parse copied Info.plist")
+        }
+        plist["CFBundleShortVersionString"] = "99.0.0"
+        let rewritten = try PropertyListSerialization.data(fromPropertyList: plist, format: .xml, options: 0)
+        try rewritten.write(to: plistURL)
+
+        let zipURL = outputDirectory.appendingPathComponent("Redline-99.0.0.zip")
+        if fm.fileExists(atPath: zipURL.path) {
+            try fm.removeItem(at: zipURL)
+        }
+        try runDitto(arguments: ["-c", "-k", payload.path, zipURL.path])
+
+        let zipData = try Data(contentsOf: zipURL)
+        let hex = UpdateChecker.sha256Hex(zipData)
+
+        let appcastURL = outputDirectory.appendingPathComponent("appcast.json")
+        let appcast: [String: String] = [
+            "version": "99.0.0",
+            "zipURL": zipURL.absoluteString,
+            "sha256": hex,
+            "notes": "UPDATE-SELFTEST",
+        ]
+        let appcastData = try JSONSerialization.data(withJSONObject: appcast, options: [.sortedKeys])
+        try appcastData.write(to: appcastURL)
+
+        let defaults = UserDefaults.standard
+        let previous = defaults.string(forKey: UpdateChecker.appcastURLDefaultsKey)
+        defaults.set(appcastURL.absoluteString, forKey: UpdateChecker.appcastURLDefaultsKey)
+        defer {
+            if let previous {
+                defaults.set(previous, forKey: UpdateChecker.appcastURLDefaultsKey)
+            } else {
+                defaults.removeObject(forKey: UpdateChecker.appcastURLDefaultsKey)
+            }
+        }
+
+        let (model, isolatedRoot) = try makeIsolatedUpdateModel()
+        defer { try? fm.removeItem(at: isolatedRoot) }
+
+        await model.updateChecker.checkNow()
+
+        guard model.updateAvailable?.version == "99.0.0" else {
+            throw UpdateSelfTestError.detail(
+                "updateAvailable=\(model.updateAvailable?.version ?? "nil")"
+            )
+        }
+        guard let staged = model.updateChecker.stagedAppURL else {
+            throw UpdateSelfTestError.detail("staged payload missing")
+        }
+        guard staged.lastPathComponent == "Redline.app" else {
+            throw UpdateSelfTestError.detail("staged name \(staged.lastPathComponent)")
+        }
+        let stagedExe = staged.appendingPathComponent("Contents/MacOS/Shotdeck")
+        guard fm.fileExists(atPath: stagedExe.path) else {
+            throw UpdateSelfTestError.detail("staged Contents/MacOS/Shotdeck missing")
+        }
+
+        let targetRoot = outputDirectory.appendingPathComponent("target", isDirectory: true)
+        if fm.fileExists(atPath: targetRoot.path) {
+            try fm.removeItem(at: targetRoot)
+        }
+        let target = targetRoot.appendingPathComponent("Redline.app")
+        model.updateChecker.installStaged(to: target)
+
+        let installedPlist = target.appendingPathComponent("Contents/Info.plist")
+        guard let installed = NSDictionary(contentsOf: installedPlist) as? [String: Any],
+              let installedVersion = installed["CFBundleShortVersionString"] as? String
+        else {
+            throw UpdateSelfTestError.detail("installed Info.plist unreadable")
+        }
+        guard installedVersion == "99.0.0" else {
+            throw UpdateSelfTestError.detail("installed version \(installedVersion)")
+        }
+    }
+
+    private static func ownAppBundleURL() -> URL? {
+        let bundle = Bundle.main.bundleURL
+        if bundle.pathExtension == "app" { return bundle }
+        let up3 = bundle
+            .deletingLastPathComponent()
+            .deletingLastPathComponent()
+            .deletingLastPathComponent()
+        if up3.pathExtension == "app" { return up3 }
+        return nil
+    }
+
+    private static func makeIsolatedUpdateModel() throws -> (AppModel, URL) {
+        let root = FileManager.default.temporaryDirectory
+            .appendingPathComponent("shotdeck-update-selftest-\(UUID().uuidString)", isDirectory: true)
+        let paths = try AppSupportPaths(
+            root: root,
+            outbox: root.appendingPathComponent("outbox", isDirectory: true),
+            watchFolder: root.appendingPathComponent("watch", isDirectory: true)
+        )
+        let ledger = try ReturnLedger(paths: paths)
+        let model = AppModel(
+            paths: paths,
+            spool: try SpoolStore(paths: paths),
+            composer: PDFComposer(),
+            capturer: ScreenCapturer(),
+            hotkeys: HotkeyCenter(),
+            picker: RegionPickerController(),
+            ledger: ledger,
+            watcher: ReturnWatcher(paths: paths, ledger: ledger)
+        )
+        return (model, root)
+    }
+
+    private static func runDitto(arguments: [String]) throws {
+        let process = Process()
+        process.executableURL = URL(fileURLWithPath: "/usr/bin/ditto")
+        process.arguments = arguments
+        let err = Pipe()
+        process.standardError = err
+        process.standardOutput = Pipe()
+        try process.run()
+        process.waitUntilExit()
+        guard process.terminationStatus == 0 else {
+            let message = String(data: err.fileHandleForReading.readDataToEndOfFile(), encoding: .utf8) ?? ""
+            throw UpdateSelfTestError.detail("ditto failed: \(message)")
+        }
+    }
+
+    private static func updateFail(_ detail: String) -> Never {
+        print("UPDATE-SELFTEST FAIL \(detail)")
+        fflush(stdout)
+        exit(1)
+    }
+
     private static func interpolate(_ step: Int) -> NSPoint {
         let t = CGFloat(step) / CGFloat(dragSteps)
         return NSPoint(
@@ -213,3 +529,12 @@ enum PickerSelfTest {
         exit(1)
     }
 }
+
+private enum UpdateSelfTestError: Error, CustomStringConvertible {
+    case detail(String)
+    var description: String {
+        switch self {
+        case .detail(let s): return s
+        }
+    }
+}

Sources/Shotdeck/SendController.swift

@@ -3,12 +3,59 @@ import Darwin
 import Foundation
 import ShotdeckCore
 
+/// Result of composing a send PDF. Kept so the self-test can drive the share
+/// outcome without presenting a real AirDrop sheet.
+struct ComposedSend: Sendable {
+    let fileName: String
+    let fileURL: URL
+    let pageCount: Int
+}
+
 extension AppModel: SendCapable {
     public func send(anchor: NSView?) async {
         guard !session.isEmpty, !isSending else { return }
         setSending(true)
-        defer { setSending(false) }
 
+        let pending: ComposedSend
+        do {
+            pending = try await composePDFForSend()
+        } catch {
+            // Never unlink the published PDF, and never unlink the temp file either:
+            // a rename failure would leave the complete document at the temp name.
+            setStatus((error as? ShotdeckError)?.errorDescription ?? "The PDF could not be built.")
+            setSending(false)
+            return
+        }
+
+        guard let anchor else {
+            handleDidFailToShareItems(fileName: pending.fileName)
+            setSending(false)
+            return
+        }
+
+        do {
+            try Sharing.airDrop(fileURL: pending.fileURL, from: anchor) { [weak self] success in
+                guard let self else { return }
+                if success {
+                    await self.handleDidShareItems(
+                        fileName: pending.fileName,
+                        pageCount: pending.pageCount
+                    )
+                } else {
+                    self.handleDidFailToShareItems(fileName: pending.fileName)
+                }
+                self.setSending(false)
+            }
+        } catch {
+            // canPerform false, no service, or no visible window: same as cancel.
+            handleDidFailToShareItems(fileName: pending.fileName)
+            setSending(false)
+        }
+    }
+
+    /// Writes the PDF to the outbox and records its path. Does not archive the session
+    /// and does not present AirDrop — that happens only after the share completes.
+    func composePDFForSend() async throws -> ComposedSend {
         let workingSession = session
         let composer = self.composer
         // Live outbox (FolderSettings), not `paths.outbox` — Settings changes take effect.
@@ -20,7 +67,6 @@ extension AppModel: SendCapable {
         let tempURL = outboxDir.appendingPathComponent(".shotdeck-\(UUID().uuidString).pdf")
         let title = "Redline – \(DubaiTime.stamp(workingSession.createdAt))"
 
-        do {
         // D-13: build off the main actor. Only Sendable values cross into the
         // detached task — never `anchor` (NSView is not Sendable).
         try await Task.detached(priority: .userInitiated) {
@@ -40,32 +86,35 @@ extension AppModel: SendCapable {
             try AtomicFile.fsyncDirectory(at: outboxDir)
         }.value
 
-            // File exists on disk now — archive only after that (D-13). A later AirDrop
-            // failure never deletes this file.
         guard FileManager.default.fileExists(atPath: finalURL.path) else {
             throw ShotdeckError.pdfCompositionFailed(reason: "the PDF was not written to disk")
         }
-            _ = try await spool.archiveCurrent(pdfFileName: fileName)
-            replaceSession(try await spool.currentSession())
-
-            let pageWord = workingSession.captures.count == 1 ? "page" : "pages"
-            setStatus("Sent — \(workingSession.captures.count) \(pageWord).")
-
-            guard let anchor else {
-                setStatus("PDF saved to \(outboxDisplayName). Open the panel to AirDrop it.")
-                return
-            }
-            do {
-                try Sharing.airDrop(fileURL: finalURL, from: anchor)
-            } catch {
-                setStatus(
-                    "AirDrop is not available right now — the PDF is on your \(outboxDisplayName)."
+        rememberLastComposedPDF(finalURL)
+        return ComposedSend(
+            fileName: fileName,
+            fileURL: finalURL,
+            pageCount: workingSession.captures.count
         )
     }
+
+    /// `NSSharingServiceDelegate.sharingService(_:didShareItems:)` seam.
+    func handleDidShareItems(fileName: String, pageCount: Int) async {
+        guard !session.isEmpty else { return }
+        do {
+            _ = try await spool.archiveCurrent(pdfFileName: fileName)
+            replaceSession(try await spool.currentSession())
+            let pageWord = pageCount == 1 ? "page" : "pages"
+            setStatus("Sent — \(pageCount) \(pageWord).")
         } catch {
-            // Never unlink the published PDF, and never unlink `tempURL` either:
-            // a rename failure would leave the complete document at the temp name.
-            setStatus((error as? ShotdeckError)?.errorDescription ?? "The PDF could not be built.")
+            setStatus((error as? ShotdeckError)?.errorDescription ?? "Could not archive the session.")
         }
     }
+
+    /// `NSSharingServiceDelegate.sharingService(_:didFailToShareItems:error:)` seam,
+    /// also used when `canPerform` is false or the user cancels. Does not archive.
+    func handleDidFailToShareItems(fileName: String) {
+        setStatus(
+            "AirDrop didn't complete — nothing was sent. Your captures are still here; the PDF is on your \(outboxDisplayName) as \(fileName)."
+        )
+    }
 }

Sources/Shotdeck/Sharing.swift

@@ -7,7 +7,14 @@ enum Sharing {
     /// Throws `ShotdeckError.airDropUnavailable` when the service cannot be created,
     /// `canPerform` is false, or `view` is not in a visible window (a detached view
     /// never produces an on-screen sheet).
-    static func airDrop(fileURL: URL, from view: NSView) throws {
+    ///
+    /// `onFinished` is invoked on the main actor when the sheet completes: `true` for
+    /// `didShareItems`, `false` for `didFailToShareItems` (including user cancel).
+    static func airDrop(
+        fileURL: URL,
+        from view: NSView,
+        onFinished: @escaping @MainActor @Sendable (Bool) async -> Void
+    ) throws {
         guard let service = NSSharingService(named: .sendViaAirDrop),
               service.canPerform(withItems: [fileURL]) else {
             throw ShotdeckError.airDropUnavailable
@@ -21,7 +28,12 @@ enum Sharing {
         window.makeKeyAndOrderFront(nil)
 
         service.subject = fileURL.lastPathComponent
-        let session = AirDropSession(service: service, window: window, view: view)
+        let session = AirDropSession(
+            service: service,
+            window: window,
+            view: view,
+            onFinished: onFinished
+        )
         AirDropSession.keepAlive(session)
         service.delegate = session
         service.perform(withItems: [fileURL])
@@ -29,7 +41,9 @@ enum Sharing {
 }
 
 /// Retains the sharing service for the life of the picker and supplies the real
-/// on-screen window as the sheet parent. `NSSharingService.delegate` is weak.
+/// on-screen window as the sheet parent. `NSSharingService.delegate` is weak, so
+/// `live` is the strong reference that keeps this object alive until the sheet
+/// reports success or failure (including cancel).
 @MainActor
 private final class AirDropSession: NSObject, NSSharingServiceDelegate {
     static var live: [AirDropSession] = []
@@ -37,11 +51,19 @@ private final class AirDropSession: NSObject, NSSharingServiceDelegate {
     let service: NSSharingService
     let window: NSWindow
     let view: NSView
+    let onFinished: @MainActor @Sendable (Bool) async -> Void
+    private var reported = false
 
-    init(service: NSSharingService, window: NSWindow, view: NSView) {
+    init(
+        service: NSSharingService,
+        window: NSWindow,
+        view: NSView,
+        onFinished: @escaping @MainActor @Sendable (Bool) async -> Void
+    ) {
         self.service = service
         self.window = window
         self.view = view
+        self.onFinished = onFinished
     }
 
     static func keepAlive(_ session: AirDropSession) {
@@ -52,6 +74,15 @@ private final class AirDropSession: NSObject, NSSharingServiceDelegate {
         Self.live.removeAll { $0 === self }
     }
 
+    private func report(_ success: Bool) {
+        guard !reported else { return }
+        reported = true
+        Task { @MainActor in
+            await self.onFinished(success)
+            self.drop()
+        }
+    }
+
     func sharingService(
         _ sharingService: NSSharingService,
         sourceWindowForShareItems items: [Any],
@@ -70,7 +101,7 @@ private final class AirDropSession: NSObject, NSSharingServiceDelegate {
     }
 
     func sharingService(_ sharingService: NSSharingService, didShareItems items: [Any]) {
-        drop()
+        report(true)
     }
 
     func sharingService(
@@ -78,6 +109,6 @@ private final class AirDropSession: NSObject, NSSharingServiceDelegate {
         didFailToShareItems items: [Any],
         error: any Error
     ) {
-        drop()
+        report(false)
     }
 }

Sources/Shotdeck/UpdateChecker.swift

@@ -0,0 +1,281 @@
+import AppKit
+import CryptoKit
+import Foundation
+
+/// Built-in updater. Checks an appcast, stages a verified payload, and installs
+/// only when the user clicks the menu row — never automatically.
+@MainActor
+final class UpdateChecker {
+    static let appcastURLDefaultsKey = "ai.flowmaster.shotdeck.appcastURL"
+    static let defaultAppcastURL = URL(string: "https://get.baobab-ts.com/cowork/redline/appcast.json")!
+    static let defaultInstallTarget = URL(fileURLWithPath: "/Applications/Redline.app")
+
+    private(set) var availableUpdate: (version: String, notes: String)?
+    private(set) var stagedAppURL: URL?
+    private(set) var statusMessage: String?
+
+    var onChecked: (() -> Void)?
+
+    private let urlSession: URLSession
+    private var repeatingTimer: Timer?
+    private var firstCheckTask: Task<Void, Never>?
+    private var isChecking = false
+    private var stagingDirectory: URL?
+
+    init() {
+        let config = URLSessionConfiguration.ephemeral
+        config.timeoutIntervalForRequest = 15
+        config.timeoutIntervalForResource = 15
+        config.httpCookieAcceptPolicy = .never
+        config.httpShouldSetCookies = false
+        config.httpCookieStorage = nil
+        config.urlCache = nil
+        urlSession = URLSession(configuration: config)
+    }
+
+    /// First check 10 seconds after start, then every 6 hours. Stages only — never installs.
+    func startSchedule() {
+        firstCheckTask?.cancel()
+        firstCheckTask = Task { [weak self] in
+            try? await Task.sleep(for: .seconds(10))
+            guard !Task.isCancelled else { return }
+            await self?.checkNow()
+        }
+        repeatingTimer?.invalidate()
+        let timer = Timer(timeInterval: 6 * 60 * 60, repeats: true) { [weak self] _ in
+            Task { @MainActor in
+                await self?.checkNow()
+            }
+        }
+        RunLoop.main.add(timer, forMode: .common)
+        repeatingTimer = timer
+    }
+
+    func checkNow() async {
+        guard !isChecking else { return }
+        isChecking = true
+        defer { isChecking = false }
+
+        let appcast: Appcast
+        do {
+            appcast = try await fetchAppcast()
+        } catch {
+            statusMessage = "Could not check for updates."
+            onChecked?()
+            return
+        }
+
+        guard Self.isNewer(appcast.version, than: Self.currentVersion()) else {
+            clearOffer()
+            statusMessage = nil
+            onChecked?()
+            return
+        }
+
+        do {
+            try await downloadAndStage(appcast)
+            availableUpdate = (version: appcast.version, notes: appcast.notes ?? "")
+            statusMessage = nil
+        } catch UpdateCheckError.checksumMismatch {
+            discardStaging()
+            availableUpdate = nil
+            statusMessage = "Update file failed the checksum — not installed."
+        } catch {
+            discardStaging()
+            availableUpdate = nil
+            statusMessage = "The update could not be prepared."
+        }
+        onChecked?()
+    }
+
+    /// Copies the staged app onto `target` with ditto (in place; never deletes the old app).
+    /// Relaunches unless `SHOTDECK_UPDATE_SELFTEST` is set, so the in-process self-test
+    /// can assert the installed Info.plist without killing the process.
+    func installStaged(to target: URL = UpdateChecker.defaultInstallTarget) {
+        guard let staged = stagedAppURL else {
+            statusMessage = "No update is staged."
+            onChecked?()
+            return
+        }
+
+        do {
+            try FileManager.default.createDirectory(
+                at: target.deletingLastPathComponent(),
+                withIntermediateDirectories: true
+            )
+            try Self.runProcess(executable: "/usr/bin/ditto", arguments: [staged.path, target.path])
+        } catch {
+            statusMessage = "The update could not be installed."
+            onChecked?()
+            return
+        }
+
+        let isSelfTest = ProcessInfo.processInfo.environment["SHOTDECK_UPDATE_SELFTEST"] != nil
+        if isSelfTest { return }
+
+        do {
+            try Self.runProcess(executable: "/usr/bin/open", arguments: ["-n", target.path])
+        } catch {
+            statusMessage = "The update was installed but Redline could not relaunch. Open it from Applications."
+            onChecked?()
+            return
+        }
+        NSApp.terminate(nil)
+    }
+
+    static func resolvedAppcastURL() -> URL {
+        if let env = ProcessInfo.processInfo.environment["REDLINE_APPCAST_URL"],
+           !env.isEmpty,
+           let url = URL(string: env)
+        {
+            return url
+        }
+        if let stored = UserDefaults.standard.string(forKey: appcastURLDefaultsKey),
+           !stored.isEmpty,
+           let url = URL(string: stored)
+        {
+            return url
+        }
+        return defaultAppcastURL
+    }
+
+    static func currentVersion() -> String {
+        Bundle.main.object(forInfoDictionaryKey: "CFBundleShortVersionString") as? String ?? "0.0.0"
+    }
+
+    static func isNewer(_ candidate: String, than current: String) -> Bool {
+        let a = semverParts(candidate)
+        let b = semverParts(current)
+        for i in 0..<3 {
+            if a[i] != b[i] { return a[i] > b[i] }
+        }
+        return false
+    }
+
+    static func sha256Hex(_ data: Data) -> String {
+        SHA256.hash(data: data).map { String(format: "%02x", $0) }.joined()
+    }
+
+    // MARK: - Private
+
+    private struct Appcast: Decodable {
+        var version: String
+        var zipURL: URL
+        var sha256: String
+        var notes: String?
+    }
+
+    private enum UpdateCheckError: Error {
+        case checksumMismatch
+        case invalidPayload
+        case httpStatus(Int)
+        case processFailed(String)
+    }
+
+    private func fetchAppcast() async throws -> Appcast {
+        let data = try await fetchData(from: Self.resolvedAppcastURL())
+        return try JSONDecoder().decode(Appcast.self, from: data)
+    }
+
+    private func fetchData(from url: URL) async throws -> Data {
+        if url.isFileURL {
+            return try Data(contentsOf: url)
+        }
+        let (data, response) = try await urlSession.data(from: url)
+        if let http = response as? HTTPURLResponse, !(200...299).contains(http.statusCode) {
+            throw UpdateCheckError.httpStatus(http.statusCode)
+        }
+        return data
+    }
+
+    private func downloadAndStage(_ appcast: Appcast) async throws {
+        let zipData = try await fetchData(from: appcast.zipURL)
+        let expected = appcast.sha256.trimmingCharacters(in: .whitespacesAndNewlines)
+        let actual = Self.sha256Hex(zipData)
+        guard actual.caseInsensitiveCompare(expected) == .orderedSame else {
+            throw UpdateCheckError.checksumMismatch
+        }
+
+        discardStaging()
+        let root = FileManager.default.temporaryDirectory
+            .appendingPathComponent("shotdeck-update-\(UUID().uuidString)", isDirectory: true)
+        try FileManager.default.createDirectory(at: root, withIntermediateDirectories: true)
+        stagingDirectory = root
+
+        let zipURL = root.appendingPathComponent("update.zip")
+        try zipData.write(to: zipURL)
+
+        let extracted = root.appendingPathComponent("extracted", isDirectory: true)
+        try FileManager.default.createDirectory(at: extracted, withIntermediateDirectories: true)
+        try Self.runProcess(
+            executable: "/usr/bin/ditto",
+            arguments: ["-x", "-k", zipURL.path, extracted.path]
+        )
+
+        guard let appURL = Self.findRedlineApp(in: extracted) else {
+            throw UpdateCheckError.invalidPayload
+        }
+        let executable = appURL.appendingPathComponent("Contents/MacOS/Shotdeck")
+        guard FileManager.default.fileExists(atPath: executable.path) else {
+            throw UpdateCheckError.invalidPayload
+        }
+        stagedAppURL = appURL
+    }
+
+    private func clearOffer() {
+        availableUpdate = nil
+        discardStaging()
+    }
+
+    private func discardStaging() {
+        if let stagingDirectory {
+            try? FileManager.default.removeItem(at: stagingDirectory)
+        }
+        stagingDirectory = nil
+        stagedAppURL = nil
+    }
+
+    private static func findRedlineApp(in directory: URL) -> URL? {
+        let fm = FileManager.default
+        let direct = directory.appendingPathComponent("Redline.app")
+        if fm.fileExists(atPath: direct.path) { return direct }
+
+        guard let enumerator = fm.enumerator(
+            at: directory,
+            includingPropertiesForKeys: [.isDirectoryKey],
+            options: [.skipsHiddenFiles]
+        ) else { return nil }
+
+        while let item = enumerator.nextObject() as? URL {
+            if item.lastPathComponent == "Redline.app" {
+                return item
+            }
+            if item.pathExtension == "app" {
+                enumerator.skipDescendants()
+            }
+        }
+        return nil
+    }
+
+    private static func semverParts(_ string: String) -> [Int] {
+        let core = string.split(separator: "-").first.map(String.init) ?? string
+        var parts = core.split(separator: ".").prefix(3).map { Int($0) ?? 0 }
+        while parts.count < 3 { parts.append(0) }
+        return parts
+    }
+
+    private static func runProcess(executable: String, arguments: [String]) throws {
+        let process = Process()
+        process.executableURL = URL(fileURLWithPath: executable)
+        process.arguments = arguments
+        let err = Pipe()
+        process.standardError = err
+        process.standardOutput = Pipe()
+        try process.run()
+        process.waitUntilExit()
+        guard process.terminationStatus == 0 else {
+            let message = String(data: err.fileHandleForReading.readDataToEndOfFile(), encoding: .utf8) ?? ""
+            throw UpdateCheckError.processFailed("\(executable) failed: \(message)")
+        }
+    }
+}

Sources/ShotdeckCore/PDF/PDFComposer.swift

@@ -70,8 +70,8 @@ public struct PDFComposer: Sendable {
         }
     }
 
-    public static func fileName(for session: CaptureSession) -> String {
-        "Redline-\(DubaiTime.fileStamp(session.createdAt)).pdf"
+    public static func fileName(for _: CaptureSession) -> String {
+        "Redline-\(DubaiTime.fileStamp(Date())).pdf"
     }
 
     private static func writePDF(

Tests/ShotdeckCoreTests/PDFComposerTests.swift

@@ -203,6 +203,17 @@ private func pixelWindow(
     return (pixelX0, pixelY0, pixelX1, pixelY1)
 }
 
+@Test("fileName uses compose time, not session.createdAt, and matches Redline-yyyyMMdd-HHmmss.pdf")
+func fileNameUsesComposeTimeNotSessionCreatedAt() {
+    let old = Date(timeIntervalSince1970: 1_600_000_000) // 2020-09-13
+    let session = makeSession(captures: [], createdAt: old)
+    let name = PDFComposer.fileName(for: session)
+    #expect(name.wholeMatch(of: /^Redline-\d{8}-\d{6}\.pdf$/) != nil)
+    #expect(!name.contains(DubaiTime.fileStamp(old)))
+    let today = String(DubaiTime.fileStamp(Date()).prefix(8))
+    #expect(name.contains(today))
+}
+
 @Test("Three-page basic compose")
 func threePageBasicCompose() throws {
     let directory = try makeScratchDirectory()