feature: sent-PDF history (10) + image retention (30) with pruning per Ben's 2026-09-02 ruling

# 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>0.2.0</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

@@ -36,6 +36,8 @@ 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 }
@@ -50,6 +52,7 @@ public final class AppModel {
     let picker: RegionPickerController
     let ledger: ReturnLedger
     let watcher: ReturnWatcher
+    let historyStore: HistoryStore
     let updateChecker: UpdateChecker
 
     public init(
@@ -61,7 +64,7 @@ public final class AppModel {
         picker: RegionPickerController,
         ledger: ReturnLedger,
         watcher: ReturnWatcher
-    ) {
+    ) throws {
         self.paths = paths
         self.spool = spool
         self.composer = composer
@@ -70,6 +73,7 @@ public final class AppModel {
         self.picker = picker
         self.ledger = ledger
         self.watcher = watcher
+        self.historyStore = try HistoryStore(paths: paths)
         self.session = CaptureSession(
             id: UUID(),
             createdAt: Date(),
@@ -116,6 +120,42 @@ 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 }
@@ -170,6 +210,7 @@ public final class AppModel {
             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_HISTORY_SELFTEST"] != nil
         if !skipSchedule {
             updateChecker.startSchedule()
         }

Sources/Shotdeck/MenuBarView.swift

@@ -95,6 +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/PanelSnapshot.swift

@@ -163,7 +163,7 @@ enum PanelSnapshot {
             watchFolder: root.appendingPathComponent("watch", isDirectory: true)
         )
         let ledger = try ReturnLedger(paths: paths)
-        let model = AppModel(
+        let model = try AppModel(
             paths: paths,
             spool: try SpoolStore(paths: paths),
             composer: PDFComposer(),

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`.
@@ -28,6 +30,20 @@ enum PickerSelfTest {
         }
     }
 
+    /// Standalone HISTORY phase when `SHOTDECK_HISTORY_SELFTEST` is set without
+    /// the picker chain. Waits for NSApp like the other phases, then exits.
+    static func runHistoryIfRequested() {
+        guard let raw = ProcessInfo.processInfo.environment["SHOTDECK_HISTORY_SELFTEST"],
+              !raw.isEmpty
+        else { return }
+        _ = raw
+        DispatchQueue.main.async {
+            MainActor.assumeIsolated {
+                runHistoryPhase()
+            }
+        }
+    }
+
     private static func execute(outputDirectory: URL) {
         do {
             try FileManager.default.createDirectory(
@@ -113,10 +129,11 @@ enum PickerSelfTest {
         fflush(stdout)
 
         runRegionPersistPhase()
-        if !startUpdateSelfTestIfRequested() {
-            exit(0)
-        }
-        // UPDATE-SELFTEST hops to a later main-actor turn and exits itself.
+        // 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 HISTORY, then UPDATE-SELFTEST (or exits if that phase is
+        // not requested).
+        runSendTruthPhase()
     }
 
     /// Phase 2: writes a known region under `CaptureRegion.defaultsKey`, reloads it through
@@ -160,7 +177,290 @@ enum PickerSelfTest {
         fflush(stdout)
     }
 
-    /// Phase 3: builds a fake 99.0.0 bundle, serves a local appcast, stages via
+    /// 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 HISTORY instead of exiting.
+    private static func runSendTruthPhase() {
+        Task { @MainActor in
+            do {
+                try await executeSendTruth()
+                print("SEND-TRUTH PASS")
+                fflush(stdout)
+            } catch {
+                print("SEND-TRUTH FAIL \(error)")
+                fflush(stdout)
+                exit(1)
+            }
+            runHistoryPhase()
+        }
+    }
+
+    /// Phase 4: drive HistoryStore record/prune in a temp root. Env-gated by
+    /// `SHOTDECK_HISTORY_SELFTEST` the same way UPDATE is gated, and also runs
+    /// whenever the picker self-test chain is already in flight so a full
+    /// self-test prints HISTORY PASS|FAIL. Chains to UPDATE-SELFTEST (or exits).
+    private static func runHistoryPhase() {
+        let historyRequested = ProcessInfo.processInfo.environment["SHOTDECK_HISTORY_SELFTEST"]
+        let pickerRequested = ProcessInfo.processInfo.environment["SHOTDECK_PICKER_SELFTEST"]
+        let shouldRun = (historyRequested.map { !$0.isEmpty } ?? false)
+            || (pickerRequested.map { !$0.isEmpty } ?? false)
+        guard shouldRun else {
+            if !startUpdateSelfTestIfRequested() {
+                exit(0)
+            }
+            return
+        }
+
+        Task { @MainActor in
+            do {
+                try await executeHistorySelfTest()
+                print("HISTORY PASS")
+                fflush(stdout)
+                if !startUpdateSelfTestIfRequested() {
+                    exit(0)
+                }
+            } catch {
+                print("HISTORY FAIL \(error)")
+                fflush(stdout)
+                exit(1)
+            }
+        }
+    }
+
+    private static func executeHistorySelfTest() async throws {
+        let fm = FileManager.default
+        let root = fm.temporaryDirectory
+            .appendingPathComponent("shotdeck-history-selftest-\(UUID().uuidString)", isDirectory: true)
+        defer { try? fm.removeItem(at: root) }
+
+        let paths = try AppSupportPaths(
+            root: root.appendingPathComponent("root", isDirectory: true),
+            outbox: root.appendingPathComponent("outbox", isDirectory: true),
+            watchFolder: root.appendingPathComponent("watch", isDirectory: true)
+        )
+        let store = try HistoryStore(paths: paths)
+        let sources = root.appendingPathComponent("user-sources", isDirectory: true)
+        try fm.createDirectory(at: sources, withIntermediateDirectories: true)
+
+        var recorded: [HistoryEntry] = []
+        for i in 0..<12 {
+            let source = sources.appendingPathComponent("source-\(i).pdf")
+            try Data("%PDF-1.4\n%hist-\(i)\n%%EOF\n".utf8).write(to: source)
+            let entry = try await store.recordSentPDF(
+                sourceURL: source,
+                sessionID: UUID(),
+                pageCount: 1,
+                sentAt: Date(timeIntervalSince1970: 1_800_000_000 + TimeInterval(i))
+            )
+            recorded.append(entry)
+            let onDisk = try Data(contentsOf: source)
+            guard onDisk == Data("%PDF-1.4\n%hist-\(i)\n%%EOF\n".utf8) else {
+                throw HistorySelfTestError.detail("user source PDF was modified: \(source.path)")
+            }
+        }
+
+        let listed = await store.listPDFs()
+        guard listed.count == 10 else {
+            throw HistorySelfTestError.detail("listPDFs count \(listed.count) want 10")
+        }
+        let wantNewest = Array(recorded.suffix(10).reversed())
+        guard listed.map(\.id) == wantNewest.map(\.id) else {
+            throw HistorySelfTestError.detail("listPDFs did not return the 10 newest")
+        }
+        let pdfsDir = paths.root.appendingPathComponent("history/pdfs", isDirectory: true)
+        for entry in recorded.prefix(2) {
+            let gone = pdfsDir.appendingPathComponent(entry.fileName)
+            guard !fm.fileExists(atPath: gone.path) else {
+                throw HistorySelfTestError.detail("oldest PDF still on disk: \(gone.path)")
+            }
+        }
+
+        let same = sources.appendingPathComponent("same.pdf")
+        try Data("%PDF-1.4\n%same\n%%EOF\n".utf8).write(to: same)
+        let first = try await store.recordSentPDF(
+            sourceURL: same, sessionID: nil, pageCount: 1,
+            sentAt: Date(timeIntervalSince1970: 1_800_000_100)
+        )
+        let second = try await store.recordSentPDF(
+            sourceURL: same, sessionID: nil, pageCount: 1,
+            sentAt: Date(timeIntervalSince1970: 1_800_000_101)
+        )
+        guard first.id != second.id, first.fileURL.path != second.fileURL.path,
+              fm.fileExists(atPath: first.fileURL.path),
+              fm.fileExists(atPath: second.fileURL.path),
+              fm.fileExists(atPath: same.path)
+        else {
+            throw HistorySelfTestError.detail("re-record same source did not produce two distinct copies")
+        }
+
+        let spool = try SpoolStore(paths: paths)
+        let png = try makeTinyPNGData()
+        let base = Date(timeIntervalSince1970: 1_800_100_000)
+        var n = 0
+        var oldestSessionID: UUID?
+        for count in [5, 15, 15] {
+            if n == 0 {
+                oldestSessionID = try await spool.currentSession().id
+            }
+            for _ in 0..<count {
+                _ = try await spool.append(
+                    pngData: png, pixelWidth: 64, pixelHeight: 48, scale: 1,
+                    capturedAt: base.addingTimeInterval(TimeInterval(n))
+                )
+                n += 1
+            }
+            _ = try await spool.archiveCurrent(pdfFileName: "Redline-hist-\(n).pdf")
+        }
+        let openCapture = try await spool.append(
+            pngData: png, pixelWidth: 64, pixelHeight: 48, scale: 1,
+            capturedAt: Date(timeIntervalSince1970: 1_900_000_000)
+        )
+        let openSession = try await spool.currentSession()
+        let openPNG = paths.sessionDirectory(openSession.id).appendingPathComponent(openCapture.fileName)
+        let openBytes = try Data(contentsOf: openPNG)
+
+        try await store.pruneImages()
+
+        let images = try await store.listImages(limit: 50)
+        guard images.count == 30 else {
+            throw HistorySelfTestError.detail("listImages count \(images.count) want 30")
+        }
+        if let oldestSessionID {
+            let oldDir = paths.archiveDirectory(oldestSessionID)
+            guard !fm.fileExists(atPath: oldDir.path) else {
+                throw HistorySelfTestError.detail("emptied archive session still on disk")
+            }
+        }
+        guard fm.fileExists(atPath: openPNG.path), try Data(contentsOf: openPNG) == openBytes else {
+            throw HistorySelfTestError.detail("open session PNG was touched")
+        }
+        let remainingOpen = try await spool.currentSession()
+        guard remainingOpen.id == openSession.id,
+              remainingOpen.captures.map(\.id) == [openCapture.id]
+        else {
+            throw HistorySelfTestError.detail("open session manifest was touched")
+        }
+    }
+
+    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 = try 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 5: 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
@@ -299,7 +599,7 @@ enum PickerSelfTest {
             watchFolder: root.appendingPathComponent("watch", isDirectory: true)
         )
         let ledger = try ReturnLedger(paths: paths)
-        let model = AppModel(
+        let model = try AppModel(
             paths: paths,
             spool: try SpoolStore(paths: paths),
             composer: PDFComposer(),
@@ -398,3 +698,12 @@ private enum UpdateSelfTestError: Error, CustomStringConvertible {
         }
     }
 }
+
+private enum HistorySelfTestError: 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.
@@ -20,52 +67,70 @@ 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) {
-                _ = try composer.compose(
-                    session: workingSession,
-                    imageURL: { capture in sourceDir.appendingPathComponent(capture.fileName) },
-                    title: title,
-                    to: tempURL
+        // 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) {
+            _ = try composer.compose(
+                session: workingSession,
+                imageURL: { capture in sourceDir.appendingPathComponent(capture.fileName) },
+                title: title,
+                to: tempURL
+            )
+            // POSIX rename onto `finalURL` replaces any same-name file in one
+            // directory operation; there is never a window where the PDF is gone.
+            if Darwin.rename(tempURL.path, finalURL.path) != 0 {
+                throw ShotdeckError.pdfCompositionFailed(
+                    reason: "could not publish the PDF: \(String(cString: strerror(errno)))"
                 )
-                // POSIX rename onto `finalURL` replaces any same-name file in one
-                // directory operation; there is never a window where the PDF is gone.
-                if Darwin.rename(tempURL.path, finalURL.path) != 0 {
-                    throw ShotdeckError.pdfCompositionFailed(
-                        reason: "could not publish the PDF: \(String(cString: strerror(errno)))"
-                    )
-                }
-                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 AtomicFile.fsyncDirectory(at: outboxDir)
+        }.value
+
+        guard FileManager.default.fileExists(atPath: finalURL.path) else {
+            throw ShotdeckError.pdfCompositionFailed(reason: "the PDF was not written to disk")
+        }
+        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 }
+        let sentSessionID = session.id
+        let sourceURL = lastComposedPDFURL ?? outboxURL.appendingPathComponent(fileName)
+        do {
             _ = 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)."
-                )
-            }
+            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.")
+            return
+        }
+        do {
+            _ = try await historyStore.recordSentPDF(
+                sourceURL: sourceURL,
+                sessionID: sentSessionID,
+                pageCount: pageCount,
+                sentAt: Date()
+            )
+            try await historyStore.pruneImages()
+        } catch {
+            Log.spool.error(
+                "Could not record sent PDF into history at \(sourceURL.path, privacy: .public): \(error.localizedDescription, privacy: .public)"
+            )
         }
     }
+
+    /// `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/main.swift

@@ -9,6 +9,8 @@ if ProcessInfo.processInfo.environment["SHOTDECK_SNAPSHOT_DIR"] != nil {
 }
 if ProcessInfo.processInfo.environment["SHOTDECK_PICKER_SELFTEST"] != nil {
     MainActor.assumeIsolated { PickerSelfTest.runIfRequested() }
+} else if ProcessInfo.processInfo.environment["SHOTDECK_HISTORY_SELFTEST"] != nil {
+    MainActor.assumeIsolated { PickerSelfTest.runHistoryIfRequested() }
 }
 ShotdeckApp.main()
 
@@ -67,7 +69,7 @@ final class AppDelegate: NSObject, NSApplicationDelegate {
 
     private static func makeModel(paths: AppSupportPaths) throws -> AppModel {
         let ledger = try ReturnLedger(paths: paths)
-        return AppModel(
+        return try AppModel(
             paths: paths,
             spool: try SpoolStore(paths: paths),
             composer: PDFComposer(),

Sources/ShotdeckCore/History/HistoryStore.swift

@@ -0,0 +1,446 @@
+import Foundation
+
+/// Retention ruling (2026-09-02). Ben's instruction is the authority that
+/// supersedes the earlier D-11 never-delete rule FOR THIS STORE only:
+///
+///     "the last 10 files are saved, and the past 30 images, and cleared up
+///     afterwards. user should be able to select from those and send again."
+///
+/// App-managed copies live under `AppSupportPaths.root/history/`. Pruning
+/// unlinks files under `history/pdfs/` and archived capture PNGs beyond the
+/// newest 30. It never deletes a user file, never touches the outbox PDF, and
+/// never touches the open spool session (D-11 still applies there).
+
+/// One sent-PDF copy retained for re-send. The file at `fileURL` is the
+/// app-managed copy under `history/pdfs/`, not the user's original.
+public struct HistoryEntry: Codable, Sendable, Equatable, Identifiable {
+    public let id: UUID
+    public let fileName: String
+    public let fileURL: URL
+    public let originalFileName: String
+    public let sessionID: UUID?
+    public let pageCount: Int
+    public let sentAt: Date
+
+    public init(
+        id: UUID,
+        fileName: String,
+        fileURL: URL,
+        originalFileName: String,
+        sessionID: UUID?,
+        pageCount: Int,
+        sentAt: Date
+    ) {
+        self.id = id
+        self.fileName = fileName
+        self.fileURL = fileURL
+        self.originalFileName = originalFileName
+        self.sessionID = sessionID
+        self.pageCount = pageCount
+        self.sentAt = sentAt
+    }
+}
+
+/// A capture PNG on disk under an archived session, listed for re-send.
+/// `path` is the real file; HistoryStore never copies images.
+public struct ImageRef: Sendable, Equatable {
+    public let path: URL
+    public let capturedAt: Date
+    public let sessionID: UUID
+
+    public init(path: URL, capturedAt: Date, sessionID: UUID) {
+        self.path = path
+        self.capturedAt = capturedAt
+        self.sessionID = sessionID
+    }
+}
+
+public actor HistoryStore {
+    public static let pdfRetentionCount = 10
+    public static let imageRetentionCount = 30
+
+    private let paths: AppSupportPaths
+    private let historyRoot: URL
+    private let pdfsDirectory: URL
+    private let manifestURL: URL
+    private var entries: [HistoryEntry]
+
+    public init(paths: AppSupportPaths) throws {
+        self.paths = paths
+        self.historyRoot = paths.root.appendingPathComponent("history", isDirectory: true)
+        self.pdfsDirectory = historyRoot.appendingPathComponent("pdfs", isDirectory: true)
+        self.manifestURL = historyRoot.appendingPathComponent("history.json")
+        do {
+            try FileManager.default.createDirectory(at: historyRoot, withIntermediateDirectories: true)
+            try FileManager.default.createDirectory(at: pdfsDirectory, withIntermediateDirectories: true)
+        } catch {
+            throw ShotdeckError.spoolWriteFailed(
+                path: historyRoot.path,
+                underlying: error.localizedDescription
+            )
+        }
+        self.entries = try Self.loadEntries(from: manifestURL, pdfsDirectory: pdfsDirectory)
+    }
+
+    /// Copies `sourceURL` into `history/pdfs/` (never moves or writes the
+    /// user's file), appends an entry, then keeps the 10 newest PDF copies.
+    public func recordSentPDF(
+        sourceURL: URL,
+        sessionID: UUID?,
+        pageCount: Int,
+        sentAt: Date
+    ) throws -> HistoryEntry {
+        let fm = FileManager.default
+        guard fm.fileExists(atPath: sourceURL.path) else {
+            throw ShotdeckError.spoolWriteFailed(
+                path: sourceURL.path,
+                underlying: "source PDF does not exist"
+            )
+        }
+        let data: Data
+        do {
+            data = try Data(contentsOf: sourceURL)
+        } catch {
+            throw ShotdeckError.spoolWriteFailed(
+                path: sourceURL.path,
+                underlying: error.localizedDescription
+            )
+        }
+
+        let id = UUID()
+        let fileName = "\(DubaiTime.fileStamp(sentAt))-\(id.uuidString.lowercased()).pdf"
+        let destURL = pdfsDirectory.appendingPathComponent(fileName)
+        try AtomicFile.write(data, to: destURL)
+
+        let entry = HistoryEntry(
+            id: id,
+            fileName: fileName,
+            fileURL: destURL,
+            originalFileName: sourceURL.lastPathComponent,
+            sessionID: sessionID,
+            pageCount: pageCount,
+            sentAt: sentAt
+        )
+        entries.append(entry)
+        try prunePDFEntries()
+        return entry
+    }
+
+    /// Newest first, at most `pdfRetentionCount`.
+    public func listPDFs() -> [HistoryEntry] {
+        Array(sortedPDFs().prefix(Self.pdfRetentionCount))
+    }
+
+    /// The newest capture PNGs across `archive/` sessions (including
+    /// `removed/`). Does not copy files and does not look at the open spool.
+    public func listImages(limit: Int = 30) throws -> [ImageRef] {
+        let images = try collectArchivedImages()
+        return images.prefix(max(limit, 0)).map(\.ref)
+    }
+
+    /// Across archived sessions only: keep the 30 newest PNGs total (including
+    /// `removed/`); delete older PNGs, drop them from `session.json`, and
+    /// remove a session directory left with zero PNGs. Never touches spool/.
+    public func pruneImages() throws {
+        let fm = FileManager.default
+        let images = try collectArchivedImages()
+        let keepCount = Self.imageRetentionCount
+        let doomed = Array(images.dropFirst(keepCount))
+        guard !doomed.isEmpty else { return }
+
+        var remainingBySession: [UUID: CaptureSession] = [:]
+        var dirBySession: [UUID: URL] = [:]
+        for item in images {
+            remainingBySession[item.session.id] = item.session
+            dirBySession[item.session.id] = item.sessionDir
+        }
+
+        var droppedIDs: [UUID: Set<UUID>] = [:]
+        for item in doomed {
+            try deleteIfPrunableImage(item.ref.path)
+            if let captureID = item.captureID {
+                droppedIDs[item.session.id, default: []].insert(captureID)
+            }
+        }
+
+        for (sessionID, ids) in droppedIDs {
+            guard var session = remainingBySession[sessionID] else { continue }
+            for id in ids {
+                session = session.removing(captureID: id)
+            }
+            remainingBySession[sessionID] = session
+        }
+
+        let touchedIDs = Set(doomed.map(\.session.id))
+        for sessionID in touchedIDs {
+            guard let sessionDir = dirBySession[sessionID] else { continue }
+            guard isUnderArchive(sessionDir), !isUnderSpool(sessionDir) else { continue }
+
+            if pngsRemaining(in: sessionDir).isEmpty {
+                if fm.fileExists(atPath: sessionDir.path) {
+                    try fm.removeItem(at: sessionDir)
+                    Log.spool.warning("Pruned \(sessionDir.path, privacy: .public)")
+                }
+                try AtomicFile.fsyncDirectory(at: paths.archive)
+                continue
+            }
+
+            if let session = remainingBySession[sessionID], droppedIDs[sessionID] != nil {
+                try AtomicFile.writeJSON(
+                    session,
+                    to: sessionDir.appendingPathComponent("session.json")
+                )
+            }
+        }
+    }
+
+    // MARK: - PDF retention
+
+    private func prunePDFEntries() throws {
+        let sorted = sortedPDFs()
+        let kept = Array(sorted.prefix(Self.pdfRetentionCount))
+        let discarded = sorted.dropFirst(Self.pdfRetentionCount)
+        for entry in discarded {
+            let url = pdfsDirectory.appendingPathComponent(entry.fileName)
+            try deleteIfAppManagedPDF(url)
+        }
+        entries = kept
+        try persistEntries()
+    }
+
+    private func sortedPDFs() -> [HistoryEntry] {
+        entries.sorted { lhs, rhs in
+            if lhs.sentAt != rhs.sentAt { return lhs.sentAt > rhs.sentAt }
+            return lhs.id.uuidString > rhs.id.uuidString
+        }
+    }
+
+    private func persistEntries() throws {
+        try AtomicFile.writeJSON(entries, to: manifestURL)
+    }
+
+    private func deleteIfAppManagedPDF(_ url: URL) throws {
+        guard isUnderPDFs(url) else { return }
+        let fm = FileManager.default
+        guard fm.fileExists(atPath: url.path) else { return }
+        do {
+            try fm.removeItem(at: url)
+        } catch {
+            throw ShotdeckError.spoolWriteFailed(
+                path: url.path,
+                underlying: error.localizedDescription
+            )
+        }
+        Log.spool.warning("Pruned \(url.path, privacy: .public)")
+        try AtomicFile.fsyncDirectory(at: pdfsDirectory)
+    }
+
+    // MARK: - Archived images
+
+    private struct ArchivedImage {
+        let ref: ImageRef
+        let session: CaptureSession
+        let sessionDir: URL
+        let captureID: UUID?
+    }
+
+    private func collectArchivedImages() throws -> [ArchivedImage] {
+        let dirs = try archivedSessionDirectories()
+        var collected: [ArchivedImage] = []
+        for dir in dirs {
+            let sessionID = UUID(uuidString: dir.lastPathComponent) ?? UUID()
+            let session = (try? loadSession(at: dir, id: sessionID))
+                ?? CaptureSession(
+                    id: sessionID,
+                    createdAt: fileDate(dir) ?? Date(),
+                    state: .archived,
+                    captures: [],
+                    pdfFileName: nil
+                )
+            var referenced = Set<String>()
+            for capture in session.captures {
+                let url = dir.appendingPathComponent(capture.fileName)
+                guard FileManager.default.fileExists(atPath: url.path) else { continue }
+                referenced.insert(capture.fileName)
+                collected.append(
+                    ArchivedImage(
+                        ref: ImageRef(path: url, capturedAt: capture.capturedAt, sessionID: session.id),
+                        session: session,
+                        sessionDir: dir,
+                        captureID: capture.id
+                    )
+                )
+            }
+            let removedDir = dir.appendingPathComponent("removed", isDirectory: true)
+            for url in pngFiles(in: dir) where !referenced.contains(url.lastPathComponent) {
+                collected.append(
+                    ArchivedImage(
+                        ref: ImageRef(
+                            path: url,
+                            capturedAt: fileDate(url) ?? .distantPast,
+                            sessionID: session.id
+                        ),
+                        session: session,
+                        sessionDir: dir,
+                        captureID: nil
+                    )
+                )
+            }
+            for url in pngFiles(in: removedDir) {
+                collected.append(
+                    ArchivedImage(
+                        ref: ImageRef(
+                            path: url,
+                            capturedAt: fileDate(url) ?? .distantPast,
+                            sessionID: session.id
+                        ),
+                        session: session,
+                        sessionDir: dir,
+                        captureID: nil
+                    )
+                )
+            }
+        }
+        return collected.sorted { lhs, rhs in
+            if lhs.ref.capturedAt != rhs.ref.capturedAt {
+                return lhs.ref.capturedAt > rhs.ref.capturedAt
+            }
+            return lhs.ref.path.path > rhs.ref.path.path
+        }
+    }
+
+    private func archivedSessionDirectories() throws -> [URL] {
+        let fm = FileManager.default
+        let entries: [URL]
+        do {
+            entries = try fm.contentsOfDirectory(
+                at: paths.archive,
+                includingPropertiesForKeys: [.isDirectoryKey],
+                options: []
+            )
+        } catch {
+            throw ShotdeckError.spoolWriteFailed(
+                path: paths.archive.path,
+                underlying: error.localizedDescription
+            )
+        }
+        return entries.filter { url in
+            let isDirectory = (try? url.resourceValues(forKeys: [.isDirectoryKey]).isDirectory) ?? false
+            return isDirectory && UUID(uuidString: url.lastPathComponent) != nil
+        }
+    }
+
+    private func loadSession(at dir: URL, id: UUID) throws -> CaptureSession {
+        let url = dir.appendingPathComponent("session.json")
+        let data = try Data(contentsOf: url)
+        let decoder = JSONDecoder()
+        decoder.dateDecodingStrategy = .iso8601
+        let session = try decoder.decode(CaptureSession.self, from: data)
+        guard session.id == id else {
+            throw ShotdeckError.manifestCorrupt(path: url.path)
+        }
+        return session
+    }
+
+    private func pngFiles(in dir: URL) -> [URL] {
+        let fm = FileManager.default
+        guard fm.fileExists(atPath: dir.path) else { return [] }
+        let entries = (try? fm.contentsOfDirectory(
+            at: dir,
+            includingPropertiesForKeys: [.isDirectoryKey],
+            options: []
+        )) ?? []
+        return entries.filter { url in
+            let isDirectory = (try? url.resourceValues(forKeys: [.isDirectoryKey]).isDirectory) ?? false
+            return !isDirectory && url.pathExtension.lowercased() == "png"
+        }
+    }
+
+    private func pngsRemaining(in sessionDir: URL) -> [URL] {
+        pngFiles(in: sessionDir)
+            + pngFiles(in: sessionDir.appendingPathComponent("removed", isDirectory: true))
+    }
+
+    private func deleteIfPrunableImage(_ url: URL) throws {
+        guard isUnderArchive(url), !isUnderSpool(url) else { return }
+        let fm = FileManager.default
+        guard fm.fileExists(atPath: url.path) else { return }
+        do {
+            try fm.removeItem(at: url)
+        } catch {
+            throw ShotdeckError.spoolWriteFailed(
+                path: url.path,
+                underlying: error.localizedDescription
+            )
+        }
+        Log.spool.warning("Pruned \(url.path, privacy: .public)")
+        try AtomicFile.fsyncDirectory(at: url.deletingLastPathComponent())
+    }
+
+    private func fileDate(_ url: URL) -> Date? {
+        let values = try? url.resourceValues(forKeys: [.creationDateKey, .contentModificationDateKey])
+        return values?.creationDate ?? values?.contentModificationDate
+    }
+
+    // MARK: - Path guards
+
+    private func isUnderPDFs(_ url: URL) -> Bool {
+        isUnderDirectory(url, parent: pdfsDirectory)
+    }
+
+    private func isUnderArchive(_ url: URL) -> Bool {
+        isUnderDirectory(url, parent: paths.archive)
+    }
+
+    private func isUnderSpool(_ url: URL) -> Bool {
+        isUnderDirectory(url, parent: paths.spool)
+    }
+
+    private func isUnderDirectory(_ url: URL, parent: URL) -> Bool {
+        let parentPath = parent.standardizedFileURL.path
+        let path = url.standardizedFileURL.path
+        if path == parentPath { return true }
+        let prefix = parentPath.hasSuffix("/") ? parentPath : parentPath + "/"
+        return path.hasPrefix(prefix)
+    }
+
+    // MARK: - Manifest load
+
+    private static func loadEntries(from url: URL, pdfsDirectory: URL) throws -> [HistoryEntry] {
+        let fm = FileManager.default
+        guard fm.fileExists(atPath: url.path) else { return [] }
+        let data: Data
+        do {
+            data = try Data(contentsOf: url)
+        } catch {
+            throw ShotdeckError.spoolWriteFailed(
+                path: url.path,
+                underlying: error.localizedDescription
+            )
+        }
+        let decoder = JSONDecoder()
+        decoder.dateDecodingStrategy = .iso8601
+        do {
+            let decoded = try decoder.decode([HistoryEntry].self, from: data)
+            return decoded.map { entry in
+                HistoryEntry(
+                    id: entry.id,
+                    fileName: entry.fileName,
+                    fileURL: pdfsDirectory.appendingPathComponent(entry.fileName),
+                    originalFileName: entry.originalFileName,
+                    sessionID: entry.sessionID,
+                    pageCount: entry.pageCount,
+                    sentAt: entry.sentAt
+                )
+            }
+        } catch {
+            let corruptURL = url.deletingLastPathComponent()
+                .appendingPathComponent("history.json.corrupt-\(DubaiTime.fileStamp(Date()))")
+            try? fm.moveItem(at: url, to: corruptURL)
+            Log.spool.error(
+                "history.json could not be decoded; moved to \(corruptURL.path, privacy: .public): \(error.localizedDescription, privacy: .public)"
+            )
+            return []
+        }
+    }
+}

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/HistoryStoreTests.swift

@@ -0,0 +1,319 @@
+import CoreGraphics
+import Foundation
+import ImageIO
+import Testing
+import ShotdeckCore
+
+@Test
+func recordTwelvePDFsKeepsTenNewestAndDeletesOldestCopies() async throws {
+    let (root, paths) = try makeHistoryPaths()
+    defer { try? FileManager.default.removeItem(at: root) }
+
+    let store = try HistoryStore(paths: paths)
+    let sources = root.appendingPathComponent("user-sources", isDirectory: true)
+    try FileManager.default.createDirectory(at: sources, withIntermediateDirectories: true)
+
+    var recorded: [HistoryEntry] = []
+    for i in 0..<12 {
+        let source = sources.appendingPathComponent("source-\(i).pdf")
+        try writeDummyPDF(to: source, marker: "pdf-\(i)")
+        let sentAt = Date(timeIntervalSince1970: 1_800_000_000 + TimeInterval(i))
+        let entry = try await store.recordSentPDF(
+            sourceURL: source,
+            sessionID: UUID(),
+            pageCount: i + 1,
+            sentAt: sentAt
+        )
+        recorded.append(entry)
+    }
+
+    let listed = await store.listPDFs()
+    #expect(listed.count == 10)
+    #expect(listed.map(\.id) == recorded.suffix(10).reversed().map(\.id))
+    #expect(listed.map(\.sentAt) == recorded.suffix(10).reversed().map(\.sentAt))
+
+    let pdfsDir = paths.root.appendingPathComponent("history/pdfs", isDirectory: true)
+    for entry in recorded.prefix(2) {
+        #expect(!FileManager.default.fileExists(atPath: pdfsDir.appendingPathComponent(entry.fileName).path))
+    }
+    for entry in recorded.suffix(10) {
+        #expect(FileManager.default.fileExists(atPath: pdfsDir.appendingPathComponent(entry.fileName).path))
+    }
+}
+
+@Test
+func pruneImagesKeepsThirtyNewestAcrossThreeArchivedSessionsAndLeavesOpenSessionAlone() async throws {
+    let (root, paths) = try makeHistoryPaths()
+    defer { try? FileManager.default.removeItem(at: root) }
+
+    let spool = try SpoolStore(paths: paths)
+    let base = Date(timeIntervalSince1970: 1_800_100_000)
+    var captures: [(id: UUID, capturedAt: Date, sessionID: UUID)] = []
+
+    // 5 oldest + 15 + 15 = 35 archived PNGs. The oldest session is emptied by prune.
+    let perSession = [5, 15, 15]
+    var index = 0
+    for count in perSession {
+        let sessionID = try await spool.currentSession().id
+        for _ in 0..<count {
+            let capturedAt = base.addingTimeInterval(TimeInterval(index))
+            let capture = try await spool.append(
+                pngData: try makeHistoryPNGData(width: 6, height: 4, red: 0.2, green: 0.3, blue: 0.4),
+                pixelWidth: 6,
+                pixelHeight: 4,
+                scale: 1.0,
+                capturedAt: capturedAt
+            )
+            captures.append((capture.id, capturedAt, sessionID))
+            index += 1
+        }
+        _ = try await spool.archiveCurrent(pdfFileName: "Redline-hist-\(sessionID.uuidString).pdf")
+    }
+
+    let openBefore = try await spool.currentSession()
+    let openCapture = try await spool.append(
+        pngData: try makeHistoryPNGData(width: 8, height: 6, red: 0.9, green: 0.1, blue: 0.1),
+        pixelWidth: 8,
+        pixelHeight: 6,
+        scale: 1.0,
+        capturedAt: Date(timeIntervalSince1970: 1_900_000_000)
+    )
+    let openSession = try await spool.currentSession()
+    #expect(openSession.id == openBefore.id)
+    let openDir = paths.sessionDirectory(openSession.id)
+    let openPNG = openDir.appendingPathComponent(openCapture.fileName)
+    let openPNGBytes = try Data(contentsOf: openPNG)
+    let openManifest = try Data(contentsOf: openDir.appendingPathComponent("session.json"))
+
+    let store = try HistoryStore(paths: paths)
+    try await store.pruneImages()
+
+    let remaining = try await store.listImages(limit: 50)
+    #expect(remaining.count == 30)
+
+    let newestThirty = Array(captures.suffix(30))
+    let remainingDates = Set(remaining.map(\.capturedAt))
+    #expect(remainingDates == Set(newestThirty.map(\.capturedAt)))
+    #expect(remaining.map(\.sessionID).allSatisfy { $0 != openSession.id })
+
+    let oldestFive = Array(captures.prefix(5))
+    for old in oldestFive {
+        let archiveDir = paths.archiveDirectory(old.sessionID)
+        #expect(!FileManager.default.fileExists(atPath: archiveDir.path))
+    }
+
+    #expect(pngFiles(under: paths.archive).count == 30)
+    try assertManifestsMatchDisk(archiveRoot: paths.archive)
+
+    #expect(FileManager.default.fileExists(atPath: openPNG.path))
+    #expect(try Data(contentsOf: openPNG) == openPNGBytes)
+    #expect(try Data(contentsOf: openDir.appendingPathComponent("session.json")) == openManifest)
+    #expect(try await spool.currentSession().captures.map(\.id) == [openCapture.id])
+}
+
+@Test
+func recordSentPDFLeavesTheUserSourceUntouched() async throws {
+    let (root, paths) = try makeHistoryPaths()
+    defer { try? FileManager.default.removeItem(at: root) }
+
+    let source = root.appendingPathComponent("outside-appsupport.pdf")
+    let payload = Data("%PDF-1.4\n%user-original\n%%EOF\n".utf8)
+    try payload.write(to: source)
+
+    let store = try HistoryStore(paths: paths)
+    let entry = try await store.recordSentPDF(
+        sourceURL: source,
+        sessionID: UUID(),
+        pageCount: 2,
+        sentAt: Date(timeIntervalSince1970: 1_800_200_000)
+    )
+
+    #expect(FileManager.default.fileExists(atPath: source.path))
+    #expect(try Data(contentsOf: source) == payload)
+    #expect(entry.fileURL.path != source.path)
+    #expect(try Data(contentsOf: entry.fileURL) == payload)
+    #expect(entry.fileURL.path.hasPrefix(
+        paths.root.appendingPathComponent("history/pdfs", isDirectory: true).path
+    ))
+}
+
+@Test
+func recordingTheSameSourceTwiceMakesTwoDistinctCopies() async throws {
+    let (root, paths) = try makeHistoryPaths()
+    defer { try? FileManager.default.removeItem(at: root) }
+
+    let source = root.appendingPathComponent("resend.pdf")
+    try writeDummyPDF(to: source, marker: "same-source")
+
+    let store = try HistoryStore(paths: paths)
+    let first = try await store.recordSentPDF(
+        sourceURL: source,
+        sessionID: nil,
+        pageCount: 1,
+        sentAt: Date(timeIntervalSince1970: 1_800_300_000)
+    )
+    let second = try await store.recordSentPDF(
+        sourceURL: source,
+        sessionID: nil,
+        pageCount: 1,
+        sentAt: Date(timeIntervalSince1970: 1_800_300_001)
+    )
+
+    #expect(first.id != second.id)
+    #expect(first.fileName != second.fileName)
+    #expect(first.fileURL.path != second.fileURL.path)
+    #expect(FileManager.default.fileExists(atPath: first.fileURL.path))
+    #expect(FileManager.default.fileExists(atPath: second.fileURL.path))
+    let firstBytes = try Data(contentsOf: first.fileURL)
+    let secondBytes = try Data(contentsOf: second.fileURL)
+    #expect(firstBytes == secondBytes)
+    #expect(FileManager.default.fileExists(atPath: source.path))
+
+    let listed = await store.listPDFs()
+    #expect(listed.count == 2)
+    #expect(Set(listed.map(\.id)) == [first.id, second.id])
+}
+
+@Test
+func pruneImagesDeletesOlderPNGsInRemovedFolders() async throws {
+    let (root, paths) = try makeHistoryPaths()
+    defer { try? FileManager.default.removeItem(at: root) }
+
+    let spool = try SpoolStore(paths: paths)
+    let base = Date(timeIntervalSince1970: 1_800_400_000)
+    for i in 0..<30 {
+        _ = try await spool.append(
+            pngData: try makeHistoryPNGData(width: 4, height: 4, red: 0.1, green: 0.2, blue: 0.3),
+            pixelWidth: 4,
+            pixelHeight: 4,
+            scale: 1.0,
+            capturedAt: base.addingTimeInterval(TimeInterval(10 + i))
+        )
+    }
+    _ = try await spool.archiveCurrent(pdfFileName: "Redline-keep.pdf")
+
+    let oldSessionID = UUID()
+    let oldDir = paths.archiveDirectory(oldSessionID)
+    let removedDir = oldDir.appendingPathComponent("removed", isDirectory: true)
+    try FileManager.default.createDirectory(at: removedDir, withIntermediateDirectories: true)
+    let oldPNG = removedDir.appendingPathComponent("001-DEADBEEF.png")
+    try makeHistoryPNGData(width: 4, height: 4, red: 0.5, green: 0.5, blue: 0.5).write(to: oldPNG)
+    try FileManager.default.setAttributes(
+        [.creationDate: base],
+        ofItemAtPath: oldPNG.path
+    )
+    let oldSession = CaptureSession(
+        id: oldSessionID,
+        createdAt: base,
+        state: .archived,
+        captures: [],
+        pdfFileName: "Redline-old.pdf"
+    )
+    try AtomicFile.writeJSON(oldSession, to: oldDir.appendingPathComponent("session.json"))
+
+    let store = try HistoryStore(paths: paths)
+    try await store.pruneImages()
+
+    #expect(!FileManager.default.fileExists(atPath: oldPNG.path))
+    #expect(pngFiles(under: paths.archive).count == 30)
+}
+
+// MARK: - Fixtures
+
+private func makeHistoryPaths() throws -> (root: URL, paths: AppSupportPaths) {
+    let root = FileManager.default.temporaryDirectory
+        .appendingPathComponent("shotdeck-history-\(UUID().uuidString)", isDirectory: true)
+    let paths = try AppSupportPaths(
+        root: root.appendingPathComponent("root", isDirectory: true),
+        outbox: root.appendingPathComponent("outbox", isDirectory: true),
+        watchFolder: root.appendingPathComponent("watch", isDirectory: true)
+    )
+    return (root, paths)
+}
+
+private func writeDummyPDF(to url: URL, marker: String) throws {
+    try Data("%PDF-1.4\n%\(marker)\n%%EOF\n".utf8).write(to: url)
+}
+
+private func makeHistoryPNGData(
+    width: Int,
+    height: Int,
+    red: CGFloat,
+    green: CGFloat,
+    blue: CGFloat
+) throws -> Data {
+    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 {
+        throw HistoryFixtureError.pngGenerationFailed
+    }
+    context.setFillColor(red: red, green: green, blue: blue, alpha: 1)
+    context.fill(CGRect(x: 0, y: 0, width: width, height: height))
+    guard let image = context.makeImage() else {
+        throw HistoryFixtureError.pngGenerationFailed
+    }
+    let buffer = NSMutableData()
+    guard let destination = CGImageDestinationCreateWithData(buffer, "public.png" as CFString, 1, nil) else {
+        throw HistoryFixtureError.pngGenerationFailed
+    }
+    CGImageDestinationAddImage(destination, image, nil)
+    guard CGImageDestinationFinalize(destination) else {
+        throw HistoryFixtureError.pngGenerationFailed
+    }
+    return buffer as Data
+}
+
+private func pngFiles(under root: URL) -> [URL] {
+    let fm = FileManager.default
+    guard let enumerator = fm.enumerator(
+        at: root,
+        includingPropertiesForKeys: [.isRegularFileKey],
+        options: []
+    ) else { return [] }
+    var urls: [URL] = []
+    for case let url as URL in enumerator {
+        let isFile = (try? url.resourceValues(forKeys: [.isRegularFileKey]).isRegularFile) ?? false
+        if isFile, url.pathExtension.lowercased() == "png" {
+            urls.append(url)
+        }
+    }
+    return urls
+}
+
+private func assertManifestsMatchDisk(archiveRoot: URL) throws {
+    let fm = FileManager.default
+    let sessions = (try fm.contentsOfDirectory(
+        at: archiveRoot,
+        includingPropertiesForKeys: [.isDirectoryKey],
+        options: []
+    )).filter {
+        ((try? $0.resourceValues(forKeys: [.isDirectoryKey]).isDirectory) ?? false)
+            && UUID(uuidString: $0.lastPathComponent) != nil
+    }
+    let decoder = JSONDecoder()
+    decoder.dateDecodingStrategy = .iso8601
+    for dir in sessions {
+        let manifestURL = dir.appendingPathComponent("session.json")
+        #expect(fm.fileExists(atPath: manifestURL.path))
+        let session = try decoder.decode(CaptureSession.self, from: Data(contentsOf: manifestURL))
+        for capture in session.captures {
+            let url = dir.appendingPathComponent(capture.fileName)
+            #expect(fm.fileExists(atPath: url.path))
+        }
+        let topLevelPNGs = (try fm.contentsOfDirectory(at: dir, includingPropertiesForKeys: nil, options: []))
+            .filter { $0.pathExtension.lowercased() == "png" }
+        let manifestNames = Set(session.captures.map(\.fileName))
+        #expect(Set(topLevelPNGs.map(\.lastPathComponent)) == manifestNames)
+    }
+}
+
+private enum HistoryFixtureError: Error {
+    case pngGenerationFailed
+}

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()