feature: OneDrive folder as a second send transport

send(anchor:) now branches on TransportSettings.transport(). OneDrive mode
skips AirDrop entirely: it verifies the resolved OneDrive folder exists right
before composing (never trusts stale state), archives the session immediately
after the PDF lands, and sets "Saved to OneDrive — N page(s). Open it in Files
on your iPad." AirDrop's existing behaviour, including handleDidFailToShareItems,
is untouched and only reached from the .airDrop branch.

AppModel seeds outbox/watch from TransportSettings.effectiveFolders() instead
of FolderSettings.resolve() directly, tracks the live `transport`, and
bootstrap() creates the OneDrive folder and sets the watcher's
recordUncommented flag (true only for AirDrop) before the watcher starts.

Settings gets a "Send via" segmented picker above Folders. AirDrop shows the
existing watch/output rows; OneDrive shows a single read-only OneDrive folder
row (Choose... reuses the existing directory picker) plus one caption
explaining the same-folder round trip, or a "No OneDrive folder found" prompt
when nothing resolves (Choose... stays usable). Switching transport re-points
the watcher's folder and recordUncommended live; AirDrop's own folder
overrides are stored separately and are untouched by a OneDrive-and-back
round trip.

Menu's "Send..." row reads "Send to OneDrive" when that transport is active.

Co-Authored-By: Claude Fable 5.1 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_012ZiTXPbPCSjzPVsfoweAbp

Sources/Shotdeck/AppModel.swift

@@ -32,6 +32,9 @@ public final class AppModel {
     public private(set) var isSending: Bool = false
     public private(set) var outboxDisplayName: String
     public private(set) var watchFolderDisplayName: String
+    /// Live transport choice; WP-onedrive reads this to pick the send path and to drive
+    /// the Settings "Send via" picker and the menu's "Send…" label.
+    public private(set) var transport: SendTransport
     /// Live outbox; WP-4b reads this (not `paths.outbox`) so Settings folder changes take effect.
     public private(set) var outboxURL: URL
     /// Live watch folder; WP-4c updates this alongside `ReturnWatcher.updateWatchFolder`.
@@ -81,12 +84,15 @@ public final class AppModel {
         )
         self.region = Self.loadPersistedRegion()
         self.screenRecordingGranted = ScreenCapturer.isScreenRecordingGranted
-        // Seeded from FolderSettings.resolve() via resolvedAppSupportPaths — never .standard().
+        // Seeded from TransportSettings.effectiveFolders() — the one place that combines
-        let folders = FolderSettings.resolve()
+        // the transport choice with FolderSettings/OneDriveLocator. Never call
+        // FolderSettings.resolve() directly outside that function.
+        let folders = TransportSettings.effectiveFolders()
         self.outboxURL = folders.outbox
         self.watchFolderURL = folders.watch
         self.outboxDisplayName = folders.outbox.lastPathComponent
         self.watchFolderDisplayName = folders.watch.lastPathComponent
+        self.transport = folders.transport
         self.captureHotkey = HotkeyPreference.load()
         self.updateChecker = UpdateChecker()
         self.updateChecker.onChecked = { [weak self] in
@@ -118,6 +124,7 @@ public final class AppModel {
         watchFolderURL = watch
         setFolderDisplayNames(outbox: outbox.lastPathComponent, watch: watch.lastPathComponent)
     }
+    func setTransport(_ value: SendTransport) { transport = value }
     func rememberLastComposedPDF(_ url: URL) { lastComposedPDFURL = url }
 
     /// True when a last-composed PDF path is known this run, or the newest
@@ -185,6 +192,16 @@ public final class AppModel {
             // Empty ledger on first run is not an error.
         }
 
+        // OneDrive mode: outbox == watch folder, so a freshly written, unmarked PDF must
+        // never show up as a return; only a document that already carries a mark does.
+        // Also make sure the resolved OneDrive folder actually exists before the
+        // watcher starts watching it (bootstrap is the other creation trigger besides
+        // chooseTransport/chooseOneDriveFolder — see TransportSettings.effectiveFolders).
+        if transport == .oneDrive {
+            try? FileManager.default.createDirectory(at: outboxURL, withIntermediateDirectories: true)
+        }
+        await watcher.setRecordUncommented(transport == .airDrop)
+
         do {
             try await watcher.start { [weak self] _ in
                 Task { @MainActor in
@@ -208,6 +225,8 @@ 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_ONEDRIVE_SELFTEST"] != nil
+            || ProcessInfo.processInfo.environment["REDLINE_SELFTEST_PHASE"] != nil
         if !skipSchedule {
             updateChecker.startSchedule()
         }

Sources/Shotdeck/MenuBarView.swift

@@ -91,7 +91,7 @@ struct MenuBarView: View {
                     model.setStatus("Send is not available in this build.")
                 }
             } label: {
-                actionLabel("Send…")
+                actionLabel(model.transport == .oneDrive ? "Send to OneDrive" : "Send…")
             }
             .disabled(model.session.isEmpty || model.isSending)
 

Sources/Shotdeck/SendController.swift

@@ -16,6 +16,31 @@ extension AppModel: SendCapable {
         guard !session.isEmpty, !isSending else { return }
         setSending(true)
 
+        let transport = TransportSettings.transport()
+
+        // OneDrive mode: verify the real destination exists RIGHT NOW, before composing
+        // anything. `outboxURL` is kept in sync with the resolved OneDrive folder by
+        // bootstrap/chooseTransport/chooseOneDriveFolder, but this is re-resolved fresh
+        // here (never trusted stale) so a folder that vanished since then (OneDrive
+        // signed out, external volume unmounted, folder deleted) is caught instead of
+        // silently writing into whatever `outboxURL` happens to hold.
+        if transport == .oneDrive {
+            guard let folder = OneDriveLocator.resolveOneDriveFolder(),
+                  Self.directoryExists(at: folder)
+            else {
+                let path = OneDriveLocator.resolveOneDriveFolder()?.path
+                    ?? TransportSettings.storedOneDriveFolderPath()
+                    ?? "no OneDrive folder found"
+                setStatus(ShotdeckError.oneDriveFolderUnavailable(path: path).errorDescription)
+                setSending(false)
+                return
+            }
+            if outboxURL != folder || watchFolderURL != folder {
+                setFolderURLs(outbox: folder, watch: folder)
+                try? await watcher.updateWatchFolder(folder)
+            }
+        }
+
         let pending: ComposedSend
         do {
             pending = try await composePDFForSend()
@@ -27,32 +52,51 @@ extension AppModel: SendCapable {
             return
         }
 
-        guard let anchor else {
+        switch transport {
-            handleDidFailToShareItems(fileName: pending.fileName)
+        case .oneDrive:
+            // No AirDrop, no anchor needed — the PDF is already in the watched
+            // OneDrive folder. Archive immediately; the iPad marks it up in place.
+            await handleDidShareItems(fileName: pending.fileName, pageCount: pending.pageCount)
+            let pageWord = pending.pageCount == 1 ? "page" : "pages"
+            setStatus(
+                "Saved to OneDrive — \(pending.pageCount) \(pageWord). Open it in Files on your iPad."
+            )
             setSending(false)
-            return
-        }
 
-        do {
+        case .airDrop:
-            try Sharing.airDrop(fileURL: pending.fileURL, from: anchor) { [weak self] success in
+            guard let anchor else {
-                guard let self else { return }
+                handleDidFailToShareItems(fileName: pending.fileName)
-                if success {
+                setSending(false)
-                    await self.handleDidShareItems(
+                return
-                        fileName: pending.fileName,
+            }
-                        pageCount: pending.pageCount
+
-                    )
+            do {
-                } else {
+                try Sharing.airDrop(fileURL: pending.fileURL, from: anchor) { [weak self] success in
-                    self.handleDidFailToShareItems(fileName: pending.fileName)
+                    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)
                 }
-                self.setSending(false)
+            } catch {
+                // canPerform false, no service, or no visible window: same as cancel.
+                handleDidFailToShareItems(fileName: pending.fileName)
+                setSending(false)
             }
-        } catch {
-            // canPerform false, no service, or no visible window: same as cancel.
-            handleDidFailToShareItems(fileName: pending.fileName)
-            setSending(false)
         }
     }
 
+    private static func directoryExists(at url: URL) -> Bool {
+        var isDirectory: ObjCBool = false
+        let exists = FileManager.default.fileExists(atPath: url.path, isDirectory: &isDirectory)
+        return exists && isDirectory.boolValue
+    }
+
     /// 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 {

Sources/Shotdeck/SettingsView.swift

@@ -33,6 +33,25 @@ struct SettingsView: View {
                 .frame(minHeight: 22)
             }
 
+            GridRow {
+                Text("Send via")
+                    .font(.headline)
+                    .frame(maxWidth: .infinity, alignment: .leading)
+                    .gridCellColumns(2)
+                    .padding(.top, 6)
+            }
+
+            GridRow {
+                Picker("Send via", selection: transportBinding) {
+                    ForEach(SendTransport.allCases, id: \.self) { transport in
+                        Text(transport.displayName).tag(transport)
+                    }
+                }
+                .labelsHidden()
+                .pickerStyle(.segmented)
+                .gridCellColumns(2)
+            }
+
             GridRow {
                 Text("Folders")
                     .font(.headline)
@@ -41,17 +60,48 @@ struct SettingsView: View {
                     .padding(.top, 6)
             }
 
-            GridRow(alignment: .center) {
+            if model.transport == .airDrop {
-                fieldLabel("Watch folder")
+                GridRow(alignment: .center) {
-                folderValue(path: model.watchFolderURL.path) {
+                    fieldLabel("Watch folder")
-                    model.chooseWatchFolder()
+                    folderValue(path: model.watchFolderURL.path) {
+                        model.chooseWatchFolder()
+                    }
                 }
-            }
 
-            GridRow(alignment: .center) {
+                GridRow(alignment: .center) {
-                fieldLabel("Output folder")
+                    fieldLabel("Output folder")
-                folderValue(path: model.outboxURL.path) {
+                    folderValue(path: model.outboxURL.path) {
-                    model.chooseOutboxFolder()
+                        model.chooseOutboxFolder()
+                    }
+                }
+            } else {
+                GridRow(alignment: .center) {
+                    fieldLabel("OneDrive folder")
+                    if let folder = resolvedOneDriveFolder {
+                        folderValue(path: folder.path) {
+                            model.chooseOneDriveFolder()
+                        }
+                    } else {
+                        HStack(spacing: 8) {
+                            Text("No OneDrive folder found — sign in to OneDrive or choose a folder.")
+                                .font(.caption)
+                                .foregroundStyle(.secondary)
+                                .fixedSize(horizontal: false, vertical: true)
+                                .frame(maxWidth: .infinity, alignment: .leading)
+                            Button("Choose…") { model.chooseOneDriveFolder() }
+                        }
+                        .frame(minHeight: 22)
+                    }
+                }
+
+                GridRow {
+                    Text(
+                        "The PDF is saved here and this same folder is watched for the marked-up copy. On the iPad open it from Files > OneDrive."
+                    )
+                    .font(.caption)
+                    .foregroundStyle(.secondary)
+                    .fixedSize(horizontal: false, vertical: true)
+                    .gridCellColumns(2)
                 }
             }
 
@@ -68,6 +118,17 @@ struct SettingsView: View {
         .onDisappear { disarmHotkeyRecorder() }
     }
 
+    private var transportBinding: Binding<SendTransport> {
+        Binding(get: { model.transport }, set: { model.chooseTransport($0) })
+    }
+
+    /// Ground truth from OneDriveLocator, not `model.outboxURL` — the model may be
+    /// showing an AirDrop-folder fallback when no real OneDrive folder resolves, and
+    /// the Settings row must say so plainly rather than repeat that fallback path.
+    private var resolvedOneDriveFolder: URL? {
+        OneDriveLocator.resolveOneDriveFolder()
+    }
+
     private func armHotkeyRecorder() {
         guard !isRecordingHotkey else { return }
         isRecordingHotkey = true
@@ -190,6 +251,53 @@ extension AppModel: SettingsWindowPresenting {
         }
     }
 
+    /// Settings "Send via" picker action. Persists the choice, recomputes the effective
+    /// outbox/watch folder for the new transport, creates the OneDrive folder if it
+    /// doesn't exist yet, and re-points the running watcher (folder + recordUncommented)
+    /// at the new state. Switching back to AirDrop restores its own stored overrides
+    /// untouched, since AirDrop and OneDrive folder settings are stored under separate keys.
+    func chooseTransport(_ value: SendTransport) {
+        guard value != transport else { return }
+        TransportSettings.setTransport(value)
+        setTransport(value)
+        let folders = TransportSettings.effectiveFolders()
+        if value == .oneDrive {
+            try? FileManager.default.createDirectory(
+                at: folders.outbox, withIntermediateDirectories: true
+            )
+        }
+        setFolderURLs(outbox: folders.outbox, watch: folders.watch)
+        Task {
+            await watcher.setRecordUncommented(value == .airDrop)
+            do {
+                try await watcher.updateWatchFolder(folders.watch)
+            } catch {
+                setStatus(
+                    (error as? ShotdeckError)?.errorDescription ?? "Could not switch the watch folder."
+                )
+            }
+        }
+    }
+
+    func chooseOneDriveFolder() {
+        let start = OneDriveLocator.resolveOneDriveFolder() ?? FileManager.default.homeDirectoryForCurrentUser
+        guard let url = chooseDirectory(startingAt: start) else { return }
+        TransportSettings.setOneDriveFolder(url)
+        try? FileManager.default.createDirectory(at: url, withIntermediateDirectories: true)
+        guard transport == .oneDrive else { return }
+        setFolderURLs(outbox: url, watch: url)
+        Task {
+            do {
+                try await watcher.updateWatchFolder(url)
+                setStatus("OneDrive folder set to \(url.lastPathComponent).")
+            } catch {
+                setStatus(
+                    (error as? ShotdeckError)?.errorDescription ?? "Could not switch the watch folder."
+                )
+            }
+        }
+    }
+
     private func chooseDirectory(startingAt directory: URL) -> URL? {
         let panel = NSOpenPanel()
         panel.canChooseDirectories = true