adds quick question UI for mac catalyst target

ios/Apps/Sybil/Info.plist

@@ -2,6 +2,9 @@
 <!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
 <plist version="1.0">
 <dict>
+	<!-- macOS-only: keep the global Quick Question shortcut available with no windows. -->
+	<key>NSSupportsAutomaticTermination</key>
+	<false/>
 	<key>UIApplicationShortcutItems</key>
 	<array>
 		<dict>

ios/Apps/Sybil/Sources/SybilApp.swift

@@ -8,7 +8,7 @@ struct SybilApp: App
     @UIApplicationDelegateAdaptor(SybilAppDelegate.self) private var appDelegate
 
     var body: some Scene {
-        WindowGroup {
+        WindowGroup(id: SybilCommands.workspaceWindowID) {
             SplitView()
         }
         .commands {
@@ -24,9 +24,18 @@ final class SybilAppDelegate: NSObject, UIApplicationDelegate {
         didFinishLaunchingWithOptions launchOptions: [UIApplication.LaunchOptionsKey: Any]? = nil
     ) -> Bool {
         SybilHomeScreenQuickActionHandler.configureQuickActions()
+        #if targetEnvironment(macCatalyst)
+        SybilMacQuickQuestionController.shared.start()
+        #endif
         return true
     }
 
+    #if targetEnvironment(macCatalyst)
+    func applicationWillTerminate(_ application: UIApplication) {
+        SybilMacQuickQuestionController.shared.stop()
+    }
+    #endif
+
     func application(
         _ application: UIApplication,
         configurationForConnecting connectingSceneSession: UISceneSession,
@@ -56,11 +65,22 @@ final class SybilSceneDelegate: NSObject, UIWindowSceneDelegate {
         willConnectTo session: UISceneSession,
         options connectionOptions: UIScene.ConnectionOptions
     ) {
+        #if targetEnvironment(macCatalyst)
+        if scene is UIWindowScene, session.role == .windowApplication {
+            SybilMacWindowCommands.shared.windowConnected(sessionID: session.persistentIdentifier)
+        }
+        #endif
         if let shortcutItem = connectionOptions.shortcutItem {
             _ = SybilHomeScreenQuickActionHandler.handle(shortcutItem)
         }
     }
 
+    #if targetEnvironment(macCatalyst)
+    func sceneDidDisconnect(_ scene: UIScene) {
+        SybilMacWindowCommands.shared.windowDisconnected(sessionID: scene.session.persistentIdentifier)
+    }
+    #endif
+
     func windowScene(
         _ windowScene: UIWindowScene,
         performActionFor shortcutItem: UIApplicationShortcutItem,

ios/Apps/Sybil/project.yml

@@ -11,6 +11,13 @@ targets:
     dependencies:
       - package: Sybil
         product: Sybil
+      - target: SybilMacQuickQuestion
+        destinationFilters: [macCatalyst]
+        embed: true
+        link: false
+        codeSign: true
+        copy:
+          destination: plugins
     settings:
       base:
         PRODUCT_BUNDLE_IDENTIFIER: net.buzzert.sybil2
@@ -29,6 +36,7 @@ targets:
         INFOPLIST_KEY_CFBundleDisplayName: Sybil
         INFOPLIST_KEY_ITSAppUsesNonExemptEncryption: NO
         INFOPLIST_KEY_UIApplicationSupportsIndirectInputEvents: YES
+        "INFOPLIST_KEY_UIApplicationSceneManifest_Generation[sdk=macosx*]": YES
         INFOPLIST_KEY_UILaunchScreen_Generation: YES
         INFOPLIST_KEY_UISupportedInterfaceOrientations_iPhone: UIInterfaceOrientationPortrait
         INFOPLIST_KEY_UISupportedInterfaceOrientations_iPad: UIInterfaceOrientationPortrait UIInterfaceOrientationPortraitUpsideDown UIInterfaceOrientationLandscapeLeft UIInterfaceOrientationLandscapeRight

ios/Apps/SybilMacQuickQuestion/Sources/MacQuickQuestionPlugin.swift

@@ -0,0 +1,229 @@
+import AppKit
+import Carbon
+
+// AppKit is unavailable to Catalyst targets. This native bundle uses only
+// public AppKit/Carbon APIs and communicates with the client through Foundation.
+@MainActor
+@objc(SybilMacQuickQuestionPlugin)
+final class MacQuickQuestionPlugin: NSObject, SybilQuickQuestionPanelBridging, NSWindowDelegate {
+    private weak var delegate: (any SybilQuickQuestionPanelDelegate)?
+    private var panel: QuickQuestionPanel?
+    private var panelView: QuickQuestionPanelView?
+    private var hotKey: EventHotKeyRef?
+    private var eventHandler: EventHandlerRef?
+    private var outsideClickMonitor: Any?
+    private var hotKeyState = SybilQuickQuestionHotKeyState()
+    private var isDismissing = false
+    private var shortcutAvailable = false
+    private var windowlessActivity: NSObjectProtocol?
+    private var latestState = SybilQuickQuestionPanelState()
+    private var previousApplication: NSRunningApplication?
+
+    required override init() {
+        super.init()
+    }
+
+    var isVisible: Bool { panel?.isVisible == true }
+
+    func start(delegate: any SybilQuickQuestionPanelDelegate) -> Int32 {
+        self.delegate = delegate
+        if windowlessActivity == nil {
+            // Keep the hotkey service alive with no windows. This option does
+            // not prevent sleep/App Nap or intercept an explicit Quit command.
+            windowlessActivity = ProcessInfo.processInfo.beginActivity(
+                options: .automaticTerminationDisabled,
+                reason: "Quick Question global shortcut"
+            )
+        }
+        guard eventHandler == nil else { return noErr }
+        var eventTypes = [
+            EventTypeSpec(eventClass: OSType(kEventClassKeyboard), eventKind: UInt32(kEventHotKeyPressed)),
+            EventTypeSpec(eventClass: OSType(kEventClassKeyboard), eventKind: UInt32(kEventHotKeyReleased))
+        ]
+        let context = Unmanaged.passUnretained(self).toOpaque()
+        let handlerStatus = InstallEventHandler(
+            GetApplicationEventTarget(),
+            { _, event, context in
+                guard let event, let context else { return OSStatus(eventNotHandledErr) }
+                var identifier = EventHotKeyID()
+                let status = GetEventParameter(
+                    event, EventParamName(kEventParamDirectObject), EventParamType(typeEventHotKeyID),
+                    nil, MemoryLayout<EventHotKeyID>.size, nil, &identifier
+                )
+                guard status == noErr, identifier.signature == 0x53595151, identifier.id == 1 else {
+                    return OSStatus(eventNotHandledErr)
+                }
+                let isKeyDown = GetEventKind(event) == UInt32(kEventHotKeyPressed)
+                let plugin = Unmanaged<MacQuickQuestionPlugin>.fromOpaque(context).takeUnretainedValue()
+                // Application event handlers run on the main event loop.
+                MainActor.assumeIsolated {
+                    if plugin.hotKeyState.shouldToggle(isKeyDown: isKeyDown) {
+                        plugin.delegate?.quickQuestionToggleRequested()
+                    }
+                }
+                return noErr
+            },
+            eventTypes.count, &eventTypes, context, &eventHandler
+        )
+        guard handlerStatus == noErr else { return handlerStatus }
+        let status = RegisterEventHotKey(
+            UInt32(kVK_Space), UInt32(optionKey),
+            EventHotKeyID(signature: 0x53595151, id: 1),
+            GetApplicationEventTarget(), 0, &hotKey
+        )
+        shortcutAvailable = status == noErr
+        return status
+    }
+
+    func updateState(_ data: Data) {
+        guard let state = try? JSONDecoder().decode(SybilQuickQuestionPanelState.self, from: data) else { return }
+        // Updating a background request must not create a non-hosting window.
+        // The controller creates/orders the panel only after UIKit is foreground.
+        latestState = state
+        panelView?.update(state, shortcutAvailable: shortcutAvailable)
+        if isVisible { resizePanel() }
+    }
+
+    func show() {
+        createPanelIfNeeded()
+        guard let panel, let panelView else { return }
+        panelView.update(latestState, shortcutAvailable: shortcutAvailable)
+        let screen = NSScreen.screens.first { $0.frame.contains(NSEvent.mouseLocation) } ?? NSScreen.main
+        let visibleFrame = screen?.visibleFrame ?? NSRect(x: 0, y: 0, width: 1280, height: 800)
+        let width = min(680, visibleFrame.width - 48)
+        panel.setContentSize(NSSize(width: width, height: 240))
+        panelView.layoutSubtreeIfNeeded()
+        let height = min(panelView.preferredHeight, visibleFrame.height - 64)
+        let top = visibleFrame.maxY - min(visibleFrame.height * 0.18, 160)
+        let y = max(visibleFrame.minY + 24, top - height)
+        panel.setFrame(NSRect(x: visibleFrame.midX - width / 2, y: y, width: width, height: height), display: true)
+        // The controller has verified UIKit foreground readiness. A
+        // nonactivating panel can then take focus without raising a workspace.
+        panel.makeKeyAndOrderFront(nil)
+        panel.makeFirstResponder(panelView.promptView)
+        panelView.preparePromptForPresentation()
+        installOutsideClickMonitor()
+    }
+
+    func hide() {
+        dismissPanel(restoringPreviousApplication: true)
+    }
+
+    func activateForQuickQuestion() {
+        if let frontmost = NSWorkspace.shared.frontmostApplication,
+           frontmost != NSRunningApplication.current {
+            previousApplication = frontmost
+        }
+        // Do not order a window here. Catalyst must finish its own foreground
+        // transition before the controller calls show().
+        NSApp.activate()
+    }
+
+    func activateMainWindow() {
+        // An explicit Open in Chat/Open Sybil action keeps focus in Sybil.
+        previousApplication = nil
+        NSApp.activate()
+        NSApp.windows.first { $0 !== panel && $0.canBecomeMain }?.makeKeyAndOrderFront(nil)
+    }
+
+    private func dismissPanel(restoringPreviousApplication: Bool) {
+        guard !isDismissing else { return }
+        let wasVisible = isVisible
+        isDismissing = true
+        if wasVisible { panel?.orderOut(nil) }
+        removeOutsideClickMonitor()
+        isDismissing = false
+        let applicationToRestore = previousApplication
+        previousApplication = nil
+        if restoringPreviousApplication, NSApp.isActive,
+           let applicationToRestore, !applicationToRestore.isTerminated {
+            NSApp.yieldActivation(to: applicationToRestore)
+            applicationToRestore.activate(options: [])
+        }
+        if wasVisible { delegate?.quickQuestionPanelDismissed() }
+    }
+
+    func stop() {
+        previousApplication = nil
+        hide()
+        removeOutsideClickMonitor()
+        if let hotKey { UnregisterEventHotKey(hotKey) }
+        if let eventHandler { RemoveEventHandler(eventHandler) }
+        hotKey = nil
+        eventHandler = nil
+        hotKeyState = SybilQuickQuestionHotKeyState()
+        if let windowlessActivity {
+            ProcessInfo.processInfo.endActivity(windowlessActivity)
+        }
+        windowlessActivity = nil
+        delegate = nil
+    }
+
+    func windowDidResignKey(_ notification: Notification) {
+        // Focus is already moving to a window/app the user chose.
+        dismissPanel(restoringPreviousApplication: false)
+    }
+
+    private func createPanelIfNeeded() {
+        guard panel == nil else { return }
+        let panel = QuickQuestionPanel(
+            contentRect: NSRect(x: 0, y: 0, width: 680, height: 240),
+            styleMask: [.borderless, .nonactivatingPanel], backing: .buffered, defer: false
+        )
+        panel.title = "Quick Question"
+        panel.level = .floating
+        panel.collectionBehavior = [.canJoinAllSpaces, .fullScreenAuxiliary, .transient, .ignoresCycle]
+        panel.isFloatingPanel = true
+        panel.hidesOnDeactivate = false
+        panel.becomesKeyOnlyIfNeeded = false
+        panel.worksWhenModal = true
+        panel.isReleasedWhenClosed = false
+        panel.isOpaque = false
+        panel.backgroundColor = .clear
+        panel.hasShadow = true
+        panel.isMovableByWindowBackground = true
+        panel.appearance = NSAppearance(named: .darkAqua)
+        panel.delegate = self
+        panel.onDismiss = { [weak self] in self?.hide() }
+        let view = QuickQuestionPanelView()
+        view.delegate = delegate
+        view.onDismiss = { [weak self] in self?.hide() }
+        panel.contentView = view
+        panelView = view
+        self.panel = panel
+    }
+
+    private func resizePanel() {
+        guard let panel, let panelView else { return }
+        panelView.layoutSubtreeIfNeeded()
+        let visibleFrame = panel.screen?.visibleFrame ?? panel.frame
+        let height = min(panelView.preferredHeight, visibleFrame.height - 64)
+        guard abs(height - panel.frame.height) > 1 else { return }
+        var frame = panel.frame
+        frame.origin.y = max(visibleFrame.minY + 24, frame.maxY - height)
+        frame.size.height = height
+        panel.setFrame(frame, display: true)
+    }
+
+    private func installOutsideClickMonitor() {
+        guard outsideClickMonitor == nil else { return }
+        // Mouse-only monitoring does not require Accessibility or Input
+        // Monitoring permission. No global keyboard event tap is installed.
+        outsideClickMonitor = NSEvent.addGlobalMonitorForEvents(matching: [.leftMouseDown, .rightMouseDown]) { [weak self] _ in
+            Task { @MainActor [weak self] in self?.hide() }
+        }
+    }
+
+    private func removeOutsideClickMonitor() {
+        if let outsideClickMonitor { NSEvent.removeMonitor(outsideClickMonitor) }
+        outsideClickMonitor = nil
+    }
+}
+
+@MainActor
+private final class QuickQuestionPanel: NSPanel {
+    var onDismiss: (() -> Void)?
+    override var canBecomeKey: Bool { true }
+    override var canBecomeMain: Bool { false }
+    override func cancelOperation(_ sender: Any?) { onDismiss?() }
+}

ios/Apps/SybilMacQuickQuestion/Sources/QuickQuestionPanelView.swift

@@ -0,0 +1,300 @@
+import AppKit
+
+@MainActor
+final class QuickQuestionPanelView: NSVisualEffectView, NSTextViewDelegate {
+    weak var delegate: (any SybilQuickQuestionPanelDelegate)?
+    var onDismiss: (() -> Void)?
+
+    let promptView = QuickQuestionPromptView()
+    private let stack = NSStackView()
+    private let answerView = NSTextView()
+    private let answerScroll = NSScrollView()
+    private let statusLabel = NSTextField(wrappingLabelWithString: "")
+    private let providerPopup = NSPopUpButton()
+    private let modelPopup = NSPopUpButton()
+    private let convertButton = NSButton(title: "Open in Chat", target: nil, action: nil)
+    private let openAppButton = NSButton(title: "Open Sybil", target: nil, action: nil)
+    private let sendButton = NSButton()
+    private let shortcutLabel = NSTextField(labelWithString: "⌥ Space")
+    private var panelState = SybilQuickQuestionPanelState()
+
+    var preferredHeight: CGFloat { stack.fittingSize.height + 40 }
+
+    override init(frame frameRect: NSRect) {
+        super.init(frame: frameRect)
+        material = .hudWindow
+        blendingMode = .behindWindow
+        state = .active
+        wantsLayer = true
+        layer?.cornerRadius = 18
+        layer?.masksToBounds = true
+        layer?.borderWidth = 1
+        layer?.borderColor = NSColor.white.withAlphaComponent(0.14).cgColor
+
+        stack.orientation = .vertical
+        stack.alignment = .leading
+        stack.spacing = 12
+        stack.detachesHiddenViews = true
+        stack.translatesAutoresizingMaskIntoConstraints = false
+        addSubview(stack)
+        NSLayoutConstraint.activate([
+            stack.leadingAnchor.constraint(equalTo: leadingAnchor, constant: 20),
+            stack.trailingAnchor.constraint(equalTo: trailingAnchor, constant: -20),
+            stack.topAnchor.constraint(equalTo: topAnchor, constant: 20),
+            stack.bottomAnchor.constraint(equalTo: bottomAnchor, constant: -20)
+        ])
+
+        addRow(makeHeader())
+        configureTextView(promptView, fontSize: 22)
+        promptView.delegate = self
+        promptView.isRichText = false
+        promptView.allowsUndo = true
+        promptView.setAccessibilityLabel("Quick question prompt")
+        promptView.onSubmit = { [weak self] in self?.submit() }
+        promptView.onToggle = { [weak self] in self?.delegate?.quickQuestionToggleRequested() }
+        let promptScroll = makeScrollView(documentView: promptView)
+        promptScroll.heightAnchor.constraint(equalToConstant: 64).isActive = true
+        addRow(promptScroll)
+
+        configureTextView(answerView, fontSize: 15)
+        answerView.isEditable = false
+        answerView.isSelectable = true
+        answerView.setAccessibilityLabel("Quick question answer")
+        answerView.linkTextAttributes = [.foregroundColor: NSColor.systemPurple, .underlineStyle: NSUnderlineStyle.single.rawValue]
+        answerScroll.drawsBackground = false
+        answerScroll.hasVerticalScroller = true
+        answerScroll.autohidesScrollers = true
+        answerScroll.documentView = answerView
+        answerScroll.heightAnchor.constraint(equalToConstant: 280).isActive = true
+        addRow(answerScroll)
+
+        statusLabel.font = .systemFont(ofSize: 12)
+        statusLabel.textColor = .secondaryLabelColor
+        statusLabel.maximumNumberOfLines = 3
+        addRow(statusLabel)
+        addRow(makeControls())
+        let hint = NSTextField(labelWithString: "Return to ask   ·   Shift+Return for a new line   ·   Esc to close")
+        hint.font = .systemFont(ofSize: 11)
+        hint.textColor = .secondaryLabelColor
+        addRow(hint)
+        update(SybilQuickQuestionPanelState(), shortcutAvailable: true)
+    }
+
+    required init?(coder: NSCoder) { fatalError("init(coder:) has not been implemented") }
+
+    func update(_ next: SybilQuickQuestionPanelState, shortcutAvailable: Bool) {
+        let previous = panelState
+        panelState = next
+        if promptView.string != next.prompt, !promptView.hasMarkedText() {
+            promptView.string = next.prompt
+            promptView.setSelectedRange(NSRange(location: (next.prompt as NSString).length, length: 0))
+        }
+        promptView.isEditable = !next.isBusy
+        promptView.needsDisplay = true
+        if previous.answer != next.answer {
+            let wasAtBottom = answerScroll.contentView.bounds.maxY >= answerView.bounds.maxY - 36
+            answerView.textStorage?.setAttributedString(Self.renderAnswer(next.answer))
+            if wasAtBottom { answerView.scrollToEndOfDocument(nil) }
+        }
+        answerScroll.isHidden = next.answer.isEmpty
+
+        if providerPopup.numberOfItems == 0 || previous.providers != next.providers {
+            providerPopup.removeAllItems()
+            for provider in next.providers {
+                providerPopup.addItem(withTitle: provider.title)
+                providerPopup.lastItem?.representedObject = provider.id
+            }
+        }
+        if let index = next.providers.firstIndex(where: { $0.id == next.provider }) {
+            providerPopup.selectItem(at: index)
+        }
+        if modelPopup.numberOfItems == 0 || previous.models != next.models || previous.model != next.model {
+            modelPopup.removeAllItems()
+            var models = next.models
+            if !next.model.isEmpty, !models.contains(next.model) { models.insert(next.model, at: 0) }
+            modelPopup.addItems(withTitles: models)
+            modelPopup.selectItem(withTitle: next.model)
+        }
+        providerPopup.isEnabled = next.isAuthenticated && !next.isBusy
+        modelPopup.isEnabled = next.isAuthenticated && !next.isBusy
+        convertButton.isEnabled = next.canConvert
+        sendButton.isEnabled = next.canSend
+        openAppButton.isHidden = next.isAuthenticated
+        convertButton.isHidden = !next.isAuthenticated
+        shortcutLabel.stringValue = shortcutAvailable ? "⌥ Space" : "Shortcut unavailable"
+        shortcutLabel.toolTip = shortcutAvailable ? "Option+Space toggles Quick Question" : "Another app may be using Option+Space. Open Quick Question from Sybil’s File menu."
+
+        let status: String
+        if let error = next.error {
+            status = error
+            statusLabel.textColor = .systemRed
+        } else {
+            statusLabel.textColor = .secondaryLabelColor
+            if next.isCheckingSession {
+                status = "Connecting to Sybil…"
+            } else if !next.isAuthenticated {
+                status = "Connect in Sybil before asking a question."
+            } else if next.isConverting {
+                status = "Opening in chat…"
+            } else if next.isSending {
+                status = next.toolSummaries.last ?? "Thinking…"
+            } else {
+                status = ""
+            }
+        }
+        statusLabel.stringValue = status
+        statusLabel.isHidden = status.isEmpty
+    }
+
+    func preparePromptForPresentation() {
+        // Select only when invoked, never on streamed updates or normal edits.
+        promptView.selectAll(nil)
+    }
+
+    func textDidChange(_ notification: Notification) {
+        guard !panelState.isBusy else { return }
+        promptView.needsDisplay = true
+        delegate?.quickQuestionPromptChanged(promptView.string)
+    }
+
+    private func addRow(_ view: NSView) {
+        stack.addArrangedSubview(view)
+        view.widthAnchor.constraint(equalTo: stack.widthAnchor).isActive = true
+    }
+
+    private func makeHeader() -> NSView {
+        let icon = NSImageView(image: NSImage(systemSymbolName: "sparkles", accessibilityDescription: nil)!)
+        icon.contentTintColor = .systemPurple
+        icon.widthAnchor.constraint(equalToConstant: 18).isActive = true
+        let title = NSTextField(labelWithString: "Quick Question")
+        title.font = .systemFont(ofSize: 14, weight: .semibold)
+        shortcutLabel.font = .monospacedSystemFont(ofSize: 11, weight: .medium)
+        shortcutLabel.textColor = .secondaryLabelColor
+        let close = NSButton(image: NSImage(systemSymbolName: "xmark", accessibilityDescription: "Close Quick Question")!, target: self, action: #selector(closePanel))
+        close.isBordered = false
+        close.toolTip = "Close (Esc)"
+        close.setAccessibilityLabel("Close Quick Question")
+        close.widthAnchor.constraint(equalToConstant: 24).isActive = true
+        let row = NSStackView(views: [icon, title, NSView(), shortcutLabel, close])
+        row.spacing = 8
+        row.alignment = .centerY
+        row.heightAnchor.constraint(equalToConstant: 24).isActive = true
+        return row
+    }
+
+    private func makeControls() -> NSView {
+        providerPopup.target = self
+        providerPopup.action = #selector(changeProvider)
+        providerPopup.setAccessibilityLabel("Quick question provider")
+        providerPopup.widthAnchor.constraint(equalToConstant: 120).isActive = true
+        modelPopup.target = self
+        modelPopup.action = #selector(changeModel)
+        modelPopup.setAccessibilityLabel("Quick question model")
+        modelPopup.widthAnchor.constraint(lessThanOrEqualToConstant: 230).isActive = true
+        modelPopup.setContentCompressionResistancePriority(.defaultLow, for: .horizontal)
+        convertButton.target = self
+        convertButton.action = #selector(convertToChat)
+        convertButton.bezelStyle = .rounded
+        openAppButton.target = self
+        openAppButton.action = #selector(openApp)
+        openAppButton.bezelStyle = .rounded
+        sendButton.image = NSImage(systemSymbolName: "arrow.up", accessibilityDescription: "Ask Quick Question")
+        sendButton.imagePosition = .imageOnly
+        sendButton.bezelStyle = .circular
+        sendButton.contentTintColor = .systemPurple
+        sendButton.target = self
+        sendButton.action = #selector(submit)
+        sendButton.setAccessibilityLabel("Ask Quick Question")
+        sendButton.toolTip = "Ask (Return)"
+        sendButton.widthAnchor.constraint(equalToConstant: 32).isActive = true
+        let row = NSStackView(views: [providerPopup, modelPopup, NSView(), openAppButton, convertButton, sendButton])
+        row.spacing = 8
+        row.alignment = .centerY
+        row.detachesHiddenViews = true
+        row.heightAnchor.constraint(equalToConstant: 32).isActive = true
+        return row
+    }
+
+    private func configureTextView(_ view: NSTextView, fontSize: CGFloat) {
+        view.drawsBackground = false
+        view.textColor = .labelColor
+        view.insertionPointColor = .labelColor
+        view.font = .systemFont(ofSize: fontSize)
+        view.textContainerInset = NSSize(width: 0, height: 4)
+        view.isHorizontallyResizable = false
+        view.isVerticallyResizable = true
+        view.autoresizingMask = [.width]
+        view.textContainer?.widthTracksTextView = true
+        view.textContainer?.lineFragmentPadding = 0
+    }
+
+    private func makeScrollView(documentView: NSView) -> NSScrollView {
+        let scroll = NSScrollView()
+        scroll.drawsBackground = false
+        scroll.hasVerticalScroller = true
+        scroll.autohidesScrollers = true
+        scroll.documentView = documentView
+        return scroll
+    }
+
+    private static func renderAnswer(_ text: String) -> NSAttributedString {
+        let parsed = (try? AttributedString(markdown: text, options: .init(interpretedSyntax: .inlineOnlyPreservingWhitespace))) ?? AttributedString(text)
+        let rendered = NSMutableAttributedString(attributedString: NSAttributedString(parsed))
+        let paragraph = NSMutableParagraphStyle()
+        paragraph.lineSpacing = 4
+        rendered.addAttributes([.foregroundColor: NSColor.labelColor, .paragraphStyle: paragraph], range: NSRange(location: 0, length: rendered.length))
+        for run in parsed.runs {
+            let intent = run.inlinePresentationIntent ?? []
+            var font = intent.contains(.code) ? NSFont.monospacedSystemFont(ofSize: 14, weight: .regular) : NSFont.systemFont(ofSize: 15)
+            if intent.contains(.stronglyEmphasized) { font = NSFontManager.shared.convert(font, toHaveTrait: .boldFontMask) }
+            if intent.contains(.emphasized) { font = NSFontManager.shared.convert(font, toHaveTrait: .italicFontMask) }
+            rendered.addAttribute(.font, value: font, range: NSRange(run.range, in: parsed))
+        }
+        return rendered
+    }
+
+    @objc private func closePanel() { onDismiss?() }
+    @objc private func changeProvider() {
+        guard let provider = providerPopup.selectedItem?.representedObject as? String else { return }
+        delegate?.quickQuestionProviderChanged(provider)
+    }
+    @objc private func changeModel() {
+        guard let model = modelPopup.titleOfSelectedItem else { return }
+        delegate?.quickQuestionModelChanged(model)
+    }
+    @objc private func convertToChat() { delegate?.quickQuestionConvertRequested() }
+    @objc private func openApp() { delegate?.quickQuestionOpenAppRequested() }
+    @objc private func submit() {
+        guard panelState.canSend, !promptView.hasMarkedText() else { return }
+        delegate?.quickQuestionSubmitRequested()
+    }
+}
+
+@MainActor
+final class QuickQuestionPromptView: NSTextView {
+    var onSubmit: (() -> Void)?
+    var onToggle: (() -> Void)?
+
+    override func draw(_ dirtyRect: NSRect) {
+        super.draw(dirtyRect)
+        guard string.isEmpty else { return }
+        ("Ask anything…" as NSString).draw(
+            at: NSPoint(x: textContainerInset.width, y: textContainerInset.height),
+            withAttributes: [.font: font ?? NSFont.systemFont(ofSize: 22), .foregroundColor: NSColor.placeholderTextColor]
+        )
+    }
+
+    override func keyDown(with event: NSEvent) {
+        let modifiers = event.modifierFlags.intersection([.command, .control, .option, .shift])
+        if event.keyCode == 49, modifiers == .option {
+            if !event.isARepeat { onToggle?() }
+            return
+        }
+        if (event.keyCode == 36 || event.keyCode == 76), modifiers.isEmpty, !hasMarkedText() {
+            if !event.isARepeat { onSubmit?() }
+            return
+        }
+        // Let the text input system handle Shift+Return and IME confirmation.
+        super.keyDown(with: event)
+    }
+}

ios/Apps/SybilMacQuickQuestion/project.yml

@@ -0,0 +1,25 @@
+targets:
+  SybilMacQuickQuestion:
+    type: bundle
+    platform: macOS
+    deploymentTarget: "15.0"
+    sources:
+      - Sources
+      - ../../Packages/Sybil/Sources/Sybil/SybilMacQuickQuestionBridge.swift
+    dependencies:
+      - sdk: AppKit.framework
+      - sdk: Carbon.framework
+    settings:
+      base:
+        PRODUCT_BUNDLE_IDENTIFIER: net.buzzert.sybil2.quick-question-panel
+        PRODUCT_NAME: SybilMacQuickQuestion
+        PRODUCT_MODULE_NAME: SybilMacQuickQuestion
+        DEVELOPMENT_TEAM: DQQH5H6GBD
+        CODE_SIGN_STYLE: Automatic
+        SWIFT_VERSION: 6.0
+        SUPPORTS_MACCATALYST: NO
+        GENERATE_INFOPLIST_FILE: YES
+        INFOPLIST_KEY_CFBundleExecutable: $(EXECUTABLE_NAME)
+        INFOPLIST_KEY_NSPrincipalClass: SybilMacQuickQuestionPlugin
+        MACH_O_TYPE: mh_bundle
+        SKIP_INSTALL: YES

ios/Packages/Sybil/Sources/Sybil/SplitView.swift

@@ -78,6 +78,7 @@ public struct SplitView: View {
         .font(.sybil(.body))
         .preferredColorScheme(.dark)
         .focusedSceneValue(\.sybilKeyboardActions, keyboardActions)
+        #if !targetEnvironment(macCatalyst)
         .sheet(isPresented: $isQuickQuestionPresented, onDismiss: handleQuickQuestionDismissed) {
             SybilQuickQuestionView(
                 viewModel: viewModel,
@@ -85,7 +86,11 @@ public struct SplitView: View {
             )
             .presentationDragIndicator(.visible)
         }
+        #endif
         .task {
+            #if targetEnvironment(macCatalyst)
+            SybilMacQuickQuestionController.shared.attach(viewModel)
+            #endif
             await viewModel.bootstrap()
             presentPendingQuickQuestionIfPossible()
         }
@@ -107,6 +112,9 @@ public struct SplitView: View {
                 shouldRefreshOnForeground = true
                 viewModel.markAppInactiveForNetwork()
             case .active:
+                #if targetEnvironment(macCatalyst)
+                SybilMacQuickQuestionController.shared.attach(viewModel)
+                #endif
                 viewModel.markAppActiveForNetwork()
                 guard shouldRefreshOnForeground, horizontalSizeClass != .compact else {
                     return
@@ -151,8 +159,13 @@ public struct SplitView: View {
         }
 
         hasPendingQuickQuestionPresentation = false
+        #if targetEnvironment(macCatalyst)
+        SybilMacQuickQuestionController.shared.attach(viewModel)
+        SybilMacQuickQuestionController.shared.show()
+        #else
         quickQuestionFocusRequest += 1
         isQuickQuestionPresented = true
+        #endif
     }
 
     private func handleQuickQuestionDismissed() {
@@ -161,23 +174,57 @@ public struct SplitView: View {
 }
 
 public struct SybilCommands: Commands {
+    public static let workspaceWindowID = "sybil-workspace"
+
     @FocusedValue(\.sybilKeyboardActions) private var keyboardActions
+    #if targetEnvironment(macCatalyst)
+    @Environment(\.openWindow) private var openWindow
+    @ObservedObject private var windowCommands = SybilMacWindowCommands.shared
+    #endif
 
     public init() {}
 
     public var body: some Commands {
         CommandGroup(replacing: .newItem) {
             Button("New Chat") {
+                #if targetEnvironment(macCatalyst)
+                windowCommands.newChatOrWindow(
+                    newChat: keyboardActions?.newChat,
+                    openWindow: openNewWindow
+                )
+                #else
                 keyboardActions?.newChat()
+                #endif
             }
             .keyboardShortcut("n", modifiers: .command)
+            #if targetEnvironment(macCatalyst)
+            .disabled(!windowCommands.canStartNewChat(hasFocusedActions: keyboardActions != nil))
+            #else
             .disabled(keyboardActions == nil)
+            #endif
+
+            #if targetEnvironment(macCatalyst)
+            Button("New Window", action: openNewWindow)
+                .keyboardShortcut("n", modifiers: [.command, .shift])
+            #endif
 
             Button("New Search") {
                 keyboardActions?.newSearch()
             }
+            #if targetEnvironment(macCatalyst)
+            .keyboardShortcut("n", modifiers: [.command, .option])
+            #else
             .keyboardShortcut("n", modifiers: [.command, .shift])
+            #endif
             .disabled(keyboardActions == nil)
+
+            #if targetEnvironment(macCatalyst)
+            Divider()
+            Button("Quick Question") {
+                SybilMacQuickQuestionController.shared.toggle()
+            }
+            .keyboardShortcut(.space, modifiers: .option)
+            #endif
         }
 
         CommandMenu("Conversation") {
@@ -194,6 +241,13 @@ public struct SybilCommands: Commands {
             .disabled(keyboardActions == nil)
         }
     }
+    #if targetEnvironment(macCatalyst)
+    private func openNewWindow() {
+        // Targeting a WindowGroup without a value creates a fresh scene every
+        // time, even when another workspace window is already open.
+        openWindow(id: Self.workspaceWindowID)
+    }
+    #endif
 }
 
 private struct SybilKeyboardActions {

ios/Packages/Sybil/Sources/Sybil/SybilMacQuickQuestionBridge.swift

@@ -0,0 +1,71 @@
+import Foundation
+
+// This Foundation-only contract is compiled into both the Catalyst client and the
+// native macOS bundle. Only Objective-C-compatible values cross the bundle boundary.
+@MainActor
+@objc(SybilQuickQuestionPanelBridging)
+protocol SybilQuickQuestionPanelBridging: NSObjectProtocol {
+    init()
+    var isVisible: Bool { get }
+    func start(delegate: any SybilQuickQuestionPanelDelegate) -> Int32
+    func updateState(_ data: Data)
+    func show()
+    func hide()
+    func activateForQuickQuestion()
+    func activateMainWindow()
+    func stop()
+}
+
+@MainActor
+@objc(SybilQuickQuestionPanelDelegate)
+protocol SybilQuickQuestionPanelDelegate: NSObjectProtocol {
+    func quickQuestionToggleRequested()
+    func quickQuestionPromptChanged(_ prompt: String)
+    func quickQuestionSubmitRequested()
+    func quickQuestionProviderChanged(_ provider: String)
+    func quickQuestionModelChanged(_ model: String)
+    func quickQuestionConvertRequested()
+    func quickQuestionOpenAppRequested()
+    func quickQuestionPanelDismissed()
+}
+
+struct SybilQuickQuestionPanelState: Codable, Equatable, Sendable {
+    struct ProviderOption: Codable, Equatable, Sendable {
+        var id: String
+        var title: String
+    }
+
+    var prompt = ""
+    var answer = ""
+    var toolSummaries: [String] = []
+    var provider = ""
+    var providers: [ProviderOption] = []
+    var model = ""
+    var models: [String] = []
+    var isSending = false
+    var isConverting = false
+    var canSend = false
+    var canConvert = false
+    var isAuthenticated = false
+    var isCheckingSession = true
+    var error: String?
+
+    var isBusy: Bool { isSending || isConverting }
+    var hasResponse: Bool { !answer.isEmpty || !toolSummaries.isEmpty || isSending || error != nil }
+}
+
+// Carbon can deliver multiple presses while a key is held. Consume one toggle
+// per press/release pair, without suppressing a second deliberate press.
+struct SybilQuickQuestionHotKeyState {
+    private var isPressed = false
+
+    mutating func shouldToggle(isKeyDown: Bool) -> Bool {
+        if !isKeyDown {
+            isPressed = false
+            return false
+        }
+        guard !isPressed else { return false }
+        isPressed = true
+        return true
+    }
+}

ios/Packages/Sybil/Sources/Sybil/SybilMacQuickQuestionController.swift

@@ -0,0 +1,257 @@
+#if targetEnvironment(macCatalyst)
+import Combine
+import Foundation
+import Observation
+import UIKit
+
+@MainActor
+public final class SybilMacQuickQuestionController: NSObject, SybilQuickQuestionPanelDelegate {
+    public static let shared = SybilMacQuickQuestionController()
+
+    private var pluginBundle: Bundle?
+    private var bridge: (any SybilQuickQuestionPanelBridging)?
+    private var viewModel: SybilViewModel?
+    private var observationGeneration = 0
+    private var isPresentationRequested = false
+    private var activationRequested = false
+    private var presentationTask: Task<Void, Never>?
+    private var foregroundObservation: AnyCancellable?
+    private var notificationCenter = NotificationCenter.default
+    private var isApplicationInForeground: @MainActor () -> Bool = {
+        UIApplication.shared.applicationState != .background
+    }
+
+    private override init() {
+        super.init()
+    }
+
+    // Inject foreground readiness as well as the panel so tests can exercise
+    // windowless activation without activating apps or showing real windows.
+    init(
+        bridge: any SybilQuickQuestionPanelBridging,
+        isApplicationInForeground: @escaping @MainActor () -> Bool = { true },
+        notificationCenter: NotificationCenter = NotificationCenter()
+    ) {
+        self.bridge = bridge
+        self.isApplicationInForeground = isApplicationInForeground
+        self.notificationCenter = notificationCenter
+        super.init()
+        _ = bridge.start(delegate: self)
+        observeForegroundTransitionsIfNeeded()
+    }
+
+    public func start() {
+        observeForegroundTransitionsIfNeeded()
+        guard bridge == nil else { return }
+        guard let url = Bundle.main.builtInPlugInsURL?.appendingPathComponent("SybilMacQuickQuestion.bundle"),
+              let bundle = Bundle(url: url)
+        else {
+            SybilLog.error(SybilLog.app, "The macOS Quick Question bundle is missing.")
+            return
+        }
+
+        do {
+            try bundle.loadAndReturnError()
+            guard let pluginClass = bundle.principalClass as? any SybilQuickQuestionPanelBridging.Type else {
+                SybilLog.error(SybilLog.app, "The macOS Quick Question bundle has an invalid principal class.")
+                return
+            }
+            let plugin = pluginClass.init()
+            pluginBundle = bundle
+            bridge = plugin
+            let status = plugin.start(delegate: self)
+            if status != 0 {
+                SybilLog.warning(SybilLog.app, "Option+Space could not be registered (status \(status)). Quick Question remains available in the app menu.")
+            }
+        } catch {
+            SybilLog.error(SybilLog.app, "Could not load the macOS Quick Question panel", error: error)
+        }
+    }
+
+    func attach(_ viewModel: SybilViewModel) {
+        guard self.viewModel !== viewModel else { return }
+        // A window becoming active must not replace an in-flight quick question.
+        if self.viewModel != nil,
+           isPresentationRequested || bridge?.isVisible == true || self.viewModel?.isQuickQuestionSending == true || self.viewModel?.isConvertingQuickQuestion == true {
+            return
+        }
+        self.viewModel = viewModel
+        if bridge?.isVisible == true { updateAndObserve() }
+    }
+
+    public func toggle() {
+        start()
+        if isPresentationRequested || bridge?.isVisible == true {
+            cancelPresentation()
+            bridge?.hide()
+        } else {
+            show()
+        }
+    }
+
+    public func show() {
+        start()
+        isPresentationRequested = true
+        schedulePresentationIfNeeded()
+    }
+
+    public func stop() {
+        cancelPresentation()
+        foregroundObservation = nil
+        viewModel?.cancelQuickQuestion()
+        bridge?.stop()
+        bridge = nil
+        // Keep the loaded bundle alive for the lifetime of its code.
+    }
+
+    private func observeForegroundTransitionsIfNeeded() {
+        guard foregroundObservation == nil else { return }
+        foregroundObservation = notificationCenter.publisher(for: UIApplication.willEnterForegroundNotification)
+            .merge(with: notificationCenter.publisher(for: UIApplication.didBecomeActiveNotification))
+            .sink { [weak self] _ in
+                Task { @MainActor [weak self] in
+                    self?.schedulePresentationIfNeeded()
+                }
+            }
+    }
+
+    private func schedulePresentationIfNeeded() {
+        guard isPresentationRequested, bridge?.isVisible != true, presentationTask == nil else { return }
+        // Leave the Carbon/NSApplication event callback before touching windows.
+        // AppKit activation is asynchronous; an arbitrary delay or NSApp.isActive
+        // is not a substitute for checking UIKit's foreground lifecycle state.
+        presentationTask = Task { @MainActor [weak self] in
+            guard let self, !Task.isCancelled else { return }
+            self.presentationTask = nil
+            guard self.isPresentationRequested else { return }
+            guard self.isApplicationInForeground() else {
+                guard !self.activationRequested else { return }
+                self.activationRequested = true
+                SybilLog.debug(SybilLog.ui, "Waiting for Catalyst foreground before showing Quick Question")
+                self.bridge?.activateForQuickQuestion()
+                // Also handle an activation that completes synchronously. If it
+                // has not completed, subsequent UIKit notifications resume us.
+                self.schedulePresentationIfNeeded()
+                return
+            }
+            self.activationRequested = false
+            self.updateAndObserve()
+            self.bridge?.show()
+        }
+    }
+
+    private func cancelPresentation() {
+        isPresentationRequested = false
+        activationRequested = false
+        presentationTask?.cancel()
+        presentationTask = nil
+        observationGeneration += 1
+    }
+
+    private func updateAndObserve() {
+        guard let bridge else { return }
+        observationGeneration += 1
+        let generation = observationGeneration
+        let state = withObservationTracking {
+            viewModel?.macQuickQuestionPanelState ?? SybilQuickQuestionPanelState()
+        } onChange: { [weak self] in
+            Task { @MainActor [weak self] in
+                guard let self, self.observationGeneration == generation, self.bridge?.isVisible == true else { return }
+                self.updateAndObserve()
+            }
+        }
+        do {
+            bridge.updateState(try JSONEncoder().encode(state))
+        } catch {
+            SybilLog.error(SybilLog.ui, "Could not update the macOS Quick Question panel", error: error)
+        }
+    }
+
+    func quickQuestionToggleRequested() {
+        toggle()
+    }
+
+    func quickQuestionPromptChanged(_ prompt: String) {
+        guard let viewModel, !viewModel.isQuickQuestionSending, !viewModel.isConvertingQuickQuestion else { return }
+        viewModel.updateQuickQuestionPrompt(prompt)
+        updateAndObserve()
+    }
+
+    func quickQuestionSubmitRequested() {
+        guard let viewModel, viewModel.isAuthenticated, !viewModel.isCheckingSession else { return }
+        viewModel.sendQuickQuestion()
+        updateAndObserve()
+    }
+
+    func quickQuestionProviderChanged(_ provider: String) {
+        guard let viewModel, let provider = Provider(rawValue: provider),
+              !viewModel.isQuickQuestionSending, !viewModel.isConvertingQuickQuestion else { return }
+        viewModel.setQuickQuestionProvider(provider)
+        updateAndObserve()
+    }
+
+    func quickQuestionModelChanged(_ model: String) {
+        guard let viewModel, !viewModel.isQuickQuestionSending, !viewModel.isConvertingQuickQuestion else { return }
+        viewModel.setQuickQuestionModel(model)
+        updateAndObserve()
+    }
+
+    func quickQuestionConvertRequested() {
+        guard let viewModel, viewModel.canConvertQuickQuestion else { return }
+        Task { @MainActor [weak self] in
+            guard let self else { return }
+            if await viewModel.convertQuickQuestionToChat() {
+                self.cancelPresentation()
+                self.openMainWindow()
+                self.bridge?.hide()
+            } else {
+                self.updateAndObserve()
+            }
+        }
+    }
+
+    func quickQuestionOpenAppRequested() {
+        cancelPresentation()
+        openMainWindow()
+        bridge?.hide()
+    }
+
+    private func openMainWindow() {
+        let session = UIApplication.shared.connectedScenes
+            .compactMap { $0 as? UIWindowScene }
+            .first?.session
+        UIApplication.shared.requestSceneSessionActivation(session, userActivity: nil, options: nil)
+        bridge?.activateMainWindow()
+    }
+
+    func quickQuestionPanelDismissed() {
+        // Toggling out preserves the draft and lets an answer finish. Reopening
+        // reads the latest state, without starting a new request.
+        cancelPresentation()
+    }
+}
+
+extension SybilViewModel {
+    var macQuickQuestionPanelState: SybilQuickQuestionPanelState {
+        SybilQuickQuestionPanelState(
+            prompt: quickQuestionPrompt,
+            answer: quickQuestionAnswerText,
+            toolSummaries: quickQuestionMessages.compactMap { message in
+                guard let metadata = message.toolCallMetadata else { return nil }
+                return metadata.summary ?? message.content
+            },
+            provider: quickQuestionProvider.rawValue,
+            providers: providerOptions.map { .init(id: $0.rawValue, title: $0.displayName) },
+            model: quickQuestionModel,
+            models: quickQuestionProviderModelOptions,
+            isSending: isQuickQuestionSending,
+            isConverting: isConvertingQuickQuestion,
+            canSend: isAuthenticated && !isCheckingSession && canSendQuickQuestion,
+            canConvert: canConvertQuickQuestion,
+            isAuthenticated: isAuthenticated,
+            isCheckingSession: isCheckingSession,
+            error: quickQuestionError
+        )
+    }
+}
+#endif

ios/Packages/Sybil/Sources/Sybil/SybilMacWindowCommands.swift

@@ -0,0 +1,37 @@
+#if targetEnvironment(macCatalyst)
+import Combine
+
+// Scene lifetime is independent of focused commands: a connected window may
+// still be authenticating, inactive, or minimized. The native Quick Question
+// panel is not a workspace scene and does not count as an open window here.
+@MainActor
+public final class SybilMacWindowCommands: ObservableObject {
+    public static let shared = SybilMacWindowCommands()
+
+    @Published private var connectedWindowIDs: Set<String> = []
+
+    init() {}
+
+    var hasOpenWindows: Bool { !connectedWindowIDs.isEmpty }
+
+    public func windowConnected(sessionID: String) {
+        connectedWindowIDs.insert(sessionID)
+    }
+
+    public func windowDisconnected(sessionID: String) {
+        connectedWindowIDs.remove(sessionID)
+    }
+
+    func canStartNewChat(hasFocusedActions: Bool) -> Bool {
+        !hasOpenWindows || hasFocusedActions
+    }
+
+    func newChatOrWindow(newChat: (() -> Void)?, openWindow: () -> Void) {
+        if hasOpenWindows {
+            newChat?()
+        } else {
+            openWindow()
+        }
+    }
+}
+#endif

ios/Packages/Sybil/Sources/Sybil/SybilQuickQuestionView.swift

@@ -8,6 +8,7 @@ struct SybilQuickQuestionView: View {
 
     @Environment(\.dismiss) private var dismiss
     @FocusState private var promptFocused: Bool
+    @State private var promptSelection: TextSelection?
 
     private var hasAnswerContent: Bool {
         !viewModel.quickQuestionMessages.isEmpty || viewModel.quickQuestionError != nil
@@ -36,6 +37,8 @@ struct SybilQuickQuestionView: View {
                 return
             }
             promptFocused = true
+            let prompt = viewModel.quickQuestionPrompt
+            promptSelection = TextSelection(range: prompt.startIndex..<prompt.endIndex)
         }
     }
 
@@ -94,6 +97,7 @@ struct SybilQuickQuestionView: View {
                         get: { viewModel.quickQuestionPrompt },
                         set: { viewModel.updateQuickQuestionPrompt($0) }
                     ),
+                    selection: $promptSelection,
                     axis: .vertical
                 )
                 .focused($promptFocused)

ios/Packages/Sybil/Sources/Sybil/SybilReturnKeySubmission.swift

@@ -0,0 +1,35 @@
+import SwiftUI
+
+// A vertical TextField treats Return as editing, not form submission. Handle
+// unmodified Return explicitly on Mac, leaving Shift+Return and other modified
+// keys to the native text field. iOS keeps its software-keyboard behavior.
+@MainActor
+enum SybilReturnKeySubmission {
+    static func handle(
+        phase: KeyPress.Phases,
+        modifiers: EventModifiers,
+        submit: () -> Void
+    ) -> KeyPress.Result {
+        guard modifiers.intersection([.shift, .command, .control, .option]).isEmpty else {
+            return .ignored
+        }
+        if phase == .down {
+            submit()
+        }
+        // Consume autorepeat without submitting or inserting a newline.
+        return .handled
+    }
+}
+
+extension View {
+    @ViewBuilder
+    func submitOnMacReturn(_ submit: @escaping () -> Void) -> some View {
+        #if targetEnvironment(macCatalyst)
+        onKeyPress(keys: [.return, KeyEquivalent("\u{3}")], phases: [.down, .repeat]) { press in
+            SybilReturnKeySubmission.handle(phase: press.phase, modifiers: press.modifiers, submit: submit)
+        }
+        #else
+        self
+        #endif
+    }
+}

ios/Packages/Sybil/Sources/Sybil/SybilViewModel.swift

@@ -636,9 +636,12 @@ final class SybilViewModel {
         }
 
         cancelQuickQuestion()
+        // Lock submission before the task starts, including repeated Return
+        // events delivered in the same main-actor turn.
+        isQuickQuestionSending = true
         let selectedProvider = quickQuestionProvider
         let task = Task { [weak self] in
-            guard let self else {
+            guard let self, !Task.isCancelled else {
                 return
             }
             await self.runQuickQuestion(prompt: content, provider: selectedProvider, model: selectedModel)

ios/Packages/Sybil/Sources/Sybil/SybilWorkspaceView.swift

@@ -601,6 +601,7 @@ struct SybilWorkspaceView: View {
                 .onSubmit {
                     submitComposer()
                 }
+                .submitOnMacReturn(submitComposer)
                 .padding(.horizontal, 12)
                 .padding(.vertical, 10)
                 .background(

ios/Packages/Sybil/Tests/SybilTests/SybilTests.swift

@@ -1,6 +1,10 @@
 import CoreGraphics
 import Foundation
+import SwiftUI
 import Testing
+#if targetEnvironment(macCatalyst)
+import UIKit
+#endif
 @testable import Sybil
 
 private struct MockClientCallSnapshot: Sendable {
@@ -951,6 +955,76 @@ private func makeToolCallMessage(id: String, date: Date, summary: String = "Ran
     await sendTask.value
 }
 
+@MainActor
+@Test func composerReturnSubmitsOnceAndConsumesRepeats() {
+    var submissions = 0
+    let initial = SybilReturnKeySubmission.handle(phase: .down, modifiers: []) { submissions += 1 }
+    let repeated = SybilReturnKeySubmission.handle(phase: .repeat, modifiers: []) { submissions += 1 }
+    #expect(initial == .handled)
+    #expect(repeated == .handled)
+    #expect(submissions == 1)
+}
+
+@MainActor
+@Test func composerModifiedReturnPreservesNativeEditing() {
+    var submissions = 0
+    for modifiers: EventModifiers in [.shift, .command, .control, .option, [.shift, .command]] {
+        let result = SybilReturnKeySubmission.handle(phase: .down, modifiers: modifiers) { submissions += 1 }
+        #expect(result == .ignored)
+    }
+    #expect(submissions == 0)
+}
+
+@MainActor
+@Test func composerReturnStillSubmitsWithCapsLock() {
+    var submissions = 0
+    let result = SybilReturnKeySubmission.handle(phase: .down, modifiers: .capsLock) { submissions += 1 }
+    #expect(result == .handled)
+    #expect(submissions == 1)
+}
+
+@Test func quickQuestionHotKeyTogglesOncePerPress() {
+    var keyState = SybilQuickQuestionHotKeyState()
+    let keyDownEvents = [true, true, true, false, true, false, false, true]
+    let toggles = keyDownEvents.map { keyState.shouldToggle(isKeyDown: $0) }
+    #expect(toggles == [true, false, false, false, true, false, false, true])
+}
+
+@MainActor
+@Test func quickQuestionRejectsDuplicateSubmissionBeforeTaskStarts() async throws {
+    let client = MockSybilClient()
+    await client.setCompletionStreamEvents([.done(CompletionStreamDone(text: "One answer."))])
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.quickQuestionPrompt = "One question"
+
+    let first = viewModel.sendQuickQuestion()
+    let duplicate = viewModel.sendQuickQuestion()
+    #expect(first != nil)
+    #expect(duplicate == nil)
+    #expect(viewModel.isQuickQuestionSending)
+    await first?.value
+
+    let calls = await client.currentSnapshot()
+    #expect(calls.runCompletionStream == 1)
+    #expect(viewModel.quickQuestionAnswerText == "One answer.")
+    #expect(!viewModel.isQuickQuestionSending)
+}
+
+@MainActor
+@Test func quickQuestionCancelledBeforeTaskStartsDoesNotSend() async throws {
+    let client = MockSybilClient()
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.quickQuestionPrompt = "Do not send this"
+
+    let task = viewModel.sendQuickQuestion()
+    viewModel.cancelQuickQuestion()
+    await task?.value
+
+    let calls = await client.currentSnapshot()
+    #expect(calls.runCompletionStream == 0)
+    #expect(!viewModel.isQuickQuestionSending)
+}
+
 @MainActor
 @Test func quickQuestionRunsNonPersistentCompletionStream() async throws {
     let client = MockSybilClient()
@@ -1220,3 +1294,365 @@ private func makeToolCallMessage(id: String, date: Date, summary: String = "Ran
     #expect(BackSwipeMetrics.shouldComplete(offset: 24, velocityX: 800, width: width, isLatched: false))
     #expect(!BackSwipeMetrics.shouldComplete(offset: latchDistance + 1, velocityX: -800, width: width, isLatched: true))
 }
+
+#if targetEnvironment(macCatalyst)
+@MainActor
+@Test func macNewChatCommandOpensWindowWhenNoWorkspacesRemain() {
+    let commands = SybilMacWindowCommands()
+    var chats = 0
+    var windows = 0
+
+    #expect(commands.canStartNewChat(hasFocusedActions: false))
+    commands.newChatOrWindow(newChat: nil, openWindow: { windows += 1 })
+    // A focused value can briefly outlive a closing scene. It must not route
+    // Command+N back into a closed workspace.
+    commands.newChatOrWindow(newChat: { chats += 1 }, openWindow: { windows += 1 })
+    #expect(windows == 2)
+    #expect(chats == 0)
+}
+
+@MainActor
+@Test func macNewChatCommandUsesExistingWorkspace() {
+    let commands = SybilMacWindowCommands()
+    commands.windowConnected(sessionID: "first")
+    var chats = 0
+    var windows = 0
+
+    #expect(commands.canStartNewChat(hasFocusedActions: true))
+    commands.newChatOrWindow(newChat: { chats += 1 }, openWindow: { windows += 1 })
+    #expect(chats == 1)
+    #expect(windows == 0)
+}
+
+@MainActor
+@Test func macNewChatCommandDoesNotMistakeUnavailableActionsForNoWindows() {
+    let commands = SybilMacWindowCommands()
+    commands.windowConnected(sessionID: "authenticating")
+    var windows = 0
+
+    #expect(!commands.canStartNewChat(hasFocusedActions: false))
+    commands.newChatOrWindow(newChat: nil, openWindow: { windows += 1 })
+    #expect(windows == 0)
+}
+
+@MainActor
+@Test func macWindowCommandsTrackLastWindowClosureAndReconnection() {
+    let commands = SybilMacWindowCommands()
+    commands.windowConnected(sessionID: "first")
+    commands.windowConnected(sessionID: "first")
+    commands.windowConnected(sessionID: "second")
+    commands.windowDisconnected(sessionID: "first")
+    #expect(commands.hasOpenWindows)
+    commands.windowDisconnected(sessionID: "first")
+    #expect(commands.hasOpenWindows)
+    commands.windowDisconnected(sessionID: "second")
+    #expect(!commands.hasOpenWindows)
+    #expect(commands.canStartNewChat(hasFocusedActions: false))
+    commands.windowConnected(sessionID: "third")
+    #expect(commands.hasOpenWindows)
+    #expect(!commands.canStartNewChat(hasFocusedActions: false))
+}
+
+@MainActor
+private final class MockQuickQuestionPanel: NSObject, SybilQuickQuestionPanelBridging {
+    private weak var delegate: (any SybilQuickQuestionPanelDelegate)?
+    var isVisible = false
+    var state = SybilQuickQuestionPanelState()
+    var presentationCount = 0
+    var activationCount = 0
+    var stateUpdateCount = 0
+    var events: [String] = []
+    var onShow: (() -> Void)?
+
+    required override init() { super.init() }
+    func start(delegate: any SybilQuickQuestionPanelDelegate) -> Int32 {
+        self.delegate = delegate
+        return 0
+    }
+    func updateState(_ data: Data) {
+        state = try! JSONDecoder().decode(SybilQuickQuestionPanelState.self, from: data)
+        stateUpdateCount += 1
+        events.append("update")
+    }
+    func show() {
+        onShow?()
+        isVisible = true
+        presentationCount += 1
+        events.append("show")
+    }
+    func hide() {
+        isVisible = false
+        delegate?.quickQuestionPanelDismissed()
+    }
+    func activateForQuickQuestion() {
+        activationCount += 1
+        events.append("activate")
+    }
+    func activateMainWindow() {}
+    func stop() { hide() }
+}
+
+@MainActor
+private func waitForQuickQuestion(_ condition: @MainActor () -> Bool) async throws {
+    for _ in 0..<100 {
+        if condition() { return }
+        try await Task.sleep(for: .milliseconds(2))
+    }
+    try #require(condition())
+}
+
+@MainActor
+private final class MockQuickQuestionLifecycle {
+    var isForeground = false
+    let notifications = NotificationCenter()
+
+    func notify(_ name: Notification.Name) {
+        notifications.post(name: name, object: nil)
+    }
+}
+
+@MainActor
+@Test func macQuickQuestionWaitsForUIKitForegroundBeforeOpeningPanel() async throws {
+    let lifecycle = MockQuickQuestionLifecycle()
+    let panel = MockQuickQuestionPanel()
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in MockSybilClient() }
+    viewModel.quickQuestionPrompt = "Original prompt"
+    let controller = SybilMacQuickQuestionController(
+        bridge: panel,
+        isApplicationInForeground: { lifecycle.isForeground },
+        notificationCenter: lifecycle.notifications
+    )
+    defer { controller.stop() }
+    controller.attach(viewModel)
+    panel.onShow = { #expect(lifecycle.isForeground) }
+
+    controller.toggle()
+    // Never create/order a window inline in the hotkey's event callback.
+    #expect(panel.presentationCount == 0)
+    #expect(panel.activationCount == 0)
+    try await waitForQuickQuestion { panel.activationCount == 1 }
+    #expect(panel.stateUpdateCount == 0)
+    #expect(!panel.isVisible)
+
+    // "Will enter" is not proof of readiness: UIKit can still be backgrounded.
+    lifecycle.notify(UIApplication.willEnterForegroundNotification)
+    try await Task.sleep(for: .milliseconds(10))
+    #expect(panel.activationCount == 1)
+    #expect(panel.presentationCount == 0)
+    #expect(panel.stateUpdateCount == 0)
+
+    viewModel.quickQuestionPrompt = "The latest prompt while waiting"
+    lifecycle.isForeground = true
+    lifecycle.notify(UIApplication.didBecomeActiveNotification)
+    try await waitForQuickQuestion { panel.isVisible }
+    #expect(panel.events == ["activate", "update", "show"])
+    #expect(panel.state.prompt == "The latest prompt while waiting")
+}
+
+@MainActor
+@Test func macQuickQuestionSecondToggleCancelsPendingActivation() async throws {
+    let lifecycle = MockQuickQuestionLifecycle()
+    let panel = MockQuickQuestionPanel()
+    let controller = SybilMacQuickQuestionController(
+        bridge: panel,
+        isApplicationInForeground: { lifecycle.isForeground },
+        notificationCenter: lifecycle.notifications
+    )
+    defer { controller.stop() }
+    controller.toggle()
+    try await waitForQuickQuestion { panel.activationCount == 1 }
+    controller.toggle()
+
+    lifecycle.isForeground = true
+    lifecycle.notify(UIApplication.didBecomeActiveNotification)
+    try await Task.sleep(for: .milliseconds(10))
+    #expect(!panel.isVisible)
+    #expect(panel.presentationCount == 0)
+    #expect(panel.stateUpdateCount == 0)
+
+    controller.toggle()
+    try await waitForQuickQuestion { panel.isVisible }
+    #expect(panel.presentationCount == 1)
+    #expect(panel.activationCount == 1)
+}
+
+@MainActor
+@Test func macQuickQuestionRapidTogglesKeepOnlyLatestPresentation() async throws {
+    let lifecycle = MockQuickQuestionLifecycle()
+    lifecycle.isForeground = true
+    let panel = MockQuickQuestionPanel()
+    let controller = SybilMacQuickQuestionController(
+        bridge: panel,
+        isApplicationInForeground: { lifecycle.isForeground },
+        notificationCenter: lifecycle.notifications
+    )
+    defer { controller.stop() }
+    controller.toggle()
+    controller.toggle()
+    controller.toggle()
+    #expect(panel.presentationCount == 0)
+    try await waitForQuickQuestion { panel.isVisible }
+    #expect(panel.presentationCount == 1)
+    #expect(panel.activationCount == 0)
+
+    // Lifecycle notifications must not present/select the prompt a second time.
+    lifecycle.notify(UIApplication.willEnterForegroundNotification)
+    lifecycle.notify(UIApplication.didBecomeActiveNotification)
+    try await Task.sleep(for: .milliseconds(10))
+    #expect(panel.presentationCount == 1)
+}
+
+@MainActor
+@Test func macQuickQuestionStopCancelsPendingPresentation() async throws {
+    let lifecycle = MockQuickQuestionLifecycle()
+    let panel = MockQuickQuestionPanel()
+    let controller = SybilMacQuickQuestionController(
+        bridge: panel,
+        isApplicationInForeground: { lifecycle.isForeground },
+        notificationCenter: lifecycle.notifications
+    )
+    controller.show()
+    try await waitForQuickQuestion { panel.activationCount == 1 }
+    controller.stop()
+    lifecycle.isForeground = true
+    lifecycle.notify(UIApplication.didBecomeActiveNotification)
+    try await Task.sleep(for: .milliseconds(10))
+    #expect(panel.presentationCount == 0)
+    #expect(panel.stateUpdateCount == 0)
+}
+
+@MainActor
+@Test func macQuickQuestionRechecksForegroundAfterLeavingHotKeyCallback() async throws {
+    let lifecycle = MockQuickQuestionLifecycle()
+    lifecycle.isForeground = true
+    let panel = MockQuickQuestionPanel()
+    let controller = SybilMacQuickQuestionController(
+        bridge: panel,
+        isApplicationInForeground: { lifecycle.isForeground },
+        notificationCenter: lifecycle.notifications
+    )
+    defer { controller.stop() }
+    controller.show()
+    lifecycle.isForeground = false
+    try await waitForQuickQuestion { panel.activationCount == 1 }
+    #expect(!panel.isVisible)
+    #expect(panel.stateUpdateCount == 0)
+    lifecycle.isForeground = true
+    lifecycle.notify(UIApplication.didBecomeActiveNotification)
+    try await waitForQuickQuestion { panel.isVisible }
+    #expect(panel.presentationCount == 1)
+}
+
+@MainActor
+@Test func macQuickQuestionTogglePreservesDraftAndUsesLatestAnswer() async throws {
+    let client = MockSybilClient()
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    viewModel.isCheckingSession = false
+    viewModel.quickQuestionPrompt = "Keep this draft"
+    let panel = MockQuickQuestionPanel()
+    let controller = SybilMacQuickQuestionController(bridge: panel)
+    controller.attach(viewModel)
+
+    controller.toggle()
+    try await waitForQuickQuestion { panel.isVisible }
+    #expect(panel.isVisible)
+    #expect(panel.state.prompt == "Keep this draft")
+    #expect(panel.state.canSend)
+    controller.toggle()
+    #expect(!panel.isVisible)
+
+    viewModel.quickQuestionMessages = [
+        Message(id: "temp-assistant-quick-test", createdAt: Date(), role: .assistant, content: "An answer arrived while hidden.", name: nil)
+    ]
+    controller.toggle()
+    try await waitForQuickQuestion { panel.isVisible }
+    #expect(panel.isVisible)
+    #expect(panel.presentationCount == 2)
+    #expect(panel.state.prompt == "Keep this draft")
+    #expect(panel.state.answer == "An answer arrived while hidden.")
+    let calls = await client.currentSnapshot()
+    #expect(calls.runCompletionStream == 0)
+    controller.stop()
+}
+
+@MainActor
+@Test func macQuickQuestionObservesStreamingAndKeepsItsOwner() async throws {
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in MockSybilClient() }
+    viewModel.isAuthenticated = true
+    viewModel.isCheckingSession = false
+    viewModel.quickQuestionPrompt = "Original window"
+    let panel = MockQuickQuestionPanel()
+    let controller = SybilMacQuickQuestionController(bridge: panel)
+    controller.attach(viewModel)
+    controller.show()
+
+    let otherWindow = SybilViewModel(settings: testSettings(named: #function + "-other")) { _ in MockSybilClient() }
+    otherWindow.quickQuestionPrompt = "Other window"
+    controller.attach(otherWindow)
+    viewModel.quickQuestionMessages = [
+        Message(id: "temp-assistant-quick-test", createdAt: Date(), role: .assistant, content: "Streaming update", name: nil)
+    ]
+    for _ in 0..<30 {
+        if panel.state.answer == "Streaming update" { break }
+        try await Task.sleep(for: .milliseconds(5))
+    }
+    #expect(panel.state.answer == "Streaming update")
+    #expect(panel.state.prompt == "Original window")
+    controller.stop()
+}
+
+@MainActor
+@Test func macQuickQuestionRetainsStateAfterLastWorkspaceCloses() async throws {
+    let client = MockSybilClient()
+    var windowViewModel: SybilViewModel? = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    windowViewModel?.isAuthenticated = true
+    windowViewModel?.isCheckingSession = false
+    windowViewModel?.quickQuestionPrompt = "A question from the closed window"
+    windowViewModel?.quickQuestionMessages = [
+        Message(id: "temp-assistant-quick-windowless", createdAt: Date(), role: .assistant, content: "Keep this answer too.", name: nil)
+    ]
+    let panel = MockQuickQuestionPanel()
+    let controller = SybilMacQuickQuestionController(bridge: panel)
+    controller.attach(try #require(windowViewModel))
+
+    // Releasing the workspace must not release the global shortcut's model.
+    windowViewModel = nil
+    controller.toggle()
+    try await waitForQuickQuestion { panel.isVisible }
+    #expect(panel.isVisible)
+    #expect(panel.state.prompt == "A question from the closed window")
+    #expect(panel.state.answer == "Keep this answer too.")
+    controller.toggle()
+    #expect(!panel.isVisible)
+    controller.toggle()
+    try await waitForQuickQuestion { panel.isVisible }
+    #expect(panel.presentationCount == 2)
+    #expect(panel.state.canSend)
+    let calls = await client.currentSnapshot()
+    #expect(calls.runCompletionStream == 0)
+    controller.stop()
+}
+
+@MainActor
+@Test func macQuickQuestionCannotSubmitBeforeAuthentication() async throws {
+    let client = MockSybilClient()
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = false
+    viewModel.isCheckingSession = false
+    let panel = MockQuickQuestionPanel()
+    let controller = SybilMacQuickQuestionController(bridge: panel)
+    controller.attach(viewModel)
+    controller.show()
+    try await waitForQuickQuestion { panel.isVisible }
+    controller.quickQuestionPromptChanged("A signed-out question")
+    controller.quickQuestionSubmitRequested()
+
+    #expect(!panel.state.canSend)
+    #expect(panel.state.prompt == "A signed-out question")
+    #expect(!viewModel.isQuickQuestionSending)
+    let calls = await client.currentSnapshot()
+    #expect(calls.runCompletionStream == 0)
+    controller.stop()
+}
+#endif

ios/README.md

@@ -0,0 +1,76 @@
+# Sybil for iOS and Mac Catalyst
+
+Run `just run` for the iPhone simulator, or `just run-mac` for Mac Catalyst.
+`just build-mac` builds without launching the Mac app. Both regenerate the Xcode
+project from `project.yml`. The Mac recipes use ad-hoc signing for local development;
+release/archive signing settings are unchanged.
+
+## Quick Question on macOS
+
+While the Catalyst app is running, **Option+Space** toggles a floating Quick
+Question panel, including over other applications. The prompt is focused as soon
+as it opens, with any existing prompt selected so typing replaces it. The same
+select-on-open behavior applies to Quick Question on iPhone and iPad.
+**Return** submits; **Shift+Return** inserts a new line. **Escape**, a
+second **Option+Space**, the close button, or clicking outside dismisses it.
+Hiding the panel preserves the draft and answer and lets an in-flight answer finish.
+**Open in Chat** saves the question and answer in the regular workspace.
+
+The regular Mac chat/search composer uses the same Return/Shift+Return rules.
+Holding Return does not repeatedly submit. The iOS software keyboard is unchanged.
+
+Closing the last Mac window leaves Sybil running, so Option+Space still works.
+Use **Sybil → Quit Sybil** or **Command+Q** to quit the application. The Catalyst
+build opts out of automatic termination, and the native shortcut service holds a
+matching automatic-termination activity until it stops. No hidden keep-alive
+window or sleep-preventing activity is used. Mac scene support also allows the
+workspace to reopen after its last window is closed.
+
+When Catalyst is backgrounded, opening Quick Question first requests app
+activation and waits for UIKit to enter the foreground before creating or ordering
+the native panel. Presentation is deferred out of the hotkey event callback.
+Pressing Option+Space again cancels a pending presentation. Dismissing a panel
+that required activation returns focus to the previous app; explicitly opening
+the workspace keeps focus in Sybil.
+
+On Mac, **Command+N** starts a new chat in the focused workspace, or opens a new
+workspace window when none are open. **Command+Shift+N** always opens a new window,
+including while signed out. **Command+Option+N** starts a new search; iOS retains
+its existing Command+Shift+N search shortcut.
+
+The shortcut is also shown under **File → Quick Question**. If another application
+already owns Option+Space, the panel reports that the shortcut is unavailable;
+the menu item can still be clicked. No Accessibility or Input Monitoring grant is
+needed for the registered hotkey.
+
+The native AppKit panel and Carbon hotkey live in `Apps/SybilMacQuickQuestion`,
+a macOS bundle embedded only for the Mac Catalyst destination. Catalyst loads it
+through the Foundation-only `SybilMacQuickQuestionBridge` contract. Requests,
+provider/model preferences, streaming, and conversion to chat remain in the
+existing `SybilViewModel`; there is no separate backend or API contract. The panel
+uses AppKit controls rather than trying to load the macOS SwiftUI runtime into a
+Catalyst process.
+
+The iPhone/iPad app keeps its existing Quick Question sheet and Home Screen quick
+action, and does not build or embed the macOS helper.
+
+## Verification
+
+- `just test`: existing Swift package tests on the iPhone simulator.
+- From `Packages/Sybil`, run `xcodebuild test -scheme Sybil -destination 'platform=macOS,variant=Mac Catalyst' -parallel-testing-enabled NO` for package tests including the Catalyst panel controller.
+- For a manual Mac check, open the panel from another app, type immediately,
+  submit, hide/reopen during streaming, and verify Escape/outside-click dismissal
+  returns input to the previous app. Check a second display and a full-screen Space
+  when available.
+- Close every Mac window, invoke Option+Space, and verify the saved question and
+  answer remain available. Reopen the workspace from the panel, then explicitly
+  quit with Command+Q. Rebuild and relaunch after changing lifecycle plist keys.
+- In both Mac and iOS Quick Question, reopen an existing prompt and type to replace
+  it. In the Mac workspace, verify Return submits and Shift+Return adds a newline.
+- Check Command+N both with a workspace open and after closing every workspace.
+  Command+Shift+N must open another window even when one already exists, and
+  Command+Option+N must start a search without opening a window.
+- With all workspace windows closed, switch to another app and repeatedly open
+  and dismiss Quick Question, including two quick Option+Space presses while it
+  is opening. Check that no late panel appears after cancellation and that no
+  `UINSAppLifecycleStateRunningNoOpenWindows` assertion occurs.

ios/justfile

@@ -24,6 +24,12 @@ run: generate
   xcrun simctl install booted '{{derived_data}}/Build/Products/Debug-iphonesimulator/Sybil.app'
   xcrun simctl launch booted net.buzzert.sybil2
 
+build-mac: generate
+  xcodebuild -scheme Sybil -destination 'platform=macOS,variant=Mac Catalyst' -derivedDataPath '{{derived_data}}' CODE_SIGN_IDENTITY=- CODE_SIGNING_REQUIRED=NO
+
+run-mac: build-mac
+  open '{{derived_data}}/Build/Products/Debug-maccatalyst/Sybil.app'
+
 beta:
   fastlane ios beta
 

ios/project.yml

@@ -7,3 +7,4 @@ packages:
     path: Packages/Sybil
 include:
   - Apps/Sybil/project.yml
+  - Apps/SybilMacQuickQuestion/project.yml

scripts/devbox-start.sh

@@ -0,0 +1,90 @@
+#!/usr/bin/env bash
+set -euo pipefail
+
+ROOT="$(cd "$(dirname "${BASH_SOURCE[0]}")/.." && pwd)"
+SESSION="${SYBIL_TMUX_SESSION:-sybil-dev}"
+LOG_DIR="$ROOT/.devbox/logs"
+PID_DIR="$ROOT/.devbox/pids"
+
+require_env() {
+  local name="$1"
+  if [[ -z "${!name:-}" ]]; then
+    echo "Missing required environment variable: $name" >&2
+    exit 1
+  fi
+}
+
+require_env OPENAI_API_KEY
+require_env EXA_API_KEY
+
+mkdir -p "$LOG_DIR" "$PID_DIR"
+
+export HOST="${HOST:-0.0.0.0}"
+export PORT="${PORT:-8787}"
+export DATABASE_URL="${DATABASE_URL:-file:$ROOT/server/dev.db}"
+
+echo "Installing server dependencies..."
+npm ci --prefix "$ROOT/server" --no-audit --no-fund
+
+echo "Installing web dependencies..."
+npm ci --prefix "$ROOT/web" --no-audit --no-fund
+
+if command -v tmux >/dev/null 2>&1; then
+  tmux kill-session -t "$SESSION" >/dev/null 2>&1 || true
+  tmux new-session -d -s "$SESSION" -n server -c "$ROOT/server" "sleep infinity"
+  tmux set-environment -t "$SESSION" OPENAI_API_KEY "$OPENAI_API_KEY"
+  tmux set-environment -t "$SESSION" EXA_API_KEY "$EXA_API_KEY"
+  tmux set-environment -t "$SESSION" HOST "$HOST"
+  tmux set-environment -t "$SESSION" PORT "$PORT"
+  tmux set-environment -t "$SESSION" DATABASE_URL "$DATABASE_URL"
+  if [[ -n "${BRIX_CLUSTER:-}" ]]; then
+    tmux set-environment -t "$SESSION" BRIX_CLUSTER "$BRIX_CLUSTER"
+  fi
+  for name in \
+    CHAT_CODEX_TOOL_ENABLED \
+    CHAT_CODEX_REMOTE_HOST \
+    CHAT_CODEX_REMOTE_USER \
+    CHAT_CODEX_REMOTE_PORT \
+    CHAT_CODEX_REMOTE_WORKDIR \
+    CHAT_CODEX_SSH_KEY_PATH \
+    CHAT_CODEX_SSH_PRIVATE_KEY_B64 \
+    CHAT_CODEX_EXEC_TIMEOUT_MS \
+    CHAT_SHELL_TOOL_ENABLED \
+    CHAT_SHELL_EXEC_TIMEOUT_MS; do
+    if [[ -n "${!name:-}" ]]; then
+      tmux set-environment -t "$SESSION" "$name" "${!name}"
+    fi
+  done
+  tmux respawn-pane -k -t "$SESSION:server.0" -c "$ROOT/server" "npm run dev"
+  tmux new-window -t "$SESSION" -n web -c "$ROOT/web" \
+    "npm run dev -- --host 0.0.0.0 --port 5173"
+  echo "Started Sybil in tmux session '$SESSION'."
+  echo "Server: http://127.0.0.1:8787"
+  echo "Web:    http://127.0.0.1:5173"
+  exit 0
+fi
+
+echo "tmux not found; starting background processes with nohup."
+
+if [[ -f "$PID_DIR/server.pid" ]]; then
+  kill "$(cat "$PID_DIR/server.pid")" >/dev/null 2>&1 || true
+fi
+if [[ -f "$PID_DIR/web.pid" ]]; then
+  kill "$(cat "$PID_DIR/web.pid")" >/dev/null 2>&1 || true
+fi
+
+(
+  cd "$ROOT/server"
+  exec env HOST="$HOST" PORT="$PORT" DATABASE_URL="$DATABASE_URL" npm run dev
+) >"$LOG_DIR/server.log" 2>&1 &
+echo "$!" >"$PID_DIR/server.pid"
+
+(
+  cd "$ROOT/web"
+  exec npm run dev -- --host 0.0.0.0 --port 5173
+) >"$LOG_DIR/web.log" 2>&1 &
+echo "$!" >"$PID_DIR/web.pid"
+
+echo "Started Sybil background processes."
+echo "Server log: $LOG_DIR/server.log"
+echo "Web log:    $LOG_DIR/web.log"

scripts/devbox-update.sh

@@ -0,0 +1,357 @@
+#!/usr/bin/env bash
+set -euo pipefail
+
+ROOT="$(cd "$(dirname "${BASH_SOURCE[0]}")/.." && pwd)"
+REPO="${REPO:-Sybil-2}"
+WORKLOAD="${WORKLOAD:-sybil-dev}"
+CLUSTER="${CLUSTER:-viper}"
+NAMESPACE="${NAMESPACE:-buzzert}"
+QUOTA="${QUOTA:-research-api}"
+SECRET="${SECRET:-sybil-dev-env}"
+REMOTE_ROOT="${REMOTE_ROOT:-/root/code/$REPO}"
+INGRESS_PORT="${INGRESS_PORT:-5173}"
+CODEX_IMAGE="${CODEX_IMAGE:-openai.azurecr.io/rcall:crow-1b540b5e15f9-2026-01-22-2404-312}"
+CODEX_SERVICE="${CODEX_SERVICE:-sybil-codex-devbox}"
+CODEX_CONTAINER="${CODEX_CONTAINER:-codex-devbox}"
+CODEX_SSH_SECRET="${CODEX_SSH_SECRET:-sybil-codex-ssh}"
+CODEX_SSH_PORT="${CODEX_SSH_PORT:-2222}"
+CODEX_WORKDIR="${CODEX_WORKDIR:-/workspace/sybil-codex}"
+CODEX_SSH_KEY_PATH="${CODEX_SSH_KEY_PATH:-/run/secrets/sybil-codex-ssh/id_ed25519}"
+
+echo "Syncing $REPO to $WORKLOAD on $CLUSTER/$NAMESPACE..."
+brix create \
+  --project-root "$(dirname "$ROOT")" \
+  --path "$REPO=$ROOT" \
+  --repositories "$REPO" \
+  --include-untracked \
+  --reconcile-policy continuous \
+  -- \
+  "cluster=$CLUSTER" \
+  "namespace=$NAMESPACE" \
+  "name=$WORKLOAD" \
+  "pool.spec.quota=$QUOTA" \
+  "pool.spec.size.resource=cpu" \
+  "pool.spec.size.quantity=1" \
+  "pool.spec.priority=low"
+
+if [[ "$REPO" != "openai" ]]; then
+  if kubectl --context "$CLUSTER" -n "$NAMESPACE" get git "$WORKLOAD" -o json 2>/dev/null | jq -e '.spec.repositories.openai?' >/dev/null; then
+    kubectl --context "$CLUSTER" -n "$NAMESPACE" patch git "$WORKLOAD" --type=json -p='[{"op":"remove","path":"/spec/repositories/openai"}]'
+  fi
+fi
+
+if [[ -n "${OPENAI_API_KEY:-}" && -n "${EXA_API_KEY:-}" ]]; then
+  kubectl --context "$CLUSTER" -n "$NAMESPACE" create secret generic "$SECRET" \
+    --from-literal=OPENAI_API_KEY="$OPENAI_API_KEY" \
+    --from-literal=EXA_API_KEY="$EXA_API_KEY" \
+    --dry-run=client -o yaml | kubectl --context "$CLUSTER" -n "$NAMESPACE" apply -f -
+elif [[ -n "${OPENAI_API_KEY:-}" || -n "${EXA_API_KEY:-}" ]]; then
+  echo "Only one API key env var is set; keeping existing Kubernetes secret $SECRET." >&2
+fi
+
+if [[ "$(kubectl --context "$CLUSTER" -n "$NAMESPACE" get secret "$SECRET" -o name 2>/dev/null || true)" == "" ]]; then
+  echo "Secret $SECRET does not exist. Re-run with OPENAI_API_KEY and EXA_API_KEY set." >&2
+  exit 1
+fi
+
+if [[ "$(kubectl --context "$CLUSTER" -n "$NAMESPACE" get secret "$CODEX_SSH_SECRET" -o name 2>/dev/null || true)" == "" ]]; then
+  tmpdir="$(mktemp -d)"
+  trap 'rm -rf "$tmpdir"' EXIT
+  ssh-keygen -t ed25519 -N "" -C "sybil-codex@$WORKLOAD" -f "$tmpdir/id_ed25519" >/dev/null
+  kubectl --context "$CLUSTER" -n "$NAMESPACE" create secret generic "$CODEX_SSH_SECRET" \
+    --from-file=id_ed25519="$tmpdir/id_ed25519" \
+    --from-file=id_ed25519.pub="$tmpdir/id_ed25519.pub" \
+    --dry-run=client -o yaml | kubectl --context "$CLUSTER" -n "$NAMESPACE" apply -f -
+fi
+
+kubectl --context "$CLUSTER" -n "$NAMESPACE" patch secret "$SECRET" --type=merge -p "$(jq -n \
+  --arg host "$CODEX_SERVICE" \
+  --arg port "$CODEX_SSH_PORT" \
+  --arg workdir "$CODEX_WORKDIR" \
+  --arg keyPath "$CODEX_SSH_KEY_PATH" \
+  '{
+    stringData: {
+      CHAT_CODEX_TOOL_ENABLED: "true",
+      CHAT_CODEX_REMOTE_HOST: $host,
+      CHAT_CODEX_REMOTE_USER: "root",
+      CHAT_CODEX_REMOTE_PORT: $port,
+      CHAT_CODEX_REMOTE_WORKDIR: $workdir,
+      CHAT_CODEX_SSH_KEY_PATH: $keyPath,
+      CHAT_CODEX_EXEC_TIMEOUT_MS: "600000",
+      CHAT_SHELL_TOOL_ENABLED: "true"
+    }
+  }')"
+
+ensure_codex_deployment() {
+  kubectl --context "$CLUSTER" -n "$NAMESPACE" apply -f - <<KUBE_MANIFEST
+apiVersion: apps/v1
+kind: Deployment
+metadata:
+  name: $CODEX_SERVICE
+  labels:
+    app.kubernetes.io/name: $CODEX_SERVICE
+    app.kubernetes.io/part-of: sybil-dev
+spec:
+  replicas: 1
+  selector:
+    matchLabels:
+      app.kubernetes.io/name: $CODEX_SERVICE
+  template:
+    metadata:
+      labels:
+        app.kubernetes.io/name: $CODEX_SERVICE
+        app.kubernetes.io/part-of: sybil-dev
+    spec:
+      tolerations:
+        - key: openai.com/team
+          operator: Exists
+          effect: NoSchedule
+      containers:
+        - name: $CODEX_CONTAINER
+          image: $CODEX_IMAGE
+          imagePullPolicy: IfNotPresent
+          command: ["/bin/bash", "-lc"]
+          args:
+            - |
+              set -euo pipefail
+              export DEBIAN_FRONTEND=noninteractive
+              if ! command -v sshd >/dev/null 2>&1; then
+                apt-get update
+                apt-get install -y --no-install-recommends openssh-server ca-certificates git curl
+                rm -rf /var/lib/apt/lists/*
+              fi
+              if ! command -v codex >/dev/null 2>&1; then
+                npm install -g @openai/codex
+              fi
+              mkdir -p /run/sshd /root/.ssh "$CODEX_WORKDIR"
+              cp /run/secrets/sybil-codex-ssh/id_ed25519.pub /root/.ssh/authorized_keys
+              chmod 700 /root/.ssh
+              chmod 600 /root/.ssh/authorized_keys
+              {
+                if [[ -n "\${OPENAI_API_KEY:-}" ]]; then
+                  printf 'export OPENAI_API_KEY=%q\n' "\$OPENAI_API_KEY"
+                fi
+                if [[ -n "\${EXA_API_KEY:-}" ]]; then
+                  printf 'export EXA_API_KEY=%q\n' "\$EXA_API_KEY"
+                fi
+              } >/root/.sybil-codex-env
+              chmod 600 /root/.sybil-codex-env
+              cat >/usr/local/bin/sybil-codex-ssh-command <<'SSH_COMMAND'
+              #!/usr/bin/env bash
+              set -euo pipefail
+              if [[ -f /root/.sybil-codex-env ]]; then
+                source /root/.sybil-codex-env
+              fi
+              if [[ -n "\${SSH_ORIGINAL_COMMAND:-}" ]]; then
+                exec /bin/bash -lc "\$SSH_ORIGINAL_COMMAND"
+              fi
+              exec /bin/bash -l
+              SSH_COMMAND
+              chmod 700 /usr/local/bin/sybil-codex-ssh-command
+              ssh-keygen -A
+              cat >/tmp/sybil-codex-sshd_config <<SSHD_CONFIG
+              Port $CODEX_SSH_PORT
+              ListenAddress 0.0.0.0
+              PermitRootLogin prohibit-password
+              PasswordAuthentication no
+              PubkeyAuthentication yes
+              AcceptEnv OPENAI_API_KEY EXA_API_KEY
+              AuthorizedKeysFile .ssh/authorized_keys
+              PermitUserEnvironment no
+              ForceCommand /usr/local/bin/sybil-codex-ssh-command
+              AllowTcpForwarding no
+              X11Forwarding no
+              Subsystem sftp internal-sftp
+              PidFile /run/sshd/sybil-codex.pid
+              SSHD_CONFIG
+              exec \$(command -v sshd) -D -e -f /tmp/sybil-codex-sshd_config
+          ports:
+            - name: ssh
+              containerPort: $CODEX_SSH_PORT
+          envFrom:
+            - secretRef:
+                name: $SECRET
+          resources:
+            requests:
+              cpu: "1"
+              memory: 4Gi
+            limits:
+              cpu: "1"
+              memory: 4Gi
+          volumeMounts:
+            - name: sybil-codex-ssh
+              mountPath: /run/secrets/sybil-codex-ssh
+              readOnly: true
+            - name: sybil-codex-workspace
+              mountPath: /workspace
+      volumes:
+        - name: sybil-codex-ssh
+          secret:
+            secretName: $CODEX_SSH_SECRET
+            defaultMode: 384
+        - name: sybil-codex-workspace
+          emptyDir: {}
+---
+apiVersion: v1
+kind: Service
+metadata:
+  name: $CODEX_SERVICE
+  labels:
+    app.kubernetes.io/name: $CODEX_SERVICE
+    app.kubernetes.io/part-of: sybil-dev
+spec:
+  type: ClusterIP
+  selector:
+    app.kubernetes.io/name: $CODEX_SERVICE
+  ports:
+    - name: ssh
+      port: $CODEX_SSH_PORT
+      targetPort: ssh
+KUBE_MANIFEST
+
+  kubectl --context "$CLUSTER" -n "$NAMESPACE" rollout status "deployment/$CODEX_SERVICE" --timeout=300s
+}
+
+ensure_codex_deployment
+
+ensure_env_from() {
+  local resource="$1"
+  local name="$2"
+  local jsonpath="$3"
+  local patch_path="$4"
+  local existing_env_from
+
+  existing_env_from="$(kubectl --context "$CLUSTER" -n "$NAMESPACE" get "$resource" "$name" \
+    -o "jsonpath=$jsonpath" 2>/dev/null || true)"
+
+  if [[ "$existing_env_from" == *"$SECRET"* ]]; then
+    return
+  fi
+
+  local patch
+  if [[ -z "$existing_env_from" ]]; then
+    patch="[{\"op\":\"add\",\"path\":\"$patch_path\",\"value\":[{\"secretRef\":{\"name\":\"$SECRET\"}}]}]"
+  else
+    patch="[{\"op\":\"add\",\"path\":\"$patch_path/-\",\"value\":{\"secretRef\":{\"name\":\"$SECRET\"}}}]"
+  fi
+  kubectl --context "$CLUSTER" -n "$NAMESPACE" patch "$resource" "$name" --type=json -p "$patch"
+}
+
+ensure_env_from \
+  workload \
+  "$WORKLOAD" \
+  "{.spec.pools[0].template.template.spec.workers.template.spec.containers[0].envFrom}" \
+  "/spec/pools/0/template/template/spec/workers/template/spec/containers/0/envFrom"
+
+ensure_env_from \
+  pool \
+  "$WORKLOAD" \
+  "{.spec.workers.template.spec.containers[0].envFrom}" \
+  "/spec/workers/template/spec/containers/0/envFrom"
+
+codex_ssh_volume_json="$(jq -n --arg secret "$CODEX_SSH_SECRET" '{
+  name: "sybil-codex-ssh",
+  secret: {
+    secretName: $secret,
+    defaultMode: 384
+  }
+}')"
+codex_main_mount_json="$(jq -n '{name: "sybil-codex-ssh", mountPath: "/run/secrets/sybil-codex-ssh", readOnly: true}')"
+
+patch_pool_codex_mount() {
+  local pool_json containers volumes patch
+  pool_json="$(kubectl --context "$CLUSTER" -n "$NAMESPACE" get pool "$WORKLOAD" -o json)"
+  containers="$(jq \
+    --arg sidecarName "$CODEX_CONTAINER" \
+    --argjson mainMount "$codex_main_mount_json" \
+    '
+    def ensure_mount($mount):
+      .volumeMounts = (((.volumeMounts // []) | map(select(.name != $mount.name))) + [$mount]);
+    (.spec.workers.template.spec.containers // [])
+    | map(if .name == "main" then ensure_mount($mainMount) else . end)
+    | map(select(.name != $sidecarName))
+    ' <<<"$pool_json")"
+  volumes="$(jq \
+    --argjson sshVolume "$codex_ssh_volume_json" \
+    '
+    (.spec.workers.template.spec.volumes // [])
+    | map(select(.name != $sshVolume.name and .name != "sybil-codex-workspace"))
+    + [$sshVolume]
+    ' <<<"$pool_json")"
+  patch="$(jq -n --argjson containers "$containers" --argjson volumes "$volumes" '{
+    spec: {
+      workers: {
+        template: {
+          spec: {
+            containers: $containers,
+            volumes: $volumes
+          }
+        }
+      }
+    }
+  }')"
+  kubectl --context "$CLUSTER" -n "$NAMESPACE" patch pool "$WORKLOAD" --type=merge -p "$patch"
+}
+
+patch_workload_codex_mount() {
+  local workload_json pools patch
+  workload_json="$(kubectl --context "$CLUSTER" -n "$NAMESPACE" get workload "$WORKLOAD" -o json)"
+  pools="$(jq \
+    --arg groupName "$WORKLOAD" \
+    --arg sidecarName "$CODEX_CONTAINER" \
+    --argjson mainMount "$codex_main_mount_json" \
+    --argjson sshVolume "$codex_ssh_volume_json" \
+    '
+    def ensure_mount($mount):
+      .volumeMounts = (((.volumeMounts // []) | map(select(.name != $mount.name))) + [$mount]);
+    .spec.pools
+    | map(
+        if .groupName == $groupName then
+          .template.template.spec.workers.template.spec.containers =
+            ((.template.template.spec.workers.template.spec.containers // [])
+              | map(if .name == "main" then ensure_mount($mainMount) else . end)
+              | map(select(.name != $sidecarName)))
+          | .template.template.spec.workers.template.spec.volumes =
+            ((.template.template.spec.workers.template.spec.volumes // [])
+              | map(select(.name != $sshVolume.name and .name != "sybil-codex-workspace"))
+              + [$sshVolume])
+        else
+          .
+        end
+      )
+    ' <<<"$workload_json")"
+  patch="$(jq -n --argjson pools "$pools" '{spec: {pools: $pools}}')"
+  kubectl --context "$CLUSTER" -n "$NAMESPACE" patch workload "$WORKLOAD" --type=merge -p "$patch"
+}
+
+patch_workload_codex_mount
+patch_pool_codex_mount
+
+echo "Waiting for $WORKLOAD-0 to run the current pool revision..."
+deadline=$((SECONDS + 300))
+while true; do
+  pool_revision="$(kubectl --context "$CLUSTER" -n "$NAMESPACE" get pool "$WORKLOAD" -o jsonpath='{.status.revision}' 2>/dev/null || true)"
+  pod_revision="$(kubectl --context "$CLUSTER" -n "$NAMESPACE" get pod "$WORKLOAD-0" -o jsonpath='{.metadata.labels.brix\.openai\.com/revision}' 2>/dev/null || true)"
+  pod_ready="$(kubectl --context "$CLUSTER" -n "$NAMESPACE" get pod "$WORKLOAD-0" -o jsonpath='{.status.conditions[?(@.type=="Ready")].status}' 2>/dev/null || true)"
+  pod_deletion_timestamp="$(kubectl --context "$CLUSTER" -n "$NAMESPACE" get pod "$WORKLOAD-0" -o jsonpath='{.metadata.deletionTimestamp}' 2>/dev/null || true)"
+
+  if [[ -n "$pool_revision" && "$pod_revision" == "$pool_revision" && "$pod_ready" == "True" && -z "$pod_deletion_timestamp" ]]; then
+    break
+  fi
+
+  if (( SECONDS >= deadline )); then
+    echo "Timed out waiting for current ready pod. pool_revision=$pool_revision pod_revision=$pod_revision pod_ready=$pod_ready deleting=$pod_deletion_timestamp" >&2
+    exit 1
+  fi
+
+  sleep 5
+done
+
+brix run --clusters "$CLUSTER" --namespace "$NAMESPACE" --pools "$WORKLOAD" --dir "$REMOTE_ROOT" -- ./scripts/devbox-start.sh
+
+ssh_check="ssh -n -i '$CODEX_SSH_KEY_PATH' -o BatchMode=yes -o StrictHostKeyChecking=accept-new -o UserKnownHostsFile=/tmp/sybil-codex-known-hosts -p '$CODEX_SSH_PORT' root@'$CODEX_SERVICE' true"
+brix run --clusters "$CLUSTER" --namespace "$NAMESPACE" --pools "$WORKLOAD" --dir "$REMOTE_ROOT" -- /bin/bash -lc "$ssh_check"
+
+url="$(brix ingress create --cluster "$CLUSTER" --namespace "$NAMESPACE" --pod "$WORKLOAD-0" --ports "web:$INGRESS_PORT" --root web --timeout 300 "$WORKLOAD" | tail -1)"
+
+echo "Devbox update complete: $url"