Add indexed history search across iOS and web

docs/api/rest.md

@@ -31,7 +31,7 @@ Chat upload limits:
 ```json
 {
   "providers": {
-    "openai": { "models": ["gpt-4.1-mini"], "loadedAt": "2026-02-14T00:00:00.000Z", "error": null },
+    "openai": { "models": ["chat-latest", "gpt-4.1-mini"], "loadedAt": "2026-02-14T00:00:00.000Z", "error": null },
     "anthropic": { "models": ["claude-3-5-sonnet-latest"], "loadedAt": null, "error": null },
     "xai": { "models": ["grok-3-mini"], "loadedAt": null, "error": null },
     "gemini": { "models": ["gemini-3.5-flash"], "loadedAt": null, "error": null },
@@ -39,7 +39,7 @@ Chat upload limits:
   }
 }
 ```
-- OpenAI model lists are filtered to models that are expected to work with the backend's Responses API implementation.
+- OpenAI model lists are filtered to models that are expected to work with the backend's Responses API implementation, including the exact `chat-latest` alias when returned by OpenAI. Audio, image-generation, embedding, moderation, and other specialized model ids remain excluded. See [OpenAI's Chat Latest documentation](https://developers.openai.com/api/docs/models/chat-latest) for supported capabilities.
 - Gemini model lists are loaded from Google's native Models API and filtered to Gemini `generateContent` model ids.
 - `hermes-agent` is included only when `HERMES_AGENT_API_KEY` is configured. Set it to Hermes `API_SERVER_KEY`, or any non-empty value if that local server does not require auth. `HERMES_AGENT_API_BASE_URL` defaults to `http://127.0.0.1:8642/v1`; set `HERMES_AGENT_MODEL` only when you need an additional fallback/override model id.
 - The backend loads provider model lists at startup and refreshes them about once every 24 hours. If a later provider refresh fails, the response keeps the last loaded model list for that provider and sets `error` to the latest failure message.
@@ -81,6 +81,8 @@ Behavior notes:
 
 ### `GET /v1/workspace-items`
 - Response: `{ "items": WorkspaceItem[] }`
+- Optional query: `q` (trimmed string, up to 200 characters). Omit or leave blank for the recent-items list.
+- With nonblank `q`, response: `{ "items": WorkspaceItem[], "hasMore": boolean }`; each item also has `searchSnippet: string | null` (plain text, no HTML).
 - `WorkspaceItem` is a discriminated union sorted by `updatedAt` descending:
 ```json
 {
@@ -123,6 +125,15 @@ Behavior notes:
 - Root chats have `parentChatId: null`. Every fork points directly to its single root chat, including a fork created from another fork, so clients can group rows without traversing a fork chain.
 - `starred`/`starredAt` are backed by membership in a reserved `Project` with id `starred`; future project folders can reuse the same project item model.
 
+History search (`q`) notes:
+- Searches all saved history, including items outside the recent-items window. Chats match their title or the text of a user/assistant message; saved web searches match their title, query, or generated answer. System prompts, tool logs, attachments, and raw web-result payloads are excluded.
+- Case- and diacritic-insensitive Unicode word-prefix matching: `plan` matches `planning`. All query words must match within the title, a single message, or one saved web search (across its indexed fields). Punctuation separates words; quotes, `*`, and operators have no special query syntax. Punctuation-only queries return no matches. This is word-prefix search, not arbitrary substring matching.
+- Returns at most 100 distinct matching items, newest `updatedAt` first, with ties ordered by `type` then `id`. `hasMore` indicates additional matches; refine `q` to narrow them. Unmatched fork roots are not added in search mode. Selecting a fork result opens that fork directly. Search-mode fork results carry their root's `starred`/`starredAt`; clients should star/unstar the `parentChatId`, as in the grouped sidebar.
+- `searchSnippet` is a bounded excerpt from a matching message or saved web search; title-only chat matches have `null`. Clients should render it as plain text.
+- The web and iOS sidebar search fields use this endpoint across saved history. Both display matching excerpts; web title-only chat results display “Title match”.
+- Invalid/non-string queries or queries exceeding 200 characters return `400`. Authentication is unchanged.
+- SQLite FTS5 external-content indexes and prefix indexes serve these queries without scanning or transferring every transcript. The migration backfills existing content; transactional triggers maintain the indexes on inserts, updates, deletes, and cascades. Recent chat listing also has an `updatedAt` index.
+
 ## Chats
 
 ### `GET /v1/chats`

docs/api/streaming-chat.md

@@ -1,21 +1,22 @@
 # Streaming Chat API Contract
 
-This document defines the server-sent events (SSE) contract for chat completions.
+This document defines the server-sent events (SSE) contract for chat completions and Quick Questions.
 
 Endpoint:
 - `POST /v1/chat-completions/stream`
 - `POST /v1/chats/:chatId/stream/attach`
+- `POST /v1/quick-questions/stream`
 
 Transport:
 - HTTP response uses `Content-Type: text/event-stream; charset=utf-8`
 - Events are emitted in SSE format (`event: ...`, `data: ...`)
 - Request body is JSON
-- Request body supports the same inline attachment schema and limits documented in `docs/api/rest.md`.
+- Chat completion request bodies support the same inline attachment schema and limits documented in `docs/api/rest.md`. Quick Questions accept text only.
 
 Authentication:
 - Same as REST endpoints (`Authorization: Bearer <token>` when token mode is enabled)
 
-## Request Body
+## Chat Completion Request Body
 
 ```json
 {
@@ -90,6 +91,32 @@ Persisted chat streams with a `chatId` are backend-owned active runs:
 
 This endpoint is intended for clients that restored an active `chatId` from `GET /v1/active-runs`, especially after browser refresh. Replayed `delta` events may include text that was originally emitted before the client attached.
 
+## Quick Question Endpoint
+
+`POST /v1/quick-questions/stream`
+
+Request body:
+```json
+{
+  "provider": "openai|anthropic|xai|gemini|hermes-agent",
+  "model": "string",
+  "question": "What is the capital of France?",
+  "enabledTools": ["web_search", "fetch_url"],
+  "userLocation": "optional city, region, country",
+  "temperature": 0.2,
+  "maxTokens": 256
+}
+```
+
+Behavior notes:
+- `provider` and `model` are required. Web and native clients default Quick Question to `provider: "openai"` and `model: "chat-latest"` when no Quick Question selection has been saved. Saved Quick Question choices take precedence over this default and are separate from regular chat preferences.
+- `question` is required, trimmed by the server, and must not be empty.
+- The server prepends a Quick Question system prompt that asks for a succinct, direct, self-contained answer without follow-up questions. Clients do not send or maintain this prompt.
+- Quick Questions are always non-persistent. The endpoint does not create a chat or store messages, tool-call logs, assistant output, or `LlmCall` metadata.
+- The response uses the same `meta`, `tool_call`, `delta`, `done`, and `error` SSE events as chat completion streams. The `meta` event has `chatId: null` and `callId: null`.
+- `enabledTools`, `temperature`, and `maxTokens` are optional and behave as they do for chat completion streams. When `enabledTools` is omitted, all available Sybil-managed tools are enabled by default.
+- User location is inferred from the same request headers as chat completion streams when `userLocation` is omitted.
+
 ## Event Stream Contract
 
 Event order:

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/SybilAPIClient.swift

@@ -49,6 +49,15 @@ actor SybilAPIClient: SybilAPIClienting {
         return response.items
     }
 
+    func searchWorkspaceItems(query: String) async throws -> WorkspaceSearchResponse {
+        try await request(
+            "/v1/workspace-items",
+            method: "GET",
+            queryItems: [URLQueryItem(name: "q", value: query)],
+            responseType: WorkspaceSearchResponse.self
+        )
+    }
+
     func listChats() async throws -> [ChatSummary] {
         let response = try await request("/v1/chats", method: "GET", responseType: ChatListResponse.self)
         return response.chats
@@ -74,6 +83,16 @@ actor SybilAPIClient: SybilAPIClienting {
         return response.chat
     }
 
+    func forkChat(chatID: String, messageID: String? = nil) async throws -> ChatSummary {
+        let response = try await request(
+            "/v1/chats/\(chatID)/fork",
+            method: "POST",
+            body: AnyEncodable(ChatForkBody(messageId: messageID)),
+            responseType: ChatCreateResponse.self
+        )
+        return response.chat
+    }
+
     func updateChatTitle(chatID: String, title: String) async throws -> ChatSummary {
         let response = try await request(
             "/v1/chats/\(chatID)",
@@ -183,6 +202,29 @@ actor SybilAPIClient: SybilAPIClienting {
         SybilLog.info(SybilLog.network, "Chat stream completed")
     }
 
+    func runQuickQuestionStream(
+        body: QuickQuestionStreamRequest,
+        onEvent: @escaping @Sendable (CompletionStreamEvent) async -> Void
+    ) async throws {
+        let request = try makeRequest(
+            path: "/v1/quick-questions/stream",
+            method: "POST",
+            body: AnyEncodable(body),
+            acceptsSSE: true
+        )
+
+        SybilLog.info(
+            SybilLog.network,
+            "Starting quick question stream POST \(request.url?.absoluteString ?? "<unknown>")"
+        )
+
+        try await stream(request: request) { eventName, dataText in
+            try await Self.handleCompletionStreamEvent(eventName: eventName, dataText: dataText, onEvent: onEvent)
+        }
+
+        SybilLog.info(SybilLog.network, "Quick question stream completed")
+    }
+
     func attachCompletionStream(
         chatID: String,
         onEvent: @escaping @Sendable (CompletionStreamEvent) async -> Void
@@ -257,9 +299,10 @@ actor SybilAPIClient: SybilAPIClienting {
         _ path: String,
         method: String,
         body: AnyEncodable? = nil,
+        queryItems: [URLQueryItem] = [],
         responseType: Response.Type
     ) async throws -> Response {
-        let request = try makeRequest(path: path, method: method, body: body, acceptsSSE: false)
+        let request = try makeRequest(path: path, method: method, body: body, acceptsSSE: false, queryItems: queryItems)
 
         SybilLog.debug(
             SybilLog.network,
@@ -311,9 +354,10 @@ actor SybilAPIClient: SybilAPIClienting {
         path: String,
         method: String,
         body: AnyEncodable?,
-        acceptsSSE: Bool
+        acceptsSSE: Bool,
+        queryItems: [URLQueryItem] = []
     ) throws -> URLRequest {
-        let url = try buildURL(path: path)
+        let url = try buildURL(path: path, queryItems: queryItems)
         var request = URLRequest(url: url)
         request.httpMethod = method
         request.timeoutInterval = 120
@@ -336,7 +380,7 @@ actor SybilAPIClient: SybilAPIClienting {
         return request
     }
 
-    private func buildURL(path: String) throws -> URL {
+    private func buildURL(path: String, queryItems: [URLQueryItem]) throws -> URL {
         guard var components = URLComponents(url: configuration.baseURL, resolvingAgainstBaseURL: false) else {
             throw APIError.invalidBaseURL
         }
@@ -347,6 +391,9 @@ actor SybilAPIClient: SybilAPIClienting {
             basePath.removeLast()
         }
         components.path = "\(basePath)/\(trimmedPath)"
+        if !queryItems.isEmpty {
+            components.queryItems = (components.queryItems ?? []) + queryItems
+        }
 
         guard let url = components.url else {
             throw APIError.invalidBaseURL
@@ -664,6 +711,12 @@ struct CompletionStreamRequest: Codable, Sendable {
     var userLocation: String? = nil
 }
 
+struct QuickQuestionStreamRequest: Codable, Sendable {
+    var provider: Provider
+    var model: String
+    var question: String
+}
+
 private struct ChatCreateBody: Encodable {
     var title: String?
     var provider: Provider?
@@ -675,6 +728,10 @@ private struct ChatTitleUpdateBody: Encodable {
     var title: String
 }
 
+private struct ChatForkBody: Encodable {
+    var messageId: String?
+}
+
 private struct StarUpdateBody: Encodable {
     var starred: Bool
 }

ios/Packages/Sybil/Sources/Sybil/SybilAPIClienting.swift

@@ -3,6 +3,7 @@ import Foundation
 protocol SybilAPIClienting: Sendable {
     func verifySession() async throws -> AuthSession
     func listWorkspaceItems() async throws -> [WorkspaceItem]
+    func searchWorkspaceItems(query: String) async throws -> WorkspaceSearchResponse
     func listChats() async throws -> [ChatSummary]
     func createChat(
         title: String?,
@@ -11,6 +12,7 @@ protocol SybilAPIClienting: Sendable {
         messages: [CompletionRequestMessage]?
     ) async throws -> ChatSummary
     func getChat(chatID: String) async throws -> ChatDetail
+    func forkChat(chatID: String, messageID: String?) async throws -> ChatSummary
     func updateChatTitle(chatID: String, title: String) async throws -> ChatSummary
     func updateChatStar(chatID: String, starred: Bool) async throws -> ChatSummary
     func deleteChat(chatID: String) async throws
@@ -27,6 +29,10 @@ protocol SybilAPIClienting: Sendable {
         body: CompletionStreamRequest,
         onEvent: @escaping @Sendable (CompletionStreamEvent) async -> Void
     ) async throws
+    func runQuickQuestionStream(
+        body: QuickQuestionStreamRequest,
+        onEvent: @escaping @Sendable (CompletionStreamEvent) async -> Void
+    ) async throws
     func attachCompletionStream(
         chatID: String,
         onEvent: @escaping @Sendable (CompletionStreamEvent) async -> Void

ios/Packages/Sybil/Sources/Sybil/SybilChatTranscriptView.swift

@@ -1,13 +1,17 @@
 import MarkdownUI
 import SwiftUI
+import UIKit
 
 struct SybilChatTranscriptView: View {
     var messages: [Message]
     var isLoading: Bool
     var isSending: Bool
+    var streamingAssistantPresentation: StreamingAssistantPresentation?
     var topContentInset: CGFloat = 0
     var bottomContentInset: CGFloat = 0
     var bottomPinRequestID: Int = 0
+    var isForking: Bool = false
+    var onForkResponse: ((String) -> Void)? = nil
 
     @State private var hasTrackedToolCallMessages = false
     @State private var knownToolCallMessageIDs: Set<String> = []
@@ -41,7 +45,15 @@ struct SybilChatTranscriptView: View {
                     ForEach(renderItems) { item in
                         switch item {
                         case let .message(message):
-                            MessageBubble(message: message, isSending: isSending)
+                            MessageBubble(
+                                message: message,
+                                isSending: isSending,
+                                streamingAssistantPresentation: streamingAssistantPresentation,
+                                isForking: isForking,
+                                onFork: {
+                                    onForkResponse?(message.id)
+                                }
+                            )
                                 .frame(maxWidth: .infinity)
                         case let .toolGroup(id, messages):
                             ToolCallStackView(
@@ -140,6 +152,9 @@ func buildTranscriptRenderItems(from messages: [Message]) -> [TranscriptRenderIt
 private struct MessageBubble: View {
     var message: Message
     var isSending: Bool
+    var streamingAssistantPresentation: StreamingAssistantPresentation?
+    var isForking: Bool
+    var onFork: (() -> Void)?
 
     private var toolCallMetadata: ToolCallMetadata? {
         message.toolCallMetadata
@@ -149,13 +164,46 @@ private struct MessageBubble: View {
         message.role == .user
     }
 
-    private var isPendingAssistant: Bool {
+    private var isStreamingAssistant: Bool {
-        message.id.hasPrefix("temp-assistant-") &&
+        message.role == .assistant && message.id.hasPrefix("temp-assistant-")
-            isSending &&
+    }
-            message.content.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty
+
+    private var matchingStreamingAssistantPresentation: StreamingAssistantPresentation? {
+        guard streamingAssistantPresentation?.messageID == message.id else { return nil }
+        return streamingAssistantPresentation
+    }
+
+    private var canFork: Bool {
+        message.role == .assistant &&
+            !message.id.hasPrefix("temp-") &&
+            onFork != nil
     }
 
     var body: some View {
+        Group {
+            if canFork {
+                bubbleContent
+                    .contextMenu {
+                        Button {
+                            UIPasteboard.general.string = message.content
+                        } label: {
+                            Label("Copy", systemImage: "doc.on.doc")
+                        }
+
+                        Button {
+                            onFork?()
+                        } label: {
+                            Label("Fork", systemImage: "arrow.triangle.branch")
+                        }
+                        .disabled(isForking)
+                    }
+            } else {
+                bubbleContent
+            }
+        }
+    }
+
+    private var bubbleContent: some View {
         HStack(alignment: .top, spacing: 0) {
             leadingSpacer
 
@@ -174,16 +222,12 @@ private struct MessageBubble: View {
                         )
                     }
 
-                    if isPendingAssistant {
+                    if isStreamingAssistant {
-                        HStack(spacing: 8) {
+                        StreamingAssistantContentView(
-                            ProgressView()
+                            content: message.content,
-                                .controlSize(.small)
+                            isSending: isSending,
-                                .tint(SybilTheme.primary)
+                            presentation: matchingStreamingAssistantPresentation
-                            Text("Thinking…")
+                        )
-                                .font(.sybil(.footnote))
-                                .foregroundStyle(SybilTheme.textMuted)
-                        }
-                        .padding(.vertical, 2)
                     } else if !message.content.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty {
                         Markdown(message.content)
                             .tint(SybilTheme.primary)
@@ -232,6 +276,123 @@ private struct MessageBubble: View {
     }
 }
 
+private struct StreamingTraceHeightPreferenceKey: PreferenceKey {
+    static let defaultValue: CGFloat = 0
+
+    static func reduce(value: inout CGFloat, nextValue: () -> CGFloat) {
+        value = max(value, nextValue())
+    }
+}
+
+struct StreamingAssistantContentView: View {
+    private enum Phase: Hashable {
+        case pending
+        case trace(Int)
+        case answer
+    }
+
+    var content: String
+    var isSending: Bool
+    var presentation: StreamingAssistantPresentation?
+
+    @Environment(\.accessibilityReduceMotion) private var reduceMotion
+    @State private var retainedTraceHeight: CGFloat = 0
+
+    private var traceText: String? {
+        guard let trace = presentation?.ephemeralTrace?.trimmingCharacters(in: .whitespacesAndNewlines),
+              !trace.isEmpty
+        else {
+            return nil
+        }
+        return trace
+    }
+
+    private var hasAnswer: Bool {
+        !content.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty
+    }
+
+    private var phase: Phase {
+        if hasAnswer {
+            return .answer
+        }
+        if traceText != nil {
+            return .trace(presentation?.traceRevision ?? 0)
+        }
+        return .pending
+    }
+
+    private var traceTransition: AnyTransition {
+        guard !reduceMotion else { return .identity }
+        return .asymmetric(
+            insertion: .opacity.combined(with: .offset(y: 5)),
+            removal: .opacity.combined(with: .offset(y: -5))
+        )
+    }
+
+    private var answerTransition: AnyTransition {
+        guard !reduceMotion else { return .identity }
+        return .opacity.combined(with: .offset(y: 3))
+    }
+
+    var body: some View {
+        ZStack(alignment: .topLeading) {
+            if let traceText {
+                Text(traceText)
+                    .font(.sybil(size: 15))
+                    .italic()
+                    .foregroundStyle(SybilTheme.textMuted.opacity(0.88))
+                    .lineSpacing(5)
+                    .fixedSize(horizontal: false, vertical: true)
+                    .opacity(0.78)
+                    .textSelection(.disabled)
+                    .allowsHitTesting(false)
+                    .accessibilityLabel("Assistant is working")
+                    .background {
+                        GeometryReader { geometry in
+                            Color.clear.preference(
+                                key: StreamingTraceHeightPreferenceKey.self,
+                                value: geometry.size.height
+                            )
+                        }
+                    }
+                    .id("thinking-trace-\(presentation?.traceRevision ?? 0)")
+                    .transition(traceTransition)
+                    .zIndex(1)
+            }
+
+            if hasAnswer {
+                Markdown(content)
+                    .tint(SybilTheme.primary)
+                    .foregroundStyle(SybilTheme.text.opacity(0.95))
+                    .markdownTheme(.sybilReadable)
+                    .textSelection(.enabled)
+                    .id("streaming-assistant-answer")
+                    .transition(answerTransition)
+                    .zIndex(2)
+            }
+
+            if isSending && !hasAnswer && traceText == nil {
+                HStack(spacing: 8) {
+                    ProgressView()
+                        .controlSize(.small)
+                        .tint(SybilTheme.primary)
+                    Text("Thinking…")
+                        .font(.sybil(.footnote))
+                        .foregroundStyle(SybilTheme.textMuted)
+                }
+                .padding(.vertical, 2)
+                .transition(reduceMotion ? .identity : .opacity)
+            }
+        }
+        .frame(maxWidth: .infinity, minHeight: max(24, retainedTraceHeight), alignment: .topLeading)
+        .onPreferenceChange(StreamingTraceHeightPreferenceKey.self) { measuredHeight in
+            guard measuredHeight.isFinite, measuredHeight > retainedTraceHeight else { return }
+            retainedTraceHeight = measuredHeight
+        }
+        .animation(reduceMotion ? nil : .easeOut(duration: 0.20), value: phase)
+    }
+}
+
 private struct ToolCallStackView: View {
     private struct CardLayout {
         var x: CGFloat

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/SybilModels.swift

@@ -219,6 +219,7 @@ public struct WorkspaceItem: Codable, Identifiable, Hashable, Sendable {
     public var id: String
     public var title: String?
     public var query: String?
+    public var searchSnippet: String? = nil
     public var parentChatId: String? = nil
     public var titleGenerationPending = false
     public var createdAt: Date
@@ -302,6 +303,7 @@ extension WorkspaceItem {
         case id
         case title
         case query
+        case searchSnippet
         case parentChatId
         case titleGenerationPending
         case createdAt
@@ -320,6 +322,7 @@ extension WorkspaceItem {
         id = try container.decode(String.self, forKey: .id)
         title = try container.decodeIfPresent(String.self, forKey: .title)
         query = try container.decodeIfPresent(String.self, forKey: .query)
+        searchSnippet = try container.decodeIfPresent(String.self, forKey: .searchSnippet)
         parentChatId = try container.decodeIfPresent(String.self, forKey: .parentChatId)
         titleGenerationPending = try container.decodeIfPresent(Bool.self, forKey: .titleGenerationPending) ?? false
         createdAt = try container.decode(Date.self, forKey: .createdAt)
@@ -730,6 +733,11 @@ struct SearchListResponse: Codable {
     var searches: [SearchSummary]
 }
 
+struct WorkspaceSearchResponse: Codable, Sendable {
+    var items: [WorkspaceItem]
+    var hasMore: Bool
+}
+
 struct WorkspaceListResponse: Codable {
     var items: [WorkspaceItem]
 }

ios/Packages/Sybil/Sources/Sybil/SybilPhoneShellView.swift

@@ -130,7 +130,10 @@ struct SybilPhoneShellView: View {
             route: route,
             onRequestBack: { _ in showSidebarOverlay() },
             onRequestNewChat: sidebarWorkspaceNewChatAction,
-            onShowSidebar: showSidebarOverlay
+            onShowSidebar: showSidebarOverlay,
+            onOpenForkedChat: { chatID in
+                showRoute(.chat(chatID))
+            }
         )
         .background(SybilTheme.background)
         .blur(radius: SidebarOverlaySwipeMetrics.workspaceBlurRadius(for: sidebarOverlayProgress))
@@ -239,6 +242,7 @@ struct SybilPhoneShellView: View {
     }
 
     private func showRoute(_ nextRoute: PhoneRoute) {
+        dismissSidebarKeyboard()
         let update = {
             route = nextRoute
         }
@@ -268,12 +272,19 @@ struct SybilPhoneShellView: View {
     }
 
     private func hideSidebarOverlay() {
+        dismissSidebarKeyboard()
         withAnimation(.easeOut(duration: 0.18)) {
             isSidebarOverlayPresented = false
         }
         resetSidebarSwipe(animated: false)
     }
 
+    private func dismissSidebarKeyboard() {
+        if isSidebarOverlayPresented {
+            UIApplication.shared.sendAction(#selector(UIResponder.resignFirstResponder), to: nil, from: nil, for: nil)
+        }
+    }
+
     private func openSidebarSelection(_ selection: SidebarSelection) {
         if openingSelectionRequestID != nil, sidebarHighlightSelection == selection {
             return
@@ -511,6 +522,9 @@ private struct SybilPhoneSidebarRoot: View {
                 },
                 onSelect: { item in
                     onSelect(item.selection)
+                },
+                onOpenForkedChat: { chatID in
+                    onSelect(.chat(chatID))
                 }
             )
         }
@@ -585,6 +599,7 @@ private struct SybilPhoneDestinationView: View {
     let onRequestBack: (_ animateNavigation: Bool) -> Void
     let onRequestNewChat: (() -> Void)?
     let onShowSidebar: () -> Void
+    let onOpenForkedChat: (String) -> Void
 
     var body: some View {
         SybilWorkspaceView(
@@ -593,7 +608,8 @@ private struct SybilPhoneDestinationView: View {
             navigationLeadingControl: .showSidebar,
             onShowSidebar: onShowSidebar,
             onRequestBack: onRequestBack,
-            onRequestNewChat: onRequestNewChat
+            onRequestNewChat: onRequestNewChat,
+            onOpenForkedChat: onOpenForkedChat
         )
         .frame(maxWidth: .infinity, maxHeight: .infinity, alignment: .topLeading)
         .task(id: route) {

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)
         }
     }
 
@@ -59,7 +62,11 @@ struct SybilQuickQuestionView: View {
             VStack(alignment: .leading, spacing: 12) {
                 if hasAnswerContent {
                     ForEach(viewModel.quickQuestionMessages) { message in
-                        QuickQuestionMessageView(message: message, isSending: viewModel.isQuickQuestionSending)
+                        QuickQuestionMessageView(
+                            message: message,
+                            isSending: viewModel.isQuickQuestionSending,
+                            streamingAssistantPresentation: viewModel.quickQuestionStreamingAssistantPresentation
+                        )
                     }
 
                     if let error = viewModel.quickQuestionError {
@@ -94,13 +101,13 @@ struct SybilQuickQuestionView: View {
                         get: { viewModel.quickQuestionPrompt },
                         set: { viewModel.updateQuickQuestionPrompt($0) }
                     ),
-                    axis: .vertical
+                    selection: $promptSelection,
+                    axis: .horizontal
                 )
                 .focused($promptFocused)
                 .font(.body)
                 .textInputAutocapitalization(.sentences)
                 .autocorrectionDisabled(false)
-                .lineLimit(1 ... 6)
                 .submitLabel(.send)
                 .onSubmit(submitQuestion)
                 .padding(.horizontal, 12)
@@ -259,11 +266,11 @@ private struct QuickQuestionPickerPill: View {
 private struct QuickQuestionMessageView: View {
     var message: Message
     var isSending: Bool
+    var streamingAssistantPresentation: StreamingAssistantPresentation?
 
-    private var isPendingAssistant: Bool {
+    private var matchingStreamingAssistantPresentation: StreamingAssistantPresentation? {
-        message.id.hasPrefix("temp-assistant-quick-") &&
+        guard streamingAssistantPresentation?.messageID == message.id else { return nil }
-            isSending &&
+        return streamingAssistantPresentation
-            message.content.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty
     }
 
     var body: some View {
@@ -272,15 +279,12 @@ private struct QuickQuestionMessageView: View {
                 .font(.caption)
                 .foregroundStyle(SybilTheme.textMuted)
                 .fixedSize(horizontal: false, vertical: true)
-        } else if isPendingAssistant {
+        } else if message.id.hasPrefix("temp-assistant-quick-") {
-            HStack(spacing: 8) {
+            StreamingAssistantContentView(
-                ProgressView()
+                content: message.content,
-                    .controlSize(.small)
+                isSending: isSending,
-                    .tint(SybilTheme.primary)
+                presentation: matchingStreamingAssistantPresentation
-                Text("Thinking...")
+            )
-                    .font(.caption)
-                    .foregroundStyle(SybilTheme.textMuted)
-            }
         } else if !message.content.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty {
             Markdown(message.content)
                 .font(.body)

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/SybilSettingsStore.swift

@@ -52,9 +52,9 @@ final class SybilSettingsStore {
         self.preferredModelByProvider = preferredModels
 
         self.quickQuestionPreferredProvider =
-            defaults.string(forKey: Keys.quickQuestionPreferredProvider).flatMap(Provider.init(rawValue:)) ?? provider
+            defaults.string(forKey: Keys.quickQuestionPreferredProvider).flatMap(Provider.init(rawValue:)) ?? .openai
         self.quickQuestionPreferredModelByProvider = [
-            .openai: defaults.string(forKey: Keys.quickQuestionPreferredOpenAIModel) ?? preferredModels[.openai] ?? "gpt-4.1-mini",
+            .openai: defaults.string(forKey: Keys.quickQuestionPreferredOpenAIModel) ?? "chat-latest",
             .anthropic: defaults.string(forKey: Keys.quickQuestionPreferredAnthropicModel) ?? preferredModels[.anthropic] ?? "claude-3-5-sonnet-latest",
             .xai: defaults.string(forKey: Keys.quickQuestionPreferredXAIModel) ?? preferredModels[.xai] ?? "grok-3-mini",
             .gemini: defaults.string(forKey: Keys.quickQuestionPreferredGeminiModel) ?? preferredModels[.gemini] ?? "gemini-3.5-flash",

ios/Packages/Sybil/Sources/Sybil/SybilSidebarView.swift

@@ -1,5 +1,6 @@
 import Observation
 import SwiftUI
+import UIKit
 
 struct SybilSidebarView: View {
     @Bindable var viewModel: SybilViewModel
@@ -111,8 +112,10 @@ struct SybilSidebarItemList: View {
     @Bindable var viewModel: SybilViewModel
     var isSelected: (SidebarItem) -> Bool
     var onSelect: (SidebarItem) -> Void
+    var onOpenForkedChat: ((String) -> Void)? = nil
     @State private var renameTarget: SidebarItem?
     @State private var renameTitle = ""
+    @FocusState private var isSearchFocused: Bool
 
     private var isRenameAlertPresented: Binding<Bool> {
         Binding {
@@ -126,37 +129,98 @@ struct SybilSidebarItemList: View {
     }
 
     var body: some View {
+        VStack(spacing: 0) {
+            HStack(spacing: 10) {
+                Image(systemName: "magnifyingglass")
+                    .foregroundStyle(SybilTheme.textMuted)
+                TextField("Search chats and web searches", text: Binding(
+                    get: { viewModel.sidebarSearchQuery },
+                    set: { viewModel.setSidebarSearchQuery($0) }
+                ))
+                .font(.sybil(.subheadline))
+                .foregroundStyle(SybilTheme.text)
+                .textInputAutocapitalization(.never)
+                .autocorrectionDisabled()
+                .submitLabel(.search)
+                .focused($isSearchFocused)
+                .accessibilityLabel("Search conversation history and saved web searches")
+                .onSubmit {
+                    isSearchFocused = false
+                    Task { await viewModel.refreshSidebarSearch() }
+                }
+
+                if !viewModel.sidebarSearchQuery.isEmpty {
+                    Button {
+                        viewModel.setSidebarSearchQuery("")
+                    } label: {
+                        Image(systemName: "xmark.circle.fill")
+                            .foregroundStyle(SybilTheme.textMuted)
+                    }
+                    .buttonStyle(.plain)
+                    .accessibilityLabel("Clear history search")
+                }
+            }
+            .padding(12)
+            .background(SybilTheme.surface, in: RoundedRectangle(cornerRadius: 12))
+            .overlay(RoundedRectangle(cornerRadius: 12).stroke(SybilTheme.border, lineWidth: 1))
+            .padding(10)
+
+            itemList
+        }
+    }
+
+    private var itemList: some View {
         Group {
-            if viewModel.isLoadingCollections && viewModel.sidebarItems.isEmpty {
+            if viewModel.isSearchingSidebar ||
+                (!viewModel.isSidebarSearchActive && viewModel.isLoadingCollections && viewModel.sidebarItems.isEmpty) {
                 VStack(alignment: .leading, spacing: 8) {
                     ProgressView()
                         .tint(SybilTheme.primary)
-                    Text("Loading conversations…")
+                    Text(viewModel.isSidebarSearchActive ? "Searching history…" : "Loading conversations…")
                         .font(.sybil(.footnote))
                         .foregroundStyle(SybilTheme.textMuted)
                 }
                 .frame(maxWidth: .infinity, maxHeight: .infinity, alignment: .topLeading)
                 .padding(16)
-            } else if viewModel.sidebarItems.isEmpty {
+            } else if let error = viewModel.sidebarSearchError, viewModel.isSidebarSearchActive {
+                VStack(spacing: 12) {
+                    Text(error)
+                        .font(.sybil(.footnote))
+                        .foregroundStyle(SybilTheme.danger)
+                        .multilineTextAlignment(.center)
+                    Button("Try again") {
+                        Task { await viewModel.refreshSidebarSearch() }
+                    }
+                }
+                .frame(maxWidth: .infinity, maxHeight: .infinity)
+                .padding(16)
+            } else if viewModel.visibleSidebarItems.isEmpty {
                 VStack(spacing: 10) {
-                    Image(systemName: "message.badge")
+                    Image(systemName: viewModel.isSidebarSearchActive ? "magnifyingglass" : "message.badge")
                         .font(.system(size: 20, weight: .medium))
                         .foregroundStyle(SybilTheme.textMuted)
-                    Text("Start a chat or run your first search.")
+                    Text(viewModel.isSidebarSearchActive ? "No matching chats or web searches." : "Start a chat or run your first search.")
                         .font(.sybil(.footnote))
                         .multilineTextAlignment(.center)
                         .foregroundStyle(SybilTheme.textMuted)
+                    if viewModel.isSidebarSearchActive {
+                        Text("Try a title, a query, or words from a conversation.")
+                            .font(.sybil(.caption))
+                            .multilineTextAlignment(.center)
+                            .foregroundStyle(SybilTheme.textMuted)
+                    }
                 }
                 .frame(maxWidth: .infinity, maxHeight: .infinity)
                 .padding(16)
             } else {
                 ScrollView {
                     LazyVStack(alignment: .leading, spacing: 8) {
-                        ForEach(viewModel.sidebarItems) { item in
+                        ForEach(viewModel.visibleSidebarItems) { item in
                             Button {
+                                isSearchFocused = false
                                 onSelect(item)
                             } label: {
-                                SybilSidebarRow(item: item, isSelected: isSelected(item))
+                                SybilSidebarRow(item: item, isSelected: isSelected(item), searchQuery: viewModel.sidebarSearchQuery)
                             }
                             .buttonStyle(.plain)
                             .contextMenu {
@@ -168,13 +232,26 @@ struct SybilSidebarItemList: View {
                                     Label(item.starred ? "Unstar" : "Star", systemImage: item.starred ? "star.slash" : "star")
                                 }
 
-                                if item.kind == .chat {
+                                if case let .chat(chatID) = item.selection {
+                                    Button {
+                                        forkChat(item)
+                                    } label: {
+                                        Label("Fork", systemImage: "arrow.triangle.branch")
+                                    }
+                                    .disabled(viewModel.isForkingChat || item.isRunning)
+
                                     Button {
                                         renameTarget = item
                                         renameTitle = item.title
                                     } label: {
                                         Label("Rename", systemImage: "pencil")
                                     }
+
+                                    Button {
+                                        UIPasteboard.general.string = chatID
+                                    } label: {
+                                        Label("Copy Session ID", systemImage: "doc.on.doc")
+                                    }
                                 }
 
                                 Button(role: .destructive) {
@@ -186,9 +263,16 @@ struct SybilSidebarItemList: View {
                                 }
                             }
                         }
+                        if viewModel.isSidebarSearchActive && viewModel.sidebarSearchHasMore {
+                            Text("Showing the 100 most recent matches. Refine your search to find more.")
+                                .font(.sybil(.caption))
+                                .foregroundStyle(SybilTheme.textMuted)
+                                .padding(12)
+                        }
                     }
                     .padding(10)
                 }
+                .scrollDismissesKeyboard(.interactively)
                 .refreshable {
                     await viewModel.refreshSidebarCollectionsFromPullToRefresh()
                 }
@@ -215,11 +299,52 @@ struct SybilSidebarItemList: View {
             .disabled(renameTitle.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty)
         }
     }
+
+    private func forkChat(_ item: SidebarItem) {
+        guard case let .chat(chatID) = item.selection else {
+            return
+        }
+
+        let selectionAtStart = viewModel.selectedItem
+        let draftKindAtStart = viewModel.draftKind
+        Task {
+            guard let forkedChat = await viewModel.forkChat(chatID: chatID),
+                  viewModel.selectedItem == selectionAtStart,
+                  viewModel.draftKind == draftKindAtStart else {
+                return
+            }
+
+            if let onOpenForkedChat {
+                onOpenForkedChat(forkedChat.id)
+            } else {
+                viewModel.select(.chat(forkedChat.id))
+            }
+        }
+    }
 }
 
 struct SybilSidebarRow: View {
     var item: SidebarItem
     var isSelected: Bool
+    var searchQuery = ""
+
+    private func highlightedSnippet(_ snippet: String) -> AttributedString {
+        var highlighted = AttributedString(snippet)
+        guard let words = try? NSRegularExpression(pattern: #"[\p{L}\p{N}\p{M}\p{Co}]+"#) else { return highlighted }
+        let terms = words.matches(in: searchQuery, range: NSRange(searchQuery.startIndex..., in: searchQuery)).compactMap { match -> String? in
+            guard let range = Range(match.range, in: searchQuery) else { return nil }
+            return String(searchQuery[range]).folding(options: [.diacriticInsensitive, .caseInsensitive], locale: Locale(identifier: "en_US_POSIX"))
+        }.filter { !$0.isEmpty }
+        for word in words.matches(in: snippet, range: NSRange(snippet.startIndex..., in: snippet)) {
+            guard let range = Range(word.range, in: snippet) else { continue }
+            let normalized = String(snippet[range]).folding(options: [.diacriticInsensitive, .caseInsensitive], locale: Locale(identifier: "en_US_POSIX"))
+            guard terms.contains(where: { normalized.hasPrefix($0) }),
+                  let start = AttributedString.Index(range.lowerBound, within: highlighted),
+                  let end = AttributedString.Index(range.upperBound, within: highlighted) else { continue }
+            highlighted[start..<end].font = .sybil(.caption, weight: .semibold)
+        }
+        return highlighted
+    }
 
     private var isHighlighted: Bool {
         isSelected
@@ -281,6 +406,15 @@ struct SybilSidebarRow: View {
                         .frame(maxWidth: .infinity, alignment: .trailing)
                 }
             }
+
+            if let snippet = item.searchSnippet, !snippet.isEmpty {
+                Text(highlightedSnippet(snippet.replacingOccurrences(of: #"\s+"#, with: " ", options: .regularExpression)))
+                    .font(.sybil(.caption))
+                    .foregroundStyle(SybilTheme.textMuted)
+                    .lineLimit(1)
+                    .truncationMode(.middle)
+                    .multilineTextAlignment(.leading)
+            }
         }
         .foregroundStyle(SybilTheme.text)
         .padding(.horizontal, 12)

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

@@ -38,11 +38,75 @@ struct SidebarItem: Identifiable, Hashable {
     var starredAt: Date?
     var initiatedLabel: String?
     var isRunning: Bool
+    var searchSnippet: String? = nil
+}
+
+enum StreamingAssistantContentUpdate: Equatable, Sendable {
+    case unchanged
+    case replace(String)
+}
+
+struct StreamingAssistantState: Equatable, Sendable {
+    private(set) var segmentText = ""
+    private(set) var initiatedToolCallIDs: Set<String> = []
+    private(set) var ephemeralTrace: String?
+    private(set) var traceRevision = 0
+
+    mutating func receiveDelta(_ text: String) -> StreamingAssistantContentUpdate {
+        guard !text.isEmpty else { return .unchanged }
+        segmentText += text
+        ephemeralTrace = nil
+        return .replace(segmentText)
+    }
+
+    mutating func receiveToolCall(id: String, status: String) -> StreamingAssistantContentUpdate {
+        guard status.lowercased() == "initiated", initiatedToolCallIDs.insert(id).inserted else {
+            return .unchanged
+        }
+
+        let trace = segmentText.trimmingCharacters(in: .whitespacesAndNewlines)
+        segmentText = ""
+        if !trace.isEmpty {
+            ephemeralTrace = trace
+            traceRevision += 1
+        }
+        return .replace("")
+    }
+
+    mutating func receiveDone(_ text: String) -> StreamingAssistantContentUpdate {
+        segmentText = ""
+        ephemeralTrace = nil
+        return .replace(text)
+    }
+
+    mutating func receiveError() -> StreamingAssistantContentUpdate {
+        segmentText = ""
+        ephemeralTrace = nil
+        return .unchanged
+    }
+}
+
+struct StreamingAssistantPresentation: Equatable, Sendable {
+    var messageID: String
+    var ephemeralTrace: String?
+    var traceRevision: Int
 }
 
 private struct PendingChatState {
     var chatID: String?
     var messages: [Message]
+    var streamingAssistantState = StreamingAssistantState()
+
+    var streamingAssistantPresentation: StreamingAssistantPresentation? {
+        guard let messageID = messages.last(where: { $0.id.hasPrefix("temp-assistant-") })?.id else {
+            return nil
+        }
+        return StreamingAssistantPresentation(
+            messageID: messageID,
+            ephemeralTrace: streamingAssistantState.ephemeralTrace,
+            traceRevision: streamingAssistantState.traceRevision
+        )
+    }
 }
 
 private enum ActiveSendContext: Hashable {
@@ -98,6 +162,15 @@ final class SybilViewModel {
     var chats: [ChatSummary] = []
     var searches: [SearchSummary] = []
     var workspaceItems: [WorkspaceItem] = []
+    private(set) var sidebarSearchQuery = ""
+    private(set) var sidebarSearchResults: [WorkspaceItem] = []
+    private(set) var isSearchingSidebar = false
+    private(set) var sidebarSearchError: String?
+    private(set) var sidebarSearchHasMore = false
+    @ObservationIgnored
+    private var sidebarSearchTask: Task<Void, Never>?
+    @ObservationIgnored
+    private var sidebarSearchRequestID = UUID()
 
     var selectedItem: SidebarSelection?
     var selectedChat: ChatDetail?
@@ -107,6 +180,7 @@ final class SybilViewModel {
     var isLoadingCollections = false
     var isLoadingSelection = false
     var isCreatingSearchChat = false
+    var isForkingChat = false
     var chatBottomPinRequestID = 0
     var errorMessage: String?
 
@@ -125,6 +199,7 @@ final class SybilViewModel {
     var quickQuestionSubmittedModel: String?
     var isQuickQuestionSending = false
     var isConvertingQuickQuestion = false
+    private var quickQuestionStreamingAssistantState = StreamingAssistantState()
 
     @ObservationIgnored
     private var hasBootstrapped = false
@@ -157,7 +232,7 @@ final class SybilViewModel {
     private let clientFactory: (APIConfiguration) -> any SybilAPIClienting
 
     private let fallbackModels: [Provider: [String]] = [
-        .openai: ["gpt-4.1-mini"],
+        .openai: ["gpt-4.1-mini", "chat-latest"],
         .anthropic: ["claude-3-5-sonnet-latest"],
         .xai: ["grok-3-mini"],
         .gemini: ["gemini-3.5-flash", "gemini-flash-latest"],
@@ -360,6 +435,30 @@ final class SybilViewModel {
         return canonical
     }
 
+    var displayedStreamingAssistantPresentation: StreamingAssistantPresentation? {
+        if case let .chat(chatID) = selectedItem,
+           let pending = pendingChatStates[chatID] {
+            return pending.streamingAssistantPresentation
+        }
+
+        if draftKind == .chat, let pending = pendingDraftChatState {
+            return pending.streamingAssistantPresentation
+        }
+
+        return nil
+    }
+
+    var quickQuestionStreamingAssistantPresentation: StreamingAssistantPresentation? {
+        guard let messageID = quickQuestionMessages.last(where: { $0.id.hasPrefix("temp-assistant-quick-") })?.id else {
+            return nil
+        }
+        return StreamingAssistantPresentation(
+            messageID: messageID,
+            ephemeralTrace: quickQuestionStreamingAssistantState.ephemeralTrace,
+            traceRevision: quickQuestionStreamingAssistantState.traceRevision
+        )
+    }
+
     var displayedSearch: SearchDetail? {
         if case let .search(searchID) = selectedItem,
            let activeSearch = activeSearchDetails[searchID] {
@@ -393,7 +492,19 @@ final class SybilViewModel {
     }
 
     var sidebarItems: [SidebarItem] {
-        workspaceItems.map { item in
+        makeSidebarItems(workspaceItems)
+    }
+
+    var isSidebarSearchActive: Bool {
+        !sidebarSearchQuery.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty
+    }
+
+    var visibleSidebarItems: [SidebarItem] {
+        isSidebarSearchActive ? makeSidebarItems(sidebarSearchResults) : sidebarItems
+    }
+
+    private func makeSidebarItems(_ items: [WorkspaceItem]) -> [SidebarItem] {
+        items.map { item in
             switch item.type {
             case .chat:
                 let initiatedLabel: String?
@@ -407,7 +518,8 @@ final class SybilViewModel {
                     initiatedLabel = nil
                 }
                 let starOwner = item.parentChatId.flatMap { parentChatID in
-                    workspaceItems.first(where: { $0.type == .chat && $0.id == parentChatID })
+                    workspaceItems.first(where: { $0.type == .chat && $0.id == parentChatID }) ??
+                        sidebarSearchResults.first(where: { $0.type == .chat && $0.id == parentChatID })
                 } ?? item
 
                 return SidebarItem(
@@ -418,7 +530,8 @@ final class SybilViewModel {
                     starred: starOwner.starred,
                     starredAt: starOwner.starredAt,
                     initiatedLabel: initiatedLabel,
-                    isRunning: isChatRowRunning(item.id)
+                    isRunning: isChatRowRunning(item.id),
+                    searchSnippet: item.searchSnippet
                 )
 
             case .search:
@@ -430,20 +543,70 @@ final class SybilViewModel {
                     starred: item.starred,
                     starredAt: item.starredAt,
                     initiatedLabel: "exa",
-                    isRunning: isSearchRowRunning(item.id)
+                    isRunning: isSearchRowRunning(item.id),
+                    searchSnippet: item.searchSnippet
                 )
             }
         }
     }
 
+    func setSidebarSearchQuery(_ query: String) {
+        let previous = sidebarSearchQuery.trimmingCharacters(in: .whitespacesAndNewlines)
+        sidebarSearchQuery = query
+        guard query.trimmingCharacters(in: .whitespacesAndNewlines) != previous else { return }
+        scheduleSidebarSearch()
+    }
+
+    func refreshSidebarSearch() async {
+        guard isSidebarSearchActive else { return }
+        scheduleSidebarSearch(debounce: false)
+        await sidebarSearchTask?.value
+    }
+
+    private func scheduleSidebarSearch(debounce: Bool = true) {
+        sidebarSearchTask?.cancel()
+        let requestID = UUID()
+        sidebarSearchRequestID = requestID
+        sidebarSearchResults = []
+        sidebarSearchError = nil
+        sidebarSearchHasMore = false
+        isSearchingSidebar = false
+        let query = sidebarSearchQuery.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !query.isEmpty, isAuthenticated else { return }
+        guard query.utf16.count <= 200 else {
+            sidebarSearchError = "Use 200 characters or fewer."
+            return
+        }
+        isSearchingSidebar = true
+        sidebarSearchTask = Task { [weak self] in
+            do {
+                if debounce { try await Task.sleep(for: .milliseconds(300)) }
+                guard let self, !Task.isCancelled else { return }
+                let response = try await self.client().searchWorkspaceItems(query: query)
+                guard !Task.isCancelled, self.sidebarSearchRequestID == requestID else { return }
+                self.sidebarSearchResults = response.items
+                self.sidebarSearchHasMore = response.hasMore
+                self.isSearchingSidebar = false
+            } catch {
+                guard let self, !Task.isCancelled, self.sidebarSearchRequestID == requestID else { return }
+                self.isSearchingSidebar = false
+                if !self.isCancellation(error) {
+                    self.sidebarSearchError = self.normalizeAPIError(error)
+                }
+            }
+        }
+    }
+
     var selectedChatSummary: ChatSummary? {
         guard case let .chat(chatID) = selectedItem else { return nil }
-        return chats.first(where: { $0.id == chatID })
+        return chats.first(where: { $0.id == chatID }) ??
+            sidebarSearchResults.first(where: { $0.type == .chat && $0.id == chatID })?.chatSummary
     }
 
     var selectedSearchSummary: SearchSummary? {
         guard case let .search(searchID) = selectedItem else { return nil }
-        return searches.first(where: { $0.id == searchID })
+        return searches.first(where: { $0.id == searchID }) ??
+            sidebarSearchResults.first(where: { $0.type == .search && $0.id == searchID })?.searchSummary
     }
 
     var hasRefreshableSelection: Bool {
@@ -470,6 +633,7 @@ final class SybilViewModel {
     }
 
     func reconnect() async {
+        setSidebarSearchQuery("")
         isCheckingSession = true
         authError = nil
         errorMessage = nil
@@ -620,6 +784,7 @@ final class SybilViewModel {
         quickQuestionTask = nil
         quickQuestionRunID = nil
         isQuickQuestionSending = false
+        quickQuestionStreamingAssistantState = StreamingAssistantState()
     }
 
     @discardableResult
@@ -636,9 +801,12 @@ 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)
@@ -772,6 +940,15 @@ final class SybilViewModel {
     private func beginSelecting(_ selection: SidebarSelection) -> Task<Void, Never>? {
         SybilLog.debug(SybilLog.ui, "Selecting \(selection.id)")
 
+        // Search can open history outside the recent collection. Retain its
+        // summary for provider settings, starring, and subsequent refreshes.
+        if let item = sidebarSearchResults.first(where: {
+            ($0.type == .chat ? SidebarSelection.chat($0.id) : .search($0.id)) == selection
+        }) {
+            if let chat = item.chatSummary { applyChatSummary(chat, moveToFront: false) }
+            if let search = item.searchSummary { applySearchSummary(search, moveToFront: false) }
+        }
+
         if draftKind == nil, selectedItem == selection {
             errorMessage = nil
             if case .search = selection {
@@ -822,7 +999,7 @@ final class SybilViewModel {
     }
 
     private func selectAdjacentSidebarItem(offset: Int) {
-        let items = sidebarItems
+        let items = visibleSidebarItems
         guard !items.isEmpty else {
             return
         }
@@ -858,6 +1035,7 @@ final class SybilViewModel {
                     break
                 }
                 await refreshCollections(preferredSelection: nil)
+                await refreshSidebarSearch()
             } catch {
                 errorMessage = normalizeAPIError(error)
                 SybilLog.error(SybilLog.ui, "Delete failed", error: error)
@@ -866,6 +1044,36 @@ final class SybilViewModel {
         }
     }
 
+    @discardableResult
+    func forkChat(chatID: String, messageID: String? = nil) async -> ChatSummary? {
+        guard isAuthenticated, !isForkingChat else {
+            return nil
+        }
+
+        guard messageID != nil || !isChatRowRunning(chatID) else {
+            errorMessage = "Wait for the response to finish before forking this chat."
+            return nil
+        }
+
+        let forkDescription = messageID.map { "chat \(chatID) from response \($0)" } ?? "chat \(chatID)"
+        SybilLog.info(SybilLog.ui, "Forking \(forkDescription)")
+        errorMessage = nil
+        isForkingChat = true
+        defer {
+            isForkingChat = false
+        }
+
+        do {
+            let forkedChat = try await client().forkChat(chatID: chatID, messageID: messageID)
+            applyChatSummary(forkedChat, moveToFront: true)
+            return forkedChat
+        } catch {
+            errorMessage = normalizeAPIError(error)
+            SybilLog.error(SybilLog.ui, "Fork failed", error: error)
+            return nil
+        }
+    }
+
     func renameChat(chatID: String, title: String) async {
         guard isAuthenticated else {
             return
@@ -883,6 +1091,7 @@ final class SybilViewModel {
         do {
             let updated = try await client().updateChatTitle(chatID: chatID, title: trimmedTitle)
             applyChatSummary(updated, moveToFront: true)
+            await refreshSidebarSearch()
         } catch {
             errorMessage = normalizeAPIError(error)
             SybilLog.error(SybilLog.ui, "Rename failed", error: error)
@@ -982,6 +1191,10 @@ final class SybilViewModel {
     }
 
     func refreshSidebarCollectionsFromPullToRefresh() async {
+        if isSidebarSearchActive {
+            await refreshSidebarSearch()
+            return
+        }
         guard isAuthenticated, !isCheckingSession else {
             return
         }
@@ -1137,6 +1350,7 @@ final class SybilViewModel {
         quickQuestionSubmittedPrompt = prompt
         quickQuestionSubmittedProvider = provider
         quickQuestionSubmittedModel = model
+        quickQuestionStreamingAssistantState = StreamingAssistantState()
         quickQuestionMessages = [
             Message(
                 id: "temp-assistant-quick-\(UUID().uuidString)",
@@ -1159,13 +1373,11 @@ final class SybilViewModel {
         let streamStatus = CompletionStreamStatus()
 
         do {
-            try await client().runCompletionStream(
+            try await client().runQuickQuestionStream(
-                body: CompletionStreamRequest(
+                body: QuickQuestionStreamRequest(
-                    chatId: nil,
-                    persist: false,
                     provider: provider,
                     model: model,
-                    messages: [CompletionRequestMessage(role: .user, content: prompt)]
+                    question: prompt
                 )
             ) { [weak self] event in
                 guard let self else { return }
@@ -1183,6 +1395,8 @@ final class SybilViewModel {
                 return
             }
 
+            let update = quickQuestionStreamingAssistantState.receiveError()
+            applyQuickQuestionAssistantContentUpdate(update)
             quickQuestionError = normalizeAPIError(error)
             SybilLog.error(SybilLog.ui, "Quick question failed", error: error)
         }
@@ -1197,17 +1411,16 @@ final class SybilViewModel {
             upsertQuickQuestionToolCallMessage(payload)
 
         case let .delta(payload):
-            guard !payload.text.isEmpty else { return }
+            let update = quickQuestionStreamingAssistantState.receiveDelta(payload.text)
-            mutateQuickQuestionAssistantMessage { existing in
+            applyQuickQuestionAssistantContentUpdate(update)
-                existing + payload.text
-            }
 
         case let .done(payload):
-            mutateQuickQuestionAssistantMessage { _ in
+            let update = quickQuestionStreamingAssistantState.receiveDone(payload.text)
-                payload.text
+            applyQuickQuestionAssistantContentUpdate(update)
-            }
 
         case let .error(payload):
+            let update = quickQuestionStreamingAssistantState.receiveError()
+            applyQuickQuestionAssistantContentUpdate(update)
             await streamStatus.setError(payload.message)
 
         case .ignored:
@@ -1322,7 +1535,15 @@ final class SybilViewModel {
             async let activeRunsValue = client.getActiveRuns()
             let (nextWorkspaceItems, nextActiveRuns) = try await (workspaceItemsValue, activeRunsValue)
 
-            applyWorkspaceItems(nextWorkspaceItems)
+            var items = nextWorkspaceItems
+            // A selected historical search result may be outside the latest 100.
+            if let preferredSelection,
+               let selectedSummary = workspaceItems.first(where: {
+                   ($0.type == .chat ? SidebarSelection.chat($0.id) : .search($0.id)) == preferredSelection
+               }), !items.contains(where: { $0.type == selectedSummary.type && $0.id == selectedSummary.id }) {
+                items.append(selectedSummary)
+            }
+            applyWorkspaceItems(items)
             applyActiveRuns(nextActiveRuns)
 
             SybilLog.info(
@@ -1500,6 +1721,11 @@ final class SybilViewModel {
     }
 
     private func upsertWorkspaceItem(_ item: WorkspaceItem, moveToFront: Bool) {
+        if let index = sidebarSearchResults.firstIndex(where: { $0.type == item.type && $0.id == item.id }) {
+            var updated = item
+            updated.searchSnippet = sidebarSearchResults[index].searchSnippet
+            sidebarSearchResults[index] = updated
+        }
         if let existingIndex = workspaceItems.firstIndex(where: { $0.type == item.type && $0.id == item.id }) {
             workspaceItems.remove(at: existingIndex)
             if moveToFront {
@@ -1523,6 +1749,9 @@ final class SybilViewModel {
         if let parentChatID = workspaceItems.first(where: { $0.type == .chat && $0.id == chatID })?.parentChatId {
             return parentChatID
         }
+        if let parentChatID = sidebarSearchResults.first(where: { $0.type == .chat && $0.id == chatID })?.parentChatId {
+            return parentChatID
+        }
         return chatID
     }
 
@@ -1606,21 +1835,28 @@ final class SybilViewModel {
             }
 
             serverActiveChatIDs.remove(chatID)
-            pendingChatStates[chatID] = nil
             await refreshCollections(preferredSelection: selectedItem, refreshSelection: false, attachVisibleActiveRun: false)
 
             if selectedItem == selection, draftKind == nil {
-                selectedChat = try await client.getChat(chatID: chatID)
+                let refreshedChat = try await client.getChat(chatID: chatID)
+                if selectedItem == selection, draftKind == nil {
+                    selectedChat = refreshedChat
                     selectedSearch = nil
                 }
+            }
+            pendingChatStates[chatID] = nil
         } catch {
             serverActiveChatIDs.remove(chatID)
+            defer {
                 pendingChatStates[chatID] = nil
+            }
 
             if isCancellation(error) {
                 return
             }
 
+            applyPendingAssistantError(chatID: chatID)
+
             if isActiveStreamNotFound(error) {
                 SybilLog.info(SybilLog.app, "Active chat stream \(chatID) no longer exists")
             } else if shouldSuppressInactiveTransportError(error) {
@@ -1634,8 +1870,11 @@ final class SybilViewModel {
 
             if selectedItem == selection, draftKind == nil {
                 do {
-                    selectedChat = try await client().getChat(chatID: chatID)
+                    let refreshedChat = try await client().getChat(chatID: chatID)
+                    if selectedItem == selection, draftKind == nil {
+                        selectedChat = refreshedChat
                         selectedSearch = nil
+                    }
                 } catch {
                     SybilLog.warning(SybilLog.app, "Chat refresh after attach failure failed: \(SybilLog.describe(error))")
                 }
@@ -1855,6 +2094,13 @@ final class SybilViewModel {
         } else {
             pendingDraftChatState = PendingChatState(chatID: nil, messages: optimisticMessages)
         }
+        defer {
+            if let resolvedChatID = chatID {
+                pendingChatStates[resolvedChatID] = nil
+            } else {
+                clearPendingChatState(for: sendContext)
+            }
+        }
         requestChatBottomPin()
 
         if chatID == nil {
@@ -2044,17 +2290,13 @@ final class SybilViewModel {
             upsertPendingToolCallMessage(payload, chatID: chatID)
 
         case let .delta(payload):
-            guard !payload.text.isEmpty else { return }
+            applyPendingAssistantDelta(payload.text, chatID: chatID)
-            mutatePendingAssistantMessage(chatID: chatID) { existing in
-                existing + payload.text
-            }
 
         case let .done(payload):
-            mutatePendingAssistantMessage(chatID: chatID) { _ in
+            finalizePendingAssistant(payload.text, chatID: chatID)
-                payload.text
-            }
 
         case let .error(payload):
+            applyPendingAssistantError(chatID: chatID)
             await streamStatus.setError(payload.message)
 
         case .ignored:
@@ -2232,29 +2474,68 @@ final class SybilViewModel {
         }
     }
 
-    private func mutatePendingAssistantMessage(chatID: String, _ transform: (String) -> String) {
+    private func applyPendingAssistantDelta(_ text: String, chatID: String) {
         guard var pending = pendingChatStates[chatID], !pending.messages.isEmpty else {
             return
         }
 
-        let index = pending.messages.indices.last { pending.messages[$0].id.hasPrefix("temp-assistant-") }
+        let update = pending.streamingAssistantState.receiveDelta(text)
-        guard let index else {
+        applyStreamingAssistantContentUpdate(
-            return
+            update,
-        }
+            to: &pending.messages,
-
+            assistantMessagePrefix: "temp-assistant-"
-        var message = pending.messages[index]
+        )
-        message.content = transform(message.content)
-        pending.messages[index] = message
         pendingChatStates[chatID] = pending
     }
 
-    private func mutateQuickQuestionAssistantMessage(_ transform: (String) -> String) {
+    private func finalizePendingAssistant(_ text: String, chatID: String) {
-        let index = quickQuestionMessages.indices.last { quickQuestionMessages[$0].id.hasPrefix("temp-assistant-quick-") }
+        guard var pending = pendingChatStates[chatID], !pending.messages.isEmpty else {
-        guard let index else {
             return
         }
 
-        quickQuestionMessages[index].content = transform(quickQuestionMessages[index].content)
+        let update = pending.streamingAssistantState.receiveDone(text)
+        applyStreamingAssistantContentUpdate(
+            update,
+            to: &pending.messages,
+            assistantMessagePrefix: "temp-assistant-"
+        )
+        pendingChatStates[chatID] = pending
+    }
+
+    private func applyPendingAssistantError(chatID: String) {
+        guard var pending = pendingChatStates[chatID] else {
+            return
+        }
+
+        let update = pending.streamingAssistantState.receiveError()
+        applyStreamingAssistantContentUpdate(
+            update,
+            to: &pending.messages,
+            assistantMessagePrefix: "temp-assistant-"
+        )
+        pendingChatStates[chatID] = pending
+    }
+
+    private func applyQuickQuestionAssistantContentUpdate(_ update: StreamingAssistantContentUpdate) {
+        applyStreamingAssistantContentUpdate(
+            update,
+            to: &quickQuestionMessages,
+            assistantMessagePrefix: "temp-assistant-quick-"
+        )
+    }
+
+    private func applyStreamingAssistantContentUpdate(
+        _ update: StreamingAssistantContentUpdate,
+        to messages: inout [Message],
+        assistantMessagePrefix: String
+    ) {
+        guard case let .replace(content) = update,
+              let index = messages.indices.last(where: { messages[$0].id.hasPrefix(assistantMessagePrefix) })
+        else {
+            return
+        }
+
+        messages[index].content = content
     }
 
     private func upsertPendingToolCallMessage(_ payload: CompletionStreamToolCall, chatID: String) {
@@ -2262,6 +2543,16 @@ final class SybilViewModel {
             return
         }
 
+        let update = pending.streamingAssistantState.receiveToolCall(
+            id: payload.toolCallId,
+            status: payload.status
+        )
+        applyStreamingAssistantContentUpdate(
+            update,
+            to: &pending.messages,
+            assistantMessagePrefix: "temp-assistant-"
+        )
+
         if let existingIndex = pending.messages.firstIndex(where: { $0.toolCallMetadata?.toolCallId == payload.toolCallId || $0.id == "temp-tool-\(payload.toolCallId)" }) {
             pending.messages[existingIndex] = toolCallMessage(for: payload, id: pending.messages[existingIndex].id)
             pendingChatStates[chatID] = pending
@@ -2280,6 +2571,12 @@ final class SybilViewModel {
     }
 
     private func upsertQuickQuestionToolCallMessage(_ payload: CompletionStreamToolCall) {
+        let update = quickQuestionStreamingAssistantState.receiveToolCall(
+            id: payload.toolCallId,
+            status: payload.status
+        )
+        applyQuickQuestionAssistantContentUpdate(update)
+
         if let existingIndex = quickQuestionMessages.firstIndex(where: { $0.toolCallMetadata?.toolCallId == payload.toolCallId || $0.id == "temp-tool-\(payload.toolCallId)" }) {
             quickQuestionMessages[existingIndex] = toolCallMessage(for: payload, id: quickQuestionMessages[existingIndex].id)
             return
@@ -2429,7 +2726,8 @@ final class SybilViewModel {
 
     private func clearPendingChatState(for context: ActiveSendContext) {
         switch context {
-        case .draftChat:
+        case let .draftChat(identity):
+            guard draftKind == .chat, draftIdentity == identity else { return }
             pendingDraftChatState = nil
         case let .chat(chatID):
             pendingChatStates[chatID] = nil

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

@@ -1,4 +1,3 @@
-import ImageIO
 import Observation
 import PhotosUI
 import SwiftUI
@@ -19,6 +18,7 @@ struct SybilWorkspaceView: View {
     var onShowSidebar: (() -> Void)? = nil
     var onRequestBack: ((_ animateNavigation: Bool) -> Void)? = nil
     var onRequestNewChat: (() -> Void)? = nil
+    var onOpenForkedChat: ((String) -> Void)? = nil
     @FocusState private var composerFocused: Bool
     @Environment(\.dismiss) private var dismiss
     @State private var isShowingAttachmentOptions = false
@@ -155,8 +155,6 @@ struct SybilWorkspaceView: View {
             workspaceContentStack
 
             if showsCustomWorkspaceNavigation {
-                SybilWorkspaceCharacterBackdrop(isBusy: viewModel.isActiveSelectionSending)
-                    .allowsHitTesting(false)
                 customWorkspaceNavigationBar
             }
         }
@@ -193,9 +191,12 @@ struct SybilWorkspaceView: View {
                         messages: viewModel.displayedMessages,
                         isLoading: viewModel.isLoadingSelection,
                         isSending: viewModel.isSendingVisibleChat,
+                        streamingAssistantPresentation: viewModel.displayedStreamingAssistantPresentation,
                         topContentInset: showsCustomWorkspaceNavigation ? customWorkspaceNavigationContentInset : 0,
                         bottomContentInset: viewModel.showsComposer ? composerOverlayContentInset : 0,
-                        bottomPinRequestID: viewModel.chatBottomPinRequestID
+                        bottomPinRequestID: viewModel.chatBottomPinRequestID,
+                        isForking: viewModel.isForkingChat,
+                        onForkResponse: forkResponse
                     )
                     .id(transcriptScrollContextID)
                 }
@@ -229,6 +230,28 @@ struct SybilWorkspaceView: View {
         }
     }
 
+    private func forkResponse(messageID: String) {
+        guard viewModel.draftKind == nil,
+              case let .chat(chatID) = viewModel.selectedItem else {
+            return
+        }
+
+        let selectionAtStart = viewModel.selectedItem
+        Task {
+            guard let forkedChat = await viewModel.forkChat(chatID: chatID, messageID: messageID),
+                  viewModel.selectedItem == selectionAtStart,
+                  viewModel.draftKind == nil else {
+                return
+            }
+
+            if let onOpenForkedChat {
+                onOpenForkedChat(forkedChat.id)
+            } else {
+                viewModel.select(.chat(forkedChat.id))
+            }
+        }
+    }
+
     private var customWorkspaceNavigationBar: some View {
         HStack(spacing: 14) {
             workspaceNavigationLeadingControl
@@ -601,6 +624,7 @@ struct SybilWorkspaceView: View {
                 .onSubmit {
                     submitComposer()
                 }
+                .submitOnMacReturn(submitComposer)
                 .padding(.horizontal, 12)
                 .padding(.vertical, 10)
                 .background(
@@ -1348,173 +1372,6 @@ private struct SybilNavigationFadeBackground: View {
     }
 }
 
-private struct SybilWorkspaceCharacterBackdrop: View {
-    var isBusy: Bool
-
-    var body: some View {
-        ZStack(alignment: .topTrailing) {
-            RadialGradient(
-                colors: [
-                    SybilTheme.primary.opacity(0.36),
-                    SybilTheme.primary.opacity(0.13),
-                    Color.clear
-                ],
-                center: .center,
-                startRadius: 10,
-                endRadius: 150
-            )
-            .frame(width: 136, height: 118)
-            .blur(radius: 7)
-            .offset(x: 28, y: -24)
-
-            SybilAnimatedGIFView(resourceName: isBusy ? "character-busy" : "character-idle")
-                .frame(width: 172, height: 172)
-                .opacity(0.92)
-                .mask {
-                    LinearGradient(
-                        colors: [
-                            Color.black,
-                            Color.black,
-                            Color.black.opacity(0)
-                        ],
-                        startPoint: .top,
-                        endPoint: .bottom
-                    )
-                }
-                .mask {
-                    LinearGradient(
-                        colors: [
-                            Color.clear,
-                            Color.black.opacity(0.98),
-                            Color.black
-                        ],
-                        startPoint: .leading,
-                        endPoint: .trailing
-                    )
-                }
-                .offset(x: 8, y: 4)
-        }
-        .frame(maxWidth: .infinity, minHeight: 156, maxHeight: 156, alignment: .topTrailing)
-        .clipped()
-        .ignoresSafeArea(edges: .top)
-        .accessibilityHidden(true)
-    }
-}
-
-private struct SybilAnimatedGIFView: UIViewRepresentable {
-    var resourceName: String
-
-    func makeCoordinator() -> Coordinator {
-        Coordinator()
-    }
-
-    func makeUIView(context: Context) -> UIImageView {
-        let imageView = SybilAnimatedUIImageView()
-        imageView.backgroundColor = .clear
-        imageView.contentMode = .scaleAspectFill
-        imageView.clipsToBounds = false
-        imageView.isOpaque = false
-        imageView.setContentHuggingPriority(.defaultLow, for: .horizontal)
-        imageView.setContentHuggingPriority(.defaultLow, for: .vertical)
-        imageView.setContentCompressionResistancePriority(.defaultLow, for: .horizontal)
-        imageView.setContentCompressionResistancePriority(.defaultLow, for: .vertical)
-        return imageView
-    }
-
-    func updateUIView(_ imageView: UIImageView, context: Context) {
-        guard context.coordinator.resourceName != resourceName else {
-            if !imageView.isAnimating {
-                imageView.startAnimating()
-            }
-            return
-        }
-
-        context.coordinator.resourceName = resourceName
-        imageView.image = SybilAnimatedGIFCache.image(named: resourceName)
-        imageView.startAnimating()
-    }
-
-    final class Coordinator {
-        var resourceName: String?
-    }
-}
-
-private final class SybilAnimatedUIImageView: UIImageView {
-    override var intrinsicContentSize: CGSize {
-        CGSize(width: UIView.noIntrinsicMetric, height: UIView.noIntrinsicMetric)
-    }
-}
-
-@MainActor
-private enum SybilAnimatedGIFCache {
-    private static var images: [String: UIImage] = [:]
-
-    static func image(named name: String) -> UIImage? {
-        if let cached = images[name] {
-            return cached
-        }
-
-        guard let image = loadImage(named: name) else {
-            return nil
-        }
-
-        images[name] = image
-
-        return image
-    }
-
-    private static func loadImage(named name: String) -> UIImage? {
-        let url = Bundle.main.url(forResource: name, withExtension: "gif", subdirectory: "Character") ??
-            Bundle.main.url(forResource: name, withExtension: "gif")
-
-        guard let url,
-              let data = try? Data(contentsOf: url),
-              let source = CGImageSourceCreateWithData(data as CFData, nil)
-        else {
-            return nil
-        }
-
-        let frameCount = CGImageSourceGetCount(source)
-        guard frameCount > 0 else {
-            return nil
-        }
-
-        var frames: [UIImage] = []
-        frames.reserveCapacity(frameCount)
-        var duration: TimeInterval = 0
-
-        for index in 0 ..< frameCount {
-            guard let cgImage = CGImageSourceCreateImageAtIndex(source, index, nil) else {
-                continue
-            }
-            frames.append(UIImage(cgImage: cgImage))
-            duration += frameDuration(at: index, source: source)
-        }
-
-        guard !frames.isEmpty else {
-            return nil
-        }
-
-        if frames.count == 1 {
-            return frames[0]
-        }
-
-        return UIImage.animatedImage(with: frames, duration: max(duration, 0.1))
-    }
-
-    private static func frameDuration(at index: Int, source: CGImageSource) -> TimeInterval {
-        guard let properties = CGImageSourceCopyPropertiesAtIndex(source, index, nil) as? [CFString: Any],
-              let gifProperties = properties[kCGImagePropertyGIFDictionary] as? [CFString: Any]
-        else {
-            return 0.08
-        }
-
-        let unclampedDelay = gifProperties[kCGImagePropertyGIFUnclampedDelayTime] as? TimeInterval
-        let delay = unclampedDelay ?? gifProperties[kCGImagePropertyGIFDelayTime] as? TimeInterval ?? 0.08
-        return max(delay, 0.03)
-    }
-}
-
 private struct NewChatSwipeBackdrop: View {
     var progress: CGFloat
     var hasLatched: Bool

ios/README.md

@@ -0,0 +1,91 @@
+# 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.
+
+The conversation sidebar includes **Search chats and web searches** on iPhone,
+iPad, and Mac. It searches all saved history by title, conversation text, and saved
+web-search query/answer, with single-line excerpts that bold matching words and
+truncate in the middle. Search waits briefly while typing,
+cancels superseded requests, and leaves the current conversation open. Clear the
+field to return to recent items. Searches use word prefixes (for example, `plan`
+finds `planning`); if more than 100 items match, refine the query.
+
+## 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.
+
+Quick Question defaults to OpenAI `chat-latest` on iPhone, iPad, and Mac. Its saved
+provider/model selection takes precedence and is separate from regular chat preferences.
+
+The regular Mac chat/search composer uses the same Return/Shift+Return rules.
+Holding Return does not repeatedly submit. On iOS, Return submits from Quick
+Question, while the normal chat/search composer continues to use Return for a
+new line.
+
+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. On iOS, verify Return submits Quick Question while Return in the normal
+  prompt adds a newline. 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"

server/prisma/migrations/20261007000000_add_workspace_full_text_search/migration.sql

@@ -0,0 +1,70 @@
+-- External-content indexes avoid storing a second copy of conversation text.
+-- Keep these virtual tables and triggers in SQL: Prisma does not model FTS5.
+CREATE VIRTUAL TABLE "ChatSearch" USING fts5(
+  title, content='Chat', content_rowid='rowid',
+  tokenize='unicode61 remove_diacritics 2', prefix='1 2 3'
+);
+
+-- Hidden system prompts and tool payloads are not searchable conversation text.
+CREATE VIEW "MessageSearchContent" AS
+  SELECT rowid, content FROM "Message" WHERE role IN ('user', 'assistant');
+CREATE VIRTUAL TABLE "MessageSearch" USING fts5(
+  content, content='MessageSearchContent', content_rowid='rowid',
+  tokenize='unicode61 remove_diacritics 2', prefix='1 2 3'
+);
+
+CREATE VIRTUAL TABLE "SavedSearchSearch" USING fts5(
+  title, query, answerText, content='Search', content_rowid='rowid',
+  tokenize='unicode61 remove_diacritics 2', prefix='1 2 3'
+);
+
+CREATE TRIGGER "ChatSearch_insert" AFTER INSERT ON "Chat" BEGIN
+  INSERT INTO "ChatSearch" (rowid, title) VALUES (new.rowid, new.title);
+END;
+CREATE TRIGGER "ChatSearch_delete" AFTER DELETE ON "Chat" BEGIN
+  INSERT INTO "ChatSearch" ("ChatSearch", rowid, title) VALUES ('delete', old.rowid, old.title);
+END;
+CREATE TRIGGER "ChatSearch_update" AFTER UPDATE OF title ON "Chat"
+WHEN old.title IS NOT new.title BEGIN
+  INSERT INTO "ChatSearch" ("ChatSearch", rowid, title) VALUES ('delete', old.rowid, old.title);
+  INSERT INTO "ChatSearch" (rowid, title) VALUES (new.rowid, new.title);
+END;
+
+CREATE TRIGGER "MessageSearch_insert" AFTER INSERT ON "Message"
+WHEN new.role IN ('user', 'assistant') BEGIN
+  INSERT INTO "MessageSearch" (rowid, content) VALUES (new.rowid, new.content);
+END;
+CREATE TRIGGER "MessageSearch_delete" AFTER DELETE ON "Message"
+WHEN old.role IN ('user', 'assistant') BEGIN
+  INSERT INTO "MessageSearch" ("MessageSearch", rowid, content) VALUES ('delete', old.rowid, old.content);
+END;
+CREATE TRIGGER "MessageSearch_update" AFTER UPDATE OF content, role ON "Message"
+WHEN old.content IS NOT new.content OR old.role IS NOT new.role BEGIN
+  INSERT INTO "MessageSearch" ("MessageSearch", rowid, content)
+    SELECT 'delete', old.rowid, old.content WHERE old.role IN ('user', 'assistant');
+  INSERT INTO "MessageSearch" (rowid, content)
+    SELECT new.rowid, new.content WHERE new.role IN ('user', 'assistant');
+END;
+
+CREATE TRIGGER "SavedSearchSearch_insert" AFTER INSERT ON "Search" BEGIN
+  INSERT INTO "SavedSearchSearch" (rowid, title, query, answerText)
+    VALUES (new.rowid, new.title, new.query, new.answerText);
+END;
+CREATE TRIGGER "SavedSearchSearch_delete" AFTER DELETE ON "Search" BEGIN
+  INSERT INTO "SavedSearchSearch" ("SavedSearchSearch", rowid, title, query, answerText)
+    VALUES ('delete', old.rowid, old.title, old.query, old.answerText);
+END;
+CREATE TRIGGER "SavedSearchSearch_update" AFTER UPDATE OF title, query, answerText ON "Search"
+WHEN old.title IS NOT new.title OR old.query IS NOT new.query OR old.answerText IS NOT new.answerText BEGIN
+  INSERT INTO "SavedSearchSearch" ("SavedSearchSearch", rowid, title, query, answerText)
+    VALUES ('delete', old.rowid, old.title, old.query, old.answerText);
+  INSERT INTO "SavedSearchSearch" (rowid, title, query, answerText)
+    VALUES (new.rowid, new.title, new.query, new.answerText);
+END;
+
+-- Index existing history during migration, then maintain it transactionally.
+INSERT INTO "ChatSearch" ("ChatSearch") VALUES ('rebuild');
+INSERT INTO "MessageSearch" ("MessageSearch") VALUES ('rebuild');
+INSERT INTO "SavedSearchSearch" ("SavedSearchSearch") VALUES ('rebuild');
+
+CREATE INDEX "Chat_updatedAt_idx" ON "Chat"("updatedAt");

server/prisma/schema.prisma

@@ -76,6 +76,7 @@ model Chat {
 
   @@index([userId])
   @@index([parentChatId])
+  @@index([updatedAt])
 }
 
 model Message {

server/src/llm/provider-adapters.ts

@@ -95,7 +95,7 @@ function isLikelyResponsesApiModel(model: string) {
   if (id.includes("audio") || id.includes("realtime") || id.includes("transcribe") || id.includes("tts")) return false;
   if (id.includes("image") || id.includes("dall-e") || id.includes("sora")) return false;
   if (id.includes("search") || id.includes("computer-use")) return false;
-  return /^(gpt-|o\d|chatgpt-)/.test(id);
+  return id === "chat-latest" || /^(gpt-|o\d|chatgpt-)/.test(id);
 }
 
 function isLikelyGeminiChatModel(model: string) {

server/src/llm/quick-question.ts

@@ -0,0 +1,30 @@
+import type { MultiplexRequest, Provider } from "./types.js";
+
+export const QUICK_QUESTION_SYSTEM_PROMPT =
+  "You are answering a quick question in a one-shot experience intended to replace a quick Google search. " +
+  "Give a succinct, direct, self-contained answer. Do not ask follow-up questions, invite the user to continue, " +
+  "or offer additional help. If the question is ambiguous, make the most reasonable assumption and state it briefly only when needed.";
+
+export type QuickQuestionRequest = {
+  provider: Provider;
+  model: string;
+  question: string;
+  enabledTools?: string[];
+  userLocation?: string;
+  temperature?: number;
+  maxTokens?: number;
+};
+
+export function buildQuickQuestionMultiplexRequest({
+  question,
+  ...request
+}: QuickQuestionRequest): MultiplexRequest {
+  return {
+    ...request,
+    persist: false,
+    messages: [
+      { role: "system", content: QUICK_QUESTION_SYSTEM_PROMPT },
+      { role: "user", content: question },
+    ],
+  };
+}

server/src/routes.ts

@@ -11,10 +11,12 @@ import { runMultiplex } from "./llm/multiplexer.js";
 import { runMultiplexStream, type StreamEvent } from "./llm/streaming.js";
 import { getAvailableChatTools, normalizeEnabledChatTools } from "./llm/chat-tools.js";
 import { getModelCatalogSnapshot } from "./llm/model-catalog.js";
+import { buildQuickQuestionMultiplexRequest } from "./llm/quick-question.js";
 import { openaiClient } from "./llm/providers.js";
 import { serializeProviderFields, toPrismaProvider } from "./llm/provider-ids.js";
 import { exaClient } from "./search/exa.js";
 import { isFreshSearchCacheHit, normalizeSearchQuery } from "./search-cache.js";
+import { searchWorkspace } from "./workspace-search.js";
 import type { ChatAttachment } from "./llm/types.js";
 
 const ProviderSchema = z.enum(["openai", "anthropic", "xai", "gemini", "hermes-agent"]);
@@ -205,6 +207,16 @@ const CompletionStreamBody = z
     }
   });
 
+const QuickQuestionStreamBody = z.object({
+  provider: ProviderSchema,
+  model: z.string().min(1),
+  question: z.string().trim().min(1),
+  enabledTools: EnabledToolsSchema.optional(),
+  userLocation: z.string().trim().min(1).max(200).optional(),
+  temperature: z.number().min(0).max(2).optional(),
+  maxTokens: z.number().int().positive().optional(),
+});
+
 function mergeAttachmentsIntoMetadata(metadata: unknown, attachments?: ChatAttachment[]) {
   if (!attachments?.length) return metadata as any;
   if (!metadata || typeof metadata !== "object" || Array.isArray(metadata)) {
@@ -916,6 +928,37 @@ export async function registerRoutes(app: FastifyInstance) {
 
   app.get("/v1/workspace-items", async (req) => {
     requireAdmin(req);
+    const parsed = z.object({ q: z.string().trim().max(200).optional() }).safeParse(req.query);
+    if (!parsed.success) throw app.httpErrors.badRequest("q must be a string of at most 200 characters");
+    if (parsed.data.q) {
+      const { hits, hasMore } = await searchWorkspace(parsed.data.q);
+      const [chats, searches] = await Promise.all([
+        prisma.chat.findMany({
+          where: { id: { in: hits.filter((hit) => hit.type === "chat").map((hit) => hit.id) } },
+          select: {
+            ...chatSummarySelect,
+            parentChat: { select: { projectItems: starredProjectItemsSelect } },
+          },
+        }),
+        prisma.search.findMany({
+          where: { id: { in: hits.filter((hit) => hit.type === "search").map((hit) => hit.id) } },
+          select: searchSummarySelect,
+        }),
+      ]);
+      const summaries = new Map<string, Record<string, unknown>>([
+        ...chats.map(({ parentChat, ...chat }) => [
+          `chat:${chat.id}`,
+          // Search omits unmatched roots, but sidebar fork stars belong to the root.
+          { ...serializeChatLike(chat), ...serializeStarFields(parentChat ?? chat) },
+        ] as const),
+        ...searches.map((search) => [`search:${search.id}`, serializeSearchLike(search)] as const),
+      ]);
+      const items = hits.flatMap((hit) => {
+        const summary = summaries.get(`${hit.type}:${hit.id}`);
+        return summary ? [{ ...summary, ...hit }] : [];
+      });
+      return { items, hasMore };
+    }
     return { items: await listWorkspaceItems() };
   });
 
@@ -1564,7 +1607,28 @@ export async function registerRoutes(app: FastifyInstance) {
     };
   });
 
-  // Streaming SSE endpoint.
+  // One-shot, non-persistent Quick Question SSE endpoint.
+  app.post("/v1/quick-questions/stream", async (req, reply) => {
+    requireAdmin(req);
+
+    const parsed = QuickQuestionStreamBody.safeParse(req.body);
+    if (!parsed.success) return app.httpErrors.badRequest(parsed.error.message);
+    const body = withRequestUserLocation(parsed.data, req);
+
+    reply.raw.writeHead(200, buildSseHeaders(typeof req.headers.origin === "string" ? req.headers.origin : undefined));
+    reply.raw.flushHeaders();
+
+    for await (const ev of runMultiplexStream(buildQuickQuestionMultiplexRequest(body))) {
+      writeSseEvent(reply, mapChatStreamEvent(ev));
+    }
+
+    if (!reply.raw.destroyed && !reply.raw.writableEnded) {
+      reply.raw.end();
+    }
+    return reply;
+  });
+
+  // General chat completion SSE endpoint.
   app.post("/v1/chat-completions/stream", async (req, reply) => {
     requireAdmin(req);
 

server/src/workspace-search.ts

@@ -0,0 +1,74 @@
+import { Prisma } from "@prisma/client";
+import { prisma } from "./db.js";
+
+export const WORKSPACE_SEARCH_LIMIT = 100;
+
+// Treat input as literal Unicode words, never FTS operators/column expressions.
+// Prefix matching supports type-ahead, including short terms such as "AI".
+export function workspaceSearchExpression(query: string): string | null {
+  const words = query.match(/[\p{L}\p{N}\p{M}\p{Co}]+/gu);
+  return words?.map((word) => `"${word}"*`).join(" AND ") ?? null;
+}
+
+export type WorkspaceSearchHit = {
+  type: "chat" | "search";
+  id: string;
+  searchSnippet: string | null;
+};
+
+export function workspaceSearchSQL(expression: string) {
+  // Batch excerpts after limiting matches. Unary + prevents SQLite from using
+  // the IN clause as repeated rowid lookups (and restarting FTS for every row).
+  // FTS still uses MATCH and the rowid bounds; IN filters that single scan.
+  return Prisma.sql`
+    WITH chat_hits AS (
+      SELECT c.id, NULL AS message_rowid
+      FROM "ChatSearch" JOIN "Chat" c ON c.rowid = "ChatSearch".rowid
+      WHERE "ChatSearch" MATCH ${expression}
+      UNION ALL
+      SELECT m.chatId AS id, MIN(m.rowid) AS message_rowid
+      FROM "MessageSearch" JOIN "Message" m ON m.rowid = "MessageSearch".rowid
+      WHERE "MessageSearch" MATCH ${expression}
+      GROUP BY m.chatId
+    ), matches AS (
+      SELECT 'chat' AS type, c.id, c.updatedAt, MIN(h.message_rowid) AS message_rowid,
+        NULL AS search_rowid
+      FROM chat_hits h JOIN "Chat" c ON c.id = h.id
+      GROUP BY c.id
+      UNION ALL
+      SELECT 'search' AS type, s.id, s.updatedAt, NULL AS message_rowid, s.rowid AS search_rowid
+      FROM "SavedSearchSearch" JOIN "Search" s ON s.rowid = "SavedSearchSearch".rowid
+      WHERE "SavedSearchSearch" MATCH ${expression}
+    ), limited AS MATERIALIZED (
+      SELECT * FROM matches ORDER BY updatedAt DESC, type, id LIMIT ${WORKSPACE_SEARCH_LIMIT + 1}
+    ), message_excerpts AS MATERIALIZED (
+      SELECT rowid, substr(snippet("MessageSearch", 0, '', '', ' … ', 24), 1, 480) AS snippet
+      FROM "MessageSearch"
+      WHERE "MessageSearch" MATCH ${expression}
+        AND rowid >= (SELECT MIN(message_rowid) FROM limited)
+        AND rowid <= (SELECT MAX(message_rowid) FROM limited)
+        AND +rowid IN (SELECT message_rowid FROM limited)
+    ), search_excerpts AS MATERIALIZED (
+      SELECT rowid, substr(snippet("SavedSearchSearch", -1, '', '', ' … ', 24), 1, 480) AS snippet
+      FROM "SavedSearchSearch"
+      WHERE "SavedSearchSearch" MATCH ${expression}
+        AND rowid >= (SELECT MIN(search_rowid) FROM limited)
+        AND rowid <= (SELECT MAX(search_rowid) FROM limited)
+        AND +rowid IN (SELECT search_rowid FROM limited)
+    )
+    SELECT type, id, COALESCE(m.snippet, s.snippet) AS searchSnippet
+    FROM limited
+    LEFT JOIN message_excerpts m ON m.rowid = limited.message_rowid
+    LEFT JOIN search_excerpts s ON s.rowid = limited.search_rowid
+    ORDER BY updatedAt DESC, type, id
+  `;
+}
+
+export async function searchWorkspace(query: string) {
+  const expression = workspaceSearchExpression(query);
+  if (!expression) return { hits: [], hasMore: false };
+  // Match via the inverted indexes first. Hydrate summaries and generate excerpts
+  // only for the bounded result set, never fetch full transcripts into JS.
+  const hits = await prisma.$queryRaw<WorkspaceSearchHit[]>(workspaceSearchSQL(expression));
+  return { hits: hits.slice(0, WORKSPACE_SEARCH_LIMIT), hasMore: hits.length > WORKSPACE_SEARCH_LIMIT };
+}

server/tests/chat-forks.test.ts

@@ -1,6 +1,6 @@
 import assert from "node:assert/strict";
 import { execFileSync } from "node:child_process";
-import { mkdtempSync, rmSync } from "node:fs";
+import { mkdtempSync, rmSync, writeFileSync } from "node:fs";
 import { tmpdir } from "node:os";
 import { dirname, join, resolve } from "node:path";
 import test from "node:test";
@@ -11,6 +11,7 @@ import sensible from "@fastify/sensible";
 const serverRoot = resolve(dirname(fileURLToPath(import.meta.url)), "..");
 const databaseDir = mkdtempSync(join(tmpdir(), "sybil-chat-forks-"));
 process.env.DATABASE_URL = `file:${join(databaseDir, "test.db")}`;
+writeFileSync(join(databaseDir, "test.db"), "");
 process.env.OPENAI_API_KEY = "";
 delete process.env.ADMIN_TOKEN;
 

server/tests/provider-adapters.test.ts

@@ -1,6 +1,50 @@
 import assert from "node:assert/strict";
 import test from "node:test";
-import { describeProviderChatBackend } from "../src/llm/provider-adapters.js";
+import { env } from "../src/env.js";
+import { describeProviderChatBackend, fetchProviderCatalogModels } from "../src/llm/provider-adapters.js";
+
+for (const { name, listedModels, expectedModels } of [
+  {
+    name: "OpenAI catalog includes chat-latest while excluding non-chat models",
+    listedModels: [
+      "gpt-4.1-mini",
+      "chat-latest",
+      "o3",
+      "chatgpt-4o-latest",
+      "chat-latest",
+      "text-embedding-3-small",
+      "omni-moderation-latest",
+      "gpt-4o-audio-preview",
+      "gpt-realtime",
+      "gpt-4o-transcribe",
+      "gpt-4o-mini-tts",
+      "gpt-image-1",
+      "chatgpt-image-latest",
+      "gpt-4o-search-preview",
+      "computer-use-preview",
+      "sora-2",
+    ],
+    expectedModels: ["chat-latest", "chatgpt-4o-latest", "gpt-4.1-mini", "o3"],
+  },
+  {
+    name: "OpenAI catalog does not invent models absent from the provider response",
+    listedModels: ["gpt-4.1-mini"],
+    expectedModels: ["gpt-4.1-mini"],
+  },
+]) {
+  test(name, async (t) => {
+    const originalKey = env.OPENAI_API_KEY;
+    env.OPENAI_API_KEY = "test-openai-key";
+    t.after(() => { env.OPENAI_API_KEY = originalKey; });
+    t.mock.method(globalThis, "fetch", async (input: RequestInfo | URL) => {
+      const url = input instanceof Request ? input.url : String(input);
+      assert.equal(url, "https://api.openai.com/v1/models");
+      return Response.json({ data: listedModels.map((id) => ({ id })) });
+    });
+
+    assert.deepEqual(await fetchProviderCatalogModels("openai"), expectedModels);
+  });
+}
 
 test("provider backend registry selects chat protocol and managed-tool mode", () => {
   assert.deepEqual(describeProviderChatBackend("openai", []), {

server/tests/quick-question.test.ts

@@ -0,0 +1,27 @@
+import assert from "node:assert/strict";
+import test from "node:test";
+import {
+  buildQuickQuestionMultiplexRequest,
+  QUICK_QUESTION_SYSTEM_PROMPT,
+} from "../src/llm/quick-question.js";
+
+test("quick question requests receive the server-owned one-shot system prompt", () => {
+  const request = buildQuickQuestionMultiplexRequest({
+    provider: "openai",
+    model: "gpt-4.1-mini",
+    question: "How do I reset my password?",
+    enabledTools: ["web_search"],
+    userLocation: "Los Angeles, CA",
+  });
+
+  assert.equal(request.persist, false);
+  assert.equal(request.chatId, undefined);
+  assert.deepEqual(request.messages, [
+    { role: "system", content: QUICK_QUESTION_SYSTEM_PROMPT },
+    { role: "user", content: "How do I reset my password?" },
+  ]);
+  assert.deepEqual(request.enabledTools, ["web_search"]);
+  assert.equal(request.userLocation, "Los Angeles, CA");
+  assert.match(QUICK_QUESTION_SYSTEM_PROMPT, /succinct, direct, self-contained answer/i);
+  assert.match(QUICK_QUESTION_SYSTEM_PROMPT, /do not ask follow-up questions/i);
+});

server/tests/workspace-search.test.ts

@@ -0,0 +1,188 @@
+import assert from "node:assert/strict";
+import { execFileSync } from "node:child_process";
+import { cpSync, mkdtempSync, readdirSync, rmSync, writeFileSync } from "node:fs";
+import { tmpdir } from "node:os";
+import { dirname, join, resolve } from "node:path";
+import test from "node:test";
+import { fileURLToPath } from "node:url";
+import Fastify from "fastify";
+import sensible from "@fastify/sensible";
+import { Prisma } from "@prisma/client";
+
+const serverRoot = resolve(dirname(fileURLToPath(import.meta.url)), "..");
+const databaseDir = mkdtempSync(join(tmpdir(), "sybil-workspace-search-"));
+const migration = "20261007000000_add_workspace_full_text_search";
+process.env.DATABASE_URL = `file:${join(databaseDir, "test.db")}`;
+process.env.OPENAI_API_KEY = "";
+delete process.env.ADMIN_TOKEN;
+writeFileSync(join(databaseDir, "test.db"), "");
+cpSync(join(serverRoot, "prisma/schema.prisma"), join(databaseDir, "schema.prisma"));
+for (const name of readdirSync(join(serverRoot, "prisma/migrations"))) {
+  if (name !== migration) cpSync(join(serverRoot, "prisma/migrations", name), join(databaseDir, "migrations", name), { recursive: true });
+}
+function migrate() {
+  execFileSync(process.execPath, [join(serverRoot, "node_modules/prisma/build/index.js"), "migrate", "deploy", "--schema", join(databaseDir, "schema.prisma")], {
+    cwd: serverRoot, env: process.env, stdio: "pipe",
+  });
+}
+migrate();
+const { prisma } = await import("../src/db.js");
+const oldChat = await prisma.chat.create({ data: {
+  title: "Old constellation notes",
+  messages: { create: [
+    { role: "user", content: "We photographed a nebula before the migration." },
+    { role: "system", content: "secretmigrationprompt" },
+  ] },
+} });
+const oldSearch = await prisma.search.create({ data: { query: "constellation map", answerText: "The nebula is visible." } });
+cpSync(join(serverRoot, "prisma/migrations", migration), join(databaseDir, "migrations", migration), { recursive: true });
+migrate();
+
+const { registerRoutes } = await import("../src/routes.js");
+const { workspaceSearchExpression, workspaceSearchSQL } = await import("../src/workspace-search.js");
+const app = Fastify({ logger: false });
+await app.register(sensible);
+await registerRoutes(app);
+await app.ready();
+
+async function search(query: string) {
+  const response = await app.inject({ method: "GET", url: `/v1/workspace-items?q=${encodeURIComponent(query)}` });
+  assert.equal(response.statusCode, 200, response.body);
+  return response.json();
+}
+
+test.afterEach(async () => {
+  await prisma.chat.deleteMany();
+  await prisma.search.deleteMany();
+});
+test.after(async () => {
+  await app.close();
+  await prisma.$disconnect();
+  rmSync(databaseDir, { recursive: true, force: true });
+});
+
+test("migration indexes existing titles, messages, queries, and answers", async () => {
+  assert.deepEqual(new Set((await search("nebula")).items.map((item: any) => item.id)), new Set([oldChat.id, oldSearch.id]));
+  assert.equal((await search("constellation")).items.length, 2);
+  assert.equal((await search("secretmigrationprompt")).items.length, 0);
+});
+
+test("matches full history, deduplicates messages, and excludes hidden content", async () => {
+  const chat = await prisma.chat.create({ data: {
+    title: "Travel notes", updatedAt: new Date("2000-01-01"),
+    messages: { create: [
+      { role: "user", content: "Let's discuss café planning in Zürich" },
+      { role: "assistant", content: "CAFÉ PLANNING includes booking a table" },
+      { role: "system", content: "hiddensystemvalue" },
+      { role: "tool", content: "hiddentoolvalue" },
+    ] },
+  } });
+  await prisma.chat.createMany({ data: Array.from({ length: 105 }, (_, i) => ({ title: `Recent ${i}` })) });
+  const recent = (await app.inject({ method: "GET", url: "/v1/workspace-items" })).json();
+  assert.equal(recent.items.some((item: any) => item.id === chat.id), false);
+  const result = await search("CAFE plan");
+  assert.equal(result.hasMore, false);
+  assert.deepEqual(result.items.map((item: any) => item.id), [chat.id]);
+  assert.match(result.items[0].searchSnippet, /café planning/i);
+  assert.equal(result.items[0].messages, undefined);
+  assert.equal((await search("zuri")).items.length, 1);
+  assert.equal((await search("hiddensystemvalue")).items.length, 0);
+  assert.equal((await search("hiddentoolvalue")).items.length, 0);
+});
+
+test("indexes edits, role changes, forks, rollbacks, and cascading deletes", async () => {
+  const chat = await prisma.chat.create({ data: {
+    title: "originaltitle", messages: { create: { role: "assistant", content: "originalbody" } },
+  }, include: { messages: true } });
+  const messageID = chat.messages[0].id;
+  await prisma.chat.update({ where: { id: chat.id }, data: { title: "replacementtitle" } });
+  await prisma.message.update({ where: { id: messageID }, data: { content: "replacementbody" } });
+  assert.equal((await search("original")).items.length, 0);
+  assert.equal((await search("replacementbody")).items.length, 1);
+  await prisma.message.update({ where: { id: messageID }, data: { role: "tool" } });
+  assert.equal((await search("replacementbody")).items.length, 0);
+  await prisma.message.update({ where: { id: messageID }, data: { role: "user" } });
+  assert.equal((await search("replacementbody")).items.length, 1);
+  await assert.rejects(prisma.$transaction(async (tx) => {
+    await tx.message.update({ where: { id: messageID }, data: { content: "rolledbackvalue" } });
+    throw new Error("rollback");
+  }));
+  assert.equal((await search("rolledbackvalue")).items.length, 0);
+  assert.equal((await search("replacementbody")).items.length, 1);
+  const fork = await app.inject({ method: "POST", url: `/v1/chats/${chat.id}/fork`, payload: {} });
+  assert.equal(fork.statusCode, 200, fork.body);
+  assert.equal((await search("replacementbody")).items.length, 2);
+  await prisma.message.delete({ where: { id: messageID } });
+  const onlyFork = (await search("replacementbody")).items;
+  assert.deepEqual(onlyFork.map((item: any) => item.id), [fork.json().chat.id]);
+  const starResponse = await app.inject({ method: "PATCH", url: `/v1/chats/${chat.id}/star`, payload: { starred: true } });
+  assert.equal(starResponse.statusCode, 200, starResponse.body);
+  const starredFork = (await search("replacementbody")).items[0];
+  assert.equal(starredFork.starred, true);
+  assert.ok(starredFork.starredAt);
+  assert.equal(starredFork.parentChat, undefined);
+  await prisma.chat.delete({ where: { id: chat.id } });
+  assert.equal((await search("replacement")).items.length, 0);
+  for (const table of ["ChatSearch", "MessageSearch", "SavedSearchSearch"]) {
+    await prisma.$executeRawUnsafe(`INSERT INTO "${table}" ("${table}", rank) VALUES ('integrity-check', 1)`);
+  }
+});
+
+test("saved searches match query and answer, and update/delete their index", async () => {
+  const saved = await prisma.search.create({ data: { title: "Bookmarks", query: "AI design", answerText: "Use a nebula illustration" } });
+  assert.equal((await search("ai des")).items[0].type, "search");
+  assert.match((await search("nebula")).items[0].searchSnippet, /nebula/);
+  await prisma.search.update({ where: { id: saved.id }, data: { title: "New title", query: "newquery", answerText: "newanswer" } });
+  assert.equal((await search("nebula")).items.length, 0);
+  assert.equal((await search("design")).items.length, 0);
+  assert.equal((await search("Bookmarks")).items.length, 0);
+  assert.equal((await search("newanswer")).items.length, 1);
+  await prisma.search.delete({ where: { id: saved.id } });
+  assert.equal((await search("new")).items.length, 0);
+});
+
+test("literal queries, validation, blank queries, and bounded snippets", async () => {
+  await prisma.chat.create({ data: { title: "AI OR safety", messages: { create: { role: "user", content: "longword".repeat(1000) } } } });
+  assert.equal((await search('"AI" OR safety*')).items.length, 1);
+  assert.equal((await search("AI OR other")).items.length, 0);
+  assert.equal((await search("AI")).items.length, 1);
+  assert.equal((await search("*** : () --")).items.length, 0);
+  assert.equal((await search("' UNION SELECT * FROM Chat; --")).items.length, 0);
+  assert.equal((await search("longword")).items[0].searchSnippet.length, 480);
+  const recent = (await app.inject({ method: "GET", url: "/v1/workspace-items" })).json();
+  assert.deepEqual(await search("  "), recent);
+  for (const query of ["q=" + "x".repeat(201), "q=one&q=two"]) {
+    const response = await app.inject({ method: "GET", url: `/v1/workspace-items?${query}` });
+    assert.equal(response.statusCode, 400, response.body);
+  }
+});
+
+test("caps combined results at 100 with deterministic newest-first ordering", async () => {
+  const date = new Date("2026-01-01");
+  await prisma.chat.createMany({ data: Array.from({ length: 100 }, (_, i) => ({ id: `chat-${String(i).padStart(3, "0")}`, title: "commonword", updatedAt: date })) });
+  await prisma.search.create({ data: { id: "saved", query: "commonword", updatedAt: new Date("2026-02-01") } });
+  const result = await search("common");
+  assert.equal(result.items.length, 100);
+  assert.equal(result.hasMore, true);
+  assert.equal(result.items[0].id, "saved");
+  assert.equal(result.items[1].id, "chat-000");
+  assert.equal(result.items.at(-1).id, "chat-098");
+});
+
+test("query plan uses all three FTS indexes", async () => {
+  const plan = await prisma.$queryRaw<Array<{ detail: string }>>(Prisma.sql`EXPLAIN QUERY PLAN ${workspaceSearchSQL(workspaceSearchExpression("needle")!)}`);
+  for (const table of ["ChatSearch", "MessageSearch", "SavedSearchSearch"]) {
+    assert.ok(plan.some((row) => row.detail.includes(table) && /VIRTUAL TABLE INDEX.*M\d/.test(row.detail)), plan.map((row) => row.detail).join("\n"));
+  }
+  assert.equal(plan.some((row) => row.detail.includes("CORRELATED SCALAR SUBQUERY")), false, "Excerpts must not restart FTS for each result");
+});
+
+test("vacuum preserves external-content index row identities", async () => {
+  const removed = await prisma.chat.create({ data: { title: "removed" } });
+  const kept = await prisma.chat.create({ data: { title: "kepttitle", messages: { create: { role: "user", content: "keptbody" } } } });
+  await prisma.chat.delete({ where: { id: removed.id } });
+  await prisma.$executeRaw`VACUUM`;
+  assert.equal((await search("kepttitle")).items[0].id, kept.id);
+  assert.equal((await search("kepttitle")).items[0].searchSnippet, null);
+  assert.equal((await search("keptbody")).items[0].searchSnippet, "keptbody");
+});

web/README.md

@@ -34,6 +34,13 @@ Default dev URL: `http://localhost:5173`
 ## UI
 
 - Left panel: mixed list of chat conversations and Exa searches.
+- Sidebar search uses `GET /v1/workspace-items?q=…` to search all saved titles,
+  conversation messages, and web-search queries/answers. It waits 300 ms while
+  typing and cancels superseded requests. Results include a single-line matching excerpt
+  with matching words in bold and middle truncation
+  (or “Title match” for title-only chat matches), with up to 100 newest matches.
+  Clear the field or press Escape to return to recent items. Matching uses word
+  prefixes, so `plan` also finds `planning`.
 - Right panel:
   - Chat mode: transcript + provider/model controls.
   - Search mode: top AI answer block + Google-style Exa results view.

web/src/App.tsx

@@ -1,4 +1,4 @@
-import { useEffect, useMemo, useRef, useState } from "preact/hooks";
+import { useEffect, useLayoutEffect, useMemo, useRef, useState } from "preact/hooks";
 import type { TargetedTouchEvent } from "preact";
 import {
   Check,
@@ -26,6 +26,7 @@ import { ChatAttachmentList } from "@/components/chat/chat-attachment-list";
 import { ChatComposer } from "@/components/chat/chat-composer";
 import { ChatMessagesPanel } from "@/components/chat/chat-messages-panel";
 import { SearchResultsPanel } from "@/components/search/search-results-panel";
+import { SearchMatchLabel } from "@/components/search/search-match-label";
 import { SybilCharacter } from "@/components/sybil-character";
 import {
   createChat,
@@ -43,6 +44,7 @@ import {
   getSearch,
   listWorkspaceItems,
   runCompletionStream,
+  runQuickQuestionStream,
   runSearchStream,
   suggestChatTitle,
   updateChatTitle,
@@ -65,25 +67,38 @@ import {
   type WorkspaceItem,
 } from "@/lib/api";
 import { useSessionAuth } from "@/hooks/use-session-auth";
+import { useWorkspaceSearch } from "@/hooks/use-workspace-search";
 import {
   getChatModelSelection,
   getChatModelSelectionSyncKey,
 } from "@/lib/chat-model-selection";
 import {
-  filterSidebarItemsWithForkGroups,
   getForkGroupPresentation,
   groupForkedChatItems,
   shouldRequestChatTitle,
 } from "@/lib/chat-forking";
 import {
+  retainSelectedHistoryItem,
   resolveSidebarSelectionAfterRefresh,
   type SidebarSelection,
 } from "@/lib/sidebar-selection";
+import { buildQuickQuestionRequest, pickQuickQuestionModel, QUICK_QUESTION_DEFAULT_MODEL } from "@/lib/quick-question";
+import {
+  appendStreamingDelta,
+  clearStreamingAssistantTrace,
+  createStreamingAssistantMetadata,
+  createStreamingAttemptState,
+  finalizeStreamingAssistant,
+  promoteStreamingAssistantTrace,
+  setStreamingAssistantSegment,
+  transitionStreamingToolCall,
+} from "@/lib/chat-stream-presentation";
 import { cn } from "@/lib/utils";
 
 type DraftSelectionKind = "chat" | "search";
 type SidebarItem = SidebarSelection & {
   title: string;
+  searchSnippet: string | null;
   parentChatId: string | null;
   updatedAt: string;
   createdAt: string;
@@ -149,7 +164,7 @@ function buildWorkspaceUrl(selection: SidebarSelection | null) {
 }
 
 const PROVIDER_FALLBACK_MODELS: Record<Provider, string[]> = {
-  openai: ["gpt-4.1-mini"],
+  openai: ["gpt-4.1-mini", QUICK_QUESTION_DEFAULT_MODEL],
   anthropic: ["claude-3-5-sonnet-latest"],
   xai: ["grok-3-mini"],
   gemini: ["gemini-3.5-flash", "gemini-flash-latest"],
@@ -642,9 +657,10 @@ type ModelComboboxProps = {
   value: string;
   onChange: (value: string) => void;
   disabled?: boolean;
+  className?: string;
 };
 
-function ModelCombobox({ options, value, onChange, disabled = false }: ModelComboboxProps) {
+function ModelCombobox({ options, value, onChange, disabled = false, className }: ModelComboboxProps) {
   const [open, setOpen] = useState(false);
   const [draftValue, setDraftValue] = useState(value);
   const rootRef = useRef<HTMLDivElement>(null);
@@ -698,7 +714,12 @@ function ModelCombobox({ options, value, onChange, disabled = false }: ModelComb
 
   return (
     <div className="relative" ref={rootRef}>
-      <div className="flex h-10 min-w-56 items-center rounded-lg border border-violet-300/22 bg-background/72 px-3 text-sm shadow-[inset_0_1px_0_hsl(255_100%_92%_/_0.06)]">
+      <div
+        className={cn(
+          "flex h-10 min-w-56 items-center rounded-lg border border-violet-300/22 bg-background/72 px-3 text-sm shadow-[inset_0_1px_0_hsl(255_100%_92%_/_0.06)]",
+          className
+        )}
+      >
         <input
           ref={inputRef}
           value={draftValue}
@@ -825,6 +846,7 @@ function buildSidebarItems(items: WorkspaceItem[]): SidebarItem[] {
         kind: "chat" as const,
         id: chat.id,
         title: getChatTitle(chat),
+        searchSnippet: chat.searchSnippet ?? null,
         parentChatId: chat.parentChatId,
         updatedAt: chat.updatedAt,
         createdAt: chat.createdAt,
@@ -842,6 +864,7 @@ function buildSidebarItems(items: WorkspaceItem[]): SidebarItem[] {
       kind: "search" as const,
       id: search.id,
       title: getSearchTitle(search),
+      searchSnippet: search.searchSnippet ?? null,
       parentChatId: null,
       updatedAt: search.updatedAt,
       createdAt: search.createdAt,
@@ -936,7 +959,6 @@ export default function App() {
     isCheckingSession,
     isSigningIn,
     isAuthenticated,
-    authMode,
     authError,
     handleAuthFailure: baseHandleAuthFailure,
     handleSignIn,
@@ -974,7 +996,7 @@ export default function App() {
   );
   const [quickModel, setQuickModel] = useState(() => {
     const stored = loadStoredQuickQuestionModelSelection();
-    return stored.modelPreferences[stored.provider] ?? PROVIDER_FALLBACK_MODELS[stored.provider][0];
+    return pickQuickQuestionModel(stored.provider, PROVIDER_FALLBACK_MODELS[stored.provider], stored.modelPreferences[stored.provider]);
   });
   const [isQuickQuestionOpen, setIsQuickQuestionOpen] = useState(false);
   const [quickPrompt, setQuickPrompt] = useState("");
@@ -1006,6 +1028,7 @@ export default function App() {
   const transcriptEndRef = useRef<HTMLDivElement>(null);
   const contextMenuRef = useRef<HTMLDivElement>(null);
   const renameChatInputRef = useRef<HTMLInputElement>(null);
+  const chatSettingsDialogRef = useRef<HTMLDialogElement>(null);
   const fileInputRef = useRef<HTMLInputElement>(null);
   const dragDepthRef = useRef(0);
   const pendingAttachmentsRef = useRef<ChatAttachment[]>([]);
@@ -1034,6 +1057,10 @@ export default function App() {
   const [contextMenu, setContextMenu] = useState<ContextMenuState | null>(null);
   const [isMobileSidebarOpen, setIsMobileSidebarOpen] = useState(false);
   const [sidebarQuery, setSidebarQuery] = useState("");
+  const [sidebarSearchRevision, setSidebarSearchRevision] = useState(0);
+  const sidebarSearch = useWorkspaceSearch(sidebarQuery, isAuthenticated, sidebarSearchRevision);
+  const isSidebarSearchActive = Boolean(sidebarQuery.trim());
+  const selectedHistoryItemRef = useRef<WorkspaceItem | null>(null);
   const initialRouteSelectionRef = useRef<SidebarSelection | null>(readSidebarSelectionFromUrl());
   const hasSyncedSelectionHistoryRef = useRef(false);
 
@@ -1099,19 +1126,16 @@ export default function App() {
   }, [pendingAttachments]);
 
   const sidebarItems = useMemo(() => buildSidebarItems(workspaceItems), [workspaceItems]);
-  const filteredSidebarItems = useMemo(() => {
+  const searchSidebarItems = useMemo(() => buildSidebarItems(sidebarSearch.items), [sidebarSearch.items]);
-    const query = sidebarQuery.trim().toLowerCase();
+  const knownSidebarItems = useMemo(() => {
-    if (!query) return groupForkedChatItems(sidebarItems).flat();
+    const matches = new Set(searchSidebarItems.map((item) => `${item.kind}:${item.id}`));
-    return filterSidebarItemsWithForkGroups(sidebarItems, (item) => {
+    return [...searchSidebarItems, ...sidebarItems.filter((item) => !matches.has(`${item.kind}:${item.id}`))];
-      const providerLabel = getProviderLabel(item.lastUsedProvider || item.initiatedProvider).toLowerCase();
+  }, [sidebarItems, searchSidebarItems]);
-      return [item.title, item.initiatedModel, item.lastUsedModel, providerLabel]
-        .filter(Boolean)
-        .some((value) => String(value).toLowerCase().includes(query));
-    });
-  }, [sidebarItems, sidebarQuery]);
   const sidebarSections = useMemo(
-    () => buildSidebarSections(filteredSidebarItems, sidebarItems),
+    () => isSidebarSearchActive
-    [filteredSidebarItems, sidebarItems]
+      ? (searchSidebarItems.length ? [{ label: "SEARCH RESULTS", items: searchSidebarItems }] : [])
+      : buildSidebarSections(sidebarItems),
+    [isSidebarSearchActive, searchSidebarItems, sidebarItems]
   );
   const orderedSidebarItems = useMemo(() => sidebarSections.flatMap((section) => section.items), [sidebarSections]);
 
@@ -1130,6 +1154,8 @@ export default function App() {
     setChats([]);
     setSearches([]);
     setWorkspaceItems([]);
+    setSidebarQuery("");
+    selectedHistoryItemRef.current = null;
     setSelectedItem(null);
     setSelectedChat(null);
     setSelectedSearch(null);
@@ -1181,6 +1207,10 @@ export default function App() {
     resetWorkspaceState();
   };
 
+  useEffect(() => {
+    if (sidebarSearch.error?.includes("bearer token")) handleAuthFailure(sidebarSearch.error);
+  }, [sidebarSearch.error]);
+
   const refreshCollections = async ({
     initialSelection,
     reportTransientError = true,
@@ -1193,12 +1223,14 @@ export default function App() {
     };
     setIsLoadingCollections(true);
     try {
-      const nextWorkspaceItems = await listWorkspaceItems();
+      let nextWorkspaceItems = await listWorkspaceItems();
       if (requestId !== collectionLoadRequestRef.current) return;
+      nextWorkspaceItems = retainSelectedHistoryItem(nextWorkspaceItems, selectedItemRef.current, selectedHistoryItemRef.current);
       const { chats: nextChats, searches: nextSearches } = splitWorkspaceItems(nextWorkspaceItems);
       setWorkspaceItems(nextWorkspaceItems);
       setChats(nextChats);
       setSearches(nextSearches);
+      setSidebarSearchRevision((current) => current + 1);
 
       setSelectedItem((current) => {
         const nextSelection = resolveSidebarSelectionAfterRefresh(current, nextWorkspaceItems, {
@@ -1431,7 +1463,7 @@ export default function App() {
   useEffect(() => {
     if (quickModel.trim()) return;
     setQuickModel((current) => {
-      return current.trim() || pickProviderModel(quickProviderModelOptions, quickProviderModelPreferences[quickProvider]);
+      return current.trim() || pickQuickQuestionModel(quickProvider, quickProviderModelOptions, quickProviderModelPreferences[quickProvider]);
     });
   }, [quickModel, quickProvider, quickProviderModelOptions, quickProviderModelPreferences]);
 
@@ -1494,16 +1526,16 @@ export default function App() {
   const isItemRunning = (item: SidebarSelection) =>
     item.kind === "chat" ? !!pendingChatStates[item.id] || !!activeRuns.chats[item.id] : !!runningSearchStates[item.id] || !!activeRuns.searches[item.id];
   const getChatFamilyItems = (chatId: string) => {
-    const chat = sidebarItems.find((item) => item.kind === "chat" && item.id === chatId);
+    const chat = knownSidebarItems.find((item) => item.kind === "chat" && item.id === chatId);
     if (!chat) return [];
     const rootId = chat.parentChatId ?? chat.id;
-    return sidebarItems.filter(
+    return knownSidebarItems.filter(
       (item) => item.kind === "chat" && (item.id === rootId || item.parentChatId === rootId)
     );
   };
   const isRootChat = (item: SidebarSelection) => {
     if (item.kind !== "chat") return false;
-    const chat = sidebarItems.find((candidate) => candidate.kind === "chat" && candidate.id === item.id);
+    const chat = knownSidebarItems.find((candidate) => candidate.kind === "chat" && candidate.id === item.id);
     return chat?.parentChatId === null;
   };
   const isDeleteBlocked = (item: SidebarSelection) => {
@@ -1512,9 +1544,10 @@ export default function App() {
   };
   const isSidebarTargetStarred = (item: SidebarSelection) => {
     if (item.kind === "chat") {
-      return getChatFamilyItems(item.id).find((familyItem) => familyItem.parentChatId === null)?.starred ?? false;
+      const family = getChatFamilyItems(item.id);
+      return (family.find((familyItem) => familyItem.parentChatId === null) ?? family[0])?.starred ?? false;
     }
-    return sidebarItems.find((candidate) => candidate.kind === "search" && candidate.id === item.id)?.starred ?? false;
+    return knownSidebarItems.find((candidate) => candidate.kind === "search" && candidate.id === item.id)?.starred ?? false;
   };
   const isCurrentSelection = (item: SidebarSelection) => {
     const current = selectedItemRef.current;
@@ -1910,14 +1943,26 @@ export default function App() {
         : Math.min(orderedSidebarItems.length - 1, Math.max(0, currentIndex + direction));
     const nextItem = orderedSidebarItems[nextIndex];
     const target: SidebarSelection = { kind: nextItem.kind, id: nextItem.id };
+    rememberHistoryResult(target);
     selectedItemRef.current = target;
     setSelectedItem(target);
   };
 
+  const rememberHistoryResult = (target: SidebarSelection) => {
+    const item = sidebarSearch.items.find((item) => item.type === target.kind && item.id === target.id);
+    if (!item) return;
+    selectedHistoryItemRef.current = item;
+    const { chats: matchedChats, searches: matchedSearches } = splitWorkspaceItems([item]);
+    if (matchedChats.length) setChats((current) => [...matchedChats, ...current.filter((chat) => chat.id !== item.id)]);
+    if (matchedSearches.length) setSearches((current) => [...matchedSearches, ...current.filter((search) => search.id !== item.id)]);
+    setWorkspaceItems((current) => upsertWorkspaceItem(current, item, false));
+  };
+
   useEffect(() => {
     if (!isAuthenticated) return;
 
     const handleKeyDown = (event: KeyboardEvent) => {
+      if (chatSettingsDialogRef.current?.open) return;
       const hasPrimaryModifier = event.metaKey || event.ctrlKey;
       if (!hasPrimaryModifier || event.altKey) return;
 
@@ -1956,11 +2001,15 @@ export default function App() {
     if (selectedChat?.id === chatId) return getChatTitle(selectedChat, selectedChat.messages);
     const summary = chats.find((chat) => chat.id === chatId);
     if (summary) return getChatTitle(summary);
-    const sidebarItem = sidebarItems.find((item) => item.kind === "chat" && item.id === chatId);
+    const sidebarItem = knownSidebarItems.find((item) => item.kind === "chat" && item.id === chatId);
     return sidebarItem?.title ?? "New chat";
   };
 
   const applyChatSummary = (updatedChat: ChatSummary, moveToFront = true) => {
+    setSidebarSearchRevision((current) => current + 1);
+    if (selectedHistoryItemRef.current?.type === "chat" && selectedHistoryItemRef.current.id === updatedChat.id) {
+      selectedHistoryItemRef.current = chatWorkspaceItem(updatedChat);
+    }
     supersedeCollectionLoad();
     setChats((current) => {
       const withoutExisting = current.filter((chat) => chat.id !== updatedChat.id);
@@ -1993,6 +2042,10 @@ export default function App() {
   };
 
   const applySearchSummary = (updatedSearch: SearchSummary, moveToFront = true) => {
+    setSidebarSearchRevision((current) => current + 1);
+    if (selectedHistoryItemRef.current?.type === "search" && selectedHistoryItemRef.current.id === updatedSearch.id) {
+      selectedHistoryItemRef.current = searchWorkspaceItem(updatedSearch);
+    }
     supersedeCollectionLoad();
     setSearches((current) => {
       const withoutExisting = current.filter((search) => search.id !== updatedSearch.id);
@@ -2179,7 +2232,7 @@ export default function App() {
     const family = getChatFamilyItems(chatId);
     const root = family.find((item) => item.parentChatId === null) ?? family[0];
     if (!root) return;
-    applyChatSummary(await updateChatStar(root.id, !root.starred), false);
+    applyChatSummary(await updateChatStar(root.parentChatId ?? root.id, !root.starred), false);
   };
 
   const handleToggleStar = async (target: SidebarSelection) => {
@@ -2190,7 +2243,7 @@ export default function App() {
       if (target.kind === "chat") {
         await toggleChatFamilyStar(target.id);
       } else {
-        const current = sidebarItems.find((item) => item.kind === "search" && item.id === target.id);
+        const current = knownSidebarItems.find((item) => item.kind === "search" && item.id === target.id);
         const updatedSearch = await updateSearchStar(target.id, !current?.starred);
         applySearchSummary(updatedSearch, false);
       }
@@ -2282,6 +2335,11 @@ export default function App() {
       } else {
         await deleteSearch(target.id);
       }
+      const retained = selectedHistoryItemRef.current;
+      if (retained && ((retained.type === target.kind && retained.id === target.id) ||
+          (retained.type === "chat" && target.kind === "chat" && retained.parentChatId === target.id))) {
+        selectedHistoryItemRef.current = null;
+      }
       await refreshCollections({ selectFallback: true });
     } catch (err) {
       const message = err instanceof Error ? err.message : String(err);
@@ -2319,16 +2377,16 @@ export default function App() {
     return () => window.clearTimeout(timer);
   }, [renameChatDialog]);
 
-  useEffect(() => {
+  useLayoutEffect(() => {
     if (!isChatSettingsOpen) return;
-    const handleKeyDown = (event: KeyboardEvent) => {
+    const dialog = chatSettingsDialogRef.current;
-      if (event.key !== "Escape" || isSavingChatSettings) return;
+    const previouslyFocused = document.activeElement;
-      event.preventDefault();
+    dialog?.showModal();
-      setIsChatSettingsOpen(false);
+    return () => {
+      dialog?.close();
+      if (previouslyFocused instanceof HTMLElement) previouslyFocused.focus({ preventScroll: true });
     };
-    window.addEventListener("keydown", handleKeyDown);
+  }, [isChatSettingsOpen]);
-    return () => window.removeEventListener("keydown", handleKeyDown);
-  }, [isChatSettingsOpen, isSavingChatSettings]);
 
   useEffect(() => {
     if (!isQuickQuestionOpen) return;
@@ -2484,7 +2542,7 @@ export default function App() {
       role: "assistant",
       content: "",
       name: null,
-      metadata: null,
+      metadata: createStreamingAssistantMetadata(),
     };
 
     let chatId = draftKind === "chat" ? null : selectedItem?.kind === "chat" ? selectedItem.id : null;
@@ -2589,7 +2647,7 @@ export default function App() {
 
     while (true) {
       let streamErrorMessage: string | null = null;
-      let replayedAssistantText = "";
+      let streamingAttempt = createStreamingAttemptState();
       const abortController = new AbortController();
       chatStreamAbortRefs.current.set(chatId, abortController);
 
@@ -2607,45 +2665,39 @@ export default function App() {
               if (payload.chatId !== chatId) return;
             },
             onToolCall: (payload) => {
+              const transition = transitionStreamingToolCall(streamingAttempt, payload);
+              streamingAttempt = transition.attempt;
               setPendingChatStates((current) => {
                 const pendingState = current[chatId];
                 if (!pendingState) return current;
+                const messages = transition.startedNewToolCall
+                  ? promoteStreamingAssistantTrace(pendingState.messages, "temp-assistant-", transition.traceText ?? "")
+                  : pendingState.messages;
                 return {
                   ...current,
                   [chatId]: {
-                    messages: upsertOptimisticToolMessage(pendingState.messages, payload, "temp-assistant-"),
+                    messages: upsertOptimisticToolMessage(messages, payload, "temp-assistant-"),
                   },
                 };
               });
             },
             onDelta: (payload) => {
               if (!payload.text) return;
-              replayedAssistantText += payload.text;
+              streamingAttempt = appendStreamingDelta(streamingAttempt, payload.text);
+              const segmentText = streamingAttempt.segmentText;
               setPendingChatStates((current) => {
                 const pendingState = current[chatId];
                 if (!pendingState) return current;
-                let updated = false;
+                const nextMessages = setStreamingAssistantSegment(pendingState.messages, "temp-assistant-", segmentText);
-                const nextMessages = pendingState.messages.map((message, index, all) => {
+                return nextMessages === pendingState.messages ? current : { ...current, [chatId]: { messages: nextMessages } };
-                  const isTarget = index === all.length - 1 && message.id.startsWith("temp-assistant-");
-                  if (!isTarget) return message;
-                  updated = true;
-                  return { ...message, content: replayedAssistantText };
-                });
-                return updated ? { ...current, [chatId]: { messages: nextMessages } } : current;
               });
             },
             onDone: (payload) => {
               setPendingChatStates((current) => {
                 const pendingState = current[chatId];
                 if (!pendingState) return current;
-                let updated = false;
+                const nextMessages = finalizeStreamingAssistant(pendingState.messages, "temp-assistant-", payload.text);
-                const nextMessages = pendingState.messages.map((message, index, all) => {
+                return nextMessages === pendingState.messages ? current : { ...current, [chatId]: { messages: nextMessages } };
-                  const isTarget = index === all.length - 1 && message.id.startsWith("temp-assistant-");
-                  if (!isTarget) return message;
-                  updated = true;
-                  return { ...message, content: payload.text };
-                });
-                return updated ? { ...current, [chatId]: { messages: nextMessages } } : current;
               });
             },
             onError: (payload) => {
@@ -2894,6 +2946,7 @@ export default function App() {
         const abortController = new AbortController();
         chatStreamAbortRefs.current.set(chatId, abortController);
         let streamErrorMessage: string | null = null;
+        let streamingAttempt = createStreamingAttemptState();
 
         try {
           const baseChat = await getChat(chatId);
@@ -2910,7 +2963,7 @@ export default function App() {
                   role: "assistant",
                   content: "",
                   name: null,
-                  metadata: null,
+                  metadata: createStreamingAssistantMetadata(),
                 }),
               },
             };
@@ -2920,44 +2973,39 @@ export default function App() {
             chatId,
             {
               onToolCall: (payload) => {
+                const transition = transitionStreamingToolCall(streamingAttempt, payload);
+                streamingAttempt = transition.attempt;
                 setPendingChatStates((current) => {
                   const pendingState = current[chatId];
                   if (!pendingState) return current;
+                  const messages = transition.startedNewToolCall
+                    ? promoteStreamingAssistantTrace(pendingState.messages, "temp-assistant-", transition.traceText ?? "")
+                    : pendingState.messages;
                   return {
                     ...current,
                     [chatId]: {
-                      messages: upsertOptimisticToolMessage(pendingState.messages, payload, "temp-assistant-"),
+                      messages: upsertOptimisticToolMessage(messages, payload, "temp-assistant-"),
                     },
                   };
                 });
               },
               onDelta: (payload) => {
                 if (!payload.text) return;
+                streamingAttempt = appendStreamingDelta(streamingAttempt, payload.text);
+                const segmentText = streamingAttempt.segmentText;
                 setPendingChatStates((current) => {
                   const pendingState = current[chatId];
                   if (!pendingState) return current;
-                  let updated = false;
+                  const nextMessages = setStreamingAssistantSegment(pendingState.messages, "temp-assistant-", segmentText);
-                  const nextMessages = pendingState.messages.map((message, index, all) => {
+                  return nextMessages === pendingState.messages ? current : { ...current, [chatId]: { messages: nextMessages } };
-                    const isTarget = index === all.length - 1 && message.id.startsWith("temp-assistant-");
-                    if (!isTarget) return message;
-                    updated = true;
-                    return { ...message, content: message.content + payload.text };
-                  });
-                  return updated ? { ...current, [chatId]: { messages: nextMessages } } : current;
                 });
               },
               onDone: (payload) => {
                 setPendingChatStates((current) => {
                   const pendingState = current[chatId];
                   if (!pendingState) return current;
-                  let updated = false;
+                  const nextMessages = finalizeStreamingAssistant(pendingState.messages, "temp-assistant-", payload.text);
-                  const nextMessages = pendingState.messages.map((message, index, all) => {
+                  return nextMessages === pendingState.messages ? current : { ...current, [chatId]: { messages: nextMessages } };
-                    const isTarget = index === all.length - 1 && message.id.startsWith("temp-assistant-");
-                    if (!isTarget) return message;
-                    updated = true;
-                    return { ...message, content: payload.text };
-                  });
-                  return updated ? { ...current, [chatId]: { messages: nextMessages } } : current;
                 });
               },
               onError: (payload) => {
@@ -3209,7 +3257,7 @@ export default function App() {
       role: "assistant",
       content: "",
       name: null,
-      metadata: null,
+      metadata: createStreamingAssistantMetadata(),
     };
 
     quickQuestionAbortRef.current?.abort();
@@ -3223,44 +3271,37 @@ export default function App() {
     setIsQuickQuestionSending(true);
 
     let streamErrorMessage: string | null = null;
+    let streamingAttempt = createStreamingAttemptState();
 
     try {
-      await runCompletionStream(
+      await runQuickQuestionStream(
-        {
+        buildQuickQuestionRequest({
-          persist: false,
           provider: quickProvider,
           model: selectedModel,
-          messages: [{ role: "user", content }],
+          content,
-        },
+        }),
         {
           onToolCall: (payload) => {
+            const transition = transitionStreamingToolCall(streamingAttempt, payload);
+            streamingAttempt = transition.attempt;
             setQuickQuestionMessages((current) => {
-              return upsertOptimisticToolMessage(current, payload, "temp-assistant-quick-");
+              const messages = transition.startedNewToolCall
+                ? promoteStreamingAssistantTrace(current, "temp-assistant-quick-", transition.traceText ?? "")
+                : current;
+              return upsertOptimisticToolMessage(messages, payload, "temp-assistant-quick-");
             });
           },
           onDelta: (payload) => {
             if (!payload.text) return;
+            streamingAttempt = appendStreamingDelta(streamingAttempt, payload.text);
+            const segmentText = streamingAttempt.segmentText;
             setQuickQuestionMessages((current) => {
-              let updated = false;
+              return setStreamingAssistantSegment(current, "temp-assistant-quick-", segmentText);
-              const nextMessages = current.map((message, index, all) => {
-                const isTarget = index === all.length - 1 && message.id.startsWith("temp-assistant-quick-");
-                if (!isTarget) return message;
-                updated = true;
-                return { ...message, content: message.content + payload.text };
-              });
-              return updated ? nextMessages : current;
             });
           },
           onDone: (payload) => {
             setQuickQuestionMessages((current) => {
-              let updated = false;
+              return finalizeStreamingAssistant(current, "temp-assistant-quick-", payload.text);
-              const nextMessages = current.map((message, index, all) => {
-                const isTarget = index === all.length - 1 && message.id.startsWith("temp-assistant-quick-");
-                if (!isTarget) return message;
-                updated = true;
-                return { ...message, content: payload.text };
-              });
-              return updated ? nextMessages : current;
             });
           },
           onError: (payload) => {
@@ -3275,6 +3316,7 @@ export default function App() {
       }
     } catch (err) {
       if (abortController.signal.aborted) return;
+      setQuickQuestionMessages((current) => clearStreamingAssistantTrace(current, "temp-assistant-quick-"));
       const message = err instanceof Error ? err.message : String(err);
       if (message.includes("bearer token")) {
         handleAuthFailure(message);
@@ -3437,7 +3479,7 @@ export default function App() {
 
   return (
     <div className="app-grid-surface app-safe-frame h-full">
-      <div className="workspace-shell flex h-full w-full overflow-hidden bg-transparent md:gap-2">
+      <div className="workspace-shell flex h-full w-full overflow-hidden bg-transparent">
         {isMobileSidebarOpen ? (
           <button
             type="button"
@@ -3449,20 +3491,14 @@ export default function App() {
 
         <aside
           className={cn(
-            "workspace-sidebar glass-panel fixed inset-y-0 left-0 z-40 flex w-[86vw] max-w-80 shrink-0 flex-col border-r border-violet-300/18 transition-transform md:static md:z-auto md:w-80 md:max-w-none md:rounded-2xl md:border",
+            "workspace-sidebar glass-panel fixed inset-y-0 left-0 z-40 flex w-[86vw] max-w-80 shrink-0 flex-col border-r border-violet-300/18 transition-transform md:static md:z-auto md:w-80 md:max-w-none",
             isMobileSidebarOpen ? "translate-x-0" : "-translate-x-full md:translate-x-0"
           )}
         >
-          <div className="relative min-h-24 px-4 pb-4 pt-5">
+          <div className="relative min-h-24 px-4 pb-4 pt-5 flex items-center">
-            <div className="pr-24">
             <div className="sybil-wordmark bg-[linear-gradient(90deg,#ff8df8,#9a6dff_54%,#67dfff)] bg-clip-text text-3xl text-transparent">
               SYBIL
             </div>
-              <p className="mt-2 flex items-center gap-1.5 text-xs font-medium text-muted-foreground">
-                <span className="h-1.5 w-1.5 rounded-full bg-emerald-400" />
-                Sybil Web{authMode ? ` (${authMode === "open" ? "open mode" : "token mode"})` : ""}
-              </p>
-            </div>
             <SybilCharacter
               className="absolute right-4 top-3 h-[calc(100%-1.5rem)]"
               isBusy={isActiveSelectionSending || isQuickQuestionSending}
@@ -3506,33 +3542,55 @@ export default function App() {
               <input
                 value={sidebarQuery}
                 onInput={(event) => setSidebarQuery(event.currentTarget.value)}
-                placeholder="Search chats"
+                placeholder="Search chats and web searches"
-                className="h-10 w-full rounded-lg border border-violet-300/18 bg-background/66 pl-9 pr-3 text-sm text-violet-50 outline-none shadow-[inset_0_1px_0_hsl(255_100%_92%_/_0.05)] placeholder:text-muted-foreground focus:border-violet-300/45 focus:ring-1 focus:ring-ring/70"
+                aria-label="Search conversation history and saved web searches"
+                autoComplete="off"
+                spellcheck={false}
+                onKeyDown={(event) => {
+                  if (event.key === "Escape") setSidebarQuery("");
+                }}
+                className="h-10 w-full rounded-lg border border-violet-300/18 bg-background/66 pl-9 pr-9 text-sm text-violet-50 outline-none shadow-[inset_0_1px_0_hsl(255_100%_92%_/_0.05)] placeholder:text-muted-foreground focus:border-violet-300/45 focus:ring-1 focus:ring-ring/70"
               />
+              {sidebarQuery ? (
+                <button type="button" onClick={() => setSidebarQuery("")} aria-label="Clear history search"
+                  className="absolute right-2 top-1/2 -translate-y-1/2 rounded p-1 text-violet-200/70 hover:text-violet-50">
+                  <X className="h-4 w-4" />
+                </button>
+              ) : null}
             </div>
           </div>
           <Separator className="bg-violet-300/10" />
           <div className="flex-1 overflow-y-auto px-2 py-3">
-            {isLoadingCollections && sidebarItems.length === 0 ? <p className="px-2 py-3 text-sm text-muted-foreground">Loading conversations...</p> : null}
+            {!isSidebarSearchActive && isLoadingCollections && sidebarItems.length === 0 ? <p className="px-2 py-3 text-sm text-muted-foreground">Loading conversations...</p> : null}
-            {!isLoadingCollections && sidebarItems.length === 0 ? (
+            {!isSidebarSearchActive && !isLoadingCollections && sidebarItems.length === 0 ? (
               <div className="flex h-full flex-col items-center justify-center gap-2 p-5 text-center text-sm text-muted-foreground">
                 <MessageSquare className="h-5 w-5" />
                 Start a chat or run your first search.
               </div>
             ) : null}
-            {!isLoadingCollections && sidebarItems.length > 0 && filteredSidebarItems.length === 0 ? (
+            {isSidebarSearchActive ? (
-              <p className="px-2 py-3 text-sm text-muted-foreground">No chats found.</p>
+              <div aria-live="polite" role="status">
+                {sidebarSearch.isLoading ? <p className="flex items-center gap-2 px-3 py-3 text-sm text-muted-foreground"><LoaderCircle className="h-4 w-4 animate-spin" />Searching history…</p> : null}
+                {sidebarSearch.error ? (
+                  <div className="space-y-2 px-3 py-3 text-sm">
+                    <p className="text-red-300">{sidebarSearch.error}</p>
+                    <Button variant="secondary" onClick={() => setSidebarSearchRevision((current) => current + 1)}>Try again</Button>
+                  </div>
+                ) : !sidebarSearch.isLoading && searchSidebarItems.length === 0 ? (
+                  <p className="px-3 py-3 text-sm text-muted-foreground">No matching chats or web searches. Try a title, query, or words from a conversation.</p>
+                ) : null}
+              </div>
             ) : null}
             {sidebarSections.map((section) => (
               <div key={section.label} className="mb-4">
                 <p className="px-3 pb-2 text-[11px] font-semibold text-violet-200/48">{section.label}</p>
                 {section.items.map((item) => {
                   const active = selectedItem?.kind === item.kind && selectedItem.id === item.id;
-                  const isForkChild = item.kind === "chat" && item.parentChatId !== null;
+                  const isForkChild = !isSidebarSearchActive && item.kind === "chat" && item.parentChatId !== null;
-                  const familyItems = item.kind === "chat" ? getChatFamilyItems(item.id) : [item];
+                  const familyItems = !isSidebarSearchActive && item.kind === "chat" ? getChatFamilyItems(item.id) : [item];
                   const itemIsRunning = familyItems.some((familyItem) => isItemRunning(familyItem));
                   const itemIsStarred =
-                    familyItems.find((familyItem) => familyItem.parentChatId === null)?.starred ?? false;
+                    familyItems.find((familyItem) => familyItem.parentChatId === null)?.starred ?? item.starred;
                   const itemUpdatedAt = familyItems.reduce(
                     (newest, familyItem) =>
                       new Date(familyItem.updatedAt).getTime() > new Date(newest).getTime()
@@ -3558,6 +3616,7 @@ export default function App() {
                         draftKindRef.current = null;
                         setDraftKind(null);
                         const target = { kind: item.kind, id: item.id } as SidebarSelection;
+                        rememberHistoryResult(target);
                         selectedItemRef.current = target;
                         setSelectedItem(target);
                         setIsMobileSidebarOpen(false);
@@ -3576,7 +3635,7 @@ export default function App() {
                               active ? "border-cyan-200/35 bg-cyan-300/12 text-cyan-100" : "border-violet-300/18 text-violet-200/70"
                             )}
                           >
-                            {item.kind === "chat" ? <MessageSquare className="h-3.5 w-3.5" /> : <Search className="h-3.5 w-3.5" />}
+                            {item.kind === "chat" ? (item.parentChatId ? <GitFork className="h-3.5 w-3.5" aria-label="Fork" /> : <MessageSquare className="h-3.5 w-3.5" />) : <Search className="h-3.5 w-3.5" />}
                           </span>
                           <span className="flex min-w-0 flex-1 items-center gap-1.5">
                             <span className="truncate text-sm font-semibold">{item.title}</span>
@@ -3601,6 +3660,9 @@ export default function App() {
                               </span>
                             ) : null}
                           </span>
+                          {isSidebarSearchActive ? (
+                            <SearchMatchLabel text={item.searchSnippet || "Title match"} query={item.searchSnippet ? sidebarQuery : ""} />
+                          ) : null}
                         </div>
                       )}
                     </button>
@@ -3608,11 +3670,14 @@ export default function App() {
                 })}
               </div>
             ))}
+            {isSidebarSearchActive && sidebarSearch.hasMore ? (
+              <p className="px-3 py-2 text-xs text-muted-foreground">Showing the 100 most recent matches. Refine your search to find more.</p>
+            ) : null}
           </div>
         </aside>
 
         <main
-          className="workspace-content glass-panel relative flex min-w-0 flex-1 touch-pan-y flex-col overflow-hidden border-violet-300/18 md:touch-auto md:rounded-2xl md:border"
+          className="workspace-content glass-panel relative flex min-w-0 flex-1 touch-pan-y flex-col overflow-hidden md:touch-auto"
           onTouchStart={handleMobileWorkspaceTouchStart}
           onTouchMove={handleMobileWorkspaceTouchMove}
           onTouchEnd={handleMobileWorkspaceTouchEnd}
@@ -3826,44 +3891,66 @@ export default function App() {
         </div>
       ) : null}
       {isChatSettingsOpen ? (
-        <div
+        <dialog
-          className="fixed inset-0 z-[60] flex items-center justify-center bg-black/72 p-3 backdrop-blur-md md:p-6"
+          ref={chatSettingsDialogRef}
+          aria-labelledby="chat-settings-title"
+          className="fixed inset-0 m-0 flex h-dvh max-h-none w-full max-w-none items-center justify-center overflow-hidden bg-transparent p-0 text-foreground backdrop:bg-black/70 backdrop:backdrop-blur-md md:p-6"
+          onCancel={(event) => {
+            event.preventDefault();
+            if (!isSavingChatSettings) setIsChatSettingsOpen(false);
+          }}
           onMouseDown={(event) => {
             if (event.target === event.currentTarget && !isSavingChatSettings) setIsChatSettingsOpen(false);
           }}
         >
           <form
-            role="dialog"
+            className="glass-panel flex h-full min-h-0 w-full flex-col overflow-hidden md:h-auto md:max-h-full md:max-w-2xl md:rounded-2xl md:border md:border-violet-300/24"
-            aria-modal="true"
-            aria-labelledby="chat-settings-title"
-            className="glass-panel flex max-h-[88vh] w-full max-w-2xl flex-col rounded-2xl border border-violet-300/24 p-4 shadow-2xl shadow-black/45 md:p-5"
             onSubmit={(event) => void handleChatSettingsSubmit(event)}
           >
-            <div className="mb-4 flex items-center justify-between gap-3">
+            <div className="chat-settings-header grid shrink-0 grid-cols-[minmax(0,1fr)_auto_minmax(0,1fr)] items-center gap-2 border-b border-violet-300/16 md:flex md:justify-between md:gap-3">
+              <Button
+                type="button"
+                variant="ghost"
+                className="h-11 justify-self-start px-2 text-violet-200 hover:bg-violet-400/10 hover:text-violet-100 md:hidden"
+                onClick={() => setIsChatSettingsOpen(false)}
+                disabled={isSavingChatSettings}
+              >
+                Cancel
+              </Button>
               <div className="min-w-0">
-                <h2 id="chat-settings-title" className="text-sm font-semibold text-violet-50">
+                <h2 id="chat-settings-title" className="text-base font-semibold text-violet-50 md:text-sm">
                   Chat settings
                 </h2>
-                <p className="mt-1 truncate text-xs text-muted-foreground">{chatSettingsTitleDraft.trim() || "New chat"}</p>
+                <p className="mt-1 hidden truncate text-xs text-muted-foreground md:block">{chatSettingsTitleDraft.trim() || "New chat"}</p>
               </div>
               <Button
                 type="button"
                 size="icon"
                 variant="ghost"
-                className="h-8 w-8"
+                className="hidden h-8 w-8 shrink-0 md:inline-flex"
                 onClick={() => setIsChatSettingsOpen(false)}
                 disabled={isSavingChatSettings}
                 aria-label="Close chat settings"
               >
                 <X className="h-4 w-4" />
               </Button>
+              <Button
+                type="submit"
+                variant="ghost"
+                className="h-11 justify-self-end gap-1.5 px-2 font-semibold text-violet-200 hover:bg-violet-400/10 hover:text-violet-100 md:hidden"
+                disabled={isSavingChatSettings}
+              >
+                {isSavingChatSettings ? <LoaderCircle className="h-4 w-4 animate-spin" /> : null}
+                Save
+              </Button>
             </div>
 
-            <div className="min-h-0 flex-1 space-y-4 overflow-y-auto pr-1">
+            <div className="chat-settings-content min-h-0 flex-1 space-y-5 overflow-y-auto overscroll-contain md:space-y-4">
               <div>
-                <span className="mb-1.5 block text-xs font-semibold text-violet-100/72">Chat title</span>
+                <label for="chat-settings-chat-title" className="mb-1.5 block text-xs font-semibold text-violet-100/72">Chat title</label>
                 <div className="flex items-center gap-2">
                   <input
+                    id="chat-settings-chat-title"
                     value={chatSettingsTitleDraft}
                     onInput={(event) => {
                       setChatSettingsTitleDraft(event.currentTarget.value);
@@ -3871,7 +3958,7 @@ export default function App() {
                     }}
                     maxLength={120}
                     placeholder={draftKind === null && selectedItem?.kind === "chat" ? "Chat title" : "Optional title"}
-                    className="h-11 min-w-0 flex-1 rounded-lg border border-violet-300/22 bg-background/72 px-3 text-sm text-violet-50 outline-none shadow-[inset_0_1px_0_hsl(255_100%_92%_/_0.06)] placeholder:text-muted-foreground focus:border-violet-300/45 focus:ring-1 focus:ring-ring/70"
+                    className="h-11 min-w-0 flex-1 rounded-lg border border-violet-300/22 bg-background/70 px-3 text-base text-violet-50 outline-none shadow-[inset_0_1px_0_hsl(255_100%_92%_/_0.06)] placeholder:text-muted-foreground focus:border-violet-300/45 focus:ring-1 focus:ring-ring/70 md:text-sm"
                     disabled={isSavingChatSettings}
                   />
                   {chatSettingsChatId ? (
@@ -3899,7 +3986,7 @@ export default function App() {
                 <label className="block">
                   <span className="mb-1.5 block text-xs font-semibold text-violet-100/72">Provider</span>
                   <select
-                    className="h-10 w-full rounded-lg border border-violet-300/22 bg-background/72 px-3 text-sm text-violet-50 outline-none shadow-[inset_0_1px_0_hsl(255_100%_92%_/_0.06)] focus:border-violet-300/45 focus:ring-1 focus:ring-ring/70"
+                    className="h-11 w-full rounded-lg border border-violet-300/22 bg-background/70 px-3 text-base text-violet-50 outline-none shadow-[inset_0_1px_0_hsl(255_100%_92%_/_0.06)] focus:border-violet-300/45 focus:ring-1 focus:ring-ring/70 md:h-10 md:text-sm"
                     value={chatSettingsProviderDraft}
                     onChange={(event) => {
                       const nextProvider = event.currentTarget.value as Provider;
@@ -3921,6 +4008,7 @@ export default function App() {
                 <label className="block min-w-0">
                   <span className="mb-1.5 block text-xs font-semibold text-violet-100/72">Model</span>
                   <ModelCombobox
+                    className="h-11 min-w-0 bg-background/70 text-base md:h-10 md:text-sm"
                     options={chatSettingsProviderModelOptions}
                     value={chatSettingsModelDraft}
                     disabled={isSavingChatSettings}
@@ -3942,7 +4030,7 @@ export default function App() {
                     if (chatSettingsError) setChatSettingsError(null);
                   }}
                   placeholder="Add per-chat instructions"
-                  className="min-h-32 resize-y border-violet-300/24 bg-background/72 text-sm text-violet-50 placeholder:text-violet-200/45"
+                  className="min-h-32 resize-y border-violet-300/24 bg-background/70 text-base text-violet-50 placeholder:text-violet-200/45 md:text-sm"
                   disabled={isSavingChatSettings}
                 />
               </label>
@@ -3956,6 +4044,7 @@ export default function App() {
                         type="button"
                         size="sm"
                         variant="secondary"
+                        className="h-11 gap-1.5 md:h-8"
                         onClick={() => setChatSettingsEnabledToolsDraft(getDefaultEnabledTools(availableChatTools))}
                         disabled={isSavingChatSettings}
                       >
@@ -3966,6 +4055,7 @@ export default function App() {
                         type="button"
                         size="sm"
                         variant="secondary"
+                        className="h-11 gap-1.5 md:h-8"
                         onClick={() => setChatSettingsEnabledToolsDraft([])}
                         disabled={isSavingChatSettings}
                       >
@@ -3975,31 +4065,30 @@ export default function App() {
                     </div>
                   ) : null}
                 </div>
-                <div className="space-y-2">
+                <div className="grid gap-2 md:grid-cols-2">
                   {availableChatTools.length ? (
                     availableChatTools.map((tool) => {
                       const checked = chatSettingsEnabledToolsDraft.includes(tool.name);
                       return (
                         <label
                           key={tool.name}
-                          className="flex cursor-pointer items-start gap-3 rounded-lg border border-violet-300/18 bg-background/44 px-3 py-2.5 transition hover:border-violet-300/34 hover:bg-violet-400/8"
+                          title={tool.description}
+                          className="flex min-h-11 min-w-0 cursor-pointer items-center gap-3 rounded-lg border border-violet-300/18 bg-background/44 px-3 py-2.5 transition hover:border-violet-300/34 hover:bg-violet-400/8 focus-within:border-violet-300/45 focus-within:ring-1 focus-within:ring-ring/70"
                         >
                           <input
                             type="checkbox"
                             checked={checked}
                             onChange={() => toggleChatSettingsTool(tool.name)}
-                            className="mt-1 h-4 w-4 rounded border-violet-300/35 bg-background/80 accent-violet-400"
+                            className="h-4 w-4 shrink-0 rounded border-violet-300/35 bg-background/80 accent-violet-400"
+                            aria-description={tool.description}
                             disabled={isSavingChatSettings}
                           />
-                          <span className="min-w-0">
+                          <span className="min-w-0 break-words text-sm font-medium text-violet-50">{getToolLabel(tool.name)}</span>
-                            <span className="block text-sm font-medium text-violet-50">{getToolLabel(tool.name)}</span>
-                            <span className="mt-0.5 block text-xs leading-5 text-muted-foreground">{tool.description}</span>
-                          </span>
                         </label>
                       );
                     })
                   ) : (
-                    <p className="rounded-lg border border-violet-300/18 bg-background/44 px-3 py-2.5 text-sm text-muted-foreground">
+                    <p className="rounded-lg border border-violet-300/18 bg-background/44 px-3 py-2.5 text-sm text-muted-foreground md:col-span-2">
                       No chat tools are available.
                     </p>
                   )}
@@ -4007,8 +4096,8 @@ export default function App() {
               </section>
             </div>
 
-            {chatSettingsError ? <p className="mt-3 text-sm text-rose-300">{chatSettingsError}</p> : null}
+            {chatSettingsError ? <p role="alert" className="chat-settings-error shrink-0 break-words border-t border-violet-300/16 text-sm text-rose-300">{chatSettingsError}</p> : null}
-            <div className="mt-4 flex justify-end gap-2">
+            <div className="hidden shrink-0 justify-end gap-2 border-t border-violet-300/16 p-5 md:flex">
               <Button type="button" variant="secondary" onClick={() => setIsChatSettingsOpen(false)} disabled={isSavingChatSettings}>
                 Cancel
               </Button>
@@ -4018,7 +4107,7 @@ export default function App() {
               </Button>
             </div>
           </form>
-        </div>
+        </dialog>
       ) : null}
       {renameChatDialog ? (
         <div
@@ -4077,7 +4166,7 @@ export default function App() {
       ) : null}
       {isQuickQuestionOpen ? (
         <div
-          className="fixed inset-0 z-[60] flex items-center justify-center bg-black/72 p-3 backdrop-blur-md md:p-6"
+          className="fixed inset-0 z-[60] flex items-center justify-center bg-black/40 p-3 md:p-6"
           onMouseDown={(event) => {
             if (event.target === event.currentTarget) setIsQuickQuestionOpen(false);
           }}
@@ -4155,7 +4244,7 @@ export default function App() {
                     const nextProvider = event.currentTarget.value as Provider;
                     setQuickProvider(nextProvider);
                     const options = getModelOptions(modelCatalog, nextProvider);
-                    setQuickModel(pickProviderModel(options, quickProviderModelPreferences[nextProvider]));
+                    setQuickModel(pickQuickQuestionModel(nextProvider, options, quickProviderModelPreferences[nextProvider]));
                   }}
                   disabled={isQuickQuestionSending || isConvertingQuickQuestion}
                   aria-label="Quick question provider"

web/src/components/chat/chat-messages-panel.tsx

@@ -1,8 +1,9 @@
-import { useEffect, useMemo, useRef, useState } from "preact/hooks";
+import { useEffect, useLayoutEffect, useMemo, useRef, useState } from "preact/hooks";
 import type { ComponentChildren, JSX } from "preact";
 import { cn } from "@/lib/utils";
 import { ChatAttachmentList } from "@/components/chat/chat-attachment-list";
 import { getMessageAttachments, type Message } from "@/lib/api";
+import { asStreamingAssistantMetadata } from "@/lib/chat-stream-presentation";
 import { MarkdownContent } from "@/components/markdown/markdown-content";
 import { ChevronDown, ChevronUp, Globe2, Link2, Wrench } from "lucide-preact";
 
@@ -377,13 +378,13 @@ function ToolCallStack({
           );
         })}
         {!expanded && hiddenCount ? (
-          <span className="absolute bottom-1 right-10 z-20 rounded-full border border-cyan-300/30 bg-slate-950/86 px-2 py-0.5 text-[10px] font-semibold leading-none text-cyan-100 shadow-sm">
+          <span className="absolute bottom-1 right-10 z-20 rounded-none border border-cyan-300/30 bg-slate-950/86 px-2 py-0.5 text-[10px] font-semibold leading-none text-cyan-100 shadow-sm">
             +{hiddenCount}
           </span>
         ) : null}
         <button
           type="button"
-          className="tool-call-stack-toggle absolute right-0 top-2 z-20 flex h-8 w-8 items-center justify-center rounded-full"
+          className="tool-call-stack-toggle absolute right-0 top-2 z-20 flex h-8 w-8 items-center justify-center rounded-none"
           aria-expanded={expanded ? "true" : "false"}
           aria-label={`${expanded ? "Collapse" : "Expand"} ${countLabel}`}
           title={`${expanded ? "Collapse" : "Expand"} ${countLabel}`}
@@ -396,8 +397,144 @@ function ToolCallStack({
   );
 }
 
+type RenderedThinkingTrace = {
+  text: string;
+  revision: number;
+};
+
+const THINKING_TRACE_EXIT_MS = 220;
+
+export function StreamingAssistantPresentation({ message, isSending }: { message: Message; isSending: boolean }) {
+  const metadata = asStreamingAssistantMetadata(message.metadata);
+  const traceText = metadata?.ephemeralTrace?.trim() || null;
+  const traceRevision = metadata?.traceRevision ?? 0;
+  const [activeTrace, setActiveTrace] = useState<RenderedThinkingTrace | null>(() =>
+    traceText ? { text: traceText, revision: traceRevision } : null
+  );
+  const [outgoingTrace, setOutgoingTrace] = useState<RenderedThinkingTrace | null>(null);
+  const [reservedTraceHeight, setReservedTraceHeight] = useState(0);
+  const activeTraceRef = useRef<HTMLDivElement | null>(null);
+  const outgoingTraceRef = useRef<HTMLDivElement | null>(null);
+  const exitTimerRef = useRef<number | null>(null);
+
+  useLayoutEffect(() => {
+    const isSameTrace =
+      (!activeTrace && !traceText) ||
+      (activeTrace?.text === traceText && activeTrace?.revision === traceRevision && Boolean(activeTrace) === Boolean(traceText));
+    if (isSameTrace) return;
+
+    if (exitTimerRef.current !== null) {
+      window.clearTimeout(exitTimerRef.current);
+      exitTimerRef.current = null;
+    }
+
+    if (activeTrace) {
+      setOutgoingTrace(activeTrace);
+      exitTimerRef.current = window.setTimeout(() => {
+        setOutgoingTrace(null);
+        exitTimerRef.current = null;
+      }, THINKING_TRACE_EXIT_MS);
+    } else {
+      setOutgoingTrace(null);
+    }
+
+    setActiveTrace(traceText ? { text: traceText, revision: traceRevision } : null);
+  }, [traceRevision, traceText]);
+
+  useEffect(() => {
+    return () => {
+      if (exitTimerRef.current !== null) window.clearTimeout(exitTimerRef.current);
+    };
+  }, []);
+
+  useLayoutEffect(() => {
+    const traceElements = [activeTraceRef.current, outgoingTraceRef.current].filter(
+      (element): element is HTMLDivElement => element !== null
+    );
+    if (!traceElements.length) return;
+
+    const reserveMeasuredHeight = () => {
+      const measuredHeight = Math.max(...traceElements.map((element) => element.getBoundingClientRect().height));
+      if (measuredHeight > 0) {
+        setReservedTraceHeight((current) => Math.max(current, Math.ceil(measuredHeight)));
+      }
+    };
+
+    reserveMeasuredHeight();
+    if (typeof ResizeObserver === "undefined") return;
+
+    const observer = new ResizeObserver(reserveMeasuredHeight);
+    for (const element of traceElements) observer.observe(element);
+    return () => observer.disconnect();
+  }, [activeTrace, outgoingTrace]);
+
+  const hasAnswer = message.content.trim().length > 0;
+  const showTyping = isSending && !hasAnswer && !traceText && !activeTrace && !outgoingTrace;
+  const phase = hasAnswer ? "answer" : traceText || activeTrace || outgoingTrace ? "trace" : "pending";
+
+  return (
+    <div
+      className="streaming-assistant-slot"
+      data-streaming-assistant="true"
+      data-streaming-phase={phase}
+      style={reservedTraceHeight ? { minHeight: `${reservedTraceHeight}px` } : undefined}
+    >
+      {outgoingTrace ? (
+        <div
+          ref={outgoingTraceRef}
+          key={`outgoing-trace-${outgoingTrace.revision}`}
+          className="streaming-assistant-layer ephemeral-thinking-trace ephemeral-thinking-trace-exit"
+          data-thinking-trace="true"
+          data-thinking-trace-state="outgoing"
+          aria-hidden="true"
+        >
+          <p className="whitespace-pre-wrap">{outgoingTrace.text}</p>
+        </div>
+      ) : null}
+      {activeTrace ? (
+        <div
+          ref={activeTraceRef}
+          key={`active-trace-${activeTrace.revision}`}
+          className="streaming-assistant-layer ephemeral-thinking-trace ephemeral-thinking-trace-enter"
+          data-thinking-trace="true"
+          data-thinking-trace-state="active"
+          aria-hidden="true"
+        >
+          <p className="whitespace-pre-wrap">{activeTrace.text}</p>
+        </div>
+      ) : null}
+      {activeTrace && !hasAnswer ? (
+        <span className="sr-only" role="status" aria-live="polite">
+          Assistant is working
+        </span>
+      ) : null}
+      {hasAnswer ? (
+        <div className="streaming-assistant-layer streaming-assistant-answer" data-streaming-answer="true">
+          <MarkdownContent
+            markdown={message.content}
+            openLinksInNewTab
+            className="leading-[1.82] text-violet-50 [&_a]:text-inherit [&_a]:underline"
+          />
+        </div>
+      ) : null}
+      {showTyping ? (
+        <span
+          className="streaming-assistant-layer inline-flex items-center gap-1"
+          data-streaming-pending="true"
+          aria-label="Assistant is typing"
+          role="status"
+        >
+          <span className="inline-block h-1.5 w-1.5 animate-bounce rounded-full bg-muted-foreground [animation-delay:0ms]" />
+          <span className="inline-block h-1.5 w-1.5 animate-bounce rounded-full bg-muted-foreground [animation-delay:140ms]" />
+          <span className="inline-block h-1.5 w-1.5 animate-bounce rounded-full bg-muted-foreground [animation-delay:280ms]" />
+        </span>
+      ) : null}
+    </div>
+  );
+}
+
 export function ChatMessagesPanel({ messages, isLoading, isSending, onMessageContextMenu }: Props) {
-  const hasPendingAssistant = messages.some((message) => message.id.startsWith("temp-assistant-") && message.content.trim().length === 0);
+  const hasPendingAssistant = messages.some((message) => message.id.startsWith("temp-assistant-"));
   const renderItems = useMemo(() => buildMessageRenderItems(messages), [messages]);
   const toolCallMessageIDs = useMemo(() => getToolCallMessageIDs(messages), [messages]);
   const seenToolCallMessageIDsRef = useRef<Set<string> | null>(null);
@@ -457,6 +594,7 @@ export function ChatMessagesPanel({ messages, isLoading, isSending, onMessageCon
           }
 
           const isUser = message.role === "user";
+          const streamingAssistantMetadata = asStreamingAssistantMetadata(message.metadata);
           const isPendingAssistant = message.id.startsWith("temp-assistant-") && isSending && message.content.trim().length === 0;
           const attachments = getMessageAttachments(message.metadata);
           return (
@@ -465,7 +603,7 @@ export function ChatMessagesPanel({ messages, isLoading, isSending, onMessageCon
                 className={cn(
                   "max-w-[85%] space-y-3",
                   isUser
-                    ? "rounded-xl border border-violet-300/24 bg-[linear-gradient(135deg,hsl(258_86%_48%_/_0.86),hsl(278_72%_29%_/_0.86))] px-4 py-3 text-sm leading-6 text-fuchsia-50 shadow-sm"
+                    ? "chat-user-message border border-violet-300/24 bg-[linear-gradient(135deg,hsl(258_86%_48%_/_0.86),hsl(278_72%_29%_/_0.86))] px-4 py-3 text-sm leading-6 text-fuchsia-50 shadow-sm"
                     : "text-base leading-7 text-violet-50"
                 )}
                 onContextMenu={
@@ -475,7 +613,9 @@ export function ChatMessagesPanel({ messages, isLoading, isSending, onMessageCon
                 }
               >
                 {attachments.length ? <ChatAttachmentList attachments={attachments} tone={isUser ? "user" : "assistant"} /> : null}
-                {isPendingAssistant ? (
+                {streamingAssistantMetadata ? (
+                  <StreamingAssistantPresentation message={message} isSending={isSending} />
+                ) : isPendingAssistant ? (
                   <span className="inline-flex items-center gap-1" aria-label="Assistant is typing" role="status">
                     <span className="inline-block h-1.5 w-1.5 animate-bounce rounded-full bg-muted-foreground [animation-delay:0ms]" />
                     <span className="inline-block h-1.5 w-1.5 animate-bounce rounded-full bg-muted-foreground [animation-delay:140ms]" />

web/src/components/search/search-match-label.tsx

@@ -0,0 +1,96 @@
+/// <reference lib="es2022.intl" />
+import { useLayoutEffect, useMemo, useRef, useState } from "preact/hooks";
+
+const words = /[\p{L}\p{N}\p{M}\p{Co}]+/gu;
+const fold = (text: string) => text.normalize("NFD").replace(/\p{M}/gu, "").toLowerCase();
+const graphemes = new Intl.Segmenter(undefined, { granularity: "grapheme" });
+
+export function SearchMatchLabel({ text: source, query }: { text: string; query: string }) {
+  const text = source.replace(/\s+/gu, " ").trim();
+  const containerRef = useRef<HTMLSpanElement>(null);
+  const measureRef = useRef<HTMLSpanElement>(null);
+  const ellipsisRef = useRef<HTMLSpanElement>(null);
+  const [kept, setKept] = useState<number | null>(null);
+  const boundaries = useMemo(() => [0, ...Array.from(graphemes.segment(text), ({ index, segment }) => index + segment.length)], [text]);
+  const runs = useMemo(() => {
+    const terms = (query.match(words) ?? []).map(fold).filter(Boolean);
+    const result: Array<{ start: number; end: number; match: boolean }> = [];
+    let cursor = 0;
+    for (const word of text.matchAll(words)) {
+      if (word.index > cursor) result.push({ start: cursor, end: word.index, match: false });
+      cursor = word.index + word[0].length;
+      result.push({ start: word.index, end: cursor, match: terms.some((term) => fold(word[0]).startsWith(term)) });
+    }
+    if (cursor < text.length) result.push({ start: cursor, end: text.length, match: false });
+    return result;
+  }, [text, query]);
+
+  const renderRange = (start: number, end: number) => runs.flatMap((run) => {
+    const value = text.slice(Math.max(start, run.start), Math.min(end, run.end));
+    if (run.end <= start || run.start >= end) return [];
+    return [run.match
+      ? <strong key={`${start}:${run.start}`} className="font-semibold text-violet-100/95">{value}</strong>
+      : <span key={`${start}:${run.start}`}>{value}</span>];
+  });
+
+  useLayoutEffect(() => {
+    const container = containerRef.current;
+    const measure = measureRef.current;
+    const ellipsis = ellipsisRef.current;
+    if (!container || !measure || !ellipsis) return;
+    let disposed = false;
+    const update = () => {
+      if (disposed) return;
+      const width = container.getBoundingClientRect().width;
+      if (measure.getBoundingClientRect().width <= width) { setKept(null); return; }
+      // Measure the styled DOM, including bold runs, instead of guessing a
+      // character limit. Grapheme boundaries keep accents and emoji intact.
+      const nodes = Array.from(measure.children, (child) => child.firstChild as Text);
+      const range = document.createRange();
+      const measureRange = (start: number, end: number) => {
+        if (start >= end) return 0;
+        let offset = 0;
+        let started = false;
+        for (const node of nodes) {
+          const next = offset + node.length;
+          if (!started && start <= next) { range.setStart(node, start - offset); started = true; }
+          if (end <= next) { range.setEnd(node, end - offset); break; }
+          offset = next;
+        }
+        return range.getBoundingClientRect().width;
+      };
+      const count = boundaries.length - 1;
+      const ellipsisWidth = ellipsis.getBoundingClientRect().width;
+      let low = 0;
+      let high = count - 1;
+      while (low < high) {
+        const middle = Math.ceil((low + high) / 2);
+        const prefix = boundaries[Math.ceil(middle / 2)];
+        const suffix = boundaries[count - Math.floor(middle / 2)];
+        if (measureRange(0, prefix) + ellipsisWidth + measureRange(suffix, text.length) <= width - 1) low = middle;
+        else high = middle - 1;
+      }
+      setKept(low);
+    };
+    update();
+    const observer = new ResizeObserver(update);
+    observer.observe(container);
+    void document.fonts.ready.then(update);
+    document.fonts.addEventListener("loadingdone", update);
+    return () => { disposed = true; observer.disconnect(); document.fonts.removeEventListener("loadingdone", update); };
+  }, [text, runs, boundaries]);
+
+  const count = boundaries.length - 1;
+  const truncated = kept !== null && kept < count;
+  return (
+    <span ref={containerRef} title={text} className="relative col-start-2 block min-w-0 overflow-hidden whitespace-nowrap text-xs leading-5 text-secondary-foreground/75">
+      <span className="sr-only">{text}</span>
+      <span aria-hidden="true">
+        {truncated ? <>{renderRange(0, boundaries[Math.ceil(kept / 2)])}…{renderRange(boundaries[count - Math.floor(kept / 2)], text.length)}</> : renderRange(0, text.length)}
+      </span>
+      <span aria-hidden="true" className="pointer-events-none invisible absolute left-0 top-0 whitespace-pre">
+        <span ref={measureRef}>{renderRange(0, text.length)}</span><span ref={ellipsisRef}>…</span>
+      </span>
+    </span>
+  );
+}

web/src/hooks/use-workspace-search.ts

@@ -0,0 +1,30 @@
+import { useEffect, useState } from "preact/hooks";
+import { searchWorkspaceItems, type WorkspaceItem, type WorkspaceSearchResponse } from "@/lib/api";
+import { scheduleWorkspaceSearch } from "@/lib/workspace-search";
+
+type SearchState = WorkspaceSearchResponse & { query: string; revision: number; error: string | null };
+const EMPTY_ITEMS: WorkspaceItem[] = [];
+
+export function useWorkspaceSearch(query: string, enabled: boolean, revision: number) {
+  const trimmed = query.trim();
+  const [state, setState] = useState<SearchState | null>(null);
+  const validationError = trimmed.length > 200 ? "Use 200 characters or fewer." : null;
+
+  useEffect(() => {
+    setState(null);
+    if (!enabled || !trimmed || validationError) return;
+    return scheduleWorkspaceSearch(trimmed, searchWorkspaceItems,
+      (result) => setState({ ...result, query: trimmed, revision, error: null }),
+      (error) => setState({ items: [], hasMore: false, query: trimmed, revision, error: error instanceof Error ? error.message : String(error) })
+    );
+  }, [trimmed, enabled, revision, validationError]);
+
+  // Hide obsolete results immediately, even before effect cleanup runs.
+  const current = enabled && state?.query === trimmed && state.revision === revision ? state : null;
+  return {
+    items: current?.items ?? EMPTY_ITEMS,
+    hasMore: current?.hasMore ?? false,
+    error: validationError ?? current?.error ?? null,
+    isLoading: enabled && Boolean(trimmed) && !validationError && !current,
+  };
+}

web/src/index.css

@@ -31,7 +31,7 @@
   --secondary-foreground: 254 38% 94%;
   --accent: 188 86% 50%;
   --accent-foreground: 230 45% 8%;
-  --radius: 0.5rem;
+  --radius: 0px;
 }
 
 * {
@@ -72,6 +72,7 @@ select,
 textarea {
   font: inherit;
   color-scheme: dark;
+  border-radius: var(--radius);
 }
 
 ::selection {
@@ -113,13 +114,39 @@ textarea {
     max(0.75rem, var(--safe-area-left));
 }
 
-@media (min-width: 768px) {
+.chat-settings-header {
-  .app-safe-frame {
   padding:
-      max(0.5rem, var(--safe-area-top))
+    calc(0.5rem + var(--safe-area-top))
-      max(0.5rem, var(--safe-area-right))
+    max(0.75rem, var(--safe-area-right))
-      max(0.5rem, var(--safe-area-bottom))
+    0.5rem
-      max(0.5rem, var(--safe-area-left));
+    max(0.75rem, var(--safe-area-left));
+}
+
+.chat-settings-content {
+  padding:
+    1rem
+    max(1rem, var(--safe-area-right))
+    max(1.5rem, var(--safe-area-bottom))
+    max(1rem, var(--safe-area-left));
+  scroll-padding-block: 1rem;
+}
+
+.chat-settings-error {
+  padding:
+    0.75rem
+    max(1rem, var(--safe-area-right))
+    max(0.75rem, var(--safe-area-bottom))
+    max(1rem, var(--safe-area-left));
+}
+
+@media (min-width: 768px) {
+  .chat-settings-header,
+  .chat-settings-content {
+    padding: 1.25rem;
+  }
+
+  .chat-settings-error {
+    padding: 0.75rem 1.25rem;
   }
 
   .app-search-safe-pad {
@@ -132,19 +159,11 @@ textarea {
 }
 
 @media (horizontal-viewport-segments: 2) {
-  .app-safe-frame {
-    padding:
-      max(0.5rem, var(--safe-area-top))
-      max(0.5rem, var(--safe-area-right))
-      max(0.5rem, var(--safe-area-bottom))
-      max(0.5rem, var(--safe-area-left));
-  }
-
   .workspace-shell {
     display: grid;
     grid-template-columns:
-      calc(env(viewport-segment-width 0 0) - max(0.5rem, var(--safe-area-left)))
+      calc(env(viewport-segment-width 0 0) - var(--safe-area-left))
-      calc(env(viewport-segment-width 1 0) - max(0.5rem, var(--safe-area-right)));
+      calc(env(viewport-segment-width 1 0) - var(--safe-area-right));
     column-gap: calc(env(viewport-segment-left 1 0) - env(viewport-segment-right 0 0));
   }
 
@@ -153,14 +172,10 @@ textarea {
     width: 100%;
     max-width: none;
     transform: none;
-    border-width: 1px;
-    border-radius: 1rem;
   }
 
   .workspace-content {
     min-width: 0;
-    border-width: 1px;
-    border-radius: 1rem;
     touch-action: auto;
   }
 
@@ -179,6 +194,13 @@ textarea {
     0 14px 36px hsl(240 80% 2% / 0.28);
 }
 
+.chat-user-message {
+  /* Preserve the original bubble radius independently of the square UI theme.
+     Browsers without corner-shape support fall back to circular corners. */
+  border-radius: 0.75rem;
+  corner-shape: squircle;
+}
+
 .tool-call-stack-shell {
   perspective: 900px;
   transform-style: preserve-3d;
@@ -321,6 +343,97 @@ textarea {
   }
 }
 
+.streaming-assistant-slot {
+  display: grid;
+  min-width: 0;
+  min-height: 1.82em;
+  align-items: start;
+}
+
+.streaming-assistant-layer {
+  grid-area: 1 / 1;
+  min-width: 0;
+  transform-origin: top left;
+}
+
+.ephemeral-thinking-trace {
+  position: relative;
+  z-index: 1;
+  color: hsl(252 35% 88% / 0.8);
+  font-style: italic;
+  opacity: 0.78;
+  filter: saturate(0.72);
+  will-change: opacity, transform, filter;
+}
+
+.ephemeral-thinking-trace-enter {
+  animation: ephemeral-thinking-trace-enter 200ms cubic-bezier(0.2, 0.78, 0.24, 1) both;
+}
+
+.ephemeral-thinking-trace-exit {
+  pointer-events: none;
+  animation: ephemeral-thinking-trace-exit 220ms cubic-bezier(0.4, 0, 0.8, 0.28) both;
+}
+
+.streaming-assistant-answer {
+  position: relative;
+  z-index: 2;
+  animation: streaming-assistant-answer-enter 180ms cubic-bezier(0.2, 0.78, 0.24, 1) both;
+}
+
+@keyframes ephemeral-thinking-trace-enter {
+  from {
+    opacity: 0;
+    filter: saturate(0.72) blur(1px);
+    transform: translate3d(0, 0.32rem, 0);
+  }
+
+  to {
+    opacity: 0.78;
+    filter: saturate(0.72) blur(0);
+    transform: translate3d(0, 0, 0);
+  }
+}
+
+@keyframes ephemeral-thinking-trace-exit {
+  from {
+    opacity: 0.78;
+    filter: saturate(0.72) blur(0);
+    transform: translate3d(0, 0, 0);
+  }
+
+  to {
+    opacity: 0;
+    filter: saturate(0.72) blur(1px);
+    transform: translate3d(0, -0.32rem, 0);
+  }
+}
+
+@keyframes streaming-assistant-answer-enter {
+  from {
+    opacity: 0;
+    transform: translate3d(0, 0.18rem, 0);
+  }
+
+  to {
+    opacity: 1;
+    transform: translate3d(0, 0, 0);
+  }
+}
+
+@media (prefers-reduced-motion: reduce) {
+  .ephemeral-thinking-trace-enter,
+  .ephemeral-thinking-trace-exit,
+  .streaming-assistant-answer {
+    animation: none;
+    transform: none;
+  }
+
+  .ephemeral-thinking-trace-exit {
+    opacity: 0;
+  }
+}
+
 .md-content {
   word-break: break-word;
 }
@@ -339,7 +452,7 @@ textarea {
   overflow-x: auto;
   overflow-y: hidden;
   border: 1px solid hsl(var(--border) / 0.86);
-  border-radius: 0.625rem;
+  border-radius: var(--radius);
   background: hsl(246 34% 10% / 0.76);
   box-shadow: inset 0 1px 0 hsl(258 80% 88% / 0.06);
 }
@@ -358,7 +471,7 @@ textarea {
 }
 
 .md-table-scroll::-webkit-scrollbar-thumb {
-  border-radius: 9999px;
+  border-radius: var(--radius);
   background: hsl(263 78% 72% / 0.34);
 }
 
@@ -470,7 +583,7 @@ textarea {
 
 .md-content code {
   background: hsl(249 40% 10% / 0.78);
-  border-radius: 0.3rem;
+  border-radius: var(--radius);
   padding: 0.05rem 0.3rem;
   font-size: 0.86em;
   box-decoration-break: clone;
@@ -480,7 +593,7 @@ textarea {
 .md-content pre {
   overflow-x: auto;
   border: 1px solid hsl(253 31% 29% / 0.72);
-  border-radius: 0.625rem;
+  border-radius: var(--radius);
   background: hsl(249 40% 10% / 0.82);
   padding: 0.75rem;
   box-shadow: inset 0 1px 0 hsl(258 80% 88% / 0.05);
@@ -504,7 +617,7 @@ textarea {
 .md-cite-token {
   display: inline-flex;
   align-items: center;
-  border-radius: 9999px;
+  border-radius: var(--radius);
   border: 1px solid hsl(274 40% 55%);
   background: hsl(277 33% 21%);
   color: hsl(304 42% 96%);

web/src/lib/api.ts

@@ -33,7 +33,9 @@ export type SearchWorkspaceItem = SearchSummary & {
   type: "search";
 };
 
-export type WorkspaceItem = ChatWorkspaceItem | SearchWorkspaceItem;
+export type WorkspaceItem = (ChatWorkspaceItem | SearchWorkspaceItem) & { searchSnippet?: string | null };
+
+export type WorkspaceSearchResponse = { items: WorkspaceItem[]; hasMore: boolean };
 
 export type Message = {
   id: string;
@@ -191,6 +193,14 @@ type CompletionStreamHandlers = {
   onError?: (payload: { message: string }) => void;
 };
 
+function dispatchCompletionStreamEvent(handlers: CompletionStreamHandlers, eventName: string, payload: any) {
+  if (eventName === "meta") handlers.onMeta?.(payload);
+  else if (eventName === "tool_call") handlers.onToolCall?.(payload);
+  else if (eventName === "delta") handlers.onDelta?.(payload);
+  else if (eventName === "done") handlers.onDone?.(payload);
+  else if (eventName === "error") handlers.onError?.(payload);
+}
+
 type CreateChatRequest = {
   title?: string;
   provider?: Provider;
@@ -264,6 +274,10 @@ export async function listWorkspaceItems() {
   return data.items;
 }
 
+export function searchWorkspaceItems(query: string, signal?: AbortSignal) {
+  return api<WorkspaceSearchResponse>(`/v1/workspace-items?${new URLSearchParams({ q: query })}`, { signal });
+}
+
 export async function verifySession() {
   return api<{ authenticated: true; mode: "open" | "token" }>("/v1/auth/session");
 }
@@ -627,13 +641,34 @@ export async function runCompletionStream(
     signal: options?.signal,
   });
 
-  await readSseStream(response, (eventName, payload) => {
+  await readSseStream(response, (eventName, payload) => dispatchCompletionStreamEvent(handlers, eventName, payload));
-    if (eventName === "meta") handlers.onMeta?.(payload);
+}
-    else if (eventName === "tool_call") handlers.onToolCall?.(payload);
+
-    else if (eventName === "delta") handlers.onDelta?.(payload);
+export async function runQuickQuestionStream(
-    else if (eventName === "done") handlers.onDone?.(payload);
+  body: {
-    else if (eventName === "error") handlers.onError?.(payload);
+    provider: Provider;
+    model: string;
+    question: string;
+  },
+  handlers: CompletionStreamHandlers,
+  options?: { signal?: AbortSignal }
+) {
+  const headers = new Headers({
+    Accept: "text/event-stream",
+    "Content-Type": "application/json",
   });
+  if (authToken) {
+    headers.set("Authorization", `Bearer ${authToken}`);
+  }
+
+  const response = await fetch(`${API_BASE_URL}/v1/quick-questions/stream`, {
+    method: "POST",
+    headers,
+    body: JSON.stringify(body),
+    signal: options?.signal,
+  });
+
+  await readSseStream(response, (eventName, payload) => dispatchCompletionStreamEvent(handlers, eventName, payload));
 }
 
 export async function attachCompletionStream(chatId: string, handlers: CompletionStreamHandlers, options?: { signal?: AbortSignal }) {
@@ -650,11 +685,5 @@ export async function attachCompletionStream(chatId: string, handlers: Completio
     signal: options?.signal,
   });
 
-  await readSseStream(response, (eventName, payload) => {
+  await readSseStream(response, (eventName, payload) => dispatchCompletionStreamEvent(handlers, eventName, payload));
-    if (eventName === "meta") handlers.onMeta?.(payload);
-    else if (eventName === "tool_call") handlers.onToolCall?.(payload);
-    else if (eventName === "delta") handlers.onDelta?.(payload);
-    else if (eventName === "done") handlers.onDone?.(payload);
-    else if (eventName === "error") handlers.onError?.(payload);
-  });
 }

web/src/lib/chat-stream-presentation.ts

@@ -0,0 +1,139 @@
+import type { Message, ToolCallEvent } from "@/lib/api";
+
+export const STREAMING_ASSISTANT_METADATA_KIND = "streaming_assistant";
+
+export type StreamingAssistantMetadata = {
+  kind: typeof STREAMING_ASSISTANT_METADATA_KIND;
+  ephemeralTrace: string | null;
+  traceRevision: number;
+};
+
+export type StreamingAttemptState = {
+  segmentText: string;
+  initiatedToolCallIds: string[];
+};
+
+export type StreamingToolCallTransition = {
+  attempt: StreamingAttemptState;
+  startedNewToolCall: boolean;
+  traceText: string | null;
+};
+
+export function createStreamingAssistantMetadata(): StreamingAssistantMetadata {
+  return {
+    kind: STREAMING_ASSISTANT_METADATA_KIND,
+    ephemeralTrace: null,
+    traceRevision: 0,
+  };
+}
+
+export function asStreamingAssistantMetadata(value: unknown): StreamingAssistantMetadata | null {
+  if (!value || typeof value !== "object" || Array.isArray(value)) return null;
+  const record = value as Record<string, unknown>;
+  if (record.kind !== STREAMING_ASSISTANT_METADATA_KIND) return null;
+
+  return {
+    kind: STREAMING_ASSISTANT_METADATA_KIND,
+    ephemeralTrace: typeof record.ephemeralTrace === "string" ? record.ephemeralTrace : null,
+    traceRevision:
+      typeof record.traceRevision === "number" && Number.isFinite(record.traceRevision)
+        ? Math.max(0, Math.floor(record.traceRevision))
+        : 0,
+  };
+}
+
+export function createStreamingAttemptState(): StreamingAttemptState {
+  return {
+    segmentText: "",
+    initiatedToolCallIds: [],
+  };
+}
+
+export function appendStreamingDelta(attempt: StreamingAttemptState, delta: string): StreamingAttemptState {
+  if (!delta) return attempt;
+  return {
+    ...attempt,
+    segmentText: attempt.segmentText + delta,
+  };
+}
+
+export function transitionStreamingToolCall(
+  attempt: StreamingAttemptState,
+  event: Pick<ToolCallEvent, "toolCallId" | "status">
+): StreamingToolCallTransition {
+  if (event.status !== "initiated" || attempt.initiatedToolCallIds.includes(event.toolCallId)) {
+    return { attempt, startedNewToolCall: false, traceText: null };
+  }
+
+  const traceText = attempt.segmentText.trim();
+  return {
+    attempt: {
+      segmentText: "",
+      initiatedToolCallIds: attempt.initiatedToolCallIds.concat(event.toolCallId),
+    },
+    startedNewToolCall: true,
+    traceText: traceText || null,
+  };
+}
+
+function updateStreamingAssistant(
+  messages: Message[],
+  assistantMessagePrefix: string,
+  update: (message: Message, metadata: StreamingAssistantMetadata) => Message
+) {
+  let didUpdate = false;
+  const nextMessages = messages.map((message, index, all) => {
+    const isTarget = index === all.length - 1 && message.id.startsWith(assistantMessagePrefix);
+    if (!isTarget) return message;
+    didUpdate = true;
+    return update(message, asStreamingAssistantMetadata(message.metadata) ?? createStreamingAssistantMetadata());
+  });
+  return didUpdate ? nextMessages : messages;
+}
+
+export function setStreamingAssistantSegment(messages: Message[], assistantMessagePrefix: string, segmentText: string) {
+  return updateStreamingAssistant(messages, assistantMessagePrefix, (message, metadata) => ({
+    ...message,
+    content: segmentText,
+    metadata: {
+      ...metadata,
+      ephemeralTrace: null,
+    } satisfies StreamingAssistantMetadata,
+  }));
+}
+
+export function promoteStreamingAssistantTrace(messages: Message[], assistantMessagePrefix: string, traceText: string) {
+  const normalizedTrace = traceText.trim();
+  return updateStreamingAssistant(messages, assistantMessagePrefix, (message, metadata) => ({
+    ...message,
+    content: "",
+    metadata: normalizedTrace
+      ? ({
+          ...metadata,
+          ephemeralTrace: normalizedTrace,
+          traceRevision: metadata.traceRevision + 1,
+        } satisfies StreamingAssistantMetadata)
+      : metadata,
+  }));
+}
+
+export function finalizeStreamingAssistant(messages: Message[], assistantMessagePrefix: string, finalText: string) {
+  return updateStreamingAssistant(messages, assistantMessagePrefix, (message, metadata) => ({
+    ...message,
+    content: finalText,
+    metadata: {
+      ...metadata,
+      ephemeralTrace: null,
+    } satisfies StreamingAssistantMetadata,
+  }));
+}
+
+export function clearStreamingAssistantTrace(messages: Message[], assistantMessagePrefix: string) {
+  return updateStreamingAssistant(messages, assistantMessagePrefix, (message, metadata) => ({
+    ...message,
+    metadata: {
+      ...metadata,
+      ephemeralTrace: null,
+    } satisfies StreamingAssistantMetadata,
+  }));
+}

web/src/lib/quick-question.ts

@@ -0,0 +1,25 @@
+import type { Provider } from "./api";
+
+export const QUICK_QUESTION_DEFAULT_MODEL = "chat-latest";
+
+export function pickQuickQuestionModel(provider: Provider, options: string[], preferred: string | null = null) {
+  if (preferred?.trim()) return preferred.trim();
+  if (provider === "openai") return QUICK_QUESTION_DEFAULT_MODEL;
+  return options[0] ?? "";
+}
+
+export function buildQuickQuestionRequest({
+  provider,
+  model,
+  content,
+}: {
+  provider: Provider;
+  model: string;
+  content: string;
+}) {
+  return {
+    provider,
+    model,
+    question: content,
+  };
+}

web/src/lib/sidebar-selection.ts

@@ -2,6 +2,16 @@ export type SidebarSelection = { kind: "chat" | "search"; id: string };
 
 type WorkspaceSelectionItem = { type: SidebarSelection["kind"]; id: string };
 
+export function retainSelectedHistoryItem<T extends WorkspaceSelectionItem>(
+  items: T[], selection: SidebarSelection | null, retained: T | null
+): T[] {
+  if (retained && selection?.kind === retained.type && selection.id === retained.id &&
+      !items.some((item) => item.type === retained.type && item.id === retained.id)) {
+    return [...items, retained];
+  }
+  return items;
+}
+
 type ResolveSidebarSelectionOptions = {
   initialSelection?: SidebarSelection;
   selectFallback?: boolean;

web/src/lib/workspace-search.ts

@@ -0,0 +1,24 @@
+import type { WorkspaceSearchResponse } from "./api";
+
+// Cleanup cancels both the debounce and fetch, and also rejects late responses
+// from transports that finish after cancellation.
+export function scheduleWorkspaceSearch(
+  query: string,
+  request: (query: string, signal: AbortSignal) => Promise<WorkspaceSearchResponse>,
+  onResult: (result: WorkspaceSearchResponse) => void,
+  onError: (error: unknown) => void
+) {
+  const controller = new AbortController();
+  const timer = setTimeout(async () => {
+    try {
+      const result = await request(query, controller.signal);
+      if (!controller.signal.aborted) onResult(result);
+    } catch (error) {
+      if (!controller.signal.aborted) onError(error);
+    }
+  }, 300);
+  return () => {
+    clearTimeout(timer);
+    controller.abort();
+  };
+}

web/tailwind.config.ts

@@ -29,9 +29,14 @@ const config: Config = {
         },
       },
       borderRadius: {
+        // Keep surfaces square at every size; rounded-full is reserved for dots.
+        DEFAULT: "var(--radius)",
+        sm: "var(--radius)",
+        md: "var(--radius)",
         lg: "var(--radius)",
-        md: "calc(var(--radius) - 2px)",
+        xl: "var(--radius)",
-        sm: "calc(var(--radius) - 4px)",
+        "2xl": "var(--radius)",
+        "3xl": "var(--radius)",
       },
     },
   },

web/tests/chat-stream-presentation.test.mjs

@@ -0,0 +1,148 @@
+import assert from "node:assert/strict";
+import test from "node:test";
+import {
+  appendStreamingDelta,
+  asStreamingAssistantMetadata,
+  clearStreamingAssistantTrace,
+  createStreamingAssistantMetadata,
+  createStreamingAttemptState,
+  finalizeStreamingAssistant,
+  promoteStreamingAssistantTrace,
+  setStreamingAssistantSegment,
+  transitionStreamingToolCall,
+} from "../src/lib/chat-stream-presentation.ts";
+
+function assistantMessage(content = "") {
+  return {
+    id: "temp-assistant-test",
+    createdAt: "2026-08-30T00:00:00.000Z",
+    role: "assistant",
+    content,
+    name: null,
+    metadata: createStreamingAssistantMetadata(),
+  };
+}
+
+function metadata(messages) {
+  return asStreamingAssistantMetadata(messages.at(-1)?.metadata);
+}
+
+test("a tool boundary promotes the current segment and the next delta starts the answer in its place", () => {
+  let messages = [assistantMessage()];
+  let attempt = appendStreamingDelta(createStreamingAttemptState(), "I'll search for that.");
+  messages = setStreamingAssistantSegment(messages, "temp-assistant-", attempt.segmentText);
+
+  const toolTransition = transitionStreamingToolCall(attempt, {
+    toolCallId: "search-1",
+    status: "initiated",
+  });
+  attempt = toolTransition.attempt;
+  messages = promoteStreamingAssistantTrace(messages, "temp-assistant-", toolTransition.traceText ?? "");
+
+  assert.equal(messages.at(-1).content, "");
+  assert.deepEqual(metadata(messages), {
+    kind: "streaming_assistant",
+    ephemeralTrace: "I'll search for that.",
+    traceRevision: 1,
+  });
+
+  attempt = appendStreamingDelta(attempt, "Here is the answer");
+  messages = setStreamingAssistantSegment(messages, "temp-assistant-", attempt.segmentText);
+
+  assert.equal(messages.at(-1).content, "Here is the answer");
+  assert.equal(metadata(messages)?.ephemeralTrace, null);
+
+  messages = finalizeStreamingAssistant(messages, "temp-assistant-", "Here is the answer.");
+  assert.equal(messages.at(-1).content, "Here is the answer.");
+  assert.equal(metadata(messages)?.ephemeralTrace, null);
+});
+
+test("a later tool round replaces the previous trace and parallel initiated calls do not erase it", () => {
+  let messages = [assistantMessage("First trace")];
+  let attempt = appendStreamingDelta(createStreamingAttemptState(), "First trace");
+  let transition = transitionStreamingToolCall(attempt, { toolCallId: "tool-1", status: "initiated" });
+  attempt = transition.attempt;
+  messages = promoteStreamingAssistantTrace(messages, "temp-assistant-", transition.traceText ?? "");
+
+  attempt = appendStreamingDelta(attempt, "I need one more lookup.");
+  messages = setStreamingAssistantSegment(messages, "temp-assistant-", attempt.segmentText);
+  transition = transitionStreamingToolCall(attempt, { toolCallId: "tool-2", status: "initiated" });
+  attempt = transition.attempt;
+  messages = promoteStreamingAssistantTrace(messages, "temp-assistant-", transition.traceText ?? "");
+
+  assert.equal(metadata(messages)?.ephemeralTrace, "I need one more lookup.");
+  assert.equal(metadata(messages)?.traceRevision, 2);
+
+  transition = transitionStreamingToolCall(attempt, { toolCallId: "tool-3", status: "initiated" });
+  assert.equal(transition.startedNewToolCall, true);
+  assert.equal(transition.traceText, null);
+  messages = promoteStreamingAssistantTrace(messages, "temp-assistant-", transition.traceText ?? "");
+
+  assert.equal(metadata(messages)?.ephemeralTrace, "I need one more lookup.");
+  assert.equal(metadata(messages)?.traceRevision, 2);
+});
+
+test("terminal and duplicate tool events never promote or reset the in-progress segment", () => {
+  const initial = appendStreamingDelta(createStreamingAttemptState(), "candidate");
+  const completed = transitionStreamingToolCall(initial, { toolCallId: "tool-1", status: "completed" });
+
+  assert.equal(completed.startedNewToolCall, false);
+  assert.strictEqual(completed.attempt, initial);
+
+  const initiated = transitionStreamingToolCall(initial, { toolCallId: "tool-1", status: "initiated" });
+  const withNextSegment = appendStreamingDelta(initiated.attempt, "next segment");
+  const duplicate = transitionStreamingToolCall(withNextSegment, { toolCallId: "tool-1", status: "initiated" });
+
+  assert.equal(duplicate.startedNewToolCall, false);
+  assert.strictEqual(duplicate.attempt, withNextSegment);
+  assert.equal(duplicate.attempt.segmentText, "next segment");
+});
+
+test("a fresh per-attempt accumulator can replay and reclassify an already-seen tool round", () => {
+  let messages = [assistantMessage("stale partial answer")];
+  let replayAttempt = appendStreamingDelta(createStreamingAttemptState(), "Replayed trace");
+  messages = setStreamingAssistantSegment(messages, "temp-assistant-", replayAttempt.segmentText);
+
+  const replayedTool = transitionStreamingToolCall(replayAttempt, { toolCallId: "same-tool-id", status: "initiated" });
+  messages = promoteStreamingAssistantTrace(messages, "temp-assistant-", replayedTool.traceText ?? "");
+
+  assert.equal(replayedTool.startedNewToolCall, true);
+  assert.equal(messages.at(-1).content, "");
+  assert.equal(metadata(messages)?.ephemeralTrace, "Replayed trace");
+});
+
+test("message helpers preserve identity when no matching temporary assistant exists", () => {
+  const messages = [
+    {
+      id: "persisted-assistant",
+      createdAt: "2026-08-30T00:00:00.000Z",
+      role: "assistant",
+      content: "Persisted",
+      name: null,
+      metadata: null,
+    },
+  ];
+
+  assert.strictEqual(setStreamingAssistantSegment(messages, "temp-assistant-", "new"), messages);
+  assert.strictEqual(promoteStreamingAssistantTrace(messages, "temp-assistant-", "trace"), messages);
+  assert.strictEqual(finalizeStreamingAssistant(messages, "temp-assistant-", "done"), messages);
+  assert.strictEqual(clearStreamingAssistantTrace(messages, "temp-assistant-"), messages);
+});
+
+test("a terminal error clears the ephemeral trace without discarding a partial answer", () => {
+  let messages = [
+    {
+      ...assistantMessage("Partial answer"),
+      metadata: {
+        ...createStreamingAssistantMetadata(),
+        ephemeralTrace: "Still checking one source.",
+        traceRevision: 1,
+      },
+    },
+  ];
+
+  messages = clearStreamingAssistantTrace(messages, "temp-assistant-");
+
+  assert.equal(messages.at(-1).content, "Partial answer");
+  assert.equal(metadata(messages)?.ephemeralTrace, null);
+});

web/tests/quick-question.test.mjs

@@ -0,0 +1,39 @@
+import assert from "node:assert/strict";
+import test from "node:test";
+import { buildQuickQuestionRequest, pickQuickQuestionModel } from "../src/lib/quick-question.ts";
+
+test("quick questions default to chat-latest before and after the model catalog loads", () => {
+  for (const options of [[], ["gpt-4.1-mini"], ["gpt-4.1-mini", "chat-latest"]]) {
+    const model = pickQuickQuestionModel("openai", options);
+    assert.equal(model, "chat-latest");
+    assert.deepEqual(buildQuickQuestionRequest({ provider: "openai", model, content: "What is UTC?" }), {
+      provider: "openai",
+      model: "chat-latest",
+      question: "What is UTC?",
+    });
+  }
+});
+
+test("quick questions preserve saved models and use provider-specific choices when switching providers", () => {
+  assert.equal(pickQuickQuestionModel("openai", ["chat-latest"], " gpt-4.1-mini "), "gpt-4.1-mini");
+  assert.equal(pickQuickQuestionModel("openai", ["gpt-4.1-mini"], " "), "chat-latest");
+  assert.equal(pickQuickQuestionModel("anthropic", ["claude-3-5-sonnet-latest"]), "claude-3-5-sonnet-latest");
+  assert.equal(pickQuickQuestionModel("anthropic", ["claude-3-5-sonnet-latest"], "claude-3-haiku"), "claude-3-haiku");
+  assert.equal(pickQuickQuestionModel("anthropic", []), "");
+  assert.equal(pickQuickQuestionModel("openai", ["gpt-4.1-mini", "chat-latest"]), "chat-latest");
+});
+
+test("quick question requests use the dedicated server endpoint shape", () => {
+  const request = buildQuickQuestionRequest({
+    provider: "openai",
+    model: "gpt-4.1-mini",
+    content: "How do I reset my password?",
+  });
+
+  assert.deepEqual(request, {
+    provider: "openai",
+    model: "gpt-4.1-mini",
+    question: "How do I reset my password?",
+  });
+  assert.equal("additionalSystemPrompt" in request, false);
+});

web/tests/workspace-search.test.mjs

@@ -0,0 +1,80 @@
+import assert from "node:assert/strict";
+import test from "node:test";
+import { scheduleWorkspaceSearch } from "../src/lib/workspace-search.ts";
+import { retainSelectedHistoryItem, resolveSidebarSelectionAfterRefresh } from "../src/lib/sidebar-selection.ts";
+
+const flush = async () => { await Promise.resolve(); await Promise.resolve(); };
+
+test("typing is debounced and superseded requests never start", async (t) => {
+  t.mock.timers.enable({ apis: ["setTimeout"] });
+  const queries = [];
+  const results = [];
+  const request = async (query) => { queries.push(query); return { items: [], hasMore: false }; };
+  const reportError = (error) => assert.fail(String(error));
+  const cancelFirst = scheduleWorkspaceSearch("ne", request, (result) => results.push(result), reportError);
+  t.mock.timers.tick(299);
+  assert.deepEqual(queries, []);
+  cancelFirst();
+  const cancelLast = scheduleWorkspaceSearch("nebula", request, (result) => results.push(result), reportError);
+  t.mock.timers.tick(300);
+  await flush();
+  assert.deepEqual(queries, ["nebula"]);
+  assert.deepEqual(results, [{ items: [], hasMore: false }]);
+  cancelLast();
+});
+
+test("cancellation aborts the transport and discards stale results and errors", async (t) => {
+  t.mock.timers.enable({ apis: ["setTimeout"] });
+  let resolveFirst;
+  let rejectSecond;
+  let signal;
+  const results = [];
+  const errors = [];
+  const first = scheduleWorkspaceSearch("first", (_query, value) => {
+    signal = value;
+    return new Promise((resolve) => { resolveFirst = resolve; });
+  }, (result) => results.push(result), (error) => errors.push(error));
+  t.mock.timers.tick(300);
+  first();
+  assert.equal(signal.aborted, true);
+  const second = scheduleWorkspaceSearch("second", () => new Promise((_resolve, reject) => { rejectSecond = reject; }),
+    (result) => results.push(result), (error) => errors.push(error));
+  t.mock.timers.tick(300);
+  second();
+  resolveFirst({ items: [{ id: "stale" }], hasMore: true });
+  rejectSecond(new Error("stale failure"));
+  await flush();
+  assert.deepEqual(results, []);
+  assert.deepEqual(errors, []);
+});
+
+test("search results retain excerpts and truncation info; failures reach the UI", async (t) => {
+  t.mock.timers.enable({ apis: ["setTimeout"] });
+  const expected = { items: [{ type: "chat", id: "old", searchSnippet: "A nebula in the sky" }], hasMore: true };
+  let received;
+  let error;
+  const cancel = scheduleWorkspaceSearch("nebula", async () => expected, (result) => { received = result; }, assert.fail);
+  t.mock.timers.tick(300);
+  await flush();
+  assert.deepEqual(received, expected);
+  cancel();
+  const cancelFailure = scheduleWorkspaceSearch("nebula", async () => { throw new Error("Offline"); }, assert.fail, (result) => { error = result; });
+  t.mock.timers.tick(300);
+  await flush();
+  assert.equal(error.message, "Offline");
+  cancelFailure();
+});
+
+test("opening older chat/search results survives collection refresh without restoring deleted or unrelated items", () => {
+  const recent = [{ type: "chat", id: "recent" }];
+  for (const kind of ["chat", "search"]) {
+    const selection = { kind, id: "old" };
+    const retained = { type: kind, id: "old" };
+    const refreshed = retainSelectedHistoryItem(recent, selection, retained);
+    assert.deepEqual(resolveSidebarSelectionAfterRefresh(selection, refreshed), selection);
+    assert.equal(retainSelectedHistoryItem(refreshed, selection, retained), refreshed);
+    assert.equal(retainSelectedHistoryItem(recent, { kind, id: "different" }, retained), recent);
+    assert.equal(retainSelectedHistoryItem(recent, selection, null), recent);
+    assert.equal(retainSelectedHistoryItem(recent, null, retained), recent);
+  }
+});

web/tsconfig.tsbuildinfo

@@ -1 +1 @@
-{"root":["./src/App.tsx","./src/main.tsx","./src/pwa.ts","./src/root-router.tsx","./src/vite-env.d.ts","./src/components/sybil-character.tsx","./src/components/auth/auth-screen.tsx","./src/components/chat/chat-attachment-list.tsx","./src/components/chat/chat-composer.tsx","./src/components/chat/chat-messages-panel.tsx","./src/components/markdown/markdown-content.tsx","./src/components/search/search-results-panel.tsx","./src/components/ui/button.tsx","./src/components/ui/input.tsx","./src/components/ui/scroll-area.tsx","./src/components/ui/separator.tsx","./src/components/ui/textarea.tsx","./src/hooks/use-session-auth.ts","./src/lib/api.ts","./src/lib/chat-forking.ts","./src/lib/chat-model-selection.ts","./src/lib/sidebar-selection.ts","./src/lib/utils.ts","./src/pages/search-route-page.tsx"],"version":"5.9.3"}
+{"root":["./src/App.tsx","./src/main.tsx","./src/pwa.ts","./src/root-router.tsx","./src/vite-env.d.ts","./src/components/sybil-character.tsx","./src/components/auth/auth-screen.tsx","./src/components/chat/chat-attachment-list.tsx","./src/components/chat/chat-composer.tsx","./src/components/chat/chat-messages-panel.tsx","./src/components/markdown/markdown-content.tsx","./src/components/search/search-results-panel.tsx","./src/components/ui/button.tsx","./src/components/ui/input.tsx","./src/components/ui/scroll-area.tsx","./src/components/ui/separator.tsx","./src/components/ui/textarea.tsx","./src/hooks/use-session-auth.ts","./src/lib/api.ts","./src/lib/chat-forking.ts","./src/lib/chat-model-selection.ts","./src/lib/quick-question.ts","./src/lib/sidebar-selection.ts","./src/lib/utils.ts","./src/pages/search-route-page.tsx"],"version":"5.9.3"}