ios: appearance tweaks

ios/AGENTS.md

@@ -8,8 +8,19 @@ Instructions for work under `/Users/buzzert/src/sybil-2/ios`.
 - `just build` will:
   1. generate `Sybil.xcodeproj` with `xcodegen` if missing,
   2. build scheme `Sybil` for `iPhone 16e` simulator.
+- Preferred test command: `just test`
+- `just test` runs the Swift package tests through `xcodebuild test` on the `iPhone 16e` iOS simulator from `ios/Packages/Sybil`.
+- `just test` disables Xcode parallel testing because the current async view-model tests use timing-sensitive selection tasks.
+- Do not use plain `swift test` for this package; it runs as host macOS and hits a deployment mismatch with `MarkdownUI`.
 - If `xcbeautify` is installed it is used automatically; otherwise raw `xcodebuild` output is used.
 
+## Simulator Workflow
+- Run the app in the simulator with `just run` from `/Users/buzzert/src/sybil-2/ios`.
+- `just run` boots the `iPhone 16e` simulator if needed, builds with a stable derived data path, installs `Sybil.app`, and launches bundle id `net.buzzert.sybil2`.
+- Capture a simulator screenshot with `just screenshot` from `/Users/buzzert/src/sybil-2/ios`; it writes `build/sybil-screenshot.png` by default.
+- To choose a screenshot path, run `just screenshot path=build/name.png`.
+- The underlying screenshot command is `xcrun simctl io booted screenshot <path>` and requires a booted simulator.
+
 ## App Structure
 - App target entry: `/Users/buzzert/src/sybil-2/ios/Apps/Sybil/Sources/SybilApp.swift`
 - Shared iOS app code lives in Swift package:

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

@@ -6,6 +6,7 @@ public struct SplitView: View {
     @Environment(\.scenePhase) private var scenePhase
     @State private var shouldRefreshOnForeground = false
     @State private var composerFocusRequest = 0
+    @State private var columnVisibility: NavigationSplitViewVisibility = .automatic
 
     private var keyboardActions: SybilKeyboardActions? {
         guard !viewModel.isCheckingSession, viewModel.isAuthenticated else {
@@ -50,16 +51,24 @@ public struct SplitView: View {
             } else if horizontalSizeClass == .compact {
                 SybilPhoneShellView(viewModel: viewModel)
             } else {
-                NavigationSplitView {
-                    SybilSidebarView(viewModel: viewModel)
-                } detail: {
-                    SybilWorkspaceView(viewModel: viewModel, composerFocusRequest: composerFocusRequest) {
-                        viewModel.startNewChat()
-                        composerFocusRequest += 1
+                GeometryReader { proxy in
+                    NavigationSplitView(columnVisibility: $columnVisibility) {
+                        SybilSidebarView(viewModel: viewModel)
+                    } detail: {
+                        SybilWorkspaceView(
+                            viewModel: viewModel,
+                            composerFocusRequest: composerFocusRequest,
+                            navigationLeadingControl: splitNavigationLeadingControl(for: proxy.size),
+                            onShowSidebar: showSidebar,
+                            onRequestNewChat: {
+                                viewModel.startNewChat()
+                                composerFocusRequest += 1
+                            }
+                        )
                     }
+                    .navigationSplitViewStyle(.balanced)
+                    .tint(SybilTheme.primary)
                 }
-                .navigationSplitViewStyle(.balanced)
-                .tint(SybilTheme.primary)
             }
         }
         .font(.sybil(.body))
@@ -72,24 +81,37 @@ public struct SplitView: View {
             switch nextPhase {
             case .background:
                 shouldRefreshOnForeground = true
+                viewModel.markAppInactiveForNetwork()
             case .active:
+                viewModel.markAppActiveForNetwork()
                 guard shouldRefreshOnForeground, horizontalSizeClass != .compact else {
                     return
                 }
                 shouldRefreshOnForeground = false
                 Task {
-                    await viewModel.refreshVisibleContent(
+                    await viewModel.refreshAfterAppBecameActive(
                         refreshCollections: true,
                         refreshSelection: viewModel.hasRefreshableSelection
                     )
                 }
             case .inactive:
-                break
+                shouldRefreshOnForeground = true
+                viewModel.markAppInactiveForNetwork()
             @unknown default:
                 break
             }
         }
     }
+
+    private func splitNavigationLeadingControl(for size: CGSize) -> SybilWorkspaceNavigationLeadingControl {
+        return size.width < size.height ? .showSidebar : .hidden
+    }
+
+    private func showSidebar() {
+        withAnimation(.easeInOut(duration: 0.22)) {
+            columnVisibility = .all
+        }
+    }
 }
 
 public struct SybilCommands: Commands {

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

@@ -5,7 +5,8 @@ struct SybilChatTranscriptView: View {
     var messages: [Message]
     var isLoading: Bool
     var isSending: Bool
-    @State private var hasHandledInitialTranscriptScroll = false
+    var topContentInset: CGFloat = 0
+    var bottomContentInset: CGFloat = 0
 
     private var hasPendingAssistant: Bool {
         messages.contains { message in
@@ -14,65 +15,42 @@ struct SybilChatTranscriptView: View {
     }
 
     var body: some View {
-        ScrollViewReader { proxy in
-            ScrollView {
-                LazyVStack(alignment: .leading, spacing: 26) {
-                    if isLoading && messages.isEmpty {
-                        Text("Loading messages…")
+        ScrollView {
+            LazyVStack(alignment: .leading, spacing: 26) {
+                if isSending && !hasPendingAssistant {
+                    HStack(spacing: 8) {
+                        ProgressView()
+                            .controlSize(.small)
+                            .tint(SybilTheme.textMuted)
+                        Text("Assistant is typing…")
                             .font(.sybil(.footnote))
                             .foregroundStyle(SybilTheme.textMuted)
-                            .padding(.top, 24)
                     }
-
-                    ForEach(messages) { message in
-                        MessageBubble(message: message, isSending: isSending)
-                            .frame(maxWidth: .infinity)
-                            .id(message.id)
-                    }
-
-                    if isSending && !hasPendingAssistant {
-                        HStack(spacing: 8) {
-                            ProgressView()
-                                .controlSize(.small)
-                                .tint(SybilTheme.textMuted)
-                            Text("Assistant is typing…")
-                                .font(.sybil(.footnote))
-                                .foregroundStyle(SybilTheme.textMuted)
-                        }
-                        .id("typing-indicator")
-                    }
-
-                    Color.clear
-                        .frame(height: 2)
-                        .id("chat-bottom-anchor")
+                    .scaleEffect(x: 1, y: -1)
+                }
+
+                ForEach(messages.reversed()) { message in
+                    MessageBubble(message: message, isSending: isSending)
+                        .frame(maxWidth: .infinity)
+                        .scaleEffect(x: 1, y: -1)
+                }
+
+                if isLoading && messages.isEmpty {
+                    Text("Loading messages…")
+                        .font(.sybil(.footnote))
+                        .foregroundStyle(SybilTheme.textMuted)
+                        .padding(.top, 24)
+                        .scaleEffect(x: 1, y: -1)
                 }
-                .frame(maxWidth: .infinity, alignment: .leading)
-                .padding(.horizontal, 14)
-                .padding(.vertical, 18)
             }
             .frame(maxWidth: .infinity, alignment: .leading)
-            .scrollDismissesKeyboard(.interactively)
-            .onAppear {
-                scrollToBottom(with: proxy, animated: false)
-            }
-            .onChange(of: messages.map(\.id)) { _, _ in
-                scrollToBottom(with: proxy, animated: hasHandledInitialTranscriptScroll && !isLoading)
-                hasHandledInitialTranscriptScroll = true
-            }
-            .onChange(of: isSending) { _, _ in
-                scrollToBottom(with: proxy, animated: hasHandledInitialTranscriptScroll)
-            }
-        }
-    }
-
-    private func scrollToBottom(with proxy: ScrollViewProxy, animated: Bool) {
-        if animated {
-            withAnimation(.easeOut(duration: 0.22)) {
-                proxy.scrollTo("chat-bottom-anchor", anchor: .bottom)
-            }
-        } else {
-            proxy.scrollTo("chat-bottom-anchor", anchor: .bottom)
+            .padding(.horizontal, 14)
+            .padding(.top, 18 + bottomContentInset)
+            .padding(.bottom, 18 + topContentInset)
         }
+        .frame(maxWidth: .infinity, alignment: .leading)
+        .scrollDismissesKeyboard(.interactively)
+        .scaleEffect(x: 1, y: -1)
     }
 }
 

ios/Packages/Sybil/Sources/Sybil/SybilMarkdownTheme.swift

@@ -85,7 +85,7 @@ extension Theme {
             .paragraph { configuration in
                 configuration.label
                     .fixedSize(horizontal: false, vertical: true)
-                    .relativeLineSpacing(.em(0.36))
+                    .relativeLineSpacing(.em(0.46))
                     .markdownMargin(top: .zero, bottom: .em(0.82))
             }
             .blockquote { configuration in

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

@@ -34,7 +34,7 @@ struct SybilPhoneShellView: View {
                 .navigationBarTitleDisplayMode(.inline)
                 .toolbar {
                     ToolbarItem(placement: .topBarLeading) {
-                        SybilWordmark(size: 18)
+                        SybilWordmark(size: 21)
                     }
                 }
                 .navigationDestination(for: PhoneRoute.self) { route in
@@ -51,19 +51,22 @@ struct SybilPhoneShellView: View {
             switch nextPhase {
             case .background:
                 shouldRefreshOnForeground = true
+                viewModel.markAppInactiveForNetwork()
             case .active:
+                viewModel.markAppActiveForNetwork()
                 guard shouldRefreshOnForeground else {
                     return
                 }
                 shouldRefreshOnForeground = false
                 Task {
-                    await viewModel.refreshVisibleContent(
+                    await viewModel.refreshAfterAppBecameActive(
                         refreshCollections: path.isEmpty,
                         refreshSelection: !path.isEmpty && viewModel.hasRefreshableSelection
                     )
                 }
             case .inactive:
-                break
+                shouldRefreshOnForeground = true
+                viewModel.markAppInactiveForNetwork()
             @unknown default:
                 break
             }
@@ -74,6 +77,27 @@ struct SybilPhoneShellView: View {
 private struct SybilPhoneSidebarRoot: View {
     @Bindable var viewModel: SybilViewModel
     @Binding var path: [PhoneRoute]
+    @State private var openingSelection: SidebarSelection?
+    @State private var openingRequestID: UUID?
+
+    private var highlightedSelection: SidebarSelection? {
+        if let openingSelection {
+            return openingSelection
+        }
+
+        guard let route = path.last else {
+            return nil
+        }
+
+        switch route {
+        case let .chat(chatID):
+            return .chat(chatID)
+        case let .search(searchID):
+            return .search(searchID)
+        case .draftChat, .draftSearch, .settings:
+            return nil
+        }
+    }
 
     var body: some View {
         VStack(spacing: 0) {
@@ -113,12 +137,21 @@ private struct SybilPhoneSidebarRoot: View {
                 .padding(16)
             } else {
                 ScrollView {
-                    LazyVStack(alignment: .leading, spacing: 8) {
+                    LazyVStack(alignment: .leading, spacing: 0) {
                         ForEach(viewModel.sidebarItems) { item in
-                            NavigationLink(value: PhoneRoute.from(selection: item.selection)) {
-                                SybilPhoneSidebarRow(item: item)
+                            Button {
+                                open(item.selection)
+                            } label: {
+                                VStack(spacing: 0.0) {
+                                    SybilPhoneSidebarRow(item: item)
+                                    Divider()
+                                }
                             }
-                            .buttonStyle(.plain)
+                            .buttonStyle(
+                                SybilPhoneSidebarRowButtonStyle(
+                                    isHighlighted: highlightedSelection == item.selection
+                                )
+                            )
                             .contextMenu {
                                 Button(role: .destructive) {
                                     Task {
@@ -130,7 +163,6 @@ private struct SybilPhoneSidebarRoot: View {
                             }
                         }
                     }
-                    .padding(10)
                 }
             }
         }
@@ -147,17 +179,20 @@ private struct SybilPhoneSidebarRoot: View {
 
             HStack(spacing: 12) {
                 toolbarIconButton(systemImage: "gearshape", accessibilityLabel: "Settings") {
+                    clearOpeningSelection()
                     path = [.settings]
                 }
 
                 Spacer()
 
                 toolbarIconButton(systemImage: "magnifyingglass", accessibilityLabel: "New search") {
+                    clearOpeningSelection()
                     viewModel.startNewSearch()
                     path = [.draftSearch]
                 }
 
                 toolbarIconButton(systemImage: "plus", accessibilityLabel: "New chat", isPrimary: true) {
+                    clearOpeningSelection()
                     viewModel.startNewChat()
                     path = [.draftChat]
                 }
@@ -195,25 +230,69 @@ private struct SybilPhoneSidebarRoot: View {
         .buttonStyle(.plain)
         .accessibilityLabel(accessibilityLabel)
     }
+
+    private func clearOpeningSelection() {
+        openingRequestID = nil
+        openingSelection = nil
+    }
+
+    private func open(_ selection: SidebarSelection) {
+        guard openingSelection != selection else {
+            return
+        }
+
+        let requestID = UUID()
+        openingRequestID = requestID
+        openingSelection = selection
+        Task {
+            await viewModel.selectForNavigation(selection)
+            guard openingRequestID == requestID else {
+                return
+            }
+            path = [PhoneRoute.from(selection: selection)]
+            openingRequestID = nil
+            openingSelection = nil
+        }
+    }
+}
+
+private struct SybilPhoneSidebarRowIsActiveKey: EnvironmentKey {
+    static let defaultValue = false
+}
+
+private extension EnvironmentValues {
+    var sybilPhoneSidebarRowIsActive: Bool {
+        get { self[SybilPhoneSidebarRowIsActiveKey.self] }
+        set { self[SybilPhoneSidebarRowIsActiveKey.self] = newValue }
+    }
+}
+
+private struct SybilPhoneSidebarRowButtonStyle: ButtonStyle {
+    var isHighlighted: Bool
+
+    func makeBody(configuration: Configuration) -> some View {
+        configuration.label
+            .environment(\.sybilPhoneSidebarRowIsActive, isHighlighted || configuration.isPressed)
+    }
 }
 
 private struct SybilPhoneSidebarRow: View {
+    @Environment(\.sybilPhoneSidebarRowIsActive) private var isHighlighted
     var item: SidebarItem
 
     var body: some View {
-        VStack(alignment: .leading, spacing: 6) {
+        let leadingWidth = 22.0
+        
+        VStack(alignment: .leading, spacing: 8) {
             HStack(spacing: 8) {
                 Image(systemName: item.kind == .chat ? "message" : "globe")
                     .font(.system(size: 12, weight: .semibold))
-                    .foregroundStyle(SybilTheme.textMuted)
-                    .frame(width: 22, height: 22)
+                    .foregroundStyle(isHighlighted ? SybilTheme.accent : SybilTheme.textMuted)
+                    .frame(width: leadingWidth, height: leadingWidth)
                     .background(
-                        RoundedRectangle(cornerRadius: 7)
-                            .fill(SybilTheme.surface.opacity(0.72))
-                            .overlay(
-                                RoundedRectangle(cornerRadius: 7)
-                                    .stroke(SybilTheme.border.opacity(0.72), lineWidth: 1)
-                            )
+                        Rectangle()
+                            .fill(isHighlighted ? SybilTheme.accent.opacity(0.12) : SybilTheme.surface.opacity(0.72))
+                            
                     )
 
                 Text(item.title)
@@ -222,6 +301,9 @@ private struct SybilPhoneSidebarRow: View {
             }
 
             HStack(spacing: 8) {
+                Spacer()
+                    .frame(width: leadingWidth)
+
                 Text(item.updatedAt.sybilRelativeLabel)
                     .font(.sybil(.caption2))
                     .foregroundStyle(SybilTheme.textMuted)
@@ -238,17 +320,17 @@ private struct SybilPhoneSidebarRow: View {
             }
         }
         .foregroundStyle(SybilTheme.text)
-        .padding(.horizontal, 12)
-        .padding(.vertical, 10)
+        .padding(18.0)
         .frame(maxWidth: .infinity, alignment: .leading)
         .background(
-            RoundedRectangle(cornerRadius: 12)
-                .fill(LinearGradient(colors: [SybilTheme.surface.opacity(0.56), SybilTheme.surface.opacity(0.36)], startPoint: .topLeading, endPoint: .bottomTrailing))
-        )
-        .overlay(
-            RoundedRectangle(cornerRadius: 12)
-                .stroke(SybilTheme.border.opacity(0.72), lineWidth: 1)
+            Rectangle()
+                .fill(
+                    isHighlighted
+                        ? SybilTheme.selectedRowGradient
+                        : LinearGradient(colors: [SybilTheme.surface.opacity(0.56), SybilTheme.surface.opacity(0.36)], startPoint: .topLeading, endPoint: .bottomTrailing)
+                )
         )
+
     }
 }
 
@@ -259,15 +341,19 @@ private struct SybilPhoneDestinationView: View {
     let route: PhoneRoute
 
     var body: some View {
-        SybilWorkspaceView(viewModel: viewModel, composerFocusRequest: composerFocusRequest) {
-            viewModel.startNewChat()
-            composerFocusRequest += 1
-            if path.isEmpty {
-                path = [.draftChat]
-            } else {
-                path[path.index(before: path.endIndex)] = .draftChat
+        SybilWorkspaceView(
+            viewModel: viewModel,
+            composerFocusRequest: composerFocusRequest,
+            onRequestNewChat: {
+                viewModel.startNewChat()
+                composerFocusRequest += 1
+                if path.isEmpty {
+                    path = [.draftChat]
+                } else {
+                    path[path.index(before: path.endIndex)] = .draftChat
+                }
             }
-        }
+        )
         .frame(maxWidth: .infinity, maxHeight: .infinity, alignment: .topLeading)
         .navigationBarTitleDisplayMode(.inline)
         .task(id: route) {
@@ -278,8 +364,14 @@ private struct SybilPhoneDestinationView: View {
     private func applyRoute() {
         switch route {
         case let .chat(chatID):
+            guard viewModel.draftKind != nil || viewModel.selectedItem != .chat(chatID) else {
+                return
+            }
             viewModel.select(.chat(chatID))
         case let .search(searchID):
+            guard viewModel.draftKind != nil || viewModel.selectedItem != .search(searchID) else {
+                return
+            }
             viewModel.select(.search(searchID))
         case .draftChat:
             viewModel.startNewChat()

ios/Packages/Sybil/Sources/Sybil/SybilSearchResultsView.swift

@@ -6,6 +6,8 @@ struct SybilSearchResultsView: View {
     var isLoading: Bool
     var isRunning: Bool
     var isStartingChat: Bool = false
+    var topContentInset: CGFloat = 0
+    var bottomContentInset: CGFloat = 0
     var onStartChat: (() -> Void)? = nil
 
     var body: some View {
@@ -98,7 +100,8 @@ struct SybilSearchResultsView: View {
             }
             .frame(maxWidth: .infinity, alignment: .leading)
             .padding(.horizontal, 14)
-            .padding(.vertical, 20)
+            .padding(.top, 20 + topContentInset)
+            .padding(.bottom, 20 + bottomContentInset)
         }
         .scrollDismissesKeyboard(.interactively)
         .frame(maxWidth: .infinity, alignment: .leading)

ios/Packages/Sybil/Sources/Sybil/SybilTheme.swift

@@ -9,7 +9,7 @@ enum SybilFontRegistry {
     }
 
     private static let registeredFonts: Void = {
-        for fontName in ["Inter", "Orbitron"] {
+        for fontName in ["Inter", "Orbitron", "StalinistOne-Regular"] {
             guard let url = Bundle.main.url(forResource: fontName, withExtension: "ttf", subdirectory: "Fonts") ??
                 Bundle.main.url(forResource: fontName, withExtension: "ttf")
             else {
@@ -203,7 +203,7 @@ struct SybilWordmark: View {
 
     var body: some View {
         Text("SYBIL")
-            .font(.custom("Orbitron", size: size))
+            .font(.custom("Stalinist One", size: size))
             .fontWeight(.black)
             .tracking(0)
             .foregroundStyle(SybilTheme.brandGradient)

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

@@ -42,6 +42,22 @@ private struct PendingChatState {
     var messages: [Message]
 }
 
+private enum ActiveSendContext: Equatable {
+    case draftChat(UUID)
+    case chat(String)
+    case draftSearch(UUID)
+    case search(String)
+
+    var isSearch: Bool {
+        switch self {
+        case .draftSearch, .search:
+            return true
+        case .draftChat, .chat:
+            return false
+        }
+    }
+}
+
 private actor CompletionStreamStatus {
     private var streamError: String?
 
@@ -99,11 +115,17 @@ final class SybilViewModel {
     @ObservationIgnored
     private var hasBootstrapped = false
     private var pendingChatState: PendingChatState?
+    private var activeSendContext: ActiveSendContext?
+    private var draftIdentity = UUID()
     @ObservationIgnored
     private var selectionTask: Task<Void, Never>?
     @ObservationIgnored
     private var chatBackgroundTask: SybilBackgroundTaskAssertion?
     @ObservationIgnored
+    private var isAppActive = true
+    @ObservationIgnored
+    private var appLifecycleGeneration = 0
+    @ObservationIgnored
     private let clientFactory: (APIConfiguration) -> any SybilAPIClienting
 
     private let fallbackModels: [Provider: [String]] = [
@@ -153,7 +175,7 @@ final class SybilViewModel {
 
         switch selectedItem {
         case .chat:
-            if let selectedChat {
+            if let selectedChat = currentSelectedChat {
                 return chatTitle(title: selectedChat.title, messages: selectedChat.messages)
             }
             if let summary = selectedChatSummary {
@@ -162,7 +184,7 @@ final class SybilViewModel {
             return "Chat"
 
         case .search:
-            if let selectedSearch {
+            if let selectedSearch = currentSelectedSearch {
                 return searchTitle(title: selectedSearch.title, query: selectedSearch.query)
             }
             if let summary = selectedSearchSummary {
@@ -229,7 +251,7 @@ final class SybilViewModel {
     }
 
     var displayedMessages: [Message] {
-        let canonical = displayableMessages(selectedChat?.messages ?? [])
+        let canonical = displayableMessages(currentSelectedChat?.messages ?? [])
         guard let pending = pendingChatState else {
             return canonical
         }
@@ -248,6 +270,40 @@ final class SybilViewModel {
         return canonical
     }
 
+    var displayedSearch: SearchDetail? {
+        currentSelectedSearch
+    }
+
+    var isSendingVisibleChat: Bool {
+        guard isSending, pendingChatState != nil else {
+            return false
+        }
+
+        switch activeSendContext {
+        case let .draftChat(identity):
+            return draftKind == .chat && identity == draftIdentity
+        case let .chat(chatID):
+            return selectedItem == .chat(chatID)
+        case .draftSearch, .search, nil:
+            return false
+        }
+    }
+
+    var isRunningVisibleSearch: Bool {
+        guard isSending else {
+            return false
+        }
+
+        switch activeSendContext {
+        case let .draftSearch(identity):
+            return draftKind == .search && identity == draftIdentity
+        case let .search(searchID):
+            return selectedItem == .search(searchID)
+        case .draftChat, .chat, nil:
+            return false
+        }
+    }
+
     var sidebarItems: [SidebarItem] {
         let chatItems: [SidebarItem] = chats.map { chat in
             let initiatedLabel: String?
@@ -276,7 +332,7 @@ final class SybilViewModel {
                 kind: .search,
                 title: searchTitle(title: search.title, query: search.query),
                 updatedAt: search.updatedAt,
-                initiatedLabel: nil
+                initiatedLabel: "exa"
             )
         }
 
@@ -320,7 +376,10 @@ final class SybilViewModel {
         isCheckingSession = true
         authError = nil
         errorMessage = nil
+        resetSelectionLoading()
         pendingChatState = nil
+        activeSendContext = nil
+        draftIdentity = UUID()
         composerAttachments = []
         settings.persist()
 
@@ -392,10 +451,13 @@ final class SybilViewModel {
 
     func startNewChat() {
         SybilLog.debug(SybilLog.ui, "Starting draft chat")
+        resetSelectionLoading()
+        draftIdentity = UUID()
         draftKind = .chat
         selectedItem = nil
         selectedChat = nil
         selectedSearch = nil
+        pendingChatState = nil
         errorMessage = nil
         composer = ""
         composerAttachments = []
@@ -403,10 +465,13 @@ final class SybilViewModel {
 
     func startNewSearch() {
         SybilLog.debug(SybilLog.ui, "Starting draft search")
+        resetSelectionLoading()
+        draftIdentity = UUID()
         draftKind = .search
         selectedItem = nil
         selectedChat = nil
         selectedSearch = nil
+        pendingChatState = nil
         errorMessage = nil
         composer = ""
         composerAttachments = []
@@ -414,33 +479,72 @@ final class SybilViewModel {
 
     func openSettings() {
         SybilLog.debug(SybilLog.ui, "Opening settings")
+        resetSelectionLoading()
         draftKind = nil
         selectedItem = .settings
         selectedChat = nil
         selectedSearch = nil
+        pendingChatState = nil
         errorMessage = nil
         composerAttachments = []
     }
 
     func select(_ selection: SidebarSelection) {
-        SybilLog.debug(SybilLog.ui, "Selecting \(selection.id)")
-        draftKind = nil
-        selectedItem = selection
-        errorMessage = nil
-        if case .search = selection {
-            composerAttachments = []
-        }
+        _ = beginSelecting(selection)
+    }
 
-        if case .settings = selection {
-            selectedChat = nil
-            selectedSearch = nil
+    func selectForNavigation(_ selection: SidebarSelection, preloadTimeout: Duration = .seconds(3)) async {
+        guard beginSelecting(selection) != nil else {
             return
         }
 
-        selectionTask?.cancel()
-        selectionTask = Task { [weak self] in
-            await self?.refreshSelectionIfNeeded()
+        await waitForSelectionLoad(timeout: preloadTimeout)
+    }
+
+    @discardableResult
+    private func beginSelecting(_ selection: SidebarSelection) -> Task<Void, Never>? {
+        SybilLog.debug(SybilLog.ui, "Selecting \(selection.id)")
+
+        if draftKind == nil, selectedItem == selection {
+            errorMessage = nil
+            if case .search = selection {
+                composerAttachments = []
+            }
+
+            if needsSelectionLoad(selection) {
+                return startSelectionRefreshTask()
+            }
+
+            return selectionTask
         }
+
+        resetSelectionLoading()
+        draftKind = nil
+        selectedItem = selection
+        errorMessage = nil
+
+        switch selection {
+        case let .chat(chatID):
+            if selectedChat?.id != chatID {
+                selectedChat = nil
+            }
+            selectedSearch = nil
+
+        case let .search(searchID):
+            if selectedSearch?.id != searchID {
+                selectedSearch = nil
+            }
+            selectedChat = nil
+            composerAttachments = []
+
+        case .settings:
+            selectedChat = nil
+            selectedSearch = nil
+            pendingChatState = nil
+            return nil
+        }
+
+        return startSelectionRefreshTask()
     }
 
     func selectPreviousSidebarItem() {
@@ -502,6 +606,38 @@ final class SybilViewModel {
         await reconnect()
     }
 
+    func markAppInactiveForNetwork() {
+        guard isAppActive else {
+            return
+        }
+
+        isAppActive = false
+        appLifecycleGeneration += 1
+        SybilLog.debug(SybilLog.app, "App became inactive for network lifecycle generation \(appLifecycleGeneration)")
+    }
+
+    func markAppActiveForNetwork() {
+        isAppActive = true
+    }
+
+    func refreshAfterAppBecameActive(refreshCollections shouldRefreshCollections: Bool, refreshSelection shouldRefreshSelection: Bool) async {
+        markAppActiveForNetwork()
+
+        guard isAuthenticated, !isCheckingSession else {
+            return
+        }
+
+        guard shouldRefreshCollections || shouldRefreshSelection else {
+            return
+        }
+
+        try? await Task.sleep(for: .milliseconds(150))
+        await refreshVisibleContent(
+            refreshCollections: shouldRefreshCollections,
+            refreshSelection: shouldRefreshSelection
+        )
+    }
+
     func refreshVisibleContent(refreshCollections shouldRefreshCollections: Bool, refreshSelection shouldRefreshSelection: Bool) async {
         guard isAuthenticated, !isCheckingSession else {
             return
@@ -529,12 +665,13 @@ final class SybilViewModel {
     func sendComposer() async {
         let content = composer.trimmingCharacters(in: .whitespacesAndNewlines)
         let attachments = composerAttachments
+        let sendContext = currentSendContext
 
         guard !isSending else {
             return
         }
 
-        if isSearchMode {
+        if sendContext.isSearch {
             guard !content.isEmpty else { return }
         } else if content.isEmpty && attachments.isEmpty {
             return
@@ -543,10 +680,11 @@ final class SybilViewModel {
         composer = ""
         composerAttachments = []
         errorMessage = nil
+        activeSendContext = sendContext
         isSending = true
 
         do {
-            if isSearchMode {
+            if sendContext.isSearch {
                 SybilLog.info(SybilLog.ui, "Sending search query")
                 try await sendSearch(query: content)
             } else {
@@ -554,35 +692,43 @@ final class SybilViewModel {
                 try await sendChat(content: content, attachments: attachments)
             }
         } catch {
-            errorMessage = normalizeAPIError(error)
+            let shouldSurfaceError = isSendContextVisible(sendContext) || (activeSendContext.map { isSendContextVisible($0) } ?? false)
+            if shouldSurfaceError {
+                errorMessage = normalizeAPIError(error)
+            }
             SybilLog.error(SybilLog.ui, "Send failed", error: error)
 
-            if case let .chat(chatID) = selectedItem {
+            if shouldSurfaceError, case let .chat(chatID) = selectedItem {
                 do {
                     let chat = try await client().getChat(chatID: chatID)
-                    selectedChat = chat
+                    if selectedItem == .chat(chatID), draftKind == nil {
+                        selectedChat = chat
+                    }
                 } catch {
                     SybilLog.error(SybilLog.ui, "Fallback chat refresh after failure failed", error: error)
                 }
             }
 
-            if case let .search(searchID) = selectedItem {
+            if shouldSurfaceError, case let .search(searchID) = selectedItem {
                 do {
                     let search = try await client().getSearch(searchID: searchID)
-                    selectedSearch = search
+                    if selectedItem == .search(searchID), draftKind == nil {
+                        selectedSearch = search
+                    }
                 } catch {
                     SybilLog.error(SybilLog.ui, "Fallback search refresh after failure failed", error: error)
                 }
             }
 
-            if !isSearchMode {
+            if !sendContext.isSearch, shouldSurfaceError {
                 composer = content
                 composerAttachments = attachments
-                pendingChatState = nil
             }
+            pendingChatState = nil
         }
 
         isSending = false
+        activeSendContext = nil
     }
 
     func appendComposerAttachments(_ attachments: [ChatAttachment]) throws {
@@ -608,16 +754,25 @@ final class SybilViewModel {
     }
 
     func startChatFromSelectedSearch() async {
-        guard let search = selectedSearch, !isCreatingSearchChat, !isSending else {
+        guard let search = currentSelectedSearch, !isCreatingSearchChat, !isSending else {
             return
         }
 
+        let sourceSelection = SidebarSelection.search(search.id)
         isCreatingSearchChat = true
         errorMessage = nil
 
         do {
             let client = try client()
             let chat = try await client.createChatFromSearch(searchID: search.id, title: nil)
+
+            guard selectedItem == sourceSelection, draftKind == nil else {
+                chats.removeAll(where: { $0.id == chat.id })
+                chats.insert(chat, at: 0)
+                isCreatingSearchChat = false
+                return
+            }
+
             draftKind = nil
             pendingChatState = nil
             composer = ""
@@ -729,6 +884,12 @@ final class SybilViewModel {
                 SybilLog.app,
                 "Refreshed collections: \(nextChats.count) chats, \(nextSearches.count) searches"
             )
+            errorMessage = nil
+
+            if draftKind != nil {
+                isLoadingCollections = false
+                return
+            }
 
             if case .settings = selectedItem {
                 isLoadingCollections = false
@@ -749,33 +910,79 @@ final class SybilViewModel {
                 await refreshSelectionIfNeeded()
             }
         } catch {
-            errorMessage = normalizeAPIError(error)
-            SybilLog.error(SybilLog.app, "Refresh collections failed", error: error)
+            if shouldSuppressInactiveTransportError(error) {
+                SybilLog.info(SybilLog.app, "Suppressing collection refresh transport interruption while app is inactive")
+            } else {
+                errorMessage = normalizeAPIError(error)
+                SybilLog.error(SybilLog.app, "Refresh collections failed", error: error)
+            }
         }
 
         isLoadingCollections = false
     }
 
+    private func resetSelectionLoading() {
+        selectionTask?.cancel()
+        selectionTask = nil
+        isLoadingSelection = false
+    }
+
+    private func startSelectionRefreshTask() -> Task<Void, Never> {
+        isLoadingSelection = true
+        let task = Task { [weak self] in
+            guard let self else {
+                return
+            }
+            await self.refreshSelectionIfNeeded()
+        }
+        selectionTask = task
+        return task
+    }
+
+    private func waitForSelectionLoad(timeout: Duration) async {
+        let clock = ContinuousClock()
+        let deadline = clock.now.advanced(by: timeout)
+
+        while isLoadingSelection, clock.now < deadline {
+            try? await Task.sleep(for: .milliseconds(10))
+        }
+    }
+
+    private func needsSelectionLoad(_ selection: SidebarSelection) -> Bool {
+        switch selection {
+        case let .chat(chatID):
+            return selectedChat?.id != chatID
+        case let .search(searchID):
+            return selectedSearch?.id != searchID
+        case .settings:
+            return false
+        }
+    }
+
     private func refreshSelectionIfNeeded() async {
-        guard let selectedItem else {
+        guard let target = selectedItem else {
             selectedChat = nil
             selectedSearch = nil
+            isLoadingSelection = false
             return
         }
 
-        guard case .settings = selectedItem else {
+        guard case .settings = target else {
             isLoadingSelection = true
             do {
                 let client = try client()
-                switch selectedItem {
+                switch target {
                 case let .chat(chatID):
                     SybilLog.debug(SybilLog.app, "Refreshing chat \(chatID)")
-                    selectedChat = try await client.getChat(chatID: chatID)
+                    let chat = try await client.getChat(chatID: chatID)
+                    guard selectedItem == target, draftKind == nil else {
+                        return
+                    }
+                    selectedChat = chat
                     selectedSearch = nil
 
-                    if let detail = selectedChat,
-                       let provider = detail.lastUsedProvider,
-                       let model = detail.lastUsedModel,
+                    if let provider = chat.lastUsedProvider,
+                       let model = chat.lastUsedModel,
                        !model.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty {
                         self.provider = provider
                         self.model = model
@@ -783,26 +990,37 @@ final class SybilViewModel {
 
                 case let .search(searchID):
                     SybilLog.debug(SybilLog.app, "Refreshing search \(searchID)")
-                    selectedSearch = try await client.getSearch(searchID: searchID)
+                    let search = try await client.getSearch(searchID: searchID)
+                    guard selectedItem == target, draftKind == nil else {
+                        return
+                    }
+                    selectedSearch = search
                     selectedChat = nil
 
                 case .settings:
                     break
                 }
+                errorMessage = nil
             } catch {
                 if isCancellation(error) {
-                    SybilLog.debug(SybilLog.app, "Selection refresh cancelled for \(selectedItem.id)")
-                } else {
+                    SybilLog.debug(SybilLog.app, "Selection refresh cancelled for \(target.id)")
+                } else if shouldSuppressInactiveTransportError(error) {
+                    SybilLog.info(SybilLog.app, "Suppressing selection refresh transport interruption while app is inactive")
+                } else if selectedItem == target, draftKind == nil {
                     errorMessage = normalizeAPIError(error)
                     SybilLog.error(SybilLog.app, "Selection refresh failed", error: error)
                 }
             }
-            isLoadingSelection = false
+            if selectedItem == target, draftKind == nil {
+                isLoadingSelection = false
+                selectionTask = nil
+            }
             return
         }
 
         selectedChat = nil
         selectedSearch = nil
+        isLoadingSelection = false
     }
 
     private func sendChat(content: String, attachments: [ChatAttachment]) async throws {
@@ -825,7 +1043,7 @@ final class SybilViewModel {
 
         pendingChatState = PendingChatState(
             chatID: currentChatID,
-            messages: (selectedChat?.messages ?? []) + [optimisticUser, optimisticAssistant]
+            messages: (currentSelectedChat?.messages ?? []) + [optimisticUser, optimisticAssistant]
         )
 
         let client = try client()
@@ -834,24 +1052,29 @@ final class SybilViewModel {
         if chatID == nil {
             let created = try await client.createChat(title: nil)
             chatID = created.id
-            draftKind = nil
-            selectedItem = .chat(created.id)
+            let shouldShowCreatedChat = activeSendContext.map { isSendContextVisible($0) } ?? true
+            activeSendContext = .chat(created.id)
 
             chats.removeAll(where: { $0.id == created.id })
             chats.insert(created, at: 0)
 
-            selectedChat = ChatDetail(
-                id: created.id,
-                title: created.title,
-                createdAt: created.createdAt,
-                updatedAt: created.updatedAt,
-                initiatedProvider: created.initiatedProvider,
-                initiatedModel: created.initiatedModel,
-                lastUsedProvider: created.lastUsedProvider,
-                lastUsedModel: created.lastUsedModel,
-                messages: []
-            )
-            selectedSearch = nil
+            if shouldShowCreatedChat {
+                draftKind = nil
+                selectedItem = .chat(created.id)
+
+                selectedChat = ChatDetail(
+                    id: created.id,
+                    title: created.title,
+                    createdAt: created.createdAt,
+                    updatedAt: created.updatedAt,
+                    initiatedProvider: created.initiatedProvider,
+                    initiatedModel: created.initiatedModel,
+                    lastUsedProvider: created.lastUsedProvider,
+                    lastUsedModel: created.lastUsedModel,
+                    messages: []
+                )
+                selectedSearch = nil
+            }
 
             SybilLog.info(SybilLog.app, "Created chat \(created.id)")
         }
@@ -863,7 +1086,7 @@ final class SybilViewModel {
         pendingChatState?.chatID = chatID
 
         let baseChat: ChatDetail
-        if let selectedChat, selectedChat.id == chatID {
+        if let selectedChat = currentSelectedChat, selectedChat.id == chatID {
             baseChat = selectedChat
         } else {
             baseChat = try await client.getChat(chatID: chatID)
@@ -882,8 +1105,10 @@ final class SybilViewModel {
             } + [CompletionRequestMessage(role: .user, content: content, attachments: attachments.isEmpty ? nil : attachments)]
 
         let streamStatus = CompletionStreamStatus()
+        let streamLifecycleGeneration = appLifecycleGeneration
+        let streamStartedWhileInactive = !isAppActive
 
-        if isUntitledChat(chatID: chatID, detail: selectedChat) {
+        if isUntitledChat(chatID: chatID, detail: currentSelectedChat) {
             Task { [weak self] in
                 guard let self else { return }
                 do {
@@ -917,24 +1142,79 @@ final class SybilViewModel {
             chatBackgroundTask = nil
         }
 
-        try await client.runCompletionStream(
-            body: CompletionStreamRequest(
-                chatId: chatID,
-                provider: provider,
-                model: selectedModel,
-                messages: requestMessages
-            )
-        ) { [weak self] event in
-            guard let self else { return }
-            await self.applyCompletionEvent(event, streamStatus: streamStatus)
+        do {
+            try await client.runCompletionStream(
+                body: CompletionStreamRequest(
+                    chatId: chatID,
+                    provider: provider,
+                    model: selectedModel,
+                    messages: requestMessages
+                )
+            ) { [weak self] event in
+                guard let self else { return }
+                await self.applyCompletionEvent(event, streamStatus: streamStatus)
+            }
+        } catch {
+            if shouldSuppressLifecycleTransportError(
+                error,
+                startedAt: streamLifecycleGeneration,
+                startedWhileInactive: streamStartedWhileInactive
+            ) {
+                SybilLog.info(SybilLog.app, "Suppressing chat stream transport interruption after app lifecycle change")
+                pendingChatState = nil
+                if isAppActive {
+                    await refreshInterruptedStream(preferredSelection: .chat(chatID))
+                }
+                return
+            }
+
+            throw error
         }
 
         if let streamError = await streamStatus.error() {
             throw APIError.httpError(statusCode: 502, message: streamError)
         }
 
-        await refreshCollections(preferredSelection: .chat(chatID))
-        selectedChat = try await client.getChat(chatID: chatID)
+        guard isAppActive else {
+            pendingChatState = nil
+            return
+        }
+
+        let sentChatSelection = SidebarSelection.chat(chatID)
+        let shouldKeepSentChatSelected = selectedItem == sentChatSelection && draftKind == nil
+        await refreshCollections(
+            preferredSelection: shouldKeepSentChatSelected ? sentChatSelection : selectedItem,
+            refreshSelection: false
+        )
+
+        guard selectedItem == sentChatSelection, draftKind == nil else {
+            pendingChatState = nil
+            return
+        }
+
+        do {
+            let refreshedChat = try await client.getChat(chatID: chatID)
+            guard selectedItem == sentChatSelection, draftKind == nil else {
+                pendingChatState = nil
+                return
+            }
+            selectedChat = refreshedChat
+        } catch {
+            if shouldSuppressLifecycleTransportError(
+                error,
+                startedAt: streamLifecycleGeneration,
+                startedWhileInactive: streamStartedWhileInactive
+            ) {
+                SybilLog.info(SybilLog.app, "Suppressing chat refresh transport interruption after app lifecycle change")
+                pendingChatState = nil
+                if isAppActive {
+                    await refreshInterruptedStream(preferredSelection: .chat(chatID))
+                }
+                return
+            }
+
+            throw error
+        }
         pendingChatState = nil
     }
 
@@ -972,12 +1252,17 @@ final class SybilViewModel {
         if searchID == nil {
             let created = try await client.createSearch(title: String(query.prefix(80)), query: query)
             searchID = created.id
-            draftKind = nil
-            selectedItem = .search(created.id)
+            let shouldShowCreatedSearch = activeSendContext.map { isSendContextVisible($0) } ?? true
+            activeSendContext = .search(created.id)
 
             searches.removeAll(where: { $0.id == created.id })
             searches.insert(created, at: 0)
 
+            if shouldShowCreatedSearch {
+                draftKind = nil
+                selectedItem = .search(created.id)
+            }
+
             SybilLog.info(SybilLog.app, "Created search \(created.id)")
         }
 
@@ -986,37 +1271,66 @@ final class SybilViewModel {
         }
 
         let now = Date()
-        selectedSearch = SearchDetail(
-            id: searchID,
-            title: String(query.prefix(80)),
-            query: query,
-            createdAt: selectedSearch?.createdAt ?? now,
-            updatedAt: now,
-            requestId: nil,
-            latencyMs: nil,
-            error: nil,
-            answerText: nil,
-            answerRequestId: nil,
-            answerCitations: nil,
-            answerError: nil,
-            results: []
-        )
+        if selectedItem == .search(searchID), draftKind == nil {
+            selectedSearch = SearchDetail(
+                id: searchID,
+                title: String(query.prefix(80)),
+                query: query,
+                createdAt: currentSelectedSearch?.createdAt ?? now,
+                updatedAt: now,
+                requestId: nil,
+                latencyMs: nil,
+                error: nil,
+                answerText: nil,
+                answerRequestId: nil,
+                answerCitations: nil,
+                answerError: nil,
+                results: []
+            )
+        }
 
         let streamStatus = SearchStreamStatus()
+        let streamLifecycleGeneration = appLifecycleGeneration
+        let streamStartedWhileInactive = !isAppActive
 
-        try await client.runSearchStream(
-            searchID: searchID,
-            body: SearchRunRequest(query: query, title: String(query.prefix(80)), type: "auto", numResults: 10)
-        ) { [weak self] event in
-            guard let self else { return }
-            await self.applySearchEvent(event, searchID: searchID, streamStatus: streamStatus)
+        do {
+            try await client.runSearchStream(
+                searchID: searchID,
+                body: SearchRunRequest(query: query, title: String(query.prefix(80)), type: "auto", numResults: 10)
+            ) { [weak self] event in
+                guard let self else { return }
+                await self.applySearchEvent(event, searchID: searchID, streamStatus: streamStatus)
+            }
+        } catch {
+            if shouldSuppressLifecycleTransportError(
+                error,
+                startedAt: streamLifecycleGeneration,
+                startedWhileInactive: streamStartedWhileInactive
+            ) {
+                SybilLog.info(SybilLog.app, "Suppressing search stream transport interruption after app lifecycle change")
+                if isAppActive {
+                    await refreshInterruptedStream(preferredSelection: .search(searchID))
+                }
+                return
+            }
+
+            throw error
         }
 
         if let streamError = await streamStatus.error() {
             throw APIError.httpError(statusCode: 502, message: streamError)
         }
 
-        await refreshCollections(preferredSelection: .search(searchID))
+        guard isAppActive else {
+            return
+        }
+
+        let sentSearchSelection = SidebarSelection.search(searchID)
+        let shouldKeepSentSearchSelected = selectedItem == sentSearchSelection && draftKind == nil
+        await refreshCollections(
+            preferredSelection: shouldKeepSentSearchSelected ? sentSearchSelection : selectedItem,
+            refreshSelection: false
+        )
     }
 
     private func applySearchEvent(
@@ -1024,8 +1338,10 @@ final class SybilViewModel {
         searchID: String,
         streamStatus: SearchStreamStatus
     ) async {
-        guard let current = selectedSearch, current.id == searchID else {
-            if case let .done(payload) = event {
+        guard let current = currentSelectedSearch, current.id == searchID else {
+            if case let .done(payload) = event,
+               selectedItem == .search(searchID),
+               draftKind == nil {
                 selectedSearch = payload.search
             }
             return
@@ -1132,6 +1448,22 @@ final class SybilViewModel {
         return nil
     }
 
+    private var currentSelectedChat: ChatDetail? {
+        guard case let .chat(chatID) = selectedItem,
+              selectedChat?.id == chatID else {
+            return nil
+        }
+        return selectedChat
+    }
+
+    private var currentSelectedSearch: SearchDetail? {
+        guard case let .search(searchID) = selectedItem,
+              selectedSearch?.id == searchID else {
+            return nil
+        }
+        return selectedSearch
+    }
+
     private var currentSearchID: String? {
         if draftKind == .search {
             return nil
@@ -1142,6 +1474,33 @@ final class SybilViewModel {
         return nil
     }
 
+    private var currentSendContext: ActiveSendContext {
+        if isSearchMode {
+            if let searchID = currentSearchID {
+                return .search(searchID)
+            }
+            return .draftSearch(draftIdentity)
+        }
+
+        if let chatID = currentChatID {
+            return .chat(chatID)
+        }
+        return .draftChat(draftIdentity)
+    }
+
+    private func isSendContextVisible(_ context: ActiveSendContext) -> Bool {
+        switch context {
+        case let .draftChat(identity):
+            return draftKind == .chat && draftIdentity == identity
+        case let .chat(chatID):
+            return selectedItem == .chat(chatID)
+        case let .draftSearch(identity):
+            return draftKind == .search && draftIdentity == identity
+        case let .search(searchID):
+            return selectedItem == .search(searchID)
+        }
+    }
+
     private func hasSelection(_ selection: SidebarSelection, chats: [ChatSummary], searches: [SearchSummary]) -> Bool {
         switch selection {
         case let .chat(chatID):
@@ -1250,6 +1609,57 @@ final class SybilViewModel {
         #endif
     }
 
+    private func refreshInterruptedStream(preferredSelection: SidebarSelection) async {
+        try? await Task.sleep(for: .milliseconds(150))
+        await refreshCollections(preferredSelection: preferredSelection)
+    }
+
+    private func shouldSuppressLifecycleTransportError(
+        _ error: Error,
+        startedAt generation: Int,
+        startedWhileInactive: Bool
+    ) -> Bool {
+        guard generation != appLifecycleGeneration || startedWhileInactive || !isAppActive else {
+            return false
+        }
+
+        return isTransientTransportInterruption(error)
+    }
+
+    private func shouldSuppressInactiveTransportError(_ error: Error) -> Bool {
+        !isAppActive && isTransientTransportInterruption(error)
+    }
+
+    private func isTransientTransportInterruption(_ error: Error) -> Bool {
+        if isCancellation(error) {
+            return true
+        }
+
+        if let apiError = error as? APIError,
+           case let .networkError(message) = apiError {
+            let lowercased = message.lowercased()
+            return lowercased.contains("network error -999")
+                || lowercased.contains("network error -1005")
+                || lowercased.contains("network connection was lost")
+                || lowercased.contains("software caused connection abort")
+                || lowercased.contains("socket is not connected")
+        }
+
+        let nsError = error as NSError
+        if nsError.domain == NSURLErrorDomain {
+            return nsError.code == URLError.cancelled.rawValue
+                || nsError.code == URLError.networkConnectionLost.rawValue
+                || nsError.code == URLError.notConnectedToInternet.rawValue
+                || nsError.code == URLError.timedOut.rawValue
+        }
+
+        if nsError.domain == NSPOSIXErrorDomain {
+            return nsError.code == 53 || nsError.code == 57
+        }
+
+        return false
+    }
+
     private func isCancellation(_ error: Error) -> Bool {
         if error is CancellationError {
             return true

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

@@ -1,14 +1,25 @@
+import ImageIO
 import Observation
 import PhotosUI
 import SwiftUI
 import UniformTypeIdentifiers
 import UIKit
 
+enum SybilWorkspaceNavigationLeadingControl {
+    case back
+    case hidden
+    case showSidebar
+}
+
 struct SybilWorkspaceView: View {
     @Bindable var viewModel: SybilViewModel
     var composerFocusRequest: Int = 0
+    var usesCustomWorkspaceNavigation: Bool = true
+    var navigationLeadingControl: SybilWorkspaceNavigationLeadingControl = .back
+    var onShowSidebar: (() -> Void)? = nil
     var onRequestNewChat: (() -> Void)? = nil
     @FocusState private var composerFocused: Bool
+    @Environment(\.dismiss) private var dismiss
     @State private var isShowingAttachmentOptions = false
     @State private var isShowingFileImporter = false
     @State private var isShowingPhotoPicker = false
@@ -23,6 +34,9 @@ struct SybilWorkspaceView: View {
     @State private var newChatSwipeDidTriggerHaptic = false
     @State private var newChatSwipeFeedbackGenerator: UIImpactFeedbackGenerator?
 
+    private let customWorkspaceNavigationContentInset: CGFloat = 96
+    private let composerOverlayContentInset: CGFloat = 112
+
     private var isSettingsSelected: Bool {
         if case .settings = viewModel.selectedItem {
             return true
@@ -34,6 +48,10 @@ struct SybilWorkspaceView: View {
         viewModel.errorMessage != nil
     }
 
+    private var showsCustomWorkspaceNavigation: Bool {
+        usesCustomWorkspaceNavigation && !isSettingsSelected
+    }
+
     private var transcriptScrollContextID: String {
         if viewModel.draftKind == .chat {
             return "draft-chat"
@@ -44,6 +62,14 @@ struct SybilWorkspaceView: View {
         return "chat:none"
     }
 
+    private var shouldAutoFocusComposer: Bool {
+        viewModel.draftKind == .chat && viewModel.displayedMessages.isEmpty
+    }
+
+    private var composerFocusPolicyID: String {
+        "\(transcriptScrollContextID):\(composerFocusRequest):\(shouldAutoFocusComposer)"
+    }
+
     private var canSwipeToCreateChat: Bool {
         guard onRequestNewChat != nil else {
             return false
@@ -84,16 +110,17 @@ struct SybilWorkspaceView: View {
         }
         .offset(x: newChatSwipeCompletionOffset)
         .background(SybilTheme.background)
-        .navigationTitle(viewModel.selectedTitle)
+        .navigationTitle(showsCustomWorkspaceNavigation ? "" : viewModel.selectedTitle)
         .navigationBarTitleDisplayMode(.inline)
         .toolbarRole(.editor)
+        .toolbar(showsCustomWorkspaceNavigation ? .hidden : .visible, for: .navigationBar)
         .toolbar {
-            if !isSettingsSelected {
+            if !isSettingsSelected && !showsCustomWorkspaceNavigation {
                 ToolbarItem(placement: .topBarTrailing) {
                     if viewModel.isSearchMode {
                         searchModeChip
                     } else {
-                        providerModelMenu
+                        providerModelToolbarMenu
                     }
                 }
             }
@@ -105,12 +132,24 @@ struct SybilWorkspaceView: View {
             }
             resetNewChatSwipe(animated: false)
         }
-        .task(id: composerFocusRequest) {
-            await focusComposerIfRequested()
+        .task(id: composerFocusPolicyID) {
+            await applyComposerFocusPolicy()
         }
     }
 
     private var workspaceContent: some View {
+        ZStack(alignment: .top) {
+            workspaceContentStack
+
+            if showsCustomWorkspaceNavigation {
+                SybilWorkspaceCharacterBackdrop(isBusy: viewModel.isSending)
+                    .allowsHitTesting(false)
+                customWorkspaceNavigationBar
+            }
+        }
+    }
+
+    private var workspaceContentStack: some View {
         VStack(spacing: 0) {
             if showsHeader {
                 header
@@ -119,15 +158,17 @@ struct SybilWorkspaceView: View {
                     .overlay(SybilTheme.border)
             }
 
-            Group {
+            ZStack(alignment: .bottom) {
                 if isSettingsSelected {
                     SybilSettingsView(viewModel: viewModel)
                 } else if viewModel.isSearchMode {
                     SybilSearchResultsView(
-                        search: viewModel.selectedSearch,
+                        search: viewModel.displayedSearch,
                         isLoading: viewModel.isLoadingSelection,
-                        isRunning: viewModel.isSending,
-                        isStartingChat: viewModel.isCreatingSearchChat
+                        isRunning: viewModel.isRunningVisibleSearch,
+                        isStartingChat: viewModel.isCreatingSearchChat,
+                        topContentInset: showsCustomWorkspaceNavigation ? customWorkspaceNavigationContentInset : 0,
+                        bottomContentInset: viewModel.showsComposer ? composerOverlayContentInset : 0
                     ) {
                         Task {
                             await viewModel.startChatFromSelectedSearch()
@@ -137,10 +178,16 @@ struct SybilWorkspaceView: View {
                     SybilChatTranscriptView(
                         messages: viewModel.displayedMessages,
                         isLoading: viewModel.isLoadingSelection,
-                        isSending: viewModel.isSending
+                        isSending: viewModel.isSendingVisibleChat,
+                        topContentInset: showsCustomWorkspaceNavigation ? customWorkspaceNavigationContentInset : 0,
+                        bottomContentInset: viewModel.showsComposer ? composerOverlayContentInset : 0
                     )
                     .id(transcriptScrollContextID)
                 }
+
+                if viewModel.showsComposer {
+                    composerBar
+                }
             }
             .frame(maxWidth: .infinity, maxHeight: .infinity)
             .background {
@@ -161,12 +208,55 @@ struct SybilWorkspaceView: View {
                     }
                 )
             }
+        }
+    }
 
-            if viewModel.showsComposer {
-                Divider()
-                    .overlay(SybilTheme.border)
-                composerBar
+    private var customWorkspaceNavigationBar: some View {
+        HStack(spacing: 14) {
+            workspaceNavigationLeadingControl
+
+            Text(viewModel.selectedTitle)
+                .font(.sybil(size: 16, weight: .semibold))
+                .foregroundStyle(SybilTheme.text)
+                .lineLimit(1)
+                .minimumScaleFactor(0.78)
+                .frame(maxWidth: .infinity, alignment: .leading)
+                .multilineTextAlignment(.leading)
+
+            workspaceNavigationTrailingControl
+        }
+        .padding(.horizontal, 16)
+        .padding(.top, 10)
+        .padding(.bottom, 34)
+        .background(alignment: .top) {
+            SybilNavigationFadeBackground()
+                .allowsHitTesting(false)
+        }
+    }
+
+    @ViewBuilder
+    private var workspaceNavigationLeadingControl: some View {
+        switch navigationLeadingControl {
+        case .back:
+            Button {
+                dismiss()
+            } label: {
+                SybilNavigationIcon(systemImage: "chevron.left")
             }
+            .buttonStyle(.plain)
+            .accessibilityLabel("Back")
+
+        case .showSidebar:
+            Button {
+                onShowSidebar?()
+            } label: {
+                SybilNavigationIcon(systemImage: "sidebar.left")
+            }
+            .buttonStyle(.plain)
+            .accessibilityLabel("Show sidebar")
+
+        case .hidden:
+            EmptyView()
         }
     }
 
@@ -264,15 +354,13 @@ struct SybilWorkspaceView: View {
     }
 
     @MainActor
-    private func focusComposerIfRequested() async {
-        guard composerFocusRequest > 0 else {
+    private func applyComposerFocusPolicy() async {
+        guard shouldAutoFocusComposer else {
+            composerFocused = false
             return
         }
 
-        await Task.yield()
-        try? await Task.sleep(for: .milliseconds(80))
-
-        guard viewModel.showsComposer, !viewModel.isSearchMode else {
+        guard shouldAutoFocusComposer, viewModel.showsComposer else {
             return
         }
         composerFocused = true
@@ -292,34 +380,8 @@ struct SybilWorkspaceView: View {
         .background(SybilTheme.panelGradient.opacity(0.58))
     }
 
-    private var providerModelMenu: some View {
-        Menu {
-            Text("\(viewModel.provider.displayName) • \(viewModel.model)")
-                .font(.sybil(.caption))
-
-            Divider()
-
-            ForEach(Provider.allCases, id: \.self) { candidate in
-                Menu(candidate.displayName) {
-                    let models = viewModel.modelOptions(for: candidate)
-                    if models.isEmpty {
-                        Text("No models")
-                    } else {
-                        ForEach(models, id: \.self) { candidateModel in
-                            Button {
-                                viewModel.setProvider(candidate, model: candidateModel)
-                            } label: {
-                                if viewModel.provider == candidate && viewModel.model == candidateModel {
-                                    Label(candidateModel, systemImage: "checkmark")
-                                } else {
-                                    Text(candidateModel)
-                                }
-                            }
-                        }
-                    }
-                }
-            }
-        } label: {
+    private var providerModelToolbarMenu: some View {
+        providerModelMenu {
             Image(systemName: "ellipsis")
                 .font(.system(size: 18, weight: .semibold))
                 .foregroundStyle(SybilTheme.text)
@@ -333,9 +395,68 @@ struct SybilWorkspaceView: View {
                         .stroke(SybilTheme.border.opacity(0.82), lineWidth: 1)
                 )
         }
+    }
+
+    private var providerModelNavigationMenu: some View {
+        providerModelMenu {
+            SybilNavigationIcon(systemImage: "ellipsis")
+        }
+    }
+
+    @ViewBuilder
+    private var workspaceNavigationTrailingControl: some View {
+        if viewModel.isSearchMode {
+            searchModeNavigationLabel
+        } else {
+            providerModelNavigationMenu
+        }
+    }
+
+    private var searchModeNavigationLabel: some View {
+        Label("Search", systemImage: "globe")
+            .font(.sybil(.caption, weight: .medium))
+            .foregroundStyle(SybilTheme.accent)
+            .lineLimit(1)
+    }
+
+    private func providerModelMenu<Label: View>(@ViewBuilder label: @escaping () -> Label) -> some View {
+        Menu {
+            providerModelMenuItems
+        } label: {
+            label()
+        }
         .accessibilityLabel("Provider and model")
     }
 
+    @ViewBuilder
+    private var providerModelMenuItems: some View {
+        Text("\(viewModel.provider.displayName) • \(viewModel.model)")
+            .font(.sybil(.caption))
+
+        Divider()
+
+        ForEach(Provider.allCases, id: \.self) { candidate in
+            Menu(candidate.displayName) {
+                let models = viewModel.modelOptions(for: candidate)
+                if models.isEmpty {
+                    Text("No models")
+                } else {
+                    ForEach(models, id: \.self) { candidateModel in
+                        Button {
+                            viewModel.setProvider(candidate, model: candidateModel)
+                        } label: {
+                            if viewModel.provider == candidate && viewModel.model == candidateModel {
+                                Label(candidateModel, systemImage: "checkmark")
+                            } else {
+                                Text(candidateModel)
+                            }
+                        }
+                    }
+                }
+            }
+        }
+    }
+
     private var searchModeChip: some View {
         Label("Search", systemImage: "globe")
             .font(.sybil(.caption, weight: .medium))
@@ -387,7 +508,7 @@ struct SybilWorkspaceView: View {
                 }
 
                 TextField(
-                    viewModel.isSearchMode ? "Search the web" : "Message Sybil",
+                    viewModel.isSearchMode ? "Search the web" : "Enter Prompt",
                     text: $viewModel.composer,
                     axis: .vertical
                 )
@@ -397,26 +518,19 @@ struct SybilWorkspaceView: View {
                 .lineLimit(1 ... 6)
                 .submitLabel(.send)
                 .onSubmit {
-                    Task {
-                        await viewModel.sendComposer()
-                    }
+                    submitComposer()
                 }
                 .padding(.horizontal, 12)
                 .padding(.vertical, 10)
                 .background(
                     RoundedRectangle(cornerRadius: 12)
                         .fill(SybilTheme.composerGradient)
-                        .overlay(
-                            RoundedRectangle(cornerRadius: 12)
-                                .stroke(SybilTheme.primary.opacity(0.34), lineWidth: 1)
-                        )
+                        .opacity(0.98)
                 )
                 .foregroundStyle(SybilTheme.text)
 
                 Button {
-                    Task {
-                        await viewModel.sendComposer()
-                    }
+                    submitComposer()
                 } label: {
                     Image(systemName: viewModel.isSearchMode ? "magnifyingglass" : "arrow.up")
                         .font(.system(size: 17, weight: .semibold))
@@ -436,23 +550,19 @@ struct SybilWorkspaceView: View {
             }
         }
         .padding(.horizontal, 14)
-        .padding(.vertical, 12)
-        .background(
-            LinearGradient(
-                colors: [
-                    SybilTheme.background.opacity(0.18),
-                    SybilTheme.background.opacity(0.96)
-                ],
-                startPoint: .top,
-                endPoint: .bottom
-            )
-        )
+        .padding(.top, 34)
+        .padding(.bottom, 12)
+        .background(alignment: .bottom) {
+            SybilComposerFadeBackground()
+                .allowsHitTesting(false)
+        }
         .overlay {
             if isComposerDropTargeted && !viewModel.isSearchMode {
                 RoundedRectangle(cornerRadius: 18)
                     .stroke(SybilTheme.accent.opacity(0.78), style: StrokeStyle(lineWidth: 1.5, dash: [7, 5]))
                     .padding(.horizontal, 14)
-                    .padding(.vertical, 10)
+                    .padding(.top, 32)
+                    .padding(.bottom, 10)
             }
         }
         .onDrop(of: [UTType.fileURL.identifier, UTType.image.identifier], isTargeted: $isComposerDropTargeted) { providers in
@@ -527,6 +637,22 @@ struct SybilWorkspaceView: View {
         }
     }
 
+    private func submitComposer() {
+        guard viewModel.canSendComposer else {
+            return
+        }
+
+        #if !targetEnvironment(macCatalyst)
+        if !viewModel.isSearchMode {
+            composerFocused = false
+        }
+        #endif
+
+        Task {
+            await viewModel.sendComposer()
+        }
+    }
+
     @MainActor
     private func importAttachmentsFromItemProviders(_ providers: [NSItemProvider]) async {
         do {
@@ -856,6 +982,274 @@ private extension UIView {
     }
 }
 
+private struct SybilComposerFadeBackground: View {
+    var body: some View {
+        ZStack(alignment: .bottomLeading) {
+            LinearGradient(
+                colors: [
+                    Color.clear,
+                    SybilTheme.background.opacity(0.30),
+                    SybilTheme.background.opacity(0.86),
+                    SybilTheme.background.opacity(0.86),
+                    SybilTheme.background.opacity(0.98)
+                ],
+                startPoint: .top,
+                endPoint: .bottom
+            )
+
+            LinearGradient(
+                colors: [
+                    SybilTheme.primary.opacity(0.18),
+                    SybilTheme.surface.opacity(0.16),
+                    SybilTheme.accent.opacity(0.08)
+                ],
+                startPoint: .topLeading,
+                endPoint: .bottomTrailing
+            )
+            .mask(
+                LinearGradient(
+                    colors: [
+                        Color.clear,
+                        Color.black.opacity(0.42),
+                        Color.black
+                    ],
+                    startPoint: .top,
+                    endPoint: .bottom
+                )
+            )
+            .blendMode(.screen)
+
+            RadialGradient(
+                colors: [
+                    SybilTheme.primary.opacity(0.28),
+                    SybilTheme.primary.opacity(0.08),
+                    Color.clear
+                ],
+                center: .bottomLeading,
+                startRadius: 8,
+                endRadius: 180
+            )
+            .blendMode(.screen)
+            .offset(x: -42, y: 42)
+        }
+        .ignoresSafeArea(edges: .bottom)
+    }
+}
+
+private struct SybilNavigationIcon: View {
+    var systemImage: String
+
+    var body: some View {
+        Image(systemName: systemImage)
+            .font(.system(size: 21, weight: .semibold, design: .rounded))
+            .foregroundStyle(SybilTheme.text)
+            .frame(width: 46, height: 46)
+            .contentShape(Rectangle())
+            .shadow(color: SybilTheme.primary.opacity(0.34), radius: 12, x: 0, y: 0)
+    }
+}
+
+private struct SybilNavigationFadeBackground: View {
+    var body: some View {
+        ZStack(alignment: .topLeading) {
+            LinearGradient(
+                colors: [
+                    SybilTheme.background.opacity(1.0),
+                    SybilTheme.background.opacity(0.90),
+                    SybilTheme.background.opacity(0.80),
+                    SybilTheme.background.opacity(0.80),
+                    SybilTheme.background.opacity(0.28),
+                    Color.clear
+                ],
+                startPoint: .top,
+                endPoint: .bottom
+            )
+
+            RadialGradient(
+                colors: [
+                    SybilTheme.primary.opacity(0.36),
+                    SybilTheme.primary.opacity(0.10),
+                    Color.clear
+                ],
+                center: .topLeading,
+                startRadius: 6,
+                endRadius: 210
+            )
+            .blendMode(.screen)
+            .offset(x: -44, y: -46)
+        }
+        .frame(height: 200.0)
+        .ignoresSafeArea(edges: .top)
+    }
+}
+
+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
@@ -913,15 +1307,10 @@ private struct NewChatSwipeBackdrop: View {
                     .frame(width: 72, height: 72)
                     .blur(radius: 10)
 
-                Image(systemName: hasLatched ? "checkmark" : "plus")
+                Image(systemName: "plus")
                     .font(.system(size: 31, weight: .bold, design: .rounded))
                     .foregroundStyle(SybilTheme.text)
                     .symbolEffect(.bounce, value: hasLatched)
-
-                Image(systemName: "sparkle")
-                    .font(.system(size: 11, weight: .semibold))
-                    .foregroundStyle((hasLatched ? SybilTheme.accent : SybilTheme.primary).opacity(0.90))
-                    .offset(x: -26, y: -25)
             }
             .frame(width: 92, height: 92)
             .background(

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

@@ -17,25 +17,52 @@ private actor MockSybilClient: SybilAPIClienting {
     private let searchesResponse: [SearchSummary]
     private let chatDetails: [String: ChatDetail]
     private let searchDetails: [String: SearchDetail]
+    private let createChatResponse: ChatSummary?
 
     private var snapshot = MockClientCallSnapshot()
+    private var getChatDelayNanoseconds: UInt64 = 0
+    private var getSearchDelayNanoseconds: UInt64 = 0
+    private var completionStreamNetworkErrorMessage: String?
+    private var completionStreamDelayNanoseconds: UInt64 = 0
+    private var searchStreamNetworkErrorMessage: String?
+    private var searchStreamDelayNanoseconds: UInt64 = 0
 
     init(
         chatsResponse: [ChatSummary] = [],
         searchesResponse: [SearchSummary] = [],
         chatDetails: [String: ChatDetail] = [:],
-        searchDetails: [String: SearchDetail] = [:]
+        searchDetails: [String: SearchDetail] = [:],
+        createChatResponse: ChatSummary? = nil
     ) {
         self.chatsResponse = chatsResponse
         self.searchesResponse = searchesResponse
         self.chatDetails = chatDetails
         self.searchDetails = searchDetails
+        self.createChatResponse = createChatResponse
     }
 
     func currentSnapshot() -> MockClientCallSnapshot {
         snapshot
     }
 
+    func setCompletionStreamNetworkError(_ message: String, delayNanoseconds: UInt64 = 0) {
+        completionStreamNetworkErrorMessage = message
+        completionStreamDelayNanoseconds = delayNanoseconds
+    }
+
+    func setGetChatDelay(_ delayNanoseconds: UInt64) {
+        getChatDelayNanoseconds = delayNanoseconds
+    }
+
+    func setGetSearchDelay(_ delayNanoseconds: UInt64) {
+        getSearchDelayNanoseconds = delayNanoseconds
+    }
+
+    func setSearchStreamNetworkError(_ message: String, delayNanoseconds: UInt64 = 0) {
+        searchStreamNetworkErrorMessage = message
+        searchStreamDelayNanoseconds = delayNanoseconds
+    }
+
     func verifySession() async throws -> AuthSession {
         AuthSession(authenticated: true, mode: "open")
     }
@@ -46,11 +73,17 @@ private actor MockSybilClient: SybilAPIClienting {
     }
 
     func createChat(title: String?) async throws -> ChatSummary {
+        if let createChatResponse {
+            return createChatResponse
+        }
         throw UnexpectedClientCall()
     }
 
     func getChat(chatID: String) async throws -> ChatDetail {
         snapshot.getChat += 1
+        if getChatDelayNanoseconds > 0 {
+            try await Task.sleep(nanoseconds: getChatDelayNanoseconds)
+        }
         guard let detail = chatDetails[chatID] else {
             throw UnexpectedClientCall()
         }
@@ -76,6 +109,9 @@ private actor MockSybilClient: SybilAPIClienting {
 
     func getSearch(searchID: String) async throws -> SearchDetail {
         snapshot.getSearch += 1
+        if getSearchDelayNanoseconds > 0 {
+            try await Task.sleep(nanoseconds: getSearchDelayNanoseconds)
+        }
         guard let detail = searchDetails[searchID] else {
             throw UnexpectedClientCall()
         }
@@ -98,6 +134,12 @@ private actor MockSybilClient: SybilAPIClienting {
         body: CompletionStreamRequest,
         onEvent: @escaping @Sendable (CompletionStreamEvent) async -> Void
     ) async throws {
+        if completionStreamDelayNanoseconds > 0 {
+            try await Task.sleep(nanoseconds: completionStreamDelayNanoseconds)
+        }
+        if let completionStreamNetworkErrorMessage {
+            throw APIError.networkError(message: completionStreamNetworkErrorMessage)
+        }
         throw UnexpectedClientCall()
     }
 
@@ -106,6 +148,12 @@ private actor MockSybilClient: SybilAPIClienting {
         body: SearchRunRequest,
         onEvent: @escaping @Sendable (SearchStreamEvent) async -> Void
     ) async throws {
+        if searchStreamDelayNanoseconds > 0 {
+            try await Task.sleep(nanoseconds: searchStreamDelayNanoseconds)
+        }
+        if let searchStreamNetworkErrorMessage {
+            throw APIError.networkError(message: searchStreamNetworkErrorMessage)
+        }
         throw UnexpectedClientCall()
     }
 }
@@ -267,6 +315,178 @@ private func makeSearchDetail(id: String, date: Date, answer: String) -> SearchD
     #expect(viewModel.selectedSearch?.answerText == "fresh answer")
 }
 
+@MainActor
+@Test func selectingChatClearsStaleTranscriptUntilNewDetailLoads() async throws {
+    let date = Date(timeIntervalSince1970: 1_700_000_210)
+    let staleDetail = makeChatDetail(id: "chat-old", date: date, body: "stale transcript")
+    let freshDetail = makeChatDetail(id: "chat-new", date: date, body: "fresh transcript")
+    let client = MockSybilClient(chatDetails: ["chat-new": freshDetail])
+    await client.setGetChatDelay(50_000_000)
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    viewModel.isCheckingSession = false
+    viewModel.selectedItem = .chat("chat-old")
+    viewModel.selectedChat = staleDetail
+
+    viewModel.select(.chat("chat-new"))
+
+    #expect(viewModel.displayedMessages.isEmpty)
+    #expect(viewModel.isLoadingSelection)
+
+    try await Task.sleep(nanoseconds: 90_000_000)
+
+    #expect(viewModel.displayedMessages.first?.content == "fresh transcript")
+    #expect(!viewModel.isLoadingSelection)
+}
+
+@MainActor
+@Test func navigationSelectionWaitsForFastTranscriptLoad() async throws {
+    let date = Date(timeIntervalSince1970: 1_700_000_220)
+    let detail = makeChatDetail(id: "chat-fast", date: date, body: "loaded before push")
+    let client = MockSybilClient(chatDetails: ["chat-fast": detail])
+    await client.setGetChatDelay(20_000_000)
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    viewModel.isCheckingSession = false
+
+    await viewModel.selectForNavigation(.chat("chat-fast"), preloadTimeout: .milliseconds(500))
+
+    #expect(viewModel.selectedItem == .chat("chat-fast"))
+    #expect(viewModel.displayedMessages.first?.content == "loaded before push")
+    #expect(!viewModel.isLoadingSelection)
+}
+
+@MainActor
+@Test func navigationSelectionTimesOutAndKeepsLoadingTranscript() async throws {
+    let date = Date(timeIntervalSince1970: 1_700_000_230)
+    let detail = makeChatDetail(id: "chat-slow", date: date, body: "loaded after push")
+    let client = MockSybilClient(chatDetails: ["chat-slow": detail])
+    await client.setGetChatDelay(100_000_000)
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    viewModel.isCheckingSession = false
+
+    await viewModel.selectForNavigation(.chat("chat-slow"), preloadTimeout: .milliseconds(10))
+
+    #expect(viewModel.selectedItem == .chat("chat-slow"))
+    #expect(viewModel.displayedMessages.isEmpty)
+    #expect(viewModel.isLoadingSelection)
+
+    try await Task.sleep(nanoseconds: 150_000_000)
+
+    #expect(viewModel.displayedMessages.first?.content == "loaded after push")
+    #expect(!viewModel.isLoadingSelection)
+}
+
+@MainActor
+@Test func newDraftChatDoesNotShowTypingStateFromPreviousSend() async throws {
+    let date = Date(timeIntervalSince1970: 1_700_000_240)
+    let detail = makeChatDetail(id: "chat-typing", date: date, body: "existing transcript")
+    let client = MockSybilClient(chatDetails: ["chat-typing": detail])
+    await client.setCompletionStreamNetworkError(
+        "Network error -1005 while requesting POST: The network connection was lost.",
+        delayNanoseconds: 50_000_000
+    )
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    viewModel.isCheckingSession = false
+    viewModel.selectedItem = .chat("chat-typing")
+    viewModel.selectedChat = detail
+    viewModel.composer = "continue"
+
+    let sendTask = Task {
+        await viewModel.sendComposer()
+    }
+    try await Task.sleep(nanoseconds: 10_000_000)
+
+    #expect(viewModel.isSendingVisibleChat)
+
+    viewModel.startNewChat()
+
+    #expect(viewModel.displayedMessages.isEmpty)
+    #expect(!viewModel.isSendingVisibleChat)
+
+    await sendTask.value
+}
+
+@MainActor
+@Test func backgroundChatStreamInterruptionIsSuppressedUntilForegroundRefresh() async throws {
+    let date = Date(timeIntervalSince1970: 1_700_000_300)
+    let chat = makeChatSummary(id: "chat-3", date: date)
+    let initialDetail = makeChatDetail(id: "chat-3", date: date, body: "stale transcript")
+    let refreshedDetail = makeChatDetail(id: "chat-3", date: date, body: "fresh transcript")
+    let client = MockSybilClient(
+        chatsResponse: [chat],
+        chatDetails: ["chat-3": refreshedDetail]
+    )
+    await client.setCompletionStreamNetworkError(
+        "Network error -1005 while requesting POST: The network connection was lost.",
+        delayNanoseconds: 50_000_000
+    )
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    viewModel.isCheckingSession = false
+    viewModel.selectedItem = .chat("chat-3")
+    viewModel.selectedChat = initialDetail
+    viewModel.composer = "continue"
+
+    let sendTask = Task {
+        await viewModel.sendComposer()
+    }
+    try await Task.sleep(nanoseconds: 10_000_000)
+    viewModel.markAppInactiveForNetwork()
+    await sendTask.value
+
+    #expect(viewModel.errorMessage == nil)
+    #expect(viewModel.composer.isEmpty)
+    #expect(!viewModel.isSending)
+    #expect(viewModel.selectedChat?.messages.first?.content == "stale transcript")
+
+    await viewModel.refreshAfterAppBecameActive(refreshCollections: false, refreshSelection: true)
+
+    let snapshot = await client.currentSnapshot()
+    #expect(snapshot.getChat == 1)
+    #expect(viewModel.errorMessage == nil)
+    #expect(viewModel.selectedChat?.messages.first?.content == "fresh transcript")
+}
+
+@MainActor
+@Test func backgroundSearchStreamInterruptionIsSuppressedUntilForegroundRefresh() async throws {
+    let date = Date(timeIntervalSince1970: 1_700_000_400)
+    let refreshedDetail = makeSearchDetail(id: "search-3", date: date, answer: "fresh answer")
+    let client = MockSybilClient(
+        searchDetails: ["search-3": refreshedDetail]
+    )
+    await client.setSearchStreamNetworkError(
+        "Network error -1005 while requesting POST: The network connection was lost.",
+        delayNanoseconds: 50_000_000
+    )
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    viewModel.isCheckingSession = false
+    viewModel.selectedItem = .search("search-3")
+    viewModel.selectedSearch = makeSearchDetail(id: "search-3", date: date, answer: "stale answer")
+    viewModel.composer = "refresh me"
+
+    let sendTask = Task {
+        await viewModel.sendComposer()
+    }
+    try await Task.sleep(nanoseconds: 10_000_000)
+    viewModel.markAppInactiveForNetwork()
+    await sendTask.value
+
+    #expect(viewModel.errorMessage == nil)
+    #expect(viewModel.composer.isEmpty)
+    #expect(!viewModel.isSending)
+
+    await viewModel.refreshAfterAppBecameActive(refreshCollections: false, refreshSelection: true)
+
+    let snapshot = await client.currentSnapshot()
+    #expect(snapshot.getSearch == 1)
+    #expect(viewModel.errorMessage == nil)
+    #expect(viewModel.selectedSearch?.answerText == "fresh answer")
+}
+
 @Test func newChatSwipeMetricsClampProgressAndLatch() async throws {
     let width: CGFloat = 390
     let maxTravel = NewChatSwipeMetrics.maxTravel(for: width)

ios/justfile

@@ -1,10 +1,28 @@
+simulator := "platform=iOS Simulator,name=iPhone 16e,OS=latest"
+simulator_name := "iPhone 16e"
+derived_data := "build/DerivedData"
+
 default:
   @just build
 
 build:
   if [ ! -d "Sybil.xcodeproj" ]; then xcodegen --spec project.yml; fi
   if command -v xcbeautify >/dev/null 2>&1; then \
-    xcodebuild -scheme Sybil -destination 'platform=iOS Simulator,name=iPhone 16e,OS=latest' | xcbeautify; \
+    xcodebuild -scheme Sybil -destination '{{simulator}}' | xcbeautify; \
   else \
-    xcodebuild -scheme Sybil -destination 'platform=iOS Simulator,name=iPhone 16e,OS=latest'; \
+    xcodebuild -scheme Sybil -destination '{{simulator}}'; \
   fi
+
+test:
+  cd Packages/Sybil && xcodebuild test -scheme Sybil -destination '{{simulator}}' -parallel-testing-enabled NO
+
+run:
+  if [ ! -d "Sybil.xcodeproj" ]; then xcodegen --spec project.yml; fi
+  xcrun simctl boot '{{simulator_name}}' 2>/dev/null || true
+  xcodebuild -scheme Sybil -destination '{{simulator}}' -derivedDataPath '{{derived_data}}'
+  xcrun simctl install booted '{{derived_data}}/Build/Products/Debug-iphonesimulator/Sybil.app'
+  xcrun simctl launch booted net.buzzert.sybil2
+
+screenshot path="build/sybil-screenshot.png":
+  mkdir -p "$(dirname '{{path}}')"
+  xcrun simctl io booted screenshot '{{path}}'

web/src/App.tsx

@@ -7,6 +7,7 @@ import { AuthScreen } from "@/components/auth/auth-screen";
 import { ChatAttachmentList } from "@/components/chat/chat-attachment-list";
 import { ChatMessagesPanel } from "@/components/chat/chat-messages-panel";
 import { SearchResultsPanel } from "@/components/search/search-results-panel";
+import { SybilCharacter } from "@/components/sybil-character";
 import {
   createChat,
   createChatFromSearch,
@@ -1989,14 +1990,20 @@ export default function App() {
             isMobileSidebarOpen ? "translate-x-0" : "-translate-x-full md:translate-x-0"
           )}
         >
-          <div className="px-4 pb-4 pt-5">
-            <div className="sybil-wordmark bg-[linear-gradient(90deg,#ff8df8,#9a6dff_54%,#67dfff)] bg-clip-text text-3xl text-transparent">
-              SYBIL
+          <div className="relative min-h-24 px-4 pb-4 pt-5">
+            <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 ? ` (${authMode === "open" ? "open mode" : "token mode"})` : ""}
+              </p>
             </div>
-            <p className="mt-2 flex items-center gap-1.5 text-xs font-medium text-muted-foreground">
-              <span className="h-1.5 w-1.5 rounded-full bg-emerald-400" />
-              Sybil Web{authMode ? ` (${authMode === "open" ? "open mode" : "token mode"})` : ""}
-            </p>
+            <SybilCharacter
+              className="absolute right-4 top-3 h-[calc(100%-1.5rem)]"
+              isBusy={isSending}
+            />
           </div>
 
           <div className="space-y-3 px-3 pb-3">
@@ -2246,7 +2253,7 @@ export default function App() {
                     void handleSend();
                   }
                 }}
-                placeholder={isSearchMode ? "Search the web" : "Message Sybil..."}
+                placeholder={isSearchMode ? "Search the web" : "Enter prompt..."}
                 className="max-h-40 min-h-0 resize-none overflow-y-auto border-0 bg-transparent px-3 py-3 text-base text-violet-50 shadow-none placeholder:text-violet-200/45 focus-visible:ring-0"
                 disabled={isSending}
               />

web/src/components/sybil-character.tsx

@@ -0,0 +1,31 @@
+import { useEffect } from "preact/hooks";
+import { cn } from "@/lib/utils";
+
+const CHARACTER_IDLE_SRC = "/character-idle.gif";
+const CHARACTER_BUSY_SRC = "/character-busy.gif";
+
+type SybilCharacterProps = {
+  className?: string;
+  isBusy?: boolean;
+};
+
+export function SybilCharacter({ className, isBusy = false }: SybilCharacterProps) {
+  useEffect(() => {
+    const busyImage = new Image();
+    busyImage.src = CHARACTER_BUSY_SRC;
+  }, []);
+
+  return (
+    <img
+      aria-hidden="true"
+      alt=""
+      className={cn(
+        "aspect-square rounded-xl border border-violet-200/24 bg-white/6 object-cover p-1 shadow-[inset_0_1px_0_hsl(252_90%_86%/0.12),0_10px_24px_hsl(240_80%_2%/0.3)]",
+        className
+      )}
+      data-state={isBusy ? "busy" : "idle"}
+      draggable={false}
+      src={isBusy ? CHARACTER_BUSY_SRC : CHARACTER_IDLE_SRC}
+    />
+  );
+}

web/src/index.css

@@ -4,6 +4,14 @@
 @tailwind components;
 @tailwind utilities;
 
+@font-face {
+  font-family: "StalinistOne";
+  src: url("/StalinistOne-Regular.ttf") format("truetype");
+  font-weight: 400;
+  font-style: normal;
+  font-display: swap;
+}
+
 :root {
   color-scheme: dark;
   --background: 235 45% 4%;
@@ -57,8 +65,8 @@ textarea {
 }
 
 .sybil-wordmark {
-  font-family: "Orbitron", "Inter", sans-serif;
-  font-weight: 900;
+  font-family: "StalinistOne", "Orbitron", "Inter", sans-serif;
+  font-weight: 400;
   letter-spacing: 0;
   line-height: 1;
 }
@@ -184,7 +192,13 @@ textarea {
   margin-top: 0.65rem;
   margin-left: 0;
   padding-left: 0;
-  list-style-position: inside;
+  list-style: none;
+}
+
+.md-content li > ul,
+.md-content li > ol {
+  margin-top: 0.3rem;
+  padding-left: 1.35rem;
 }
 
 .md-content li + li {

web/tsconfig.tsbuildinfo

@@ -1 +1 @@
-{"root":["./src/app.tsx","./src/main.tsx","./src/root-router.tsx","./src/vite-env.d.ts","./src/components/auth/auth-screen.tsx","./src/components/chat/chat-attachment-list.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/utils.ts","./src/pages/search-route-page.tsx"],"version":"5.9.3"}
+{"root":["./src/app.tsx","./src/main.tsx","./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-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/utils.ts","./src/pages/search-route-page.tsx"],"version":"5.9.3"}