add Character animations

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

@@ -72,19 +72,22 @@ 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
             }

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

@@ -5,6 +5,7 @@ struct SybilChatTranscriptView: View {
     var messages: [Message]
     var isLoading: Bool
     var isSending: Bool
+    var topContentInset: CGFloat = 0
     @State private var hasHandledInitialTranscriptScroll = false
 
     private var hasPendingAssistant: Bool {
@@ -48,7 +49,8 @@ struct SybilChatTranscriptView: View {
                 }
                 .frame(maxWidth: .infinity, alignment: .leading)
                 .padding(.horizontal, 14)
-                .padding(.vertical, 18)
+                .padding(.top, 18 + topContentInset)
+                .padding(.bottom, 18)
             }
             .frame(maxWidth: .infinity, alignment: .leading)
             .scrollDismissesKeyboard(.interactively)

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

@@ -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
             }
@@ -259,7 +262,11 @@ private struct SybilPhoneDestinationView: View {
     let route: PhoneRoute
 
     var body: some View {
-        SybilWorkspaceView(viewModel: viewModel, composerFocusRequest: composerFocusRequest) {
+        SybilWorkspaceView(
+            viewModel: viewModel,
+            composerFocusRequest: composerFocusRequest,
+            usesCustomChatNavigation: route.isChatTranscript
+        ) {
             viewModel.startNewChat()
             composerFocusRequest += 1
             if path.isEmpty {
@@ -290,3 +297,14 @@ private struct SybilPhoneDestinationView: View {
         }
     }
 }
+
+private extension PhoneRoute {
+    var isChatTranscript: Bool {
+        switch self {
+        case .chat, .draftChat:
+            return true
+        case .search, .draftSearch, .settings:
+            return false
+        }
+    }
+}

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

@@ -104,6 +104,10 @@ final class SybilViewModel {
     @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]] = [
@@ -502,6 +506,38 @@ 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
@@ -729,6 +765,7 @@ final class SybilViewModel {
                 SybilLog.app,
                 "Refreshed collections: \(nextChats.count) chats, \(nextSearches.count) searches"
             )
+            errorMessage = nil
 
             if case .settings = selectedItem {
                 isLoadingCollections = false
@@ -749,8 +786,12 @@ 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
@@ -789,9 +830,12 @@ final class SybilViewModel {
                 case .settings:
                     break
                 }
+                errorMessage = nil
             } catch {
                 if isCancellation(error) {
                     SybilLog.debug(SybilLog.app, "Selection refresh cancelled for \(selectedItem.id)")
+                } else if shouldSuppressInactiveTransportError(error) {
+                    SybilLog.info(SybilLog.app, "Suppressing selection refresh transport interruption while app is inactive")
                 } else {
                     errorMessage = normalizeAPIError(error)
                     SybilLog.error(SybilLog.app, "Selection refresh failed", error: error)
@@ -882,6 +926,8 @@ 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) {
             Task { [weak self] in
@@ -917,24 +963,63 @@ 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)
         }
 
+        guard isAppActive else {
+            pendingChatState = nil
+            return
+        }
+
         await refreshCollections(preferredSelection: .chat(chatID))
-        selectedChat = try await client.getChat(chatID: chatID)
+        do {
+            selectedChat = try await client.getChat(chatID: chatID)
+        } 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
     }
 
@@ -1003,19 +1088,41 @@ final class SybilViewModel {
         )
 
         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)
         }
 
+        guard isAppActive else {
+            return
+        }
+
         await refreshCollections(preferredSelection: .search(searchID))
     }
 
@@ -1250,6 +1357,57 @@ 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

@@ -1,3 +1,4 @@
+import ImageIO
 import Observation
 import PhotosUI
 import SwiftUI
@@ -7,8 +8,10 @@ import UIKit
 struct SybilWorkspaceView: View {
     @Bindable var viewModel: SybilViewModel
     var composerFocusRequest: Int = 0
+    var usesCustomChatNavigation: Bool = false
     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 +26,8 @@ struct SybilWorkspaceView: View {
     @State private var newChatSwipeDidTriggerHaptic = false
     @State private var newChatSwipeFeedbackGenerator: UIImpactFeedbackGenerator?
 
+    private let customChatNavigationContentInset: CGFloat = 96
+
     private var isSettingsSelected: Bool {
         if case .settings = viewModel.selectedItem {
             return true
@@ -34,6 +39,10 @@ struct SybilWorkspaceView: View {
         viewModel.errorMessage != nil
     }
 
+    private var showsCustomChatNavigation: Bool {
+        usesCustomChatNavigation && !isSettingsSelected && !viewModel.isSearchMode
+    }
+
     private var transcriptScrollContextID: String {
         if viewModel.draftKind == .chat {
             return "draft-chat"
@@ -84,16 +93,17 @@ struct SybilWorkspaceView: View {
         }
         .offset(x: newChatSwipeCompletionOffset)
         .background(SybilTheme.background)
-        .navigationTitle(viewModel.selectedTitle)
+        .navigationTitle(showsCustomChatNavigation ? "" : viewModel.selectedTitle)
         .navigationBarTitleDisplayMode(.inline)
         .toolbarRole(.editor)
+        .toolbar(showsCustomChatNavigation ? .hidden : .visible, for: .navigationBar)
         .toolbar {
-            if !isSettingsSelected {
+            if !isSettingsSelected && !showsCustomChatNavigation {
                 ToolbarItem(placement: .topBarTrailing) {
                     if viewModel.isSearchMode {
                         searchModeChip
                     } else {
-                        providerModelMenu
+                        providerModelToolbarMenu
                     }
                 }
             }
@@ -111,6 +121,18 @@ struct SybilWorkspaceView: View {
     }
 
     private var workspaceContent: some View {
+        ZStack(alignment: .top) {
+            workspaceContentStack
+
+            if showsCustomChatNavigation {
+                SybilChatCharacterBackdrop(isBusy: viewModel.isSending)
+                    .allowsHitTesting(false)
+                customChatNavigationBar
+            }
+        }
+    }
+
+    private var workspaceContentStack: some View {
         VStack(spacing: 0) {
             if showsHeader {
                 header
@@ -137,7 +159,8 @@ struct SybilWorkspaceView: View {
                     SybilChatTranscriptView(
                         messages: viewModel.displayedMessages,
                         isLoading: viewModel.isLoadingSelection,
-                        isSending: viewModel.isSending
+                        isSending: viewModel.isSending,
+                        topContentInset: showsCustomChatNavigation ? customChatNavigationContentInset : 0
                     )
                     .id(transcriptScrollContextID)
                 }
@@ -170,6 +193,35 @@ struct SybilWorkspaceView: View {
         }
     }
 
+    private var customChatNavigationBar: some View {
+        HStack(spacing: 14) {
+            Button {
+                dismiss()
+            } label: {
+                SybilNavigationIcon(systemImage: "chevron.left")
+            }
+            .buttonStyle(.plain)
+            .accessibilityLabel("Back")
+
+            Text(viewModel.selectedTitle)
+                .font(.sybil(size: 16, weight: .semibold))
+                .foregroundStyle(SybilTheme.text)
+                .lineLimit(1)
+                .minimumScaleFactor(0.78)
+                .frame(maxWidth: .infinity, alignment: .leading)
+                .multilineTextAlignment(.leading)
+
+            providerModelNavigationMenu
+        }
+        .padding(.horizontal, 16)
+        .padding(.top, 10)
+        .padding(.bottom, 34)
+        .background(alignment: .top) {
+            SybilNavigationFadeBackground()
+                .allowsHitTesting(false)
+        }
+    }
+
     private func beginNewChatSwipe(containerWidth: CGFloat) {
         let update = {
             newChatSwipeContainerWidth = max(containerWidth, 1)
@@ -292,34 +344,8 @@ 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 +359,52 @@ struct SybilWorkspaceView: View {
                         .stroke(SybilTheme.border.opacity(0.82), lineWidth: 1)
                 )
         }
+    }
+
+    private var providerModelNavigationMenu: some View {
+        providerModelMenu {
+            SybilNavigationIcon(systemImage: "ellipsis")
+        }
+    }
+
+    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))
@@ -397,9 +466,7 @@ struct SybilWorkspaceView: View {
                 .lineLimit(1 ... 6)
                 .submitLabel(.send)
                 .onSubmit {
-                    Task {
-                        await viewModel.sendComposer()
-                    }
+                    submitComposer()
                 }
                 .padding(.horizontal, 12)
                 .padding(.vertical, 10)
@@ -414,9 +481,7 @@ struct SybilWorkspaceView: View {
                 .foregroundStyle(SybilTheme.text)
 
                 Button {
-                    Task {
-                        await viewModel.sendComposer()
-                    }
+                    submitComposer()
                 } label: {
                     Image(systemName: viewModel.isSearchMode ? "magnifyingglass" : "arrow.up")
                         .font(.system(size: 17, weight: .semibold))
@@ -527,6 +592,22 @@ 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 +937,219 @@ private extension UIView {
     }
 }
 
+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)
+        }
+        .ignoresSafeArea(edges: .top)
+    }
+}
+
+private struct SybilChatCharacterBackdrop: 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(0.74),
+                            Color.black
+                        ],
+                        startPoint: .leading,
+                        endPoint: .trailing
+                    )
+                }
+                .offset(x: 8, y: 4)
+        }
+        .frame(maxWidth: .infinity, minHeight: 156, maxHeight: 156, alignment: .topTrailing)
+        .clipped()
+        .ignoresSafeArea(edges: .top)
+        .accessibilityHidden(true)
+    }
+}
+
+private struct SybilAnimatedGIFView: UIViewRepresentable {
+    var resourceName: String
+
+    func makeCoordinator() -> Coordinator {
+        Coordinator()
+    }
+
+    func makeUIView(context: Context) -> UIImageView {
+        let imageView = SybilAnimatedUIImageView()
+        imageView.backgroundColor = .clear
+        imageView.contentMode = .scaleAspectFill
+        imageView.clipsToBounds = false
+        imageView.isOpaque = false
+        imageView.setContentHuggingPriority(.defaultLow, for: .horizontal)
+        imageView.setContentHuggingPriority(.defaultLow, for: .vertical)
+        imageView.setContentCompressionResistancePriority(.defaultLow, for: .horizontal)
+        imageView.setContentCompressionResistancePriority(.defaultLow, for: .vertical)
+        return imageView
+    }
+
+    func updateUIView(_ imageView: UIImageView, context: Context) {
+        guard context.coordinator.resourceName != resourceName else {
+            if !imageView.isAnimating {
+                imageView.startAnimating()
+            }
+            return
+        }
+
+        context.coordinator.resourceName = resourceName
+        imageView.image = SybilAnimatedGIFCache.image(named: resourceName)
+        imageView.startAnimating()
+    }
+
+    final class Coordinator {
+        var resourceName: String?
+    }
+}
+
+private final class SybilAnimatedUIImageView: UIImageView {
+    override var intrinsicContentSize: CGSize {
+        CGSize(width: UIView.noIntrinsicMetric, height: UIView.noIntrinsicMetric)
+    }
+}
+
+@MainActor
+private enum SybilAnimatedGIFCache {
+    private static var images: [String: UIImage] = [:]
+
+    static func image(named name: String) -> UIImage? {
+        if let cached = images[name] {
+            return cached
+        }
+
+        guard let image = loadImage(named: name) else {
+            return nil
+        }
+
+        images[name] = image
+
+        return image
+    }
+
+    private static func loadImage(named name: String) -> UIImage? {
+        let url = Bundle.main.url(forResource: name, withExtension: "gif", subdirectory: "Character") ??
+            Bundle.main.url(forResource: name, withExtension: "gif")
+
+        guard let url,
+              let data = try? Data(contentsOf: url),
+              let source = CGImageSourceCreateWithData(data as CFData, nil)
+        else {
+            return nil
+        }
+
+        let frameCount = CGImageSourceGetCount(source)
+        guard frameCount > 0 else {
+            return nil
+        }
+
+        var frames: [UIImage] = []
+        frames.reserveCapacity(frameCount)
+        var duration: TimeInterval = 0
+
+        for index in 0 ..< frameCount {
+            guard let cgImage = CGImageSourceCreateImageAtIndex(source, index, nil) else {
+                continue
+            }
+            frames.append(UIImage(cgImage: cgImage))
+            duration += frameDuration(at: index, source: source)
+        }
+
+        guard !frames.isEmpty else {
+            return nil
+        }
+
+        if frames.count == 1 {
+            return frames[0]
+        }
+
+        return UIImage.animatedImage(with: frames, duration: max(duration, 0.1))
+    }
+
+    private static func frameDuration(at index: Int, source: CGImageSource) -> TimeInterval {
+        guard let properties = CGImageSourceCopyPropertiesAtIndex(source, index, nil) as? [CFString: Any],
+              let gifProperties = properties[kCGImagePropertyGIFDictionary] as? [CFString: Any]
+        else {
+            return 0.08
+        }
+
+        let unclampedDelay = gifProperties[kCGImagePropertyGIFUnclampedDelayTime] as? TimeInterval
+        let delay = unclampedDelay ?? gifProperties[kCGImagePropertyGIFDelayTime] as? TimeInterval ?? 0.08
+        return max(delay, 0.03)
+    }
+}
+
 private struct NewChatSwipeBackdrop: View {
     var progress: CGFloat
     var hasLatched: Bool

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

@@ -19,6 +19,10 @@ private actor MockSybilClient: SybilAPIClienting {
     private let searchDetails: [String: SearchDetail]
 
     private var snapshot = MockClientCallSnapshot()
+    private var completionStreamNetworkErrorMessage: String?
+    private var completionStreamDelayNanoseconds: UInt64 = 0
+    private var searchStreamNetworkErrorMessage: String?
+    private var searchStreamDelayNanoseconds: UInt64 = 0
 
     init(
         chatsResponse: [ChatSummary] = [],
@@ -36,6 +40,16 @@ private actor MockSybilClient: SybilAPIClienting {
         snapshot
     }
 
+    func setCompletionStreamNetworkError(_ message: String, delayNanoseconds: UInt64 = 0) {
+        completionStreamNetworkErrorMessage = message
+        completionStreamDelayNanoseconds = delayNanoseconds
+    }
+
+    func setSearchStreamNetworkError(_ message: String, delayNanoseconds: UInt64 = 0) {
+        searchStreamNetworkErrorMessage = message
+        searchStreamDelayNanoseconds = delayNanoseconds
+    }
+
     func verifySession() async throws -> AuthSession {
         AuthSession(authenticated: true, mode: "open")
     }
@@ -98,6 +112,12 @@ 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 +126,12 @@ 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 +293,84 @@ private func makeSearchDetail(id: String, date: Date, answer: String) -> SearchD
     #expect(viewModel.selectedSearch?.answerText == "fresh answer")
 }
 
+@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)

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

@@ -184,7 +184,13 @@ 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"}