Add per-chat settings UI in web app for additional system prompt and tool checkboxes

docs/api/rest.md

@@ -40,6 +40,7 @@ Chat upload limits:
 ```
 - OpenAI model lists are filtered to models that are expected to work with the backend's Responses API implementation.
 - `hermes-agent` is included only when `HERMES_AGENT_API_KEY` is configured. Set it to Hermes `API_SERVER_KEY`, or any non-empty value if that local server does not require auth. `HERMES_AGENT_API_BASE_URL` defaults to `http://127.0.0.1:8642/v1`; set `HERMES_AGENT_MODEL` only when you need an additional fallback/override model id.
+- The backend loads provider model lists at startup and refreshes them about once every 24 hours. If a later provider refresh fails, the response keeps the last loaded model list for that provider and sets `error` to the latest failure message.
 
 ## Active Runs
 
@@ -57,6 +58,42 @@ Behavior notes:
 - Clients should use this after app start or page refresh to restore per-row generating indicators.
 - The lists are not durable across server restarts.
 
+## Workspace Items
+
+### `GET /v1/workspace-items`
+- Response: `{ "items": WorkspaceItem[] }`
+- `WorkspaceItem` is a discriminated union sorted by `updatedAt` descending:
+```json
+{
+  "items": [
+    {
+      "type": "chat",
+      "id": "chat-id",
+      "title": "optional title",
+      "createdAt": "2026-02-14T00:00:00.000Z",
+      "updatedAt": "2026-02-14T00:00:00.000Z",
+      "initiatedProvider": "openai",
+      "initiatedModel": "gpt-4.1-mini",
+      "lastUsedProvider": "openai",
+      "lastUsedModel": "gpt-4.1-mini"
+    },
+    {
+      "type": "search",
+      "id": "search-id",
+      "title": "optional title",
+      "query": "search query",
+      "createdAt": "2026-02-14T00:00:00.000Z",
+      "updatedAt": "2026-02-14T00:00:00.000Z"
+    }
+  ]
+}
+```
+
+Behavior notes:
+- This endpoint is intended for combined conversation/search lists such as sidebars.
+- The legacy `GET /v1/chats` and `GET /v1/searches` endpoints remain available for clients that need separate collections.
+- The response currently combines up to 100 chats and up to 100 searches.
+
 ## Chats
 
 ### `GET /v1/chats`

ios/Apps/Sybil/project.yml

@@ -24,8 +24,8 @@ targets:
         GENERATE_INFOPLIST_FILE: YES
         INFOPLIST_FILE: Apps/Sybil/Info.plist
         ASSETCATALOG_COMPILER_APPICON_NAME: AppIcon
-        MARKETING_VERSION: 1.7
+        MARKETING_VERSION: 1.9
-        CURRENT_PROJECT_VERSION: 8
+        CURRENT_PROJECT_VERSION: 10
         INFOPLIST_KEY_CFBundleDisplayName: Sybil
         INFOPLIST_KEY_ITSAppUsesNonExemptEncryption: NO
         INFOPLIST_KEY_UIApplicationSupportsIndirectInputEvents: YES

ios/Packages/Sybil/Sources/Sybil/SybilAPIClient.swift

@@ -44,6 +44,11 @@ actor SybilAPIClient: SybilAPIClienting {
         try await request("/v1/auth/session", method: "GET", responseType: AuthSession.self)
     }
 
+    func listWorkspaceItems() async throws -> [WorkspaceItem] {
+        let response = try await request("/v1/workspace-items", method: "GET", responseType: WorkspaceListResponse.self)
+        return response.items
+    }
+
     func listChats() async throws -> [ChatSummary] {
         let response = try await request("/v1/chats", method: "GET", responseType: ChatListResponse.self)
         return response.chats
@@ -626,6 +631,7 @@ struct CompletionStreamRequest: Codable, Sendable {
     var provider: Provider
     var model: String
     var messages: [CompletionRequestMessage]
+    var userLocation: String? = nil
 }
 
 private struct ChatCreateBody: Encodable {

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

@@ -2,6 +2,7 @@ import Foundation
 
 protocol SybilAPIClienting: Sendable {
     func verifySession() async throws -> AuthSession
+    func listWorkspaceItems() async throws -> [WorkspaceItem]
     func listChats() async throws -> [ChatSummary]
     func createChat(
         title: String?,

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

@@ -7,9 +7,6 @@ struct SybilChatTranscriptView: View {
     var isSending: Bool
     var topContentInset: CGFloat = 0
     var bottomContentInset: CGFloat = 0
-    var tailSpacerHeight: CGFloat = 0
-    var onViewportHeightChange: ((CGFloat) -> Void)? = nil
-    var onPendingAssistantHeightChange: ((CGFloat) -> Void)? = nil
 
     private var hasPendingAssistant: Bool {
         messages.contains { message in
@@ -23,16 +20,6 @@ struct SybilChatTranscriptView: View {
                 ForEach(messages.reversed()) { message in
                     MessageBubble(message: message, isSending: isSending)
                         .frame(maxWidth: .infinity)
-                        .background {
-                            if isStreamingPendingAssistant(message) {
-                                GeometryReader { proxy in
-                                    Color.clear.preference(
-                                        key: SybilPendingAssistantHeightPreferenceKey.self,
-                                        value: proxy.size.height
-                                    )
-                                }
-                            }
-                        }
                         .scaleEffect(x: 1, y: -1)
                 }
 
@@ -46,39 +33,13 @@ struct SybilChatTranscriptView: View {
             }
             .frame(maxWidth: .infinity, alignment: .leading)
             .padding(.horizontal, 14)
-            .padding(.top, 18 + bottomContentInset + tailSpacerHeight)
+            .padding(.top, 18 + bottomContentInset)
             .padding(.bottom, 18 + topContentInset)
         }
         .frame(maxWidth: .infinity, alignment: .leading)
         .scrollDismissesKeyboard(.interactively)
-        .background {
-            GeometryReader { proxy in
-                Color.clear
-                    .onAppear {
-                        onViewportHeightChange?(proxy.size.height)
-                    }
-                    .onChange(of: proxy.size.height) { _, height in
-                        onViewportHeightChange?(height)
-                    }
-            }
-        }
-        .onPreferenceChange(SybilPendingAssistantHeightPreferenceKey.self) { height in
-            onPendingAssistantHeightChange?(height)
-        }
         .scaleEffect(x: 1, y: -1)
     }
-
-    private func isStreamingPendingAssistant(_ message: Message) -> Bool {
-        isSending && message.id.hasPrefix("temp-assistant-")
-    }
-}
-
-private struct SybilPendingAssistantHeightPreferenceKey: PreferenceKey {
-    static let defaultValue: CGFloat = 0
-
-    static func reduce(value: inout CGFloat, nextValue: () -> CGFloat) {
-        value = max(value, nextValue())
-    }
 }
 
 private struct MessageBubble: View {

ios/Packages/Sybil/Sources/Sybil/SybilModels.swift

@@ -168,6 +168,75 @@ public struct SearchSummary: Codable, Identifiable, Hashable, Sendable {
     public var updatedAt: Date
 }
 
+public enum WorkspaceItemType: String, Codable, Hashable, Sendable {
+    case chat
+    case search
+}
+
+public struct WorkspaceItem: Codable, Identifiable, Hashable, Sendable {
+    public var type: WorkspaceItemType
+    public var id: String
+    public var title: String?
+    public var query: String?
+    public var createdAt: Date
+    public var updatedAt: Date
+    public var initiatedProvider: Provider?
+    public var initiatedModel: String?
+    public var lastUsedProvider: Provider?
+    public var lastUsedModel: String?
+
+    public init(chat: ChatSummary) {
+        self.type = .chat
+        self.id = chat.id
+        self.title = chat.title
+        self.query = nil
+        self.createdAt = chat.createdAt
+        self.updatedAt = chat.updatedAt
+        self.initiatedProvider = chat.initiatedProvider
+        self.initiatedModel = chat.initiatedModel
+        self.lastUsedProvider = chat.lastUsedProvider
+        self.lastUsedModel = chat.lastUsedModel
+    }
+
+    public init(search: SearchSummary) {
+        self.type = .search
+        self.id = search.id
+        self.title = search.title
+        self.query = search.query
+        self.createdAt = search.createdAt
+        self.updatedAt = search.updatedAt
+        self.initiatedProvider = nil
+        self.initiatedModel = nil
+        self.lastUsedProvider = nil
+        self.lastUsedModel = nil
+    }
+
+    public var chatSummary: ChatSummary? {
+        guard type == .chat else { return nil }
+        return ChatSummary(
+            id: id,
+            title: title,
+            createdAt: createdAt,
+            updatedAt: updatedAt,
+            initiatedProvider: initiatedProvider,
+            initiatedModel: initiatedModel,
+            lastUsedProvider: lastUsedProvider,
+            lastUsedModel: lastUsedModel
+        )
+    }
+
+    public var searchSummary: SearchSummary? {
+        guard type == .search else { return nil }
+        return SearchSummary(
+            id: id,
+            title: title,
+            query: query,
+            createdAt: createdAt,
+            updatedAt: updatedAt
+        )
+    }
+}
+
 public struct Message: Codable, Identifiable, Hashable, Sendable {
     public var id: String
     public var createdAt: Date
@@ -524,6 +593,10 @@ struct SearchListResponse: Codable {
     var searches: [SearchSummary]
 }
 
+struct WorkspaceListResponse: Codable {
+    var items: [WorkspaceItem]
+}
+
 struct ChatDetailResponse: Codable {
     var chat: ChatDetail
 }

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

@@ -219,6 +219,11 @@ struct SybilQuickQuestionView: View {
     }
 
     private func submitQuestion() {
+        guard viewModel.canSendQuickQuestion else {
+            return
+        }
+
+        promptFocused = false
         _ = viewModel.sendQuickQuestion()
     }
 }

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

@@ -159,10 +159,7 @@ struct SybilSidebarItemList: View {
                 .padding(10)
             }
             .refreshable {
-                await viewModel.refreshVisibleContent(
+                await viewModel.refreshSidebarCollectionsFromPullToRefresh()
-                    refreshCollections: true,
-                    refreshSelection: false
-                )
             }
         }
     }

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

@@ -95,6 +95,7 @@ final class SybilViewModel {
 
     var chats: [ChatSummary] = []
     var searches: [SearchSummary] = []
+    var workspaceItems: [WorkspaceItem] = []
 
     var selectedItem: SidebarSelection?
     var selectedChat: ChatDetail?
@@ -388,10 +389,12 @@ final class SybilViewModel {
     }
 
     var sidebarItems: [SidebarItem] {
-        let chatItems: [SidebarItem] = chats.map { chat in
+        workspaceItems.map { item in
+            switch item.type {
+            case .chat:
                 let initiatedLabel: String?
-            if let model = chat.initiatedModel?.trimmingCharacters(in: .whitespacesAndNewlines), !model.isEmpty {
+                if let model = item.initiatedModel?.trimmingCharacters(in: .whitespacesAndNewlines), !model.isEmpty {
-                if let provider = chat.initiatedProvider {
+                    if let provider = item.initiatedProvider {
                         initiatedLabel = "\(provider.displayName) • \(model)"
                     } else {
                         initiatedLabel = model
@@ -401,27 +404,25 @@ final class SybilViewModel {
                 }
 
                 return SidebarItem(
-                selection: .chat(chat.id),
+                    selection: .chat(item.id),
                     kind: .chat,
-                title: chatTitle(title: chat.title, messages: nil),
+                    title: chatTitle(title: item.title, messages: nil),
-                updatedAt: chat.updatedAt,
+                    updatedAt: item.updatedAt,
                     initiatedLabel: initiatedLabel,
-                isRunning: isChatRowRunning(chat.id)
+                    isRunning: isChatRowRunning(item.id)
                 )
-        }
 
-        let searchItems: [SidebarItem] = searches.map { search in
+            case .search:
-            SidebarItem(
+                return SidebarItem(
-                selection: .search(search.id),
+                    selection: .search(item.id),
                     kind: .search,
-                title: searchTitle(title: search.title, query: search.query),
+                    title: searchTitle(title: item.title, query: item.query),
-                updatedAt: search.updatedAt,
+                    updatedAt: item.updatedAt,
                     initiatedLabel: "exa",
-                isRunning: isSearchRowRunning(search.id)
+                    isRunning: isSearchRowRunning(item.id)
                 )
             }
-
+        }
-        return (chatItems + searchItems).sorted { $0.updatedAt > $1.updatedAt }
     }
 
     var selectedChatSummary: ChatSummary? {
@@ -502,6 +503,7 @@ final class SybilViewModel {
             authMode = nil
             chats = []
             searches = []
+            workspaceItems = []
             selectedItem = .settings
             selectedChat = nil
             selectedSearch = nil
@@ -671,6 +673,7 @@ final class SybilViewModel {
             setProvider(submittedProvider, model: submittedModel)
             chats.removeAll(where: { $0.id == chat.id })
             chats.insert(chat, at: 0)
+            upsertWorkspaceChat(chat)
             draftKind = nil
             selectedItem = .chat(chat.id)
             selectedChat = ChatDetail(
@@ -911,6 +914,23 @@ final class SybilViewModel {
         }
     }
 
+    func refreshSidebarCollectionsFromPullToRefresh() async {
+        guard isAuthenticated, !isCheckingSession else {
+            return
+        }
+
+        SybilLog.info(
+            SybilLog.ui,
+            "Sidebar pull-to-refresh requested"
+        )
+
+        let preferredSelection = selectedItem
+        let refreshTask = Task { @MainActor in
+            await refreshCollections(preferredSelection: preferredSelection, refreshSelection: false)
+        }
+        await refreshTask.value
+    }
+
     func sendComposer() async {
         let content = composer.trimmingCharacters(in: .whitespacesAndNewlines)
         let attachments = composerAttachments
@@ -1017,6 +1037,7 @@ final class SybilViewModel {
             guard selectedItem == sourceSelection, draftKind == nil else {
                 chats.removeAll(where: { $0.id == chat.id })
                 chats.insert(chat, at: 0)
+                upsertWorkspaceChat(chat)
                 isCreatingSearchChat = false
                 return
             }
@@ -1028,6 +1049,7 @@ final class SybilViewModel {
 
             chats.removeAll(where: { $0.id == chat.id })
             chats.insert(chat, at: 0)
+            upsertWorkspaceChat(chat)
 
             selectedItem = .chat(chat.id)
             selectedSearch = nil
@@ -1131,18 +1153,16 @@ final class SybilViewModel {
         errorMessage = nil
 
         do {
-            async let chatsValue = client.listChats()
+            async let workspaceItemsValue = client.listWorkspaceItems()
-            async let searchesValue = client.listSearches()
             async let activeRunsValue = client.getActiveRuns()
-            let (nextChats, nextSearches, nextActiveRuns) = try await (chatsValue, searchesValue, activeRunsValue)
+            let (nextWorkspaceItems, nextActiveRuns) = try await (workspaceItemsValue, activeRunsValue)
 
-            chats = nextChats
+            applyWorkspaceItems(nextWorkspaceItems)
-            searches = nextSearches
             applyActiveRuns(nextActiveRuns)
 
             SybilLog.info(
                 SybilLog.app,
-                "Loaded collections: \(nextChats.count) chats, \(nextSearches.count) searches"
+                "Loaded collections: \(chats.count) chats, \(searches.count) searches"
             )
 
             do {
@@ -1159,7 +1179,7 @@ final class SybilViewModel {
             if case .settings = selectedItem {
                 nextSelection = .settings
             } else if let currentSelection = selectedItem,
-                      hasSelection(currentSelection, chats: nextChats, searches: nextSearches) {
+                      hasSelection(currentSelection, chats: chats, searches: searches) {
                 nextSelection = currentSelection
             } else {
                 nextSelection = sidebarItems.first?.selection
@@ -1231,18 +1251,16 @@ final class SybilViewModel {
 
         do {
             let client = try client()
-            async let chatsValue = client.listChats()
+            async let workspaceItemsValue = client.listWorkspaceItems()
-            async let searchesValue = client.listSearches()
             async let activeRunsValue = client.getActiveRuns()
-            let (nextChats, nextSearches, nextActiveRuns) = try await (chatsValue, searchesValue, activeRunsValue)
+            let (nextWorkspaceItems, nextActiveRuns) = try await (workspaceItemsValue, activeRunsValue)
 
-            chats = nextChats
+            applyWorkspaceItems(nextWorkspaceItems)
-            searches = nextSearches
             applyActiveRuns(nextActiveRuns)
 
             SybilLog.info(
                 SybilLog.app,
-                "Refreshed collections: \(nextChats.count) chats, \(nextSearches.count) searches"
+                "Refreshed collections: \(chats.count) chats, \(searches.count) searches"
             )
             errorMessage = nil
 
@@ -1260,10 +1278,10 @@ final class SybilViewModel {
             }
 
             if let preferredSelection,
-               hasSelection(preferredSelection, chats: nextChats, searches: nextSearches) {
+               hasSelection(preferredSelection, chats: chats, searches: searches) {
                 selectedItem = preferredSelection
             } else if let existing = selectedItem,
-                      hasSelection(existing, chats: nextChats, searches: nextSearches) {
+                      hasSelection(existing, chats: chats, searches: searches) {
                 selectedItem = existing
             } else {
                 selectedItem = sidebarItems.first?.selection
@@ -1276,7 +1294,9 @@ final class SybilViewModel {
                 attachToVisibleActiveRunIfNeeded()
             }
         } catch {
-            if shouldSuppressInactiveTransportError(error) {
+            if isCancellation(error) {
+                SybilLog.debug(SybilLog.app, "Collection refresh cancelled")
+            } else if shouldSuppressInactiveTransportError(error) {
                 SybilLog.info(SybilLog.app, "Suppressing collection refresh transport interruption while app is inactive")
             } else {
                 errorMessage = normalizeAPIError(error)
@@ -1355,6 +1375,34 @@ final class SybilViewModel {
         serverActiveSearchIDs = Set(activeRuns.searches)
     }
 
+    private func applyWorkspaceItems(_ items: [WorkspaceItem]) {
+        workspaceItems = items
+        chats = items.compactMap(\.chatSummary)
+        searches = items.compactMap(\.searchSummary)
+    }
+
+    private func upsertWorkspaceChat(_ chat: ChatSummary, moveToFront: Bool = true) {
+        upsertWorkspaceItem(WorkspaceItem(chat: chat), moveToFront: moveToFront)
+    }
+
+    private func upsertWorkspaceSearch(_ search: SearchSummary, moveToFront: Bool = true) {
+        upsertWorkspaceItem(WorkspaceItem(search: search), moveToFront: moveToFront)
+    }
+
+    private func upsertWorkspaceItem(_ item: WorkspaceItem, moveToFront: Bool) {
+        if let existingIndex = workspaceItems.firstIndex(where: { $0.type == item.type && $0.id == item.id }) {
+            workspaceItems.remove(at: existingIndex)
+            if moveToFront {
+                workspaceItems.insert(item, at: 0)
+            } else {
+                workspaceItems.insert(item, at: existingIndex)
+            }
+            return
+        }
+
+        workspaceItems.insert(item, at: 0)
+    }
+
     private func attachToVisibleActiveRunIfNeeded() {
         guard draftKind == nil else {
             return
@@ -1686,6 +1734,7 @@ final class SybilViewModel {
 
             chats.removeAll(where: { $0.id == created.id })
             chats.insert(created, at: 0)
+            upsertWorkspaceChat(created)
 
             if shouldShowCreatedChat {
                 draftKind = nil
@@ -1762,6 +1811,7 @@ final class SybilViewModel {
                             }
                             return existing
                         }
+                        self.upsertWorkspaceChat(updated, moveToFront: false)
 
                         if self.selectedChat?.id == updated.id {
                             self.selectedChat?.title = updated.title
@@ -1899,6 +1949,7 @@ final class SybilViewModel {
 
             searches.removeAll(where: { $0.id == created.id })
             searches.insert(created, at: 0)
+            upsertWorkspaceSearch(created)
 
             if shouldShowCreatedSearch {
                 draftKind = nil

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

@@ -26,10 +26,6 @@ struct SybilWorkspaceView: View {
     @State private var isShowingPhotoPicker = false
     @State private var photoPickerItems: [PhotosPickerItem] = []
     @State private var isComposerDropTargeted = false
-    @State private var transcriptTailSpacerHeight = SybilTranscriptTailSpacer.minimumHeight
-    @State private var transcriptTailSpacerTargetHeight = SybilTranscriptTailSpacer.minimumHeight
-    @State private var transcriptViewportHeight: CGFloat = 0
-    @State private var pendingAssistantBaselineHeight: CGFloat?
     @State private var newChatSwipeOffset: CGFloat = 0
     @State private var newChatSwipeCompletionOffset: CGFloat = 0
     @State private var newChatSwipeContainerWidth: CGFloat = NewChatSwipeMetrics.referenceWidth
@@ -42,10 +38,6 @@ struct SybilWorkspaceView: View {
     private let customWorkspaceNavigationContentInset: CGFloat = 96
     private let composerOverlayContentInset: CGFloat = 112
 
-    private var visibleTranscriptTailSpacerHeight: CGFloat {
-        viewModel.showsComposer && !viewModel.isSearchMode ? transcriptTailSpacerHeight : 0
-    }
-
     private var isSettingsSelected: Bool {
         if case .settings = viewModel.selectedItem {
             return true
@@ -153,17 +145,6 @@ struct SybilWorkspaceView: View {
             }
             resetNewChatSwipe(animated: false)
         }
-        .onChange(of: transcriptScrollContextID) { _, _ in
-            handleTranscriptContextChange()
-        }
-        .onChange(of: viewModel.isSendingVisibleChat) { wasSending, isSending in
-            handleVisibleChatSendingChange(wasSending: wasSending, isSending: isSending)
-        }
-        .onChange(of: viewModel.errorMessage) { _, message in
-            if message != nil && !viewModel.isSendingVisibleChat {
-                resetTranscriptTailSpacer(animated: true)
-            }
-        }
         .task(id: composerFocusPolicyID) {
             await applyComposerFocusPolicy()
         }
@@ -213,14 +194,7 @@ struct SybilWorkspaceView: View {
                         isLoading: viewModel.isLoadingSelection,
                         isSending: viewModel.isSendingVisibleChat,
                         topContentInset: showsCustomWorkspaceNavigation ? customWorkspaceNavigationContentInset : 0,
-                        bottomContentInset: viewModel.showsComposer ? composerOverlayContentInset : 0,
+                        bottomContentInset: viewModel.showsComposer ? composerOverlayContentInset : 0
-                        tailSpacerHeight: visibleTranscriptTailSpacerHeight,
-                        onViewportHeightChange: { height in
-                            handleTranscriptViewportHeightChange(height)
-                        },
-                        onPendingAssistantHeightChange: { height in
-                            handlePendingAssistantHeightChange(height)
-                        }
                     )
                     .id(transcriptScrollContextID)
                 }
@@ -258,13 +232,7 @@ struct SybilWorkspaceView: View {
         HStack(spacing: 14) {
             workspaceNavigationLeadingControl
 
-            Text(viewModel.selectedTitle)
+            customWorkspaceNavigationTitle
-                .font(.sybil(size: 16, weight: .semibold))
-                .foregroundStyle(SybilTheme.text)
-                .lineLimit(1)
-                .minimumScaleFactor(0.78)
-                .frame(maxWidth: .infinity, alignment: .leading)
-                .multilineTextAlignment(.leading)
 
             workspaceNavigationTrailingControl
         }
@@ -277,6 +245,32 @@ struct SybilWorkspaceView: View {
         }
     }
 
+    private var selectedProviderModelSubtitle: String {
+        let selectedModel = viewModel.model.trimmingCharacters(in: .whitespacesAndNewlines)
+        guard !selectedModel.isEmpty else {
+            return viewModel.provider.displayName
+        }
+        return "\(viewModel.provider.displayName) • \(selectedModel)"
+    }
+
+    private var customWorkspaceNavigationTitle: some View {
+        VStack(alignment: .leading, spacing: 2) {
+            Text(viewModel.selectedTitle)
+                .font(.sybil(size: 16, weight: .semibold))
+                .foregroundStyle(SybilTheme.text)
+                .lineLimit(1)
+                .minimumScaleFactor(0.78)
+
+            Text(selectedProviderModelSubtitle)
+                .font(.sybil(size: 10, weight: .medium))
+                .foregroundStyle(SybilTheme.textMuted)
+                .lineLimit(1)
+                .minimumScaleFactor(0.82)
+        }
+        .frame(maxWidth: .infinity, alignment: .leading)
+        .multilineTextAlignment(.leading)
+    }
+
     @ViewBuilder
     private var workspaceNavigationLeadingControl: some View {
         switch navigationLeadingControl {
@@ -311,86 +305,6 @@ struct SybilWorkspaceView: View {
         }
     }
 
-    private func handleTranscriptContextChange() {
-        resetTranscriptTailSpacer(animated: false)
-    }
-
-    private func handleVisibleChatSendingChange(wasSending: Bool, isSending: Bool) {
-        guard !viewModel.isSearchMode else {
-            resetTranscriptTailSpacer(animated: true)
-            return
-        }
-
-        if isSending {
-            prepareTranscriptTailSpacerForReply(animated: false)
-            return
-        }
-
-        if wasSending {
-            if viewModel.errorMessage != nil {
-                resetTranscriptTailSpacer(animated: true)
-            }
-            pendingAssistantBaselineHeight = nil
-        }
-    }
-
-    private func handleTranscriptViewportHeightChange(_ height: CGFloat) {
-        transcriptViewportHeight = height
-
-        if viewModel.isSendingVisibleChat,
-           transcriptTailSpacerTargetHeight <= SybilTranscriptTailSpacer.minimumHeight {
-            prepareTranscriptTailSpacerForReply(animated: false)
-        }
-    }
-
-    private func handlePendingAssistantHeightChange(_ height: CGFloat) {
-        guard viewModel.isSendingVisibleChat, !viewModel.isSearchMode, height > 0 else {
-            return
-        }
-
-        if pendingAssistantBaselineHeight == nil {
-            pendingAssistantBaselineHeight = height
-        }
-
-        let measuredHeight = SybilTranscriptTailSpacer.placeholderHeight(
-            targetHeight: transcriptTailSpacerTargetHeight,
-            baselineAssistantHeight: pendingAssistantBaselineHeight ?? height,
-            currentAssistantHeight: height
-        )
-        let nextHeight = min(transcriptTailSpacerHeight, measuredHeight)
-        setTranscriptTailSpacer(nextHeight, animated: false)
-    }
-
-    private func prepareTranscriptTailSpacerForReply(animated: Bool) {
-        let targetHeight = SybilTranscriptTailSpacer.replyBufferHeight(for: transcriptViewportHeight)
-        transcriptTailSpacerTargetHeight = targetHeight
-        pendingAssistantBaselineHeight = nil
-        setTranscriptTailSpacer(targetHeight, animated: animated)
-    }
-
-    private func resetTranscriptTailSpacer(animated: Bool) {
-        transcriptTailSpacerTargetHeight = SybilTranscriptTailSpacer.minimumHeight
-        pendingAssistantBaselineHeight = nil
-        setTranscriptTailSpacer(SybilTranscriptTailSpacer.minimumHeight, animated: animated)
-    }
-
-    private func setTranscriptTailSpacer(_ height: CGFloat, animated: Bool) {
-        let nextHeight = SybilTranscriptTailSpacer.clampedHeight(height)
-        guard abs(nextHeight - transcriptTailSpacerHeight) >= 0.5 else {
-            return
-        }
-
-        let update = {
-            transcriptTailSpacerHeight = nextHeight
-        }
-
-        if animated {
-            withAnimation(.easeOut(duration: 0.22), update)
-        } else {
-            update()
-        }
-    }
-
     private func beginNewChatSwipe(containerWidth: CGFloat) {
         let update = {
             newChatSwipeContainerWidth = max(containerWidth, 1)
@@ -808,14 +722,8 @@ struct SybilWorkspaceView: View {
             return
         }
 
-        if !viewModel.isSearchMode {
-            prepareTranscriptTailSpacerForReply(animated: false)
-        }
-
         #if !targetEnvironment(macCatalyst)
-        if !viewModel.isSearchMode {
         composerFocused = false
-        }
         #endif
 
         Task {
@@ -881,37 +789,6 @@ struct SybilWorkspaceView: View {
     }
 }
 
-enum SybilTranscriptTailSpacer {
-    static let minimumHeight: CGFloat = 20
-    static let replyBufferMin: CGFloat = 288
-    static let replyBufferMax: CGFloat = 576
-    static let replyBufferViewportRatio: CGFloat = 0.52
-
-    static func replyBufferHeight(for viewportHeight: CGFloat) -> CGFloat {
-        guard viewportHeight > 0 else {
-            return replyBufferMin
-        }
-
-        return min(
-            replyBufferMax,
-            max(replyBufferMin, (viewportHeight * replyBufferViewportRatio).rounded())
-        )
-    }
-
-    static func clampedHeight(_ height: CGFloat) -> CGFloat {
-        max(minimumHeight, height.rounded(.up))
-    }
-
-    static func placeholderHeight(
-        targetHeight: CGFloat,
-        baselineAssistantHeight: CGFloat,
-        currentAssistantHeight: CGFloat
-    ) -> CGFloat {
-        let consumedHeight = max(currentAssistantHeight - baselineAssistantHeight, 0)
-        return clampedHeight(targetHeight - consumedHeight)
-    }
-}
-
 enum NewChatSwipeMetrics {
     static let referenceWidth: CGFloat = 390
     static let horizontalActivationDistance: CGFloat = 18

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

@@ -4,6 +4,7 @@ import Testing
 @testable import Sybil
 
 private struct MockClientCallSnapshot: Sendable {
+    var listWorkspaceItems = 0
     var listChats = 0
     var listSearches = 0
     var createChat = 0
@@ -27,6 +28,7 @@ private struct UnexpectedClientCall: Error {}
 private actor MockSybilClient: SybilAPIClienting {
     private let chatsResponse: [ChatSummary]
     private let searchesResponse: [SearchSummary]
+    private let workspaceItemsResponse: [WorkspaceItem]
     private let chatDetails: [String: ChatDetail]
     private let searchDetails: [String: SearchDetail]
     private let createChatResponse: ChatSummary?
@@ -36,6 +38,8 @@ private actor MockSybilClient: SybilAPIClienting {
     private var lastCreateChatCall: ChatCreateCallSnapshot?
     private var lastCompletionStreamBody: CompletionStreamRequest?
     private var completionStreamEvents: [CompletionStreamEvent]?
+    private var listChatsDelayNanoseconds: UInt64 = 0
+    private var listSearchesDelayNanoseconds: UInt64 = 0
     private var getChatDelayNanoseconds: UInt64 = 0
     private var getSearchDelayNanoseconds: UInt64 = 0
     private var completionStreamNetworkErrorMessage: String?
@@ -53,16 +57,22 @@ private actor MockSybilClient: SybilAPIClienting {
         chatDetails: [String: ChatDetail] = [:],
         searchDetails: [String: SearchDetail] = [:],
         createChatResponse: ChatSummary? = nil,
-        activeRunsResponse: ActiveRunsResponse = ActiveRunsResponse()
+        activeRunsResponse: ActiveRunsResponse = ActiveRunsResponse(),
+        workspaceItemsResponse: [WorkspaceItem]? = nil
     ) {
         self.chatsResponse = chatsResponse
         self.searchesResponse = searchesResponse
+        self.workspaceItemsResponse = workspaceItemsResponse ?? Self.makeWorkspaceItems(chats: chatsResponse, searches: searchesResponse)
         self.chatDetails = chatDetails
         self.searchDetails = searchDetails
         self.createChatResponse = createChatResponse
         self.activeRunsResponse = activeRunsResponse
     }
 
+    private static func makeWorkspaceItems(chats: [ChatSummary], searches: [SearchSummary]) -> [WorkspaceItem] {
+        (chats.map { WorkspaceItem(chat: $0) } + searches.map { WorkspaceItem(search: $0) }).sorted { $0.updatedAt > $1.updatedAt }
+    }
+
     func currentSnapshot() -> MockClientCallSnapshot {
         snapshot
     }
@@ -85,6 +95,11 @@ private actor MockSybilClient: SybilAPIClienting {
         completionStreamDelayNanoseconds = delayNanoseconds
     }
 
+    func setListDelays(chats: UInt64 = 0, searches: UInt64 = 0) {
+        listChatsDelayNanoseconds = chats
+        listSearchesDelayNanoseconds = searches
+    }
+
     func setGetChatDelay(_ delayNanoseconds: UInt64) {
         getChatDelayNanoseconds = delayNanoseconds
     }
@@ -120,8 +135,20 @@ private actor MockSybilClient: SybilAPIClienting {
         AuthSession(authenticated: true, mode: "open")
     }
 
+    func listWorkspaceItems() async throws -> [WorkspaceItem] {
+        snapshot.listWorkspaceItems += 1
+        let delay = max(listChatsDelayNanoseconds, listSearchesDelayNanoseconds)
+        if delay > 0 {
+            try await Task.sleep(nanoseconds: delay)
+        }
+        return workspaceItemsResponse
+    }
+
     func listChats() async throws -> [ChatSummary] {
         snapshot.listChats += 1
+        if listChatsDelayNanoseconds > 0 {
+            try await Task.sleep(nanoseconds: listChatsDelayNanoseconds)
+        }
         return chatsResponse
     }
 
@@ -165,6 +192,9 @@ private actor MockSybilClient: SybilAPIClienting {
 
     func listSearches() async throws -> [SearchSummary] {
         snapshot.listSearches += 1
+        if listSearchesDelayNanoseconds > 0 {
+            try await Task.sleep(nanoseconds: listSearchesDelayNanoseconds)
+        }
         return searchesResponse
     }
 
@@ -376,13 +406,41 @@ private func makeSearchDetail(id: String, date: Date, answer: String) -> SearchD
     await viewModel.refreshVisibleContent(refreshCollections: true, refreshSelection: false)
 
     let snapshot = await client.currentSnapshot()
-    #expect(snapshot.listChats == 1)
+    #expect(snapshot.listWorkspaceItems == 1)
-    #expect(snapshot.listSearches == 1)
+    #expect(snapshot.listChats == 0)
+    #expect(snapshot.listSearches == 0)
     #expect(snapshot.getChat == 0)
     #expect(snapshot.getSearch == 0)
     #expect(viewModel.selectedItem == .chat("chat-1"))
 }
 
+@MainActor
+@Test func pullToRefreshCompletesWhenRefreshableTaskIsCancelled() async throws {
+    let date = Date(timeIntervalSince1970: 1_700_000_050)
+    let chat = makeChatSummary(id: "chat-cancelled", date: date)
+    let search = makeSearchSummary(id: "search-cancelled", date: date)
+    let client = MockSybilClient(
+        chatsResponse: [chat],
+        searchesResponse: [search]
+    )
+    await client.setListDelays(chats: 50_000_000, searches: 50_000_000)
+    let viewModel = SybilViewModel(settings: testSettings(named: #function)) { _ in client }
+    viewModel.isAuthenticated = true
+    viewModel.isCheckingSession = false
+
+    let refreshTask = Task {
+        await viewModel.refreshSidebarCollectionsFromPullToRefresh()
+    }
+    try await Task.sleep(nanoseconds: 10_000_000)
+    refreshTask.cancel()
+    await refreshTask.value
+
+    #expect(viewModel.errorMessage == nil)
+    #expect(!viewModel.isLoadingCollections)
+    #expect(viewModel.chats.map(\.id) == ["chat-cancelled"])
+    #expect(viewModel.searches.map(\.id) == ["search-cancelled"])
+}
+
 @MainActor
 @Test func foregroundChatRefreshReloadsSelectedTranscript() async throws {
     let date = Date(timeIntervalSince1970: 1_700_000_100)
@@ -396,6 +454,7 @@ private func makeSearchDetail(id: String, date: Date, answer: String) -> SearchD
     await viewModel.refreshVisibleContent(refreshCollections: false, refreshSelection: true)
 
     let snapshot = await client.currentSnapshot()
+    #expect(snapshot.listWorkspaceItems == 0)
     #expect(snapshot.listChats == 0)
     #expect(snapshot.listSearches == 0)
     #expect(snapshot.getChat == 1)
@@ -415,6 +474,7 @@ private func makeSearchDetail(id: String, date: Date, answer: String) -> SearchD
     await viewModel.refreshVisibleContent(refreshCollections: false, refreshSelection: true)
 
     let snapshot = await client.currentSnapshot()
+    #expect(snapshot.listWorkspaceItems == 0)
     #expect(snapshot.listChats == 0)
     #expect(snapshot.listSearches == 0)
     #expect(snapshot.getSearch == 1)
@@ -784,23 +844,3 @@ private func makeSearchDetail(id: String, date: Date, answer: String) -> SearchD
     #expect(BackSwipeMetrics.shouldComplete(offset: 24, velocityX: 800, width: width, isLatched: false))
     #expect(!BackSwipeMetrics.shouldComplete(offset: latchDistance + 1, velocityX: -800, width: width, isLatched: true))
 }
-
-@Test func transcriptTailSpacerContractsAsContentGrows() async throws {
-    let targetHeight: CGFloat = 320
-    let baselineAssistantHeight: CGFloat = 28
-
-    #expect(
-        SybilTranscriptTailSpacer.placeholderHeight(
-            targetHeight: targetHeight,
-            baselineAssistantHeight: baselineAssistantHeight,
-            currentAssistantHeight: baselineAssistantHeight + 120
-        ) == 200
-    )
-    #expect(
-        SybilTranscriptTailSpacer.placeholderHeight(
-            targetHeight: targetHeight,
-            baselineAssistantHeight: baselineAssistantHeight,
-            currentAssistantHeight: baselineAssistantHeight + 500
-        ) == SybilTranscriptTailSpacer.minimumHeight
-    )
-}

server/prisma/migrations/20260524000000_add_chat_settings/migration.sql

@@ -0,0 +1,3 @@
+-- AlterTable
+ALTER TABLE "Chat" ADD COLUMN "additionalSystemPrompt" TEXT;
+ALTER TABLE "Chat" ADD COLUMN "enabledTools" JSONB;

server/prisma/schema.prisma

@@ -51,6 +51,9 @@ model Chat {
   lastUsedProvider  Provider?
   lastUsedModel     String?
 
+  additionalSystemPrompt String?
+  enabledTools           Json?
+
   user   User?   @relation(fields: [userId], references: [id])
   userId String?
 

server/src/index.ts

@@ -5,7 +5,7 @@ import swaggerUI from "@fastify/swagger-ui";
 import sensible from "@fastify/sensible";
 import { env } from "./env.js";
 import { ensureDatabaseReady } from "./db-init.js";
-import { warmModelCatalog } from "./llm/model-catalog.js";
+import { startModelCatalogRefreshLoop, warmModelCatalog } from "./llm/model-catalog.js";
 import { registerRoutes } from "./routes.js";
 
 const app = Fastify({
@@ -21,6 +21,7 @@ const app = Fastify({
 
 await ensureDatabaseReady(app.log);
 await warmModelCatalog(app.log);
+const stopModelCatalogRefreshLoop = startModelCatalogRefreshLoop(app.log);
 
 await app.register(cors, {
   origin: true,
@@ -80,6 +81,10 @@ app.setErrorHandler((err, req, reply) => {
   });
 });
 
+app.addHook("onClose", async () => {
+  stopModelCatalogRefreshLoop();
+});
+
 await registerRoutes(app);
 
 await app.listen({ port: env.PORT, host: env.HOST });

server/src/llm/chat-tools.ts

@@ -9,7 +9,11 @@ import { z } from "zod";
 import { env } from "../env.js";
 import { exaClient } from "../search/exa.js";
 import { searchSearxng } from "../search/searxng.js";
-import { buildOpenAIConversationMessage, buildOpenAIResponsesInputMessage } from "./message-content.js";
+import {
+  buildOpenAIConversationMessage,
+  buildOpenAIResponsesInputMessage,
+  buildSystemPromptAugmentationMessage,
+} from "./message-content.js";
 import type { ChatMessage } from "./types.js";
 
 const MAX_TOOL_ROUNDS = env.CHAT_MAX_TOOL_ROUNDS;
@@ -188,7 +192,43 @@ const CHAT_TOOLS: any[] = [
   ...(env.CHAT_SHELL_TOOL_ENABLED ? [SHELL_EXEC_TOOL] : []),
 ];
 
-const RESPONSES_CHAT_TOOLS: any[] = CHAT_TOOLS.map((tool) => {
+function getToolName(tool: any) {
+  return typeof tool?.function?.name === "string" ? tool.function.name : null;
+}
+
+export function getAvailableChatTools() {
+  return CHAT_TOOLS.map((tool) => {
+    const name = getToolName(tool);
+    if (!name) return null;
+    return {
+      name,
+      description: typeof tool?.function?.description === "string" ? tool.function.description : "",
+    };
+  }).filter((tool): tool is { name: string; description: string } => tool !== null);
+}
+
+export function normalizeEnabledChatTools(value: unknown) {
+  if (!Array.isArray(value)) return getAvailableChatTools().map((tool) => tool.name);
+  const available = new Set(getAvailableChatTools().map((tool) => tool.name));
+  return [...new Set(value.filter((item): item is string => typeof item === "string").map((item) => item.trim()).filter(Boolean))].filter((name) =>
+    available.has(name)
+  );
+}
+
+function getEnabledToolSet(params: Pick<ToolAwareCompletionParams, "enabledTools">) {
+  return new Set(normalizeEnabledChatTools(params.enabledTools));
+}
+
+function getEnabledChatTools(params: Pick<ToolAwareCompletionParams, "enabledTools">) {
+  const enabled = getEnabledToolSet(params);
+  return CHAT_TOOLS.filter((tool) => {
+    const name = getToolName(tool);
+    return name ? enabled.has(name) : false;
+  });
+}
+
+function toResponsesChatTools(tools: any[]) {
+  return tools.map((tool) => {
   if (tool?.type !== "function") return tool;
   return {
     type: "function",
@@ -198,6 +238,7 @@ const RESPONSES_CHAT_TOOLS: any[] = CHAT_TOOLS.map((tool) => {
     strict: false,
   };
   });
+}
 
 export const CHAT_TOOL_SYSTEM_PROMPT =
   "You can use tools to gather up-to-date web information when needed. " +
@@ -239,6 +280,8 @@ type ToolAwareCompletionParams = {
   client: OpenAI;
   model: string;
   messages: ChatMessage[];
+  enabledTools?: string[];
+  userLocation?: string;
   temperature?: number;
   maxTokens?: number;
   onToolEvent?: (event: ToolExecutionEvent) => void | Promise<void>;
@@ -379,20 +422,38 @@ function extractHtmlTitle(html: string) {
   );
 }
 
-function normalizeIncomingMessages(messages: ChatMessage[]) {
+function buildChatToolSystemPrompt(params: Pick<ToolAwareCompletionParams, "enabledTools">) {
+  const enabled = getEnabledToolSet(params);
+  return (
+    "You can use tools to gather up-to-date web information when needed. " +
+    (enabled.has("web_search") ? "Use web_search for discovery and recent facts. " : "") +
+    (enabled.has("fetch_url") ? "Use fetch_url to read the full content of a specific page. " : "") +
+    "Prefer tools when the user asks for current events, verification, sources, or details you do not already have. " +
+    "When you decide tool use is needed, call the tool immediately in the same response; do not say you are running a tool unless you actually call it. " +
+    (enabled.has("codex_exec")
+      ? "Use codex_exec when a request needs substantial coding work, repository inspection, shell commands, tests, debugging, or another complex task suited to a persistent Codex workspace. Provide codex_exec a complete prompt with the goal, constraints, assumptions, and expected report-back format. Never ask codex_exec to wait for user input or run interactive commands. "
+      : "") +
+    (enabled.has("shell_exec")
+      ? "Use shell_exec for direct non-interactive command-line work on the remote devbox, including quick Python programs, calculations, file inspection, running tests, and small scripts. "
+      : "") +
+    "Do not fabricate tool outputs; reason only from provided tool results."
+  );
+}
+
+function normalizeIncomingMessages(messages: ChatMessage[], userLocation?: string, params: Pick<ToolAwareCompletionParams, "enabledTools"> = {}) {
   const normalized = messages.map((message) => buildOpenAIConversationMessage(message));
 
-  return [{ role: "system", content: CHAT_TOOL_SYSTEM_PROMPT }, ...normalized];
+  return [{ role: "system", content: buildChatToolSystemPrompt(params) }, buildSystemPromptAugmentationMessage(userLocation), ...normalized];
 }
 
-function normalizePlainIncomingMessages(messages: ChatMessage[]) {
+function normalizePlainIncomingMessages(messages: ChatMessage[], userLocation?: string) {
-  return messages.map((message) => buildOpenAIConversationMessage(message));
+  return [buildSystemPromptAugmentationMessage(userLocation), ...messages.map((message) => buildOpenAIConversationMessage(message))];
 }
 
-function normalizeIncomingResponsesInput(messages: ChatMessage[]) {
+function normalizeIncomingResponsesInput(messages: ChatMessage[], userLocation?: string, params: Pick<ToolAwareCompletionParams, "enabledTools"> = {}) {
   const normalized = messages.map((message) => buildOpenAIResponsesInputMessage(message));
 
-  return [{ role: "system", content: CHAT_TOOL_SYSTEM_PROMPT }, ...normalized];
+  return [{ role: "system", content: buildChatToolSystemPrompt(params) }, buildSystemPromptAugmentationMessage(userLocation), ...normalized];
 }
 
 async function runExaWebSearchTool(args: WebSearchArgs): Promise<ToolRunOutcome> {
@@ -957,7 +1018,8 @@ async function executeToolCallAndBuildEvent(
 }
 
 export async function runToolAwareOpenAIChat(params: ToolAwareCompletionParams): Promise<ToolAwareCompletionResult> {
-  const input: any[] = normalizeIncomingResponsesInput(params.messages);
+  const enabledTools = getEnabledChatTools(params);
+  const input: any[] = normalizeIncomingResponsesInput(params.messages, params.userLocation, params);
   const rawResponses: unknown[] = [];
   const toolEvents: ToolExecutionEvent[] = [];
   const usageAcc: Required<ToolAwareUsage> = { inputTokens: 0, outputTokens: 0, totalTokens: 0 };
@@ -971,7 +1033,7 @@ export async function runToolAwareOpenAIChat(params: ToolAwareCompletionParams):
       input,
       temperature: params.temperature,
       max_output_tokens: params.maxTokens,
-      tools: RESPONSES_CHAT_TOOLS,
+      tools: toResponsesChatTools(enabledTools),
       tool_choice: "auto",
       parallel_tool_calls: true,
       // Tool loops pass response output items back as input; reasoning items need persistence.
@@ -1026,7 +1088,8 @@ export async function runToolAwareOpenAIChat(params: ToolAwareCompletionParams):
 }
 
 export async function runToolAwareChatCompletions(params: ToolAwareCompletionParams): Promise<ToolAwareCompletionResult> {
-  const conversation: any[] = normalizeIncomingMessages(params.messages);
+  const enabledTools = getEnabledChatTools(params);
+  const conversation: any[] = normalizeIncomingMessages(params.messages, params.userLocation, params);
   const rawResponses: unknown[] = [];
   const toolEvents: ToolExecutionEvent[] = [];
   const usageAcc: Required<ToolAwareUsage> = { inputTokens: 0, outputTokens: 0, totalTokens: 0 };
@@ -1040,7 +1103,7 @@ export async function runToolAwareChatCompletions(params: ToolAwareCompletionPar
       messages: conversation,
       temperature: params.temperature,
       max_tokens: params.maxTokens,
-      tools: CHAT_TOOLS,
+      tools: enabledTools,
       tool_choice: "auto",
     } as any);
     rawResponses.push(completion);
@@ -1114,7 +1177,7 @@ export async function runToolAwareChatCompletions(params: ToolAwareCompletionPar
 export async function runPlainChatCompletions(params: ToolAwareCompletionParams): Promise<ToolAwareCompletionResult> {
   const completion = await params.client.chat.completions.create({
     model: params.model,
-    messages: normalizePlainIncomingMessages(params.messages),
+    messages: normalizePlainIncomingMessages(params.messages, params.userLocation),
     temperature: params.temperature,
     max_tokens: params.maxTokens,
   } as any);
@@ -1134,7 +1197,8 @@ export async function runPlainChatCompletions(params: ToolAwareCompletionParams)
 export async function* runToolAwareOpenAIChatStream(
   params: ToolAwareCompletionParams
 ): AsyncGenerator<ToolAwareStreamingEvent> {
-  const input: any[] = normalizeIncomingResponsesInput(params.messages);
+  const enabledTools = getEnabledChatTools(params);
+  const input: any[] = normalizeIncomingResponsesInput(params.messages, params.userLocation, params);
   const rawResponses: unknown[] = [];
   const toolEvents: ToolExecutionEvent[] = [];
   const usageAcc: Required<ToolAwareUsage> = { inputTokens: 0, outputTokens: 0, totalTokens: 0 };
@@ -1148,7 +1212,7 @@ export async function* runToolAwareOpenAIChatStream(
       input,
       temperature: params.temperature,
       max_output_tokens: params.maxTokens,
-      tools: RESPONSES_CHAT_TOOLS,
+      tools: toResponsesChatTools(enabledTools),
       tool_choice: "auto",
       parallel_tool_calls: true,
       // Tool loops pass response output items back as input; reasoning items need persistence.
@@ -1260,7 +1324,8 @@ export async function* runToolAwareOpenAIChatStream(
 export async function* runToolAwareChatCompletionsStream(
   params: ToolAwareCompletionParams
 ): AsyncGenerator<ToolAwareStreamingEvent> {
-  const conversation: any[] = normalizeIncomingMessages(params.messages);
+  const enabledTools = getEnabledChatTools(params);
+  const conversation: any[] = normalizeIncomingMessages(params.messages, params.userLocation, params);
   const rawResponses: unknown[] = [];
   const toolEvents: ToolExecutionEvent[] = [];
   const usageAcc: Required<ToolAwareUsage> = { inputTokens: 0, outputTokens: 0, totalTokens: 0 };
@@ -1274,7 +1339,7 @@ export async function* runToolAwareChatCompletionsStream(
       messages: conversation,
       temperature: params.temperature,
       max_tokens: params.maxTokens,
-      tools: CHAT_TOOLS,
+      tools: enabledTools,
       tool_choice: "auto",
       stream: true,
       stream_options: { include_usage: true },
@@ -1403,7 +1468,7 @@ export async function* runPlainChatCompletionsStream(
 
   const stream = await params.client.chat.completions.create({
     model: params.model,
-    messages: normalizePlainIncomingMessages(params.messages),
+    messages: normalizePlainIncomingMessages(params.messages, params.userLocation),
     temperature: params.temperature,
     max_tokens: params.maxTokens,
     stream: true,

server/src/llm/message-content.ts

@@ -1,5 +1,19 @@
 import type { ChatAttachment, ChatImageAttachment, ChatMessage, ChatTextAttachment } from "./types.js";
 
+const DEFAULT_USER_LOCATION = "San Francisco, CA";
+
+function currentDateString(now = new Date()) {
+  return now.toISOString().slice(0, 10);
+}
+
+function resolveUserLocation(userLocation?: string) {
+  return userLocation?.trim() || process.env.SYBIL_USER_LOCATION?.trim() || DEFAULT_USER_LOCATION;
+}
+
+export function buildSystemPromptAugmentation(userLocation?: string, now = new Date()) {
+  return `Current date: ${currentDateString(now)}.\nUser location: ${resolveUserLocation(userLocation)}.`;
+}
+
 function escapeAttribute(value: string) {
   return value.replace(/"/g, """);
 }
@@ -198,11 +212,18 @@ export function buildOpenAIResponsesInputMessage(message: ChatMessage) {
   };
 }
 
+export function buildSystemPromptAugmentationMessage(userLocation?: string) {
+  return {
+    role: "system",
+    content: buildSystemPromptAugmentation(userLocation),
+  };
+}
+
 const ANTHROPIC_NO_SERVER_TOOLS_PROMPT =
   "This Anthropic backend path does not have server-managed tool calls. Do not claim to run shell commands, Codex tasks, web searches, or fetch URLs. If the user asks for tool execution, explain that they should switch to OpenAI or xAI in this app for tool-enabled chat.";
 
-export function getAnthropicSystemPrompt(messages: ChatMessage[]) {
+export function getAnthropicSystemPrompt(messages: ChatMessage[], userLocation?: string) {
-  return [ANTHROPIC_NO_SERVER_TOOLS_PROMPT, messages.find((message) => message.role === "system")?.content]
+  return [ANTHROPIC_NO_SERVER_TOOLS_PROMPT, buildSystemPromptAugmentation(userLocation), messages.find((message) => message.role === "system")?.content]
     .filter(Boolean)
     .join("\n\n");
 }

server/src/llm/model-catalog.ts

@@ -13,6 +13,7 @@ export type ModelCatalogSnapshot = Partial<Record<Provider, ProviderModelSnapsho
 
 const baseProviders: Provider[] = ["openai", "anthropic", "xai"];
 const MODEL_FETCH_TIMEOUT_MS = 15000;
+const MODEL_CATALOG_REFRESH_INTERVAL_MS = 24 * 60 * 60 * 1000;
 
 const modelCatalog: ModelCatalogSnapshot = {
   openai: { models: [], loadedAt: null, error: null },
@@ -20,6 +21,8 @@ const modelCatalog: ModelCatalogSnapshot = {
   xai: { models: [], loadedAt: null, error: null },
 };
 
+let catalogRefreshPromise: Promise<void> | null = null;
+
 function getCatalogProviders(): Provider[] {
   return isHermesAgentConfigured() ? [...baseProviders, "hermes-agent"] : baseProviders;
 }
@@ -86,17 +89,42 @@ async function refreshProviderModels(provider: Provider, logger?: FastifyBaseLog
     logger?.info({ provider, modelCount: models.length }, "model catalog loaded");
   } catch (err: any) {
     const message = err?.message ?? String(err);
+    const previous = modelCatalog[provider];
+    const fallbackModels = provider === "hermes-agent" && env.HERMES_AGENT_MODEL ? [env.HERMES_AGENT_MODEL] : [];
     modelCatalog[provider] = {
-      models: provider === "hermes-agent" && env.HERMES_AGENT_MODEL ? [env.HERMES_AGENT_MODEL] : [],
+      models: previous?.models.length ? previous.models : fallbackModels,
-      loadedAt: new Date().toISOString(),
+      loadedAt: previous?.loadedAt ?? null,
       error: message,
     };
     logger?.warn({ provider, err: message }, "failed to load provider model catalog");
   }
 }
 
+export async function refreshModelCatalog(logger?: FastifyBaseLogger) {
+  if (catalogRefreshPromise) return catalogRefreshPromise;
+
+  catalogRefreshPromise = Promise.all(getCatalogProviders().map((provider) => refreshProviderModels(provider, logger)))
+    .then(() => undefined)
+    .finally(() => {
+      catalogRefreshPromise = null;
+    });
+
+  return catalogRefreshPromise;
+}
+
 export async function warmModelCatalog(logger?: FastifyBaseLogger) {
-  await Promise.all(getCatalogProviders().map((provider) => refreshProviderModels(provider, logger)));
+  await refreshModelCatalog(logger);
+}
+
+export function startModelCatalogRefreshLoop(logger?: FastifyBaseLogger) {
+  const timer = setInterval(() => {
+    void refreshModelCatalog(logger);
+  }, MODEL_CATALOG_REFRESH_INTERVAL_MS);
+  timer.unref?.();
+
+  return () => {
+    clearInterval(timer);
+  };
 }
 
 export function getModelCatalogSnapshot(): ModelCatalogSnapshot {

server/src/llm/multiplexer.ts

@@ -1,7 +1,7 @@
 import { performance } from "node:perf_hooks";
 import { prisma } from "../db.js";
 import { anthropicClient, hermesAgentClient, openaiClient, xaiClient } from "./providers.js";
-import { buildToolLogMessageData, runPlainChatCompletions, runToolAwareChatCompletions, runToolAwareOpenAIChat } from "./chat-tools.js";
+import { buildToolLogMessageData, normalizeEnabledChatTools, runPlainChatCompletions, runToolAwareChatCompletions, runToolAwareOpenAIChat } from "./chat-tools.js";
 import { buildAnthropicConversationMessage, getAnthropicSystemPrompt } from "./message-content.js";
 import { toPrismaProvider } from "./provider-ids.js";
 import type { MultiplexRequest, MultiplexResponse, Provider } from "./types.js";
@@ -47,13 +47,16 @@ export async function runMultiplex(req: MultiplexRequest): Promise<MultiplexResp
     let usage: MultiplexResponse["usage"] | undefined;
     let raw: unknown;
     let toolMessages: ReturnType<typeof buildToolLogMessageData>[] = [];
+    const enabledTools = normalizeEnabledChatTools(req.enabledTools);
 
-    if (req.provider === "openai") {
+    if (req.provider === "openai" && enabledTools.length > 0) {
       const client = openaiClient();
       const r = await runToolAwareOpenAIChat({
         client,
         model: req.model,
         messages: req.messages,
+        enabledTools,
+        userLocation: req.userLocation,
         temperature: req.temperature,
         maxTokens: req.maxTokens,
         logContext: {
@@ -66,12 +69,14 @@ export async function runMultiplex(req: MultiplexRequest): Promise<MultiplexResp
       outText = r.text;
       usage = r.usage;
       toolMessages = r.toolEvents.map((event) => buildToolLogMessageData(call.chatId, event));
-    } else if (req.provider === "xai") {
+    } else if (req.provider === "xai" && enabledTools.length > 0) {
       const client = xaiClient();
       const r = await runToolAwareChatCompletions({
         client,
         model: req.model,
         messages: req.messages,
+        enabledTools,
+        userLocation: req.userLocation,
         temperature: req.temperature,
         maxTokens: req.maxTokens,
         logContext: {
@@ -84,12 +89,13 @@ export async function runMultiplex(req: MultiplexRequest): Promise<MultiplexResp
       outText = r.text;
       usage = r.usage;
       toolMessages = r.toolEvents.map((event) => buildToolLogMessageData(call.chatId, event));
-    } else if (req.provider === "hermes-agent") {
+    } else if (req.provider === "openai" || req.provider === "xai" || req.provider === "hermes-agent") {
-      const client = hermesAgentClient();
+      const client = req.provider === "openai" ? openaiClient() : req.provider === "xai" ? xaiClient() : hermesAgentClient();
       const r = await runPlainChatCompletions({
         client,
         model: req.model,
         messages: req.messages,
+        userLocation: req.userLocation,
         temperature: req.temperature,
         maxTokens: req.maxTokens,
         logContext: {
@@ -104,7 +110,7 @@ export async function runMultiplex(req: MultiplexRequest): Promise<MultiplexResp
     } else if (req.provider === "anthropic") {
       const client = anthropicClient();
 
-      const system = getAnthropicSystemPrompt(req.messages);
+      const system = getAnthropicSystemPrompt(req.messages, req.userLocation);
       const msgs = req.messages.filter((message) => message.role !== "system").map((message) => buildAnthropicConversationMessage(message));
 
       const r = await client.messages.create({

server/src/llm/streaming.ts

@@ -3,6 +3,7 @@ import { prisma } from "../db.js";
 import { anthropicClient, hermesAgentClient, openaiClient, xaiClient } from "./providers.js";
 import {
   buildToolLogMessageData,
+  normalizeEnabledChatTools,
   runPlainChatCompletionsStream,
   runToolAwareChatCompletionsStream,
   runToolAwareOpenAIChatStream,
@@ -76,12 +77,15 @@ export async function* runMultiplexStream(req: MultiplexRequest): AsyncGenerator
   try {
     if (req.provider === "openai" || req.provider === "xai" || req.provider === "hermes-agent") {
       const client = req.provider === "openai" ? openaiClient() : req.provider === "xai" ? xaiClient() : hermesAgentClient();
+      const enabledTools = normalizeEnabledChatTools(req.enabledTools);
       const streamEvents =
-        req.provider === "openai"
+        req.provider === "openai" && enabledTools.length > 0
           ? runToolAwareOpenAIChatStream({
               client,
               model: req.model,
               messages: req.messages,
+              enabledTools,
+              userLocation: req.userLocation,
               temperature: req.temperature,
               maxTokens: req.maxTokens,
               logContext: {
@@ -90,11 +94,12 @@ export async function* runMultiplexStream(req: MultiplexRequest): AsyncGenerator
                 chatId: chatId ?? undefined,
               },
             })
-          : req.provider === "hermes-agent"
+          : req.provider === "hermes-agent" || enabledTools.length === 0
             ? runPlainChatCompletionsStream({
                 client,
                 model: req.model,
                 messages: req.messages,
+                userLocation: req.userLocation,
                 temperature: req.temperature,
                 maxTokens: req.maxTokens,
                 logContext: {
@@ -107,6 +112,8 @@ export async function* runMultiplexStream(req: MultiplexRequest): AsyncGenerator
               client,
               model: req.model,
               messages: req.messages,
+              enabledTools,
+              userLocation: req.userLocation,
               temperature: req.temperature,
               maxTokens: req.maxTokens,
               logContext: {
@@ -146,7 +153,7 @@ export async function* runMultiplexStream(req: MultiplexRequest): AsyncGenerator
     } else if (req.provider === "anthropic") {
       const client = anthropicClient();
 
-      const system = getAnthropicSystemPrompt(req.messages);
+      const system = getAnthropicSystemPrompt(req.messages, req.userLocation);
       const msgs = req.messages.filter((message) => message.role !== "system").map((message) => buildAnthropicConversationMessage(message));
 
       const stream = await client.messages.create({

server/src/llm/types.ts

@@ -36,6 +36,9 @@ export type MultiplexRequest = {
   provider: Provider;
   model: string;
   messages: ChatMessage[];
+  additionalSystemPrompt?: string;
+  enabledTools?: string[];
+  userLocation?: string;
   temperature?: number;
   maxTokens?: number;
 };

server/src/routes.ts

@@ -8,6 +8,7 @@ import { env } from "./env.js";
 import { buildComparableAttachments } from "./llm/message-content.js";
 import { runMultiplex } from "./llm/multiplexer.js";
 import { runMultiplexStream, type StreamEvent } from "./llm/streaming.js";
+import { getAvailableChatTools, normalizeEnabledChatTools } from "./llm/chat-tools.js";
 import { getModelCatalogSnapshot } from "./llm/model-catalog.js";
 import { openaiClient } from "./llm/providers.js";
 import { serializeProviderFields, toPrismaProvider } from "./llm/provider-ids.js";
@@ -15,6 +16,8 @@ import { exaClient } from "./search/exa.js";
 import type { ChatAttachment } from "./llm/types.js";
 
 const ProviderSchema = z.enum(["openai", "anthropic", "xai", "hermes-agent"]);
+const MAX_ADDITIONAL_SYSTEM_PROMPT_CHARS = 12_000;
+const EnabledToolsSchema = z.array(z.string().trim().min(1).max(80)).max(20).transform((value) => normalizeEnabledChatTools(value));
 
 type IncomingChatMessage = {
   role: "system" | "user" | "assistant" | "tool";
@@ -47,6 +50,43 @@ function isToolCallLogMessage(message: { role: string; metadata: unknown }) {
   return message.role === "tool" && isToolCallLogMetadata(message.metadata);
 }
 
+function getHeaderString(req: FastifyRequest, name: string) {
+  const value = req.headers[name.toLowerCase()];
+  if (Array.isArray(value)) return value.find((item) => item.trim());
+  return typeof value === "string" && value.trim() ? value : undefined;
+}
+
+function decodeHeaderPart(value: string | undefined) {
+  if (!value) return undefined;
+  const trimmed = value.trim();
+  if (!trimmed) return undefined;
+  try {
+    return decodeURIComponent(trimmed);
+  } catch {
+    return trimmed;
+  }
+}
+
+function inferRequestUserLocation(req: FastifyRequest) {
+  const explicit = decodeHeaderPart(getHeaderString(req, "x-user-location"));
+  if (explicit) return explicit;
+
+  const vercelCity = decodeHeaderPart(getHeaderString(req, "x-vercel-ip-city"));
+  const vercelRegion = decodeHeaderPart(getHeaderString(req, "x-vercel-ip-country-region"));
+  const vercelCountry = decodeHeaderPart(getHeaderString(req, "x-vercel-ip-country"));
+  const vercelLocation = [vercelCity, vercelRegion, vercelCountry].filter(Boolean).join(", ");
+  if (vercelLocation) return vercelLocation;
+
+  const cfCity = decodeHeaderPart(getHeaderString(req, "cf-ipcity"));
+  const cfRegion = decodeHeaderPart(getHeaderString(req, "cf-region"));
+  const cfCountry = decodeHeaderPart(getHeaderString(req, "cf-ipcountry"));
+  return [cfCity, cfRegion, cfCountry].filter(Boolean).join(", ") || undefined;
+}
+
+function withRequestUserLocation<T extends { userLocation?: string }>(body: T, req: FastifyRequest): T {
+  return body.userLocation ? body : { ...body, userLocation: inferRequestUserLocation(req) };
+}
+
 async function storeNonAssistantMessages(chatId: string, messages: IncomingChatMessage[]) {
   const incoming = messages.filter((m) => m.role !== "assistant");
   if (!incoming.length) return;
@@ -131,6 +171,9 @@ const CompletionStreamBody = z
     provider: ProviderSchema,
     model: z.string().min(1),
     messages: z.array(CompletionMessageSchema),
+    additionalSystemPrompt: z.string().max(MAX_ADDITIONAL_SYSTEM_PROMPT_CHARS).optional(),
+    enabledTools: EnabledToolsSchema.optional(),
+    userLocation: z.string().trim().min(1).max(200).optional(),
     temperature: z.number().min(0).max(2).optional(),
     maxTokens: z.number().int().positive().optional(),
   })
@@ -155,6 +198,41 @@ function mergeAttachmentsIntoMetadata(metadata: unknown, attachments?: ChatAttac
   };
 }
 
+function normalizeAdditionalSystemPrompt(value: string | null | undefined) {
+  const trimmed = value?.trim();
+  return trimmed || null;
+}
+
+function prependAdditionalSystemPrompt<T extends { messages: IncomingChatMessage[]; additionalSystemPrompt?: string | null }>(body: T): T {
+  const additionalSystemPrompt = normalizeAdditionalSystemPrompt(body.additionalSystemPrompt);
+  if (!additionalSystemPrompt) return { ...body, additionalSystemPrompt: undefined };
+  return {
+    ...body,
+    additionalSystemPrompt,
+    messages: [{ role: "system", content: additionalSystemPrompt }, ...body.messages],
+  };
+}
+
+async function applyStoredChatSettings<T extends { chatId?: string; messages: IncomingChatMessage[]; additionalSystemPrompt?: string; enabledTools?: string[] }>(
+  body: T
+) {
+  if (!body.chatId || (body.additionalSystemPrompt !== undefined && body.enabledTools !== undefined)) {
+    return prependAdditionalSystemPrompt(body);
+  }
+
+  const chat = await prisma.chat.findUnique({
+    where: { id: body.chatId },
+    select: { additionalSystemPrompt: true, enabledTools: true },
+  });
+  if (!chat) return prependAdditionalSystemPrompt(body);
+
+  return prependAdditionalSystemPrompt({
+    ...body,
+    additionalSystemPrompt: body.additionalSystemPrompt ?? chat.additionalSystemPrompt ?? undefined,
+    enabledTools: body.enabledTools ?? normalizeEnabledChatTools(chat.enabledTools),
+  });
+}
+
 const SearchRunBody = z.object({
   query: z.string().trim().min(1).optional(),
   title: z.string().trim().min(1).optional(),
@@ -326,6 +404,41 @@ function getErrorMessage(err: unknown) {
   return err instanceof Error ? err.message : String(err);
 }
 
+function compareUpdatedAtDesc(a: { updatedAt: Date | string }, b: { updatedAt: Date | string }) {
+  return new Date(b.updatedAt).getTime() - new Date(a.updatedAt).getTime();
+}
+
+async function listWorkspaceItems() {
+  const [chats, searches] = await Promise.all([
+    prisma.chat.findMany({
+      orderBy: { updatedAt: "desc" },
+      take: 100,
+      select: {
+        id: true,
+        title: true,
+        createdAt: true,
+        updatedAt: true,
+        initiatedProvider: true,
+        initiatedModel: true,
+        lastUsedProvider: true,
+        lastUsedModel: true,
+        additionalSystemPrompt: true,
+        enabledTools: true,
+      },
+    }),
+    prisma.search.findMany({
+      orderBy: { updatedAt: "desc" },
+      take: 100,
+      select: { id: true, title: true, query: true, createdAt: true, updatedAt: true },
+    }),
+  ]);
+
+  return [
+    ...chats.map((chat) => ({ type: "chat" as const, ...serializeProviderFields(chat) })),
+    ...searches.map((search) => ({ type: "search" as const, ...search })),
+  ].sort(compareUpdatedAtDesc);
+}
+
 function writeSseEvent(reply: FastifyReply, event: SseStreamEvent) {
   if (reply.raw.destroyed || reply.raw.writableEnded) return;
   reply.raw.write(`event: ${event.event}\n`);
@@ -570,6 +683,11 @@ export async function registerRoutes(app: FastifyInstance) {
     return { providers: getModelCatalogSnapshot() };
   });
 
+  app.get("/v1/chat-tools", async (req) => {
+    requireAdmin(req);
+    return { tools: getAvailableChatTools() };
+  });
+
   app.get("/v1/active-runs", async (req) => {
     requireAdmin(req);
     return {
@@ -578,6 +696,11 @@ export async function registerRoutes(app: FastifyInstance) {
     };
   });
 
+  app.get("/v1/workspace-items", async (req) => {
+    requireAdmin(req);
+    return { items: await listWorkspaceItems() };
+  });
+
   app.get("/v1/chats", async (req) => {
     requireAdmin(req);
     const chats = await prisma.chat.findMany({
@@ -592,6 +715,8 @@ export async function registerRoutes(app: FastifyInstance) {
         initiatedModel: true,
         lastUsedProvider: true,
         lastUsedModel: true,
+        additionalSystemPrompt: true,
+        enabledTools: true,
       },
     });
     return { chats: chats.map((chat) => serializeProviderFields(chat)) };
@@ -604,6 +729,8 @@ export async function registerRoutes(app: FastifyInstance) {
         title: z.string().optional(),
         provider: ProviderSchema.optional(),
         model: z.string().trim().min(1).optional(),
+        additionalSystemPrompt: z.string().max(MAX_ADDITIONAL_SYSTEM_PROMPT_CHARS).optional(),
+        enabledTools: EnabledToolsSchema.optional(),
         messages: z.array(CompletionMessageSchema).optional(),
       })
       .superRefine((value, ctx) => {
@@ -632,6 +759,8 @@ export async function registerRoutes(app: FastifyInstance) {
         initiatedModel: body.model,
         lastUsedProvider: body.provider ? (toPrismaProvider(body.provider) as any) : undefined,
         lastUsedModel: body.model,
+        additionalSystemPrompt: normalizeAdditionalSystemPrompt(body.additionalSystemPrompt),
+        enabledTools: body.enabledTools as any,
         messages: body.messages?.length
           ? {
               create: body.messages.map((message) => ({
@@ -652,6 +781,8 @@ export async function registerRoutes(app: FastifyInstance) {
         initiatedModel: true,
         lastUsedProvider: true,
         lastUsedModel: true,
+        additionalSystemPrompt: true,
+        enabledTools: true,
       },
     });
     return { chat: serializeProviderFields(chat) };
@@ -660,13 +791,22 @@ export async function registerRoutes(app: FastifyInstance) {
   app.patch("/v1/chats/:chatId", async (req) => {
     requireAdmin(req);
     const Params = z.object({ chatId: z.string() });
-    const Body = z.object({ title: z.string().trim().min(1) });
+    const Body = z.object({
+      title: z.string().trim().min(1).optional(),
+      additionalSystemPrompt: z.string().max(MAX_ADDITIONAL_SYSTEM_PROMPT_CHARS).nullable().optional(),
+      enabledTools: EnabledToolsSchema.optional(),
+    });
     const { chatId } = Params.parse(req.params);
     const body = Body.parse(req.body ?? {});
 
+    const data: Record<string, unknown> = {};
+    if (body.title !== undefined) data.title = body.title;
+    if (body.additionalSystemPrompt !== undefined) data.additionalSystemPrompt = normalizeAdditionalSystemPrompt(body.additionalSystemPrompt);
+    if (body.enabledTools !== undefined) data.enabledTools = body.enabledTools;
+
     const updated = await prisma.chat.updateMany({
       where: { id: chatId },
-      data: { title: body.title },
+      data: data as any,
     });
 
     if (updated.count === 0) return app.httpErrors.notFound("chat not found");
@@ -682,6 +822,8 @@ export async function registerRoutes(app: FastifyInstance) {
         initiatedModel: true,
         lastUsedProvider: true,
         lastUsedModel: true,
+        additionalSystemPrompt: true,
+        enabledTools: true,
       },
     });
     if (!chat) return app.httpErrors.notFound("chat not found");
@@ -707,6 +849,8 @@ export async function registerRoutes(app: FastifyInstance) {
         initiatedModel: true,
         lastUsedProvider: true,
         lastUsedModel: true,
+        additionalSystemPrompt: true,
+        enabledTools: true,
       },
     });
     if (!existing) return app.httpErrors.notFound("chat not found");
@@ -728,6 +872,8 @@ export async function registerRoutes(app: FastifyInstance) {
         initiatedModel: true,
         lastUsedProvider: true,
         lastUsedModel: true,
+        additionalSystemPrompt: true,
+        enabledTools: true,
       },
     });
 
@@ -848,6 +994,8 @@ export async function registerRoutes(app: FastifyInstance) {
         initiatedModel: true,
         lastUsedProvider: true,
         lastUsedModel: true,
+        additionalSystemPrompt: true,
+        enabledTools: true,
       },
     });
 
@@ -1047,13 +1195,16 @@ export async function registerRoutes(app: FastifyInstance) {
       provider: ProviderSchema,
       model: z.string().min(1),
       messages: z.array(CompletionMessageSchema),
+      additionalSystemPrompt: z.string().max(MAX_ADDITIONAL_SYSTEM_PROMPT_CHARS).optional(),
+      enabledTools: EnabledToolsSchema.optional(),
+      userLocation: z.string().trim().min(1).max(200).optional(),
       temperature: z.number().min(0).max(2).optional(),
       maxTokens: z.number().int().positive().optional(),
     });
 
     const parsed = Body.safeParse(req.body);
     if (!parsed.success) return app.httpErrors.badRequest(parsed.error.message);
-    const body = parsed.data;
+    const body = withRequestUserLocation(parsed.data, req);
 
     // ensure chat exists if provided
     if (body.chatId) {
@@ -1066,7 +1217,7 @@ export async function registerRoutes(app: FastifyInstance) {
       await storeNonAssistantMessages(body.chatId, body.messages);
     }
 
-    const result = await runMultiplex(body);
+    const result = await runMultiplex(await applyStoredChatSettings(body));
 
     return {
       chatId: body.chatId ?? null,
@@ -1080,7 +1231,7 @@ export async function registerRoutes(app: FastifyInstance) {
 
     const parsed = CompletionStreamBody.safeParse(req.body);
     if (!parsed.success) return app.httpErrors.badRequest(parsed.error.message);
-    const body = parsed.data;
+    const body = withRequestUserLocation(parsed.data, req);
 
     // ensure chat exists if provided
     if (body.chatId) {
@@ -1097,14 +1248,14 @@ export async function registerRoutes(app: FastifyInstance) {
       if (activeChatStreams.has(body.chatId)) {
         return app.httpErrors.conflict("chat completion already running");
       }
-      const stream = startActiveChatStream(body.chatId, body);
+      const stream = startActiveChatStream(body.chatId, await applyStoredChatSettings(body));
       return streamActiveRun(req, reply, stream);
     }
 
     reply.raw.writeHead(200, buildSseHeaders(typeof req.headers.origin === "string" ? req.headers.origin : undefined));
     reply.raw.flushHeaders();
 
-    for await (const ev of runMultiplexStream(body)) {
+    for await (const ev of runMultiplexStream(await applyStoredChatSettings(body))) {
       writeSseEvent(reply, mapChatStreamEvent(ev));
     }
 

server/tests/message-content.test.ts

@@ -0,0 +1,26 @@
+import assert from "node:assert/strict";
+import test from "node:test";
+import { buildSystemPromptAugmentation, getAnthropicSystemPrompt } from "../src/llm/message-content.js";
+
+test("system prompt augmentation includes date and default location", () => {
+  const prompt = buildSystemPromptAugmentation(undefined, new Date("2026-05-24T15:30:00Z"));
+
+  assert.equal(prompt, "Current date: 2026-05-24.\nUser location: San Francisco, CA.");
+});
+
+test("system prompt augmentation uses provided user location", () => {
+  const prompt = buildSystemPromptAugmentation("New York, NY", new Date("2026-05-24T15:30:00Z"));
+
+  assert.equal(prompt, "Current date: 2026-05-24.\nUser location: New York, NY.");
+});
+
+test("Anthropic system prompt includes runtime context with existing system messages", () => {
+  const prompt = getAnthropicSystemPrompt(
+    [{ role: "system", content: "Use concise answers." }],
+    "Los Angeles, CA"
+  );
+
+  assert.match(prompt, /Current date: \d{4}-\d{2}-\d{2}\./);
+  assert.match(prompt, /User location: Los Angeles, CA\./);
+  assert.match(prompt, /Use concise answers\./);
+});

tui/src/api.ts

@@ -10,6 +10,7 @@ import type {
   SearchStreamHandlers,
   SearchSummary,
   SessionStatus,
+  WorkspaceItem,
 } from "./types.js";
 
 type RequestOptions = {
@@ -41,6 +42,11 @@ export class SybilApiClient {
     return data.chats;
   }
 
+  async listWorkspaceItems() {
+    const data = await this.request<{ items: WorkspaceItem[] }>("/v1/workspace-items");
+    return data.items;
+  }
+
   async createChat(title?: string) {
     const data = await this.request<{ chat: ChatSummary }>("/v1/chats", {
       method: "POST",
@@ -94,6 +100,7 @@ export class SybilApiClient {
       provider: Provider;
       model: string;
       messages: CompletionRequestMessage[];
+      userLocation?: string;
     },
     handlers: CompletionStreamHandlers,
     options?: { signal?: AbortSignal }

tui/src/index.ts

@@ -11,6 +11,7 @@ import type {
   SearchDetail,
   SearchSummary,
   ToolCallEvent,
+  WorkspaceItem,
 } from "./types.js";
 
 type SidebarSelection = { kind: "chat" | "search"; id: string };
@@ -93,9 +94,38 @@ function getSearchTitle(search: Pick<SearchSummary, "title" | "query">) {
   return "New search";
 }
 
-function buildSidebarItems(chats: ChatSummary[], searches: SearchSummary[]): SidebarItem[] {
+function chatWorkspaceItem(chat: ChatSummary): WorkspaceItem {
-  const items: SidebarItem[] = [
+  return { type: "chat", ...chat };
-    ...chats.map((chat) => ({
+}
+
+function searchWorkspaceItem(search: SearchSummary): WorkspaceItem {
+  return { type: "search", ...search };
+}
+
+function splitWorkspaceItems(items: WorkspaceItem[]) {
+  const chats: ChatSummary[] = [];
+  const searches: SearchSummary[] = [];
+  for (const item of items) {
+    if (item.type === "chat") {
+      const { type: _type, ...chat } = item;
+      chats.push(chat);
+    } else {
+      const { type: _type, ...search } = item;
+      searches.push(search);
+    }
+  }
+  return { chats, searches };
+}
+
+function upsertWorkspaceItem(items: WorkspaceItem[], item: WorkspaceItem) {
+  return [item, ...items.filter((existing) => existing.type !== item.type || existing.id !== item.id)];
+}
+
+function buildSidebarItems(items: WorkspaceItem[]): SidebarItem[] {
+  return items.map((item) => {
+    if (item.type === "chat") {
+      const chat = item;
+      return {
       kind: "chat" as const,
       id: chat.id,
       title: getChatTitle(chat),
@@ -105,8 +135,11 @@ function buildSidebarItems(chats: ChatSummary[], searches: SearchSummary[]): Sid
       initiatedModel: chat.initiatedModel,
       lastUsedProvider: chat.lastUsedProvider,
       lastUsedModel: chat.lastUsedModel,
-    })),
+      };
-    ...searches.map((search) => ({
+    }
+
+    const search = item;
+    return {
       kind: "search" as const,
       id: search.id,
       title: getSearchTitle(search),
@@ -116,10 +149,8 @@ function buildSidebarItems(chats: ChatSummary[], searches: SearchSummary[]): Sid
       initiatedModel: null,
       lastUsedProvider: null,
       lastUsedModel: null,
-    })),
+    };
-  ];
+  });
-
-  return items.sort((a, b) => new Date(b.updatedAt).getTime() - new Date(a.updatedAt).getTime());
 }
 
 function asToolLogMetadata(value: unknown): ToolLogMetadata | null {
@@ -195,6 +226,7 @@ async function main() {
   let authMode: "open" | "token" | null = null;
   let chats: ChatSummary[] = [];
   let searches: SearchSummary[] = [];
+  let workspaceItems: WorkspaceItem[] = [];
   let selectedItem: SidebarSelection | null = null;
   let selectedChat: ChatDetail | null = null;
   let selectedSearch: SearchDetail | null = null;
@@ -377,7 +409,7 @@ async function main() {
   }
 
   function getSidebarItems() {
-    return buildSidebarItems(chats, searches);
+    return buildSidebarItems(workspaceItems);
   }
 
   function getSelectedChatSummary() {
@@ -701,6 +733,7 @@ async function main() {
   function resetWorkspaceState() {
     chats = [];
     searches = [];
+    workspaceItems = [];
     selectedItem = null;
     selectedChat = null;
     selectedSearch = null;
@@ -767,11 +800,13 @@ async function main() {
     updateUI();
 
     try {
-      const [nextChats, nextSearches] = await Promise.all([api.listChats(), api.listSearches()]);
+      const nextWorkspaceItems = await api.listWorkspaceItems();
+      const { chats: nextChats, searches: nextSearches } = splitWorkspaceItems(nextWorkspaceItems);
+      workspaceItems = nextWorkspaceItems;
       chats = nextChats;
       searches = nextSearches;
 
-      const nextItems = buildSidebarItems(nextChats, nextSearches);
+      const nextItems = buildSidebarItems(nextWorkspaceItems);
       if (options?.preferredSelection && hasItem(nextItems, options.preferredSelection)) {
         selectedItem = options.preferredSelection;
         draftKind = null;
@@ -876,6 +911,7 @@ async function main() {
     try {
       const updated = await api.suggestChatTitle({ chatId, content });
       chats = chats.map((chat) => (chat.id === updated.id ? { ...chat, title: updated.title, updatedAt: updated.updatedAt } : chat));
+      workspaceItems = workspaceItems.map((item) => (item.type === "chat" && item.id === updated.id ? chatWorkspaceItem(updated) : item));
       if (selectedChat?.id === updated.id) {
         selectedChat = { ...selectedChat, title: updated.title, updatedAt: updated.updatedAt };
       }
@@ -920,6 +956,7 @@ async function main() {
       chatId = chat.id;
       draftKind = null;
       chats = [chat, ...chats.filter((existing) => existing.id !== chat.id)];
+      workspaceItems = upsertWorkspaceItem(workspaceItems, chatWorkspaceItem(chat));
       selectedItem = { kind: "chat", id: chat.id };
       pendingChatState = pendingChatState ? { ...pendingChatState, chatId } : pendingChatState;
       selectedChat = {
@@ -1085,6 +1122,7 @@ async function main() {
       draftKind = null;
       selectedItem = { kind: "search", id: searchId };
       searches = [search, ...searches.filter((existing) => existing.id !== search.id)];
+      workspaceItems = upsertWorkspaceItem(workspaceItems, searchWorkspaceItem(search));
       selectedChat = null;
       forceScrollToBottom = true;
       updateUI();

tui/src/types.ts

@@ -29,6 +29,16 @@ export type SearchSummary = {
   updatedAt: string;
 };
 
+export type ChatWorkspaceItem = ChatSummary & {
+  type: "chat";
+};
+
+export type SearchWorkspaceItem = SearchSummary & {
+  type: "search";
+};
+
+export type WorkspaceItem = ChatWorkspaceItem | SearchWorkspaceItem;
+
 export type Message = {
   id: string;
   createdAt: string;

web/src/App.tsx

@@ -1,5 +1,20 @@
 import { useEffect, useMemo, useRef, useState } from "preact/hooks";
-import { Check, ChevronDown, Globe2, LoaderCircle, Menu, MessageSquare, Paperclip, Plus, Rabbit, Search, SendHorizontal, Trash2, X } from "lucide-preact";
+import {
+  Check,
+  ChevronDown,
+  Globe2,
+  LoaderCircle,
+  Menu,
+  MessageSquare,
+  Paperclip,
+  Plus,
+  Rabbit,
+  Search,
+  SendHorizontal,
+  Settings2,
+  Trash2,
+  X,
+} from "lucide-preact";
 import { Button } from "@/components/ui/button";
 import { Textarea } from "@/components/ui/textarea";
 import { Separator } from "@/components/ui/separator";
@@ -18,13 +33,14 @@ import {
   attachSearchStream,
   getActiveRuns,
   getChat,
+  listChatTools,
   listModels,
   getSearch,
-  listChats,
+  listWorkspaceItems,
-  listSearches,
   runCompletionStream,
   runSearchStream,
   suggestChatTitle,
+  updateChatSettings,
   getMessageAttachments,
   type ChatAttachment,
   type ActiveRunsResponse,
@@ -32,11 +48,13 @@ import {
   type Provider,
   type ChatDetail,
   type ChatSummary,
+  type ChatToolInfo,
   type CompletionRequestMessage,
   type Message,
   type SearchDetail,
   type SearchSummary,
   type ToolCallEvent,
+  type WorkspaceItem,
 } from "@/lib/api";
 import { useSessionAuth } from "@/hooks/use-session-auth";
 import { cn } from "@/lib/utils";
@@ -371,6 +389,30 @@ function getProviderLabel(provider: Provider | null | undefined) {
   return "";
 }
 
+function getToolLabel(name: string) {
+  if (name === "web_search") return "Web search";
+  if (name === "fetch_url") return "Fetch URL";
+  if (name === "codex_exec") return "Codex";
+  if (name === "shell_exec") return "Shell";
+  return name
+    .split("_")
+    .filter(Boolean)
+    .map((part) => part.slice(0, 1).toUpperCase() + part.slice(1))
+    .join(" ");
+}
+
+function getDefaultEnabledTools(availableTools: ChatToolInfo[]) {
+  return availableTools.map((tool) => tool.name);
+}
+
+function normalizeEnabledTools(value: unknown, availableTools: ChatToolInfo[]) {
+  const available = new Set(availableTools.map((tool) => tool.name));
+  if (!Array.isArray(value)) return getDefaultEnabledTools(availableTools);
+  return [...new Set(value.filter((item): item is string => typeof item === "string").map((item) => item.trim()).filter(Boolean))].filter((name) =>
+    available.has(name)
+  );
+}
+
 function getChatModelSelection(chat: Pick<ChatSummary, "lastUsedProvider" | "lastUsedModel"> | Pick<ChatDetail, "lastUsedProvider" | "lastUsedModel"> | null) {
   if (!chat?.lastUsedProvider || !chat.lastUsedModel?.trim()) return null;
   return {
@@ -588,9 +630,34 @@ function getSearchTitle(search: Pick<SearchSummary, "title" | "query">) {
   return "New search";
 }
 
-function buildSidebarItems(chats: ChatSummary[], searches: SearchSummary[]): SidebarItem[] {
+function chatWorkspaceItem(chat: ChatSummary): WorkspaceItem {
-  const items: SidebarItem[] = [
+  return { type: "chat", ...chat };
-    ...chats.map((chat) => ({
+}
+
+function searchWorkspaceItem(search: SearchSummary): WorkspaceItem {
+  return { type: "search", ...search };
+}
+
+function splitWorkspaceItems(items: WorkspaceItem[]) {
+  const chats: ChatSummary[] = [];
+  const searches: SearchSummary[] = [];
+  for (const item of items) {
+    if (item.type === "chat") {
+      const { type: _type, ...chat } = item;
+      chats.push(chat);
+    } else {
+      const { type: _type, ...search } = item;
+      searches.push(search);
+    }
+  }
+  return { chats, searches };
+}
+
+function buildSidebarItems(items: WorkspaceItem[]): SidebarItem[] {
+  return items.map((item) => {
+    if (item.type === "chat") {
+      const chat = item;
+      return {
         kind: "chat" as const,
         id: chat.id,
         title: getChatTitle(chat),
@@ -600,8 +667,11 @@ function buildSidebarItems(chats: ChatSummary[], searches: SearchSummary[]): Sid
         initiatedModel: chat.initiatedModel,
         lastUsedProvider: chat.lastUsedProvider,
         lastUsedModel: chat.lastUsedModel,
-    })),
+      };
-    ...searches.map((search) => ({
+    }
+
+    const search = item;
+    return {
       kind: "search" as const,
       id: search.id,
       title: getSearchTitle(search),
@@ -611,10 +681,21 @@ function buildSidebarItems(chats: ChatSummary[], searches: SearchSummary[]): Sid
       initiatedModel: null,
       lastUsedProvider: null,
       lastUsedModel: null,
-    })),
+    };
-  ];
+  });
+}
 
-  return items.sort((a, b) => new Date(b.updatedAt).getTime() - new Date(a.updatedAt).getTime());
+function upsertWorkspaceItem(items: WorkspaceItem[], item: WorkspaceItem, moveToFront = true) {
+  const withoutExisting = items.filter((existing) => existing.type !== item.type || existing.id !== item.id);
+  if (moveToFront) {
+    return [item, ...withoutExisting];
+  }
+
+  const existingIndex = items.findIndex((existing) => existing.type === item.type && existing.id === item.id);
+  if (existingIndex < 0) return [item, ...items];
+  const next = [...items];
+  next[existingIndex] = item;
+  return next;
 }
 
 function buildActiveRunsState(activeRuns: ActiveRunsResponse): ActiveRunsState {
@@ -675,6 +756,7 @@ export default function App() {
 
   const [chats, setChats] = useState<ChatSummary[]>([]);
   const [searches, setSearches] = useState<SearchSummary[]>([]);
+  const [workspaceItems, setWorkspaceItems] = useState<WorkspaceItem[]>([]);
   const [selectedItem, setSelectedItem] = useState<SidebarSelection | null>(null);
   const [selectedChat, setSelectedChat] = useState<ChatDetail | null>(null);
   const [selectedSearch, setSelectedSearch] = useState<SearchDetail | null>(null);
@@ -690,6 +772,7 @@ export default function App() {
   const [isComposerDropActive, setIsComposerDropActive] = useState(false);
   const [provider, setProvider] = useState<Provider>("openai");
   const [modelCatalog, setModelCatalog] = useState<ModelCatalogResponse["providers"]>(EMPTY_MODEL_CATALOG);
+  const [availableChatTools, setAvailableChatTools] = useState<ChatToolInfo[]>([]);
   const [providerModelPreferences, setProviderModelPreferences] = useState<ProviderModelPreferences>(() => loadStoredModelPreferences());
   const [model, setModel] = useState(() => {
     const stored = loadStoredModelPreferences();
@@ -712,6 +795,9 @@ export default function App() {
   const [isConvertingQuickQuestion, setIsConvertingQuickQuestion] = useState(false);
   const [quickQuestionError, setQuickQuestionError] = useState<string | null>(null);
   const [error, setError] = useState<string | null>(null);
+  const [isChatSettingsOpen, setIsChatSettingsOpen] = useState(false);
+  const [additionalSystemPrompt, setAdditionalSystemPrompt] = useState("");
+  const [enabledTools, setEnabledTools] = useState<string[]>([]);
   const [transcriptTailSpacerHeight, setTranscriptTailSpacerHeight] = useState(TRANSCRIPT_BOTTOM_GAP);
   const transcriptContainerRef = useRef<HTMLDivElement>(null);
   const transcriptEndRef = useRef<HTMLDivElement>(null);
@@ -801,7 +887,7 @@ export default function App() {
     pendingAttachmentsRef.current = pendingAttachments;
   }, [pendingAttachments]);
 
-  const sidebarItems = useMemo(() => buildSidebarItems(chats, searches), [chats, searches]);
+  const sidebarItems = useMemo(() => buildSidebarItems(workspaceItems), [workspaceItems]);
   const filteredSidebarItems = useMemo(() => {
     const query = sidebarQuery.trim().toLowerCase();
     if (!query) return sidebarItems;
@@ -817,6 +903,7 @@ export default function App() {
   const resetWorkspaceState = () => {
     setChats([]);
     setSearches([]);
+    setWorkspaceItems([]);
     setSelectedItem(null);
     setSelectedChat(null);
     setSelectedSearch(null);
@@ -835,6 +922,9 @@ export default function App() {
     searchRunCountersRef.current.clear();
     setComposer("");
     setPendingAttachments([]);
+    setIsChatSettingsOpen(false);
+    setAdditionalSystemPrompt("");
+    setEnabledTools([]);
     setIsQuickQuestionOpen(false);
     setQuickPrompt("");
     setQuickSubmittedPrompt(null);
@@ -852,15 +942,16 @@ export default function App() {
   const refreshCollections = async (preferredSelection?: SidebarSelection) => {
     setIsLoadingCollections(true);
     try {
-      const [nextChats, nextSearches] = await Promise.all([listChats(), listSearches()]);
+      const nextWorkspaceItems = await listWorkspaceItems();
-      const nextItems = buildSidebarItems(nextChats, nextSearches);
+      const { chats: nextChats, searches: nextSearches } = splitWorkspaceItems(nextWorkspaceItems);
+      setWorkspaceItems(nextWorkspaceItems);
       setChats(nextChats);
       setSearches(nextSearches);
 
       setSelectedItem((current) => {
         const hasItem = (candidate: SidebarSelection | null) => {
           if (!candidate) return false;
-          return nextItems.some((item) => item.kind === candidate.kind && item.id === candidate.id);
+          return nextWorkspaceItems.some((item) => item.type === candidate.kind && item.id === candidate.id);
         };
 
         if (preferredSelection && hasItem(preferredSelection)) {
@@ -869,8 +960,8 @@ export default function App() {
         if (hasItem(current)) {
           return current;
         }
-        const first = nextItems[0];
+        const first = nextWorkspaceItems[0];
-        return first ? { kind: first.kind, id: first.id } : null;
+        return first ? { kind: first.type, id: first.id } : null;
       });
     } catch (err) {
       const message = err instanceof Error ? err.message : String(err);
@@ -898,6 +989,21 @@ export default function App() {
     }
   };
 
+  const refreshChatTools = async () => {
+    try {
+      const tools = await listChatTools();
+      setAvailableChatTools(tools);
+      setEnabledTools((current) => normalizeEnabledTools(current.length ? current : null, tools));
+    } catch (err) {
+      const message = err instanceof Error ? err.message : String(err);
+      if (message.includes("bearer token")) {
+        handleAuthFailure(message);
+      } else {
+        setError(message);
+      }
+    }
+  };
+
   const refreshActiveRuns = async () => {
     try {
       const data = await getActiveRuns();
@@ -950,7 +1056,7 @@ export default function App() {
     if (!isAuthenticated) return;
     const preferredSelection = initialRouteSelectionRef.current;
     initialRouteSelectionRef.current = null;
-    void Promise.all([refreshCollections(preferredSelection ?? undefined), refreshModels(), refreshActiveRuns()]);
+    void Promise.all([refreshCollections(preferredSelection ?? undefined), refreshModels(), refreshChatTools(), refreshActiveRuns()]);
   }, [isAuthenticated]);
 
   useEffect(() => {
@@ -1212,6 +1318,19 @@ export default function App() {
     setModel(nextSelection.model);
   }, [draftKind, selectedChat, selectedChatSummary, selectedItem]);
 
+  useEffect(() => {
+    if (draftKind === "chat") {
+      setAdditionalSystemPrompt("");
+      setEnabledTools(getDefaultEnabledTools(availableChatTools));
+      return;
+    }
+    if (selectedItem?.kind !== "chat") return;
+    const chat = selectedChat?.id === selectedItem.id ? selectedChat : selectedChatSummary;
+    if (!chat) return;
+    setAdditionalSystemPrompt(chat.additionalSystemPrompt ?? "");
+    setEnabledTools(normalizeEnabledTools(chat.enabledTools, availableChatTools));
+  }, [availableChatTools, draftKind, selectedChat, selectedChatSummary, selectedItem]);
+
   const selectedTitle = useMemo(() => {
     if (draftKind === "chat") return "New chat";
     if (draftKind === "search") return "New search";
@@ -1551,6 +1670,7 @@ export default function App() {
         const withoutExisting = current.filter((existing) => existing.id !== chat.id);
         return [chat, ...withoutExisting];
       });
+      setWorkspaceItems((current) => upsertWorkspaceItem(current, chatWorkspaceItem(chat)));
       setSelectedItem({ kind: "chat", id: chatId });
       setSelectedChat({
         id: chat.id,
@@ -1616,6 +1736,7 @@ export default function App() {
               return { ...chat, title: updatedChat.title, updatedAt: updatedChat.updatedAt };
             })
           );
+          setWorkspaceItems((current) => upsertWorkspaceItem(current, chatWorkspaceItem(updatedChat), false));
           setSelectedChat((current) => {
             if (!current || current.id !== updatedChat.id) return current;
             return { ...current, title: updatedChat.title, updatedAt: updatedChat.updatedAt };
@@ -1748,6 +1869,11 @@ export default function App() {
       searchId = search.id;
       setDraftKind(null);
       setSelectedItem({ kind: "search", id: searchId });
+      setSearches((current) => {
+        const withoutExisting = current.filter((existing) => existing.id !== search.id);
+        return [search, ...withoutExisting];
+      });
+      setWorkspaceItems((current) => upsertWorkspaceItem(current, searchWorkspaceItem(search)));
     }
 
     if (!searchId) {
@@ -2121,6 +2247,7 @@ export default function App() {
         const withoutExisting = current.filter((existing) => existing.id !== chat.id);
         return [chat, ...withoutExisting];
       });
+      setWorkspaceItems((current) => upsertWorkspaceItem(current, chatWorkspaceItem(chat)));
       setSelectedItem({ kind: "chat", id: chat.id });
       setSelectedChat({
         id: chat.id,
@@ -2296,6 +2423,7 @@ export default function App() {
         const withoutExisting = current.filter((existing) => existing.id !== chat.id);
         return [chat, ...withoutExisting];
       });
+      setWorkspaceItems((current) => upsertWorkspaceItem(current, chatWorkspaceItem(chat)));
       setSelectedItem({ kind: "chat", id: chat.id });
       setSelectedChat({
         id: chat.id,
@@ -2510,7 +2638,7 @@ export default function App() {
                       onContextMenu={(event) => openContextMenu(event, { kind: item.kind, id: item.id })}
                       type="button"
                     >
-                      <div className="flex items-center gap-2">
+                      <div className="grid grid-cols-[auto_minmax(0,1fr)] gap-x-2 gap-y-1">
                         <span
                           className={cn(
                             "flex h-5 w-5 shrink-0 items-center justify-center rounded-md border",
@@ -2528,11 +2656,15 @@ export default function App() {
                             />
                           ) : null}
                         </span>
-                        <span className={cn("ml-auto shrink-0 text-xs", active ? "text-violet-100/86" : "text-violet-200/50")}>{formatDate(item.updatedAt)}</span>
+                        <span className="col-start-2 flex min-w-0 items-center gap-2">
-                      </div>
+                          <span className="shrink-0 text-xs text-secondary-foreground/70">{formatDate(item.updatedAt)}</span>
                           {initiatedLabel ? (
-                        <p className={cn("mt-1 truncate text-right text-xs", active ? "text-violet-100/62" : "text-violet-200/42")}>{initiatedLabel}</p>
+                            <span className="ml-auto min-w-0 truncate text-right text-xs text-secondary-foreground/70">
+                              {initiatedLabel}
+                            </span>
                           ) : null}
+                        </span>
+                      </div>
                     </button>
                   );
                 })}

web/src/lib/api.ts

@@ -7,6 +7,8 @@ export type ChatSummary = {
   initiatedModel: string | null;
   lastUsedProvider: Provider | null;
   lastUsedModel: string | null;
+  additionalSystemPrompt: string | null;
+  enabledTools: string[] | null;
 };
 
 export type SearchSummary = {
@@ -17,6 +19,16 @@ export type SearchSummary = {
   updatedAt: string;
 };
 
+export type ChatWorkspaceItem = ChatSummary & {
+  type: "chat";
+};
+
+export type SearchWorkspaceItem = SearchSummary & {
+  type: "search";
+};
+
+export type WorkspaceItem = ChatWorkspaceItem | SearchWorkspaceItem;
+
 export type Message = {
   id: string;
   createdAt: string;
@@ -48,6 +60,8 @@ export type ChatDetail = {
   initiatedModel: string | null;
   lastUsedProvider: Provider | null;
   lastUsedModel: string | null;
+  additionalSystemPrompt: string | null;
+  enabledTools: string[] | null;
   messages: Message[];
 };
 
@@ -139,6 +153,11 @@ export type ModelCatalogResponse = {
   providers: Partial<Record<Provider, ProviderModelInfo>>;
 };
 
+export type ChatToolInfo = {
+  name: string;
+  description: string;
+};
+
 export type ActiveRunsResponse = {
   chats: string[];
   searches: string[];
@@ -164,6 +183,8 @@ type CreateChatRequest = {
   title?: string;
   provider?: Provider;
   model?: string;
+  additionalSystemPrompt?: string;
+  enabledTools?: string[];
   messages?: CompletionRequestMessage[];
 };
 
@@ -214,6 +235,11 @@ export async function listChats() {
   return data.chats;
 }
 
+export async function listWorkspaceItems() {
+  const data = await api<{ items: WorkspaceItem[] }>("/v1/workspace-items");
+  return data.items;
+}
+
 export async function verifySession() {
   return api<{ authenticated: true; mode: "open" | "token" }>("/v1/auth/session");
 }
@@ -222,6 +248,11 @@ export async function listModels() {
   return api<ModelCatalogResponse>("/v1/models");
 }
 
+export async function listChatTools() {
+  const data = await api<{ tools: ChatToolInfo[] }>("/v1/chat-tools");
+  return data.tools;
+}
+
 export async function getActiveRuns() {
   return api<ActiveRunsResponse>("/v1/active-runs");
 }
@@ -248,6 +279,14 @@ export async function updateChatTitle(chatId: string, title: string) {
   return data.chat;
 }
 
+export async function updateChatSettings(chatId: string, body: { additionalSystemPrompt?: string | null; enabledTools?: string[] }) {
+  const data = await api<{ chat: ChatSummary }>(`/v1/chats/${chatId}`, {
+    method: "PATCH",
+    body: JSON.stringify(body),
+  });
+  return data.chat;
+}
+
 export async function suggestChatTitle(body: { chatId: string; content: string }) {
   const data = await api<{ chat: ChatSummary }>("/v1/chats/title/suggest", {
     method: "POST",
@@ -554,6 +593,9 @@ export async function runCompletion(body: {
   provider: Provider;
   model: string;
   messages: CompletionRequestMessage[];
+  additionalSystemPrompt?: string;
+  enabledTools?: string[];
+  userLocation?: string;
 }) {
   return api<CompletionResponse>("/v1/chat-completions", {
     method: "POST",
@@ -568,6 +610,9 @@ export async function runCompletionStream(
     provider: Provider;
     model: string;
     messages: CompletionRequestMessage[];
+    additionalSystemPrompt?: string;
+    enabledTools?: string[];
+    userLocation?: string;
   },
   handlers: CompletionStreamHandlers,
   options?: { signal?: AbortSignal }