fix: stabilize AI workspace QA

2026-05-26 19:15:05 +02:00
parent 8828516d43
commit 29e5dd8f7b
44 changed files with 1527 additions and 398 deletions
--- a/docs/ABSTRACTIONS.md
+++ b/docs/ABSTRACTIONS.md
@@ -846,6 +846,13 @@ Tolaria delegates remote auth to the user's system git setup:
 App-level settings persisted at `~/.config/com.tolaria.app/settings.json` (reads legacy `com.laputa.app` on upgrade):

 ```typescript
+interface AiWorkspaceConversationSetting {
+  archived: boolean | null
+  id: string
+  target_id: string | null
+  title: string
+}
+
 interface Settings {
  auto_pull_interval_minutes: number | null
  autogit_enabled: boolean | null
@@ -866,6 +873,7 @@ interface Settings {
  default_ai_agent: 'claude_code' | 'codex' | 'opencode' | 'pi' | 'gemini' | 'kiro' | null
  default_ai_target: string | null // "agent:codex" or "model:<provider>/<model>"
  ai_model_providers: AiModelProvider[] | null
+  ai_workspace_conversations: AiWorkspaceConversationSetting[] | null
  hide_gitignored_files: boolean | null // null = default true
  all_notes_show_pdfs: boolean | null // null = default false
  all_notes_show_images: boolean | null // null = default false
@@ -873,7 +881,7 @@ interface Settings {
 }
 ```

-Managed by `useSettings` hook and `SettingsPanel` component. `theme_mode` is installation-local because it controls device comfort rather than vault structure; the Settings panel and command-palette Light/Dark/System actions both update that same value. `system` remains a stored preference, while the runtime resolves it to `light` or `dark` for `data-theme` and app consumers. `ui_language` is also installation-local: `null` follows the supported system language with English fallback, while explicit values pin the UI language for this installation. Stored legacy aliases such as `zh-Hans` are normalized to canonical locale codes before the setting reaches React state. `date_display_format` is installation-local and controls rendered dates in note rows, property chips/cells, note info, table-of-contents metadata, and search result subtitles; `AppPreferencesProvider` owns the UI-level value so rendering surfaces can consume it without prop forwarding, while date picker text input remains ISO for predictable manual entry and storage. `note_width_mode` is the installation-local default for rich-editor note width; individual notes can override it with `_width` when they already have frontmatter. `sidebar_type_pluralization_enabled` is installation-local and defaults to `true`; when false, type rows use exact type names unless the type document defines an explicit `sidebar_label` override. `ai_features_enabled` is installation-local and defaults to `true`; when false, Tolaria hides AI panel controls, status bar AI indicators, command-palette AI mode, and missing-agent prompts while leaving Settings as the re-enable path. `git_enabled` is also installation-local and defaults to `true`; when false, Tolaria hides Git status-bar entries and command-palette actions, disables AutoGit controls, and avoids background Git refresh/sync work while leaving Settings as the re-enable path. `default_ai_agent` remains the legacy installation-local CLI fallback. `default_ai_target` is the active AI target used by the AI panel and status bar; it can point at a coding agent or a configured direct model. `ai_model_providers` stores non-secret provider metadata for local/API model targets, while hosted API keys live in Tolaria's local app-data secrets file or user-managed environment variables instead of being persisted in app settings. Provider defaults and local/API grouping come from the shared `src/shared/aiModelProviderCatalog.json` catalog used by both renderer settings and the Tauri direct-model runtime. `hide_gitignored_files` is also installation-local and defaults to `true`; changing it reloads entries, search, saved views, and folders without restarting. The `all_notes_show_pdfs`, `all_notes_show_images`, and `all_notes_show_unsupported` flags are installation-local All Notes category toggles that default off and update the list/counts without changing vault files. The AutoGit fields are also installation-local: `useAutoGit` consumes them to schedule automatic checkpoints, while `useCommitFlow` and the status bar quick action reuse the same checkpoint runner and deterministic automatic commit message generation.
+Managed by `useSettings` hook and `SettingsPanel` component. `theme_mode` is installation-local because it controls device comfort rather than vault structure; the Settings panel and command-palette Light/Dark/System actions both update that same value. `system` remains a stored preference, while the runtime resolves it to `light` or `dark` for `data-theme` and app consumers. `ui_language` is also installation-local: `null` follows the supported system language with English fallback, while explicit values pin the UI language for this installation. Stored legacy aliases such as `zh-Hans` are normalized to canonical locale codes before the setting reaches React state. `date_display_format` is installation-local and controls rendered dates in note rows, property chips/cells, note info, table-of-contents metadata, and search result subtitles; `AppPreferencesProvider` owns the UI-level value so rendering surfaces can consume it without prop forwarding, while date picker text input remains ISO for predictable manual entry and storage. `note_width_mode` is the installation-local default for rich-editor note width; individual notes can override it with `_width` when they already have frontmatter. `sidebar_type_pluralization_enabled` is installation-local and defaults to `true`; when false, type rows use exact type names unless the type document defines an explicit `sidebar_label` override. `ai_features_enabled` is installation-local and defaults to `true`; when false, Tolaria hides AI panel controls, status bar AI indicators, command-palette AI mode, and missing-agent prompts while leaving Settings as the re-enable path. `git_enabled` is also installation-local and defaults to `true`; when false, Tolaria hides Git status-bar entries and command-palette actions, disables AutoGit controls, and avoids background Git refresh/sync work while leaving Settings as the re-enable path. `default_ai_agent` remains the legacy installation-local CLI fallback. `default_ai_target` is the active AI target used by the AI panel and status bar; it can point at a coding agent or a configured direct model. `ai_model_providers` stores non-secret provider metadata for local/API model targets, while hosted API keys live in Tolaria's local app-data secrets file or user-managed environment variables instead of being persisted in app settings. `ai_workspace_conversations` stores installation-local AI chat sidebar metadata only: conversation ids, titles, archive state, and explicit target overrides. It does not store vault content, prompts, transcripts, or model credentials. Provider defaults and local/API grouping come from the shared `src/shared/aiModelProviderCatalog.json` catalog used by both renderer settings and the Tauri direct-model runtime. `hide_gitignored_files` is also installation-local and defaults to `true`; changing it reloads entries, search, saved views, and folders without restarting. The `all_notes_show_pdfs`, `all_notes_show_images`, and `all_notes_show_unsupported` flags are installation-local All Notes category toggles that default off and update the list/counts without changing vault files. The AutoGit fields are also installation-local: `useAutoGit` consumes them to schedule automatic checkpoints, while `useCommitFlow` and the status bar quick action reuse the same checkpoint runner and deterministic automatic commit message generation.

 ## Telemetry

--- a/docs/ARCHITECTURE.md
+++ b/docs/ARCHITECTURE.md
@@ -229,7 +229,7 @@ flowchart TD
 - **Editor** (flex, fills remaining space): Single note open at a time (no tabs — see ADR-0003). Breadcrumb bar with filename controls, read-only legacy display-title context when a no-H1 note's title differs from its filename, word count, rich-editor width toggle, and the secondary-overflow Table of Contents action, BlockNote rich text editor with wikilink support, Markdown-compatible inline/display math rendering, first-class Mermaid diagram blocks, markdown-safe formatting controls, and schema-backed fenced code block highlighting via `@blocknote/code-block`. Can toggle to diff view (modified files), raw CodeMirror view, or a wide rich-editor reading surface with preserved side margins; raw CodeMirror remains full-width and unaffected by note width mode. Inline rich-editor images open in a localized shadcn lightbox on double-click while normal single-click BlockNote selection remains untouched, and tiny tracking-style images are ignored. Binary image, audio, video, and PDF files render through `FilePreview` as ordinary vault files using Tauri asset URLs; editor-embedded audio and video use the same scoped asset sources through the CSP `media-src` allow-list. Linux AppImage builds ask the native runtime whether audio/video should fall back to external-open controls before mounting webview media elements. External-open actions call `open_vault_file_external` so the target is validated against the active vault before the native default app opens it. Unsupported/broken binaries show explicit fallback states and keyboard focus returns to the note list on `Escape`. Decomposed into `Editor` (orchestrator), `EditorContent`, `FilePreview`, `EditorRightPanel`, `TableOfContentsPanel`, `SingleEditorView`, with hooks `useDiffMode`, `useEditorFocus`, and `useEditorSave`, plus the `useRawMode`/`RawEditorView` pair for markdown source editing. Rich BlockNote input and raw CodeMirror input both route typed `->`, `<-`, and `<->` through the shared `src/utils/arrowLigatures.ts` resolver so arrow ligatures stay consistent across mode switches while escaped ASCII sequences remain literal. Navigation history (Cmd+[/]) replaces tabs.
 - **Right side panels** (200-500px or hidden): Properties and Table of Contents are mutually exclusive panels mounted by `EditorRightPanel` and coordinated by `useRightPanelExclusion`. Properties shows frontmatter, relationships, instances, backlinks, and git history; Table of Contents is lazy-mounted only while open, derives a title-rooted H1/H2/H3 hierarchy through a debounced Web Worker per ADR-0109, and reuses folder-tree indentation/guide geometry with heading icons while resolving live BlockNote block IDs at click time for navigation. The breadcrumb bar toggles Table of Contents and Properties actions. Per-note `icon` is a suggested Properties field and the command palette's "Set Note Icon" action opens that field directly. When viewing a Type note, Properties shows an **Instances** section listing all notes of that type (sorted by modified_at desc, capped at 50).

- **AI workspace** (docked panel or native window): `AiWorkspace` owns the multi-chat sidebar, installed-only target picker, permission-mode picker, and dock/pop-out controls. The status-bar AI affordance opens this workspace instead of changing the default target inline. Docked workspace mode renders as a bounded desktop tool inside the main app; pop-out mode opens a dedicated Tauri webview window labeled `ai-workspace` with macOS overlay traffic lights. Close/minimize requests from the native AI window emit a dock request back to the main window before destroying the pop-out window. Chat sessions reuse `AiPanelView` for transcript/composer rendering with the old panel header disabled, so there is one workspace header per active chat.
+- **AI workspace** (docked panel or native window): `AiWorkspace` owns the multi-chat sidebar, installed-only target picker, permission-mode picker, and dock/pop-out controls. The status-bar AI affordance opens this workspace instead of changing the default target inline. Docked workspace mode renders as a bounded, width/height-resizable desktop tool inside the main app. Pop-out mode opens a dedicated undecorated Tauri webview window labeled `ai-workspace` and boots the lightweight `AiWorkspaceWindowApp` route instead of the full vault shell. The chat header and sidebar header are draggable in native-window mode, and the in-workspace close/dock controls emit a dock request back to the main window before destroying the pop-out window. Chat sessions reuse `AiPanelView` for transcript/composer rendering with the old panel header disabled; target and permission controls live in the composer toolbar so there is one workspace header per active chat.

 Panels are separated by `ResizeHandle` components that support drag-to-resize. `useLayoutPanels` clamps the sidebar, note-list, and inspector widths before applying them, keeps the side panes from flex-shrinking below their protected widths, and persists the last chosen widths in installation-local localStorage under `tolaria:layout-panels`.

@@ -246,7 +246,7 @@ On Linux, `run()` applies WebKitGTK startup safeguards before Tauri creates the

 Notes can be opened in separate Tauri windows for focused editing. Secondary windows boot the same `App` shell and load the same active workspace graph as the main window, but they start in the editor-only view mode with side panels collapsed.

-The AI workspace can also open in a separate Tauri window through `openAiWorkspaceWindow()`. That window uses the same `App` shell with `?window=ai-workspace`, opts out of main-window size constraints and startup AI onboarding, and redocks by emitting `tolaria:ai-workspace-dock-requested` to the main window.
+The AI workspace can also open in a separate Tauri window through `openAiWorkspaceWindow()`. That window uses `?window=ai-workspace` to boot the lightweight `AiWorkspaceWindowApp` route, receives the active vault context through URL params, opts out of main-window size constraints and startup AI onboarding, and redocks by emitting `tolaria:ai-workspace-dock-requested` to the main window.

 **Triggers:**
 - `Cmd+Shift+Click` on any note in the note list or sidebar
--- a/docs/adr/0128-lightweight-ai-workspace-window.md
+++ b/docs/adr/0128-lightweight-ai-workspace-window.md
@@ -0,0 +1,35 @@
+---
+type: ADR
+id: "0128"
+title: "Lightweight AI workspace window"
+status: active
+date: 2026-05-26
+supersedes: "0127"
+---
+
+## Context
+
+ADR-0127 moved the AI workspace into a native Tauri window, but the first version booted the full `App` shell and used macOS overlay traffic lights. That made pop-out feel slow, duplicated startup work, and left the chat route dependent on main-window vault loading before agent turns could run.
+
+The AI workspace also needs installation-local chat metadata so user-facing chat titles and archive state survive dock/pop-out transitions without writing to a vault.
+
+## Decision
+
+**The AI workspace pop-out uses a lightweight renderer route backed by app settings metadata.**
+
+`openAiWorkspaceWindow()` opens the `ai-workspace` Tauri webview with `?window=ai-workspace` plus active vault context in URL params. `App` routes that window directly to `AiWorkspaceWindowApp`, which loads settings, AI agent status, and vault guidance without mounting the full vault/editor shell. The window is undecorated and relies on `AiWorkspace` headers for drag regions and the workspace close/dock controls.
+
+`settings.ai_workspace_conversations` stores only chat sidebar metadata: conversation id, title, archive state, and explicit target override. Prompt text, transcripts, note content, model credentials, and vault-local configuration stay out of app settings.
+
+## Options considered
+
+- **Lightweight AI route** (chosen): keeps pop-out startup focused on AI state and passes explicit vault context to the agent controller.
+- **Full `App` route**: preserves maximum feature parity by default, but repeats vault/editor startup work and delays a window that should contain only the AI workspace.
+- **Vault-stored chat metadata**: would travel with a vault, but chat labels and archive state are installation UI preferences rather than vault content.
+
+## Consequences
+
+- Pop-out startup avoids full note graph loading and should be close to instant after the Tauri webview is created.
+- The dedicated AI window has no native traffic lights; users close or redock it through the workspace header controls.
+- Chat titles, archived state, and target overrides persist at the installation level in `settings.json`.
+- Future transcript persistence must use a separate storage decision; `ai_workspace_conversations` is intentionally metadata-only.
--- a/docs/adr/README.md
+++ b/docs/adr/README.md
@@ -178,4 +178,5 @@ proposed → active → superseded
 | [0123](0123-full-vault-graph-for-secondary-note-windows.md) | Full vault graph for secondary note windows | superseded -> [0124](0124-cached-secondary-note-window-startup.md) |
 | [0124](0124-cached-secondary-note-window-startup.md) | Cached secondary note window startup | active |
 | [0126](0126-renderer-action-history.md) | Renderer action history for app-level undo and redo | active |
-| [0127](0127-native-ai-workspace-window.md) | Native AI workspace window | active |
+| [0127](0127-native-ai-workspace-window.md) | Native AI workspace window | superseded -> [0128](0128-lightweight-ai-workspace-window.md) |
+| [0128](0128-lightweight-ai-workspace-window.md) | Lightweight AI workspace window | active |
--- a/lara.lock
+++ b/lara.lock
@@ -314,6 +314,8 @@ files:
    ai.panel.send: 747c6a3564774149c989884e0c581d53
    ai.workspace.title: d5b381672258b0bb54ede1e886895b3e
    ai.workspace.newChat: a917baaf1484ec5dc85f19ab8fc4f4e9
+    ai.workspace.collapseSidebar: 9ecc763686b7c61547281f3e05ffd06f
+    ai.workspace.expandSidebar: 281b619f3da2ba27e604302c3c00db56
    ai.workspace.close: 184649ab030e9a609488608221c28d8c
    ai.workspace.popOut: 85ec25ec056b3082651e6e3fcfa57416
    ai.workspace.dock: 72e81ed23007ec6fb9820b9abec353c4
@@ -325,6 +327,7 @@ files:
    ai.workspace.noActiveChats: f0cdbf09f23eb9a2efbb5977bcc39c1a
    ai.workspace.noArchivedChats: 68410efd12fc0308ce1ed2225000d4d5
    ai.workspace.chatTitle: 2ecae1c7ffb3296a789ff8f3b3ed2922
+    ai.workspace.renameChat: 0feba25e166f55afc51c4ebb33d8d757
    ai.workspace.status.archived: 7d69b3cb4cada18ae61811304f8fbcb5
    ai.workspace.status.idle: e599161956d626eda4cb0a5ffb85271c
    ai.workspace.status.running: 5bda814c4aedb126839228f1a3d92f09
--- a/src-tauri/capabilities/default.json
+++ b/src-tauri/capabilities/default.json
@@ -4,6 +4,7 @@
  "description": "enables the default permissions",
  "windows": [
    "main",
+    "ai-workspace",
    "note-*"
  ],
  "platforms": ["linux", "macOS", "windows"],
--- a/src-tauri/src/settings.rs
+++ b/src-tauri/src/settings.rs
@@ -65,6 +65,14 @@ const SUPPORTED_UI_LANGUAGE_ALIASES: &[(&str, &str)] = &[
    ("vi-vn", "vi"),
 ];

+#[derive(Debug, Clone, PartialEq, Serialize, Deserialize, Default)]
+pub struct AiWorkspaceConversationSetting {
+    pub archived: Option<bool>,
+    pub id: String,
+    pub target_id: Option<String>,
+    pub title: String,
+}
+
 #[derive(Debug, Clone, PartialEq, Serialize, Deserialize, Default)]
 pub struct Settings {
    pub auto_pull_interval_minutes: Option<u32>,
@@ -88,6 +96,7 @@ pub struct Settings {
    pub default_ai_agent: Option<String>,
    pub default_ai_target: Option<String>,
    pub ai_model_providers: Option<Vec<AiModelProvider>>,
+    pub ai_workspace_conversations: Option<Vec<AiWorkspaceConversationSetting>>,
    pub hide_gitignored_files: Option<bool>,
    pub all_notes_show_pdfs: Option<bool>,
    pub all_notes_show_images: Option<bool>,
@@ -203,6 +212,9 @@ fn normalize_settings(settings: Settings) -> Settings {
        default_ai_agent: normalize_default_ai_agent(settings.default_ai_agent.as_deref()),
        default_ai_target: normalize_optional_string(settings.default_ai_target),
        ai_model_providers: normalize_ai_model_providers(settings.ai_model_providers),
+        ai_workspace_conversations: normalize_ai_workspace_conversations(
+            settings.ai_workspace_conversations,
+        ),
        hide_gitignored_files: settings.hide_gitignored_files,
        all_notes_show_pdfs: settings.all_notes_show_pdfs,
        all_notes_show_images: settings.all_notes_show_images,
@@ -211,6 +223,36 @@ fn normalize_settings(settings: Settings) -> Settings {
    }
 }

+fn normalize_ai_workspace_conversations(
+    conversations: Option<Vec<AiWorkspaceConversationSetting>>,
+) -> Option<Vec<AiWorkspaceConversationSetting>> {
+    let normalized: Vec<AiWorkspaceConversationSetting> = conversations
+        .unwrap_or_default()
+        .into_iter()
+        .filter_map(|conversation| {
+            let id = conversation.id.trim().to_string();
+            let title = conversation.title.trim().to_string();
+            if id.is_empty() || title.is_empty() {
+                return None;
+            }
+
+            Some(AiWorkspaceConversationSetting {
+                archived: conversation.archived,
+                id,
+                target_id: normalize_optional_string(conversation.target_id),
+                title,
+            })
+        })
+        .take(100)
+        .collect();
+
+    if normalized.is_empty() {
+        None
+    } else {
+        Some(normalized)
+    }
+}
+
 fn app_config_dir() -> Result<PathBuf, String> {
    dirs::config_dir().ok_or_else(|| "Could not determine config directory".to_string())
 }
@@ -357,6 +399,7 @@ mod tests {
            default_ai_agent: Some("codex".to_string()),
            default_ai_target: Some("agent:codex".to_string()),
            ai_model_providers: None,
+            ai_workspace_conversations: None,
            hide_gitignored_files: Some(false),
            multi_workspace_enabled: Some(true),
            all_notes_show_pdfs: Some(true),
--- a/src/App.tsx
+++ b/src/App.tsx
@@ -13,6 +13,7 @@ import { CommitDialog } from './components/CommitDialog'
 import { PulseView } from './components/PulseView'
 import { StatusBar } from './components/StatusBar'
 import { AppAiWorkspaceSurface } from './components/AppAiWorkspaceSurface'
+import { AiWorkspaceWindowApp } from './components/AiWorkspaceWindowApp'
 import { SettingsPanel } from './components/SettingsPanel'
 import { CloneVaultModal } from './components/CloneVaultModal'
 import { FeedbackDialog } from './components/FeedbackDialog'
@@ -82,14 +83,14 @@ import { DeleteProgressNotice } from './components/DeleteProgressNotice'
 import { UpdateBanner } from './components/UpdateBanner'
 import { invoke } from '@tauri-apps/api/core'
 import { isTauri, mockInvoke } from './mock-tauri'
-import type { GitSetupPreference, SidebarSelection, InboxPeriod, ModifiedFile, VaultEntry, ViewDefinition, ViewFile, WorkspaceIdentity } from './types'
+import type { AiWorkspaceConversationSetting, GitSetupPreference, SidebarSelection, InboxPeriod, ModifiedFile, VaultEntry, ViewDefinition, ViewFile, WorkspaceIdentity } from './types'
 import type { NoteListItem } from './utils/ai-context'
 import { initializeNoteProperties } from './utils/initializeNoteProperties'
 import { filterEntries, filterInboxEntries, type NoteListFilter } from './utils/noteListHelpers'
 import { openNoteInNewWindow } from './utils/openNoteWindow'
 import { isWindows } from './utils/platform'
 import { getPulledVaultUpdateOptions, refreshPulledVaultState } from './utils/pulledVaultRefresh'
-import { isAiWorkspaceWindow, isNoteWindow, getNoteWindowParams } from './utils/windowMode'
+import { isAiWorkspaceWindow, isNoteWindow, getNoteWindowParams, type NoteWindowParams } from './utils/windowMode'
 import { GitSetupDialog } from './components/GitRequiredModal'
 import { RenameDetectedBanner } from './components/RenameDetectedBanner'
 import { openNoteListPropertiesPicker } from './components/note-list/noteListPropertiesEvents'
@@ -132,6 +133,7 @@ import { useStartupScreenState } from './hooks/useStartupScreenState'
 import { useGitFileWorkflows } from './hooks/useGitFileWorkflows'
 import { useAutoGitWork } from './hooks/useAutoGitWork'
 import { useAppAiWorkspaceBridge } from './hooks/useAppAiWorkspaceBridge'
+import type { AiWorkspaceWindowContext } from './utils/openAiWorkspaceWindow'
 import './App.css'

 const ACTIVE_EDITOR_SURFACE_SELECTOR = '.editor__blocknote-container, .raw-editor-codemirror'
@@ -240,10 +242,25 @@ function shouldPreserveViewRootPath(views: ViewFile[], editingRootPath?: string)
  return Boolean(editingRootPath) || views.some((view) => view.rootPath)
 }

+function aiWorkspaceWindowContextForPath(resolvedPath: string): AiWorkspaceWindowContext {
+  return {
+    vaultPath: resolvedPath,
+    vaultPaths: resolvedPath ? [resolvedPath] : [],
+  }
+}
+
 /** Wraps useEditorSave to also keep outgoingLinks in sync on save and on content change. */
 function App() {
  const noteWindowParams = useMemo(() => isNoteWindow() ? getNoteWindowParams() : null, [])
  const aiWorkspaceWindow = useMemo(() => isAiWorkspaceWindow(), [])
+
+  if (aiWorkspaceWindow) return <AiWorkspaceWindowApp />
+
+  return <MainApp noteWindowParams={noteWindowParams} />
+}
+
+function MainApp({ noteWindowParams }: { noteWindowParams: NoteWindowParams | null }) {
+  const aiWorkspaceWindow = false
  const [selection, setSelection] = useState<SidebarSelection>(DEFAULT_SELECTION)
  const [noteListFilter, setNoteListFilter] = useState<NoteListFilter>('open')
  const selectionRef = useRef<SidebarSelection>(DEFAULT_SELECTION)
@@ -345,6 +362,7 @@ function App() {
      ? onboarding.state.vaultPath
      : vaultSwitcher.vaultPath
  )
+  const aiWorkspaceWindowContext = aiWorkspaceWindowContextForPath(resolvedPath)
  const [settingsInitialSectionId, setSettingsInitialSectionId] = useState<string | null>(null)
  const {
    effectiveShowAIChat,
@@ -360,6 +378,7 @@ function App() {
    openSettings: dialogs.openSettings,
    setSettingsInitialSectionId,
    showAIChat,
+    windowContext: aiWorkspaceWindowContext,
  })
  const {
    folderVaults,
@@ -1723,7 +1742,10 @@ function App() {
    vaultIsLoading: vault.isLoading,
    vaultSwitcher,
  })
-  const aiWorkspaceSurface = <AppAiWorkspaceSurface mode={aiWorkspaceWindow ? 'window' : 'docked'} open={aiWorkspaceWindow || effectiveShowAIChat} aiAgentsStatus={aiAgentsStatus} aiModelProviders={settings.ai_model_providers ?? []} defaultAiAgent={aiAgentPreferences.defaultAiAgent} defaultAiTarget={aiAgentPreferences.defaultAiTarget} defaultAiAgentReadiness={aiAgentPreferences.defaultAiAgentReadiness} defaultAiAgentReady={aiAgentPreferences.defaultAiAgentReady} activeEntry={activeTab?.entry ?? null} activeNoteContent={activeTab?.content ?? null} entries={visibleEntries} openTabs={notes.tabs.map((tab) => tab.entry)} noteList={aiNoteList} noteListFilter={aiNoteListFilter} onClose={aiWorkspaceWindow ? handleDockCurrentAiWorkspaceWindow : closeAIChat} onDock={aiWorkspaceWindow ? handleDockCurrentAiWorkspaceWindow : undefined} onPopOut={aiWorkspaceWindow ? undefined : handlePopOutAiWorkspace} onOpenAiSettings={aiWorkspaceWindow ? undefined : handleOpenAiSettings} onOpenNote={notes.handleNavigateWikilink} onRestoreVaultAiGuidance={aiFeaturesEnabled ? () => { void restoreVaultAiGuidance() } : undefined} onUnsupportedAiPaste={setToastMessage} onFileCreated={vaultBridge.handleAgentFileCreated} onFileModified={vaultBridge.handleAgentFileModified} onVaultChanged={vaultBridge.handleAgentVaultChanged} vaultAiGuidanceStatus={vaultAiGuidanceStatus} vaultPath={activeEditorVaultPath} vaultPaths={writableVaultPaths} locale={appLocale} />
+  const handleAiWorkspaceConversationsChange = useCallback((conversations: AiWorkspaceConversationSetting[]) => {
+    void saveSettings({ ...settings, ai_workspace_conversations: conversations })
+  }, [saveSettings, settings])
+  const aiWorkspaceSurface = <AppAiWorkspaceSurface mode={aiWorkspaceWindow ? 'window' : 'docked'} open={aiWorkspaceWindow || effectiveShowAIChat} aiAgentsStatus={aiAgentsStatus} aiModelProviders={settings.ai_model_providers ?? []} conversationSettings={settings.ai_workspace_conversations ?? null} conversationSettingsReady={settingsLoaded} defaultAiAgent={aiAgentPreferences.defaultAiAgent} defaultAiTarget={aiAgentPreferences.defaultAiTarget} defaultAiAgentReadiness={aiAgentPreferences.defaultAiAgentReadiness} defaultAiAgentReady={aiAgentPreferences.defaultAiAgentReady} activeEntry={activeTab?.entry ?? null} activeNoteContent={activeTab?.content ?? null} entries={visibleEntries} openTabs={notes.tabs.map((tab) => tab.entry)} noteList={aiNoteList} noteListFilter={aiNoteListFilter} onClose={aiWorkspaceWindow ? handleDockCurrentAiWorkspaceWindow : closeAIChat} onConversationSettingsChange={handleAiWorkspaceConversationsChange} onDock={aiWorkspaceWindow ? handleDockCurrentAiWorkspaceWindow : undefined} onPopOut={aiWorkspaceWindow ? undefined : handlePopOutAiWorkspace} onOpenAiSettings={aiWorkspaceWindow ? undefined : handleOpenAiSettings} onOpenNote={notes.handleNavigateWikilink} onRestoreVaultAiGuidance={aiFeaturesEnabled ? () => { void restoreVaultAiGuidance() } : undefined} onUnsupportedAiPaste={setToastMessage} onFileCreated={vaultBridge.handleAgentFileCreated} onFileModified={vaultBridge.handleAgentFileModified} onVaultChanged={vaultBridge.handleAgentVaultChanged} vaultAiGuidanceStatus={vaultAiGuidanceStatus} vaultPath={activeEditorVaultPath} vaultPaths={writableVaultPaths} locale={appLocale} />
  if (shouldShowStartupScreen) {
    return (
      <StartupScreen
--- a/src/components/AiPanel.tsx
+++ b/src/components/AiPanel.tsx
@@ -1,4 +1,4 @@
-import { useRef } from 'react'
+import { useCallback, useRef, type CSSProperties, type ReactNode, type RefObject } from 'react'
 import {
  AiPanelComposer,
  AiPanelContextBar,
@@ -58,12 +58,77 @@ interface AiPanelViewProps {
  entries?: VaultEntry[]
  interactive?: boolean
  showHeader?: boolean
+  composerControls?: ReactNode
+  onSendPrompt?: (text: string) => void
 }

 function readinessFromReadyFlag(ready: boolean | undefined): AiAgentReadiness {
  return (ready ?? true) ? 'ready' : 'missing'
 }

+interface AiPanelViewModel {
+  agentLabel: string
+  defaultAiAgent: AiAgentId
+  defaultAiAgentReadiness: AiAgentReadiness
+  targetKind: AiTarget['kind']
+}
+
+function resolveAiPanelViewModel({
+  defaultAiAgent,
+  defaultAiAgentReadiness,
+  defaultAiAgentReady,
+  defaultAiTarget,
+}: {
+  defaultAiAgent?: AiAgentId
+  defaultAiAgentReadiness?: AiAgentReadiness
+  defaultAiAgentReady?: boolean
+  defaultAiTarget?: AiTarget
+}): AiPanelViewModel {
+  const resolvedAgent = defaultAiAgent ?? DEFAULT_AI_AGENT
+  const resolvedReadiness = defaultAiAgentReadiness ?? readinessFromReadyFlag(defaultAiAgentReady)
+
+  return {
+    agentLabel: defaultAiTarget?.label ?? getAiAgentDefinition(resolvedAgent).label,
+    defaultAiAgent: resolvedAgent,
+    defaultAiAgentReadiness: resolvedReadiness,
+    targetKind: defaultAiTarget?.kind ?? 'agent',
+  }
+}
+
+function aiPanelFrameStyle(isActive: boolean): CSSProperties {
+  return {
+    outline: 'none',
+    borderLeft: isActive
+      ? '2px solid var(--accent-blue)'
+      : '1px solid var(--border)',
+    animation: isActive ? 'ai-border-pulse 2s ease-in-out infinite' : undefined,
+    transition: 'border-color 0.3s ease',
+  }
+}
+
+function AiPanelFrame({
+  children,
+  isActive,
+  panelRef,
+}: {
+  children: ReactNode
+  isActive: boolean
+  panelRef: RefObject<HTMLElement | null>
+}) {
+  return (
+    <aside
+      ref={panelRef}
+      tabIndex={-1}
+      className="flex flex-1 flex-col overflow-hidden bg-background text-foreground"
+      style={aiPanelFrameStyle(isActive)}
+      data-testid="ai-panel"
+      data-ai-active={isActive || undefined}
+    >
+      {children}
+    </aside>
+  )
+}
+
 export function AiPanelView({
  controller,
  onClose,
@@ -78,15 +143,17 @@ export function AiPanelView({
  entries,
  interactive = true,
  showHeader = true,
+  composerControls,
+  onSendPrompt,
 }: AiPanelViewProps) {
-  const defaultAiAgent = providedDefaultAiAgent ?? DEFAULT_AI_AGENT
-  const defaultAiAgentReadiness = providedDefaultAiAgentReadiness
-    ?? readinessFromReadyFlag(providedDefaultAiAgentReady)
+  const view = resolveAiPanelViewModel({
+    defaultAiAgent: providedDefaultAiAgent,
+    defaultAiAgentReadiness: providedDefaultAiAgentReadiness,
+    defaultAiAgentReady: providedDefaultAiAgentReady,
+    defaultAiTarget,
+  })
  const inputRef = useRef<HTMLDivElement>(null)
  const panelRef = useRef<HTMLElement>(null)
-  const activeTarget = defaultAiTarget
-  const agentLabel = activeTarget?.label ?? getAiAgentDefinition(defaultAiAgent).label
-  const targetKind = activeTarget?.kind ?? 'agent'
  const {
    agent,
    input,
@@ -110,28 +177,19 @@ export function AiPanelView({
    onClose,
    enabled: interactive,
  })
+  const handleComposerSend = useCallback((text: string, references: Parameters<typeof handleSend>[1]) => {
+    if (!text.trim() || isActive) return
+    onSendPrompt?.(text)
+    handleSend(text, references)
+  }, [handleSend, isActive, onSendPrompt])

  return (
-    <aside
-      ref={panelRef}
-      tabIndex={-1}
-      className="flex flex-1 flex-col overflow-hidden bg-background text-foreground"
-      style={{
-        outline: 'none',
-        borderLeft: isActive
-          ? '2px solid var(--accent-blue)'
-          : '1px solid var(--border)',
-        animation: isActive ? 'ai-border-pulse 2s ease-in-out infinite' : undefined,
-        transition: 'border-color 0.3s ease',
-      }}
-      data-testid="ai-panel"
-      data-ai-active={isActive || undefined}
-    >
+    <AiPanelFrame panelRef={panelRef} isActive={isActive}>
      {showHeader && (
        <AiPanelHeader
-          agentLabel={agentLabel}
-          agentReadiness={defaultAiAgentReadiness}
-          targetKind={targetKind}
+          agentLabel={view.agentLabel}
+          agentReadiness={view.defaultAiAgentReadiness}
+          targetKind={view.targetKind}
          locale={locale}
          permissionMode={permissionMode}
          permissionModeDisabled={isActive}
@@ -144,8 +202,8 @@ export function AiPanelView({
        <AiPanelContextBar activeEntry={activeEntry} linkedCount={linkedEntries.length} locale={locale} />
      )}
      <AiPanelMessageHistory
-        agentLabel={agentLabel}
-        agentReadiness={defaultAiAgentReadiness}
+        agentLabel={view.agentLabel}
+        agentReadiness={view.defaultAiAgentReadiness}
        locale={locale}
        messages={agent.messages}
        isActive={isActive}
@@ -155,17 +213,18 @@ export function AiPanelView({
      />
      <AiPanelComposer
        entries={entries ?? []}
-        agentLabel={agentLabel}
-        agentReadiness={defaultAiAgentReadiness}
+        agentLabel={view.agentLabel}
+        agentReadiness={view.defaultAiAgentReadiness}
        locale={locale}
        input={input}
        inputRef={inputRef}
        isActive={isActive}
+        controls={composerControls}
        onChange={setInput}
-        onSend={handleSend}
+        onSend={handleComposerSend}
        onUnsupportedAiPaste={onUnsupportedAiPaste}
      />
-    </aside>
+    </AiPanelFrame>
  )
 }

--- a/src/components/AiPanelChrome.tsx
+++ b/src/components/AiPanelChrome.tsx
@@ -1,4 +1,4 @@
-import { memo, useEffect, useRef } from 'react'
+import { memo, useEffect, useRef, type CSSProperties, type ReactNode } from 'react'
 import { Robot, X, PaperPlaneRight, Plus, Link } from '@phosphor-icons/react'
 import { AiMessage } from './AiMessage'
 import { Button } from '@/components/ui/button'
@@ -15,6 +15,7 @@ import type { AiAgentMessage } from '../hooks/useCliAiAgent'
 import type { AiAgentReadiness } from '../lib/aiAgents'
 import type { NoteReference } from '../utils/ai-context'
 import type { VaultEntry } from '../types'
+import { cn } from '@/lib/utils'

 interface AiPanelHeaderProps {
  agentLabel: string
@@ -53,6 +54,7 @@ interface AiPanelComposerProps {
  input: string
  inputRef: React.RefObject<HTMLDivElement | null>
  isActive: boolean
+  controls?: ReactNode
  onChange: (value: string) => void
  onSend: (text: string, references: NoteReference[]) => void
  onUnsupportedAiPaste?: (message: string) => void
@@ -74,6 +76,109 @@ function getComposerPlaceholder(
  return t('ai.panel.placeholder.ready', { agent: agentLabel })
 }

+function composerSendButtonStyle(canSend: boolean): CSSProperties {
+  return {
+    background: canSend ? 'var(--primary)' : 'var(--muted)',
+    color: canSend ? 'var(--primary-foreground)' : 'var(--muted-foreground)',
+    borderRadius: 8,
+    width: 32,
+    height: 34,
+    cursor: canSend ? 'pointer' : 'not-allowed',
+  }
+}
+
+function ComposerInput({
+  disabled,
+  entries,
+  hasControls,
+  input,
+  inputRef,
+  onChange,
+  onSend,
+  onUnsupportedAiPaste,
+  placeholder,
+}: {
+  disabled: boolean
+  entries: VaultEntry[]
+  hasControls: boolean
+  input: string
+  inputRef: React.RefObject<HTMLDivElement | null>
+  onChange: (value: string) => void
+  onSend: (text: string, references: NoteReference[]) => void
+  onUnsupportedAiPaste?: (message: string) => void
+  placeholder: string
+}) {
+  return (
+    <WikilinkChatInput
+      entries={entries}
+      value={input}
+      onChange={onChange}
+      onSend={onSend}
+      onUnsupportedPaste={onUnsupportedAiPaste}
+      disabled={disabled}
+      placeholder={placeholder}
+      inputRef={inputRef}
+      editorClassName={cn(
+        'max-h-[160px] overflow-y-auto overscroll-contain',
+        hasControls && 'min-h-[72px] border-0 px-2 py-2',
+      )}
+      editorStyle={{ maxHeight: 160, overflowY: 'auto', overscrollBehavior: 'contain' }}
+    />
+  )
+}
+
+function ComposerSendButton({
+  canSend,
+  entries,
+  input,
+  label,
+  onSend,
+}: {
+  canSend: boolean
+  entries: VaultEntry[]
+  input: string
+  label: string
+  onSend: (text: string, references: NoteReference[]) => void
+}) {
+  return (
+    <Button
+      type="button"
+      variant="ghost"
+      size="icon-sm"
+      className="shrink-0 flex items-center justify-center border-none cursor-pointer transition-colors"
+      style={composerSendButtonStyle(canSend)}
+      onClick={() => onSend(input, extractInlineWikilinkReferences(input, entries))}
+      disabled={!canSend}
+      aria-label={label}
+      title={label}
+      data-testid="agent-send"
+    >
+      <PaperPlaneRight size={16} />
+    </Button>
+  )
+}
+
+function ComposerControlsRow({
+  children,
+  hasControls,
+  sendButton,
+}: {
+  children?: ReactNode
+  hasControls: boolean
+  sendButton: ReactNode
+}) {
+  if (!hasControls) return <>{sendButton}</>
+
+  return (
+    <div className="mt-1 flex items-center justify-between gap-2">
+      <div className="flex min-w-0 items-center gap-1">
+        {children}
+      </div>
+      {sendButton}
+    </div>
+  )
+}
+
 function permissionModeTooltip(
  mode: AiAgentPermissionMode,
  t: ReturnType<typeof createTranslator>,
@@ -360,6 +465,7 @@ export function AiPanelComposer({
  input,
  inputRef,
  isActive,
+  controls,
  onChange,
  onSend,
  onUnsupportedAiPaste,
@@ -368,49 +474,41 @@ export function AiPanelComposer({
  const composerDisabled = isActive || agentReadiness !== 'ready'
  const canSend = !composerDisabled && input.trim().length > 0
  const placeholder = getComposerPlaceholder(agentLabel, agentReadiness, t)
-  const sendButtonStyle = {
-    background: canSend ? 'var(--primary)' : 'var(--muted)',
-    color: canSend ? 'var(--primary-foreground)' : 'var(--muted-foreground)',
-    borderRadius: 8,
-    width: 32,
-    height: 34,
-    cursor: canSend ? 'pointer' : 'not-allowed',
-  } as const
+  const hasControls = controls !== undefined && controls !== null
+  const sendButton = (
+    <ComposerSendButton
+      canSend={canSend}
+      entries={entries}
+      input={input}
+      label={t('ai.panel.send')}
+      onSend={onSend}
+    />
+  )

  return (
    <div
      className="flex shrink-0 flex-col border-t border-border"
      style={{ padding: '8px 12px' }}
    >
-      <div className="flex items-end gap-2">
-        <div className="min-w-0 flex-1">
-          <WikilinkChatInput
+      <div className={cn(
+        hasControls ? 'rounded-xl border border-border bg-background p-2 shadow-xs' : 'flex items-end gap-2',
+      )}>
+        <div className={cn('min-w-0 flex-1', hasControls && 'w-full')}>
+          <ComposerInput
+            disabled={composerDisabled}
            entries={entries}
-            value={input}
+            hasControls={hasControls}
+            input={input}
+            inputRef={inputRef}
            onChange={onChange}
            onSend={onSend}
-            onUnsupportedPaste={onUnsupportedAiPaste}
-            disabled={composerDisabled}
+            onUnsupportedAiPaste={onUnsupportedAiPaste}
            placeholder={placeholder}
-            inputRef={inputRef}
-            editorClassName="max-h-[160px] overflow-y-auto overscroll-contain"
-            editorStyle={{ maxHeight: 160, overflowY: 'auto', overscrollBehavior: 'contain' }}
          />
        </div>
-        <Button
-          type="button"
-          variant="ghost"
-          size="icon-sm"
-          className="shrink-0 flex items-center justify-center border-none cursor-pointer transition-colors"
-          style={sendButtonStyle}
-          onClick={() => onSend(input, extractInlineWikilinkReferences(input, entries))}
-          disabled={!canSend}
-          aria-label={t('ai.panel.send')}
-          title={t('ai.panel.send')}
-          data-testid="agent-send"
-        >
-          <PaperPlaneRight size={16} />
-        </Button>
+        <ComposerControlsRow hasControls={hasControls} sendButton={sendButton}>
+          {controls}
+        </ComposerControlsRow>
      </div>
    </div>
  )
--- a/src/components/AiWorkspace.test.tsx
+++ b/src/components/AiWorkspace.test.tsx
@@ -1,5 +1,6 @@
 import { beforeEach, describe, expect, it, vi } from 'vitest'
 import { act, fireEvent, render, screen, within } from '@testing-library/react'
+import type { ReactNode } from 'react'
 import { AiWorkspace } from './AiWorkspace'
 import { buildAiWorkspaceTargetGroups } from './aiWorkspaceTargetGroups'
 import {
@@ -8,13 +9,16 @@ import {
  type AiAgentsStatus,
 } from '../lib/aiAgents'
 import type { AiModelProvider } from '../lib/aiTargets'
+import type { AgentStatus } from '../hooks/useCliAiAgent'
 import { resetVaultConfigStore } from '../utils/vaultConfigStore'

+let mockedAgentStatus: AgentStatus = 'idle'
+
 vi.mock('./useAiPanelController', () => ({
  useAiPanelController: () => ({
    agent: {
      messages: [],
-      status: 'idle',
+      status: mockedAgentStatus,
      sendMessage: vi.fn(),
      clearConversation: vi.fn(),
      addLocalMarker: vi.fn(),
@@ -33,8 +37,21 @@ vi.mock('./useAiPanelController', () => ({
 }))

 vi.mock('./AiPanel', () => ({
-  AiPanelView: ({ showHeader }: { showHeader?: boolean }) => (
-    <div data-testid="ai-panel-view" data-show-header={String(showHeader)}>Chat surface</div>
+  AiPanelView: ({
+    composerControls,
+    onSendPrompt,
+    showHeader,
+  }: {
+    composerControls?: ReactNode
+    onSendPrompt?: (prompt: string) => void
+    showHeader?: boolean
+  }) => (
+    <div data-testid="ai-panel-view" data-show-header={String(showHeader)}>
+      <button type="button" onClick={() => onSendPrompt?.('summarize quarterly sponsor outreach')}>
+        Send mocked prompt
+      </button>
+      {composerControls}
+    </div>
  ),
 }))

@@ -75,6 +92,7 @@ const providers: AiModelProvider[] = [

 describe('AiWorkspace', () => {
  beforeEach(() => {
+    mockedAgentStatus = 'idle'
    resetVaultConfigStore()
  })

@@ -119,4 +137,63 @@ describe('AiWorkspace', () => {
    expect(within(menu).getByText('Ollama · Llama 3.2')).toBeTruthy()
    expect(within(menu).getByText('OpenAI · GPT-4.1')).toBeTruthy()
  })
+
+  it('renames the first chat from the first prompt and stores conversation settings', () => {
+    const onConversationSettingsChange = vi.fn()
+    render(<AiWorkspace open mode="docked" aiAgentsStatus={installedStatuses()} aiModelProviders={providers} vaultPath="/tmp/vault" onClose={vi.fn()} onConversationSettingsChange={onConversationSettingsChange} />)
+
+    fireEvent.click(screen.getByText('Send mocked prompt'))
+
+    expect(screen.getAllByText('Summarize Quarterly Sponsor Outreach').length).toBeGreaterThan(0)
+    expect(onConversationSettingsChange).toHaveBeenLastCalledWith([
+      expect.objectContaining({ title: 'Summarize Quarterly Sponsor Outreach' }),
+    ])
+  })
+
+  it('renames a persisted default chat title from the first prompt', () => {
+    const onConversationSettingsChange = vi.fn()
+    render(
+      <AiWorkspace
+        open
+        mode="docked"
+        aiAgentsStatus={installedStatuses()}
+        aiModelProviders={providers}
+        conversationSettings={[{ id: 'stored-chat', title: 'Chat 1', target_id: null, archived: false }]}
+        vaultPath="/tmp/vault"
+        onClose={vi.fn()}
+        onConversationSettingsChange={onConversationSettingsChange}
+      />,
+    )
+
+    fireEvent.click(screen.getByText('Send mocked prompt'))
+
+    expect(screen.getAllByText('Summarize Quarterly Sponsor Outreach').length).toBeGreaterThan(0)
+    expect(onConversationSettingsChange).toHaveBeenLastCalledWith([
+      expect.objectContaining({ id: 'stored-chat', title: 'Summarize Quarterly Sponsor Outreach' }),
+    ])
+  })
+
+  it('allows a chat title to be renamed from the sidebar', () => {
+    const onConversationSettingsChange = vi.fn()
+    render(<AiWorkspace open mode="docked" aiAgentsStatus={installedStatuses()} aiModelProviders={providers} vaultPath="/tmp/vault" onClose={vi.fn()} onConversationSettingsChange={onConversationSettingsChange} />)
+
+    fireEvent.doubleClick(screen.getByRole('button', { name: /chat 1/i }))
+    const input = screen.getByLabelText('Rename chat')
+    fireEvent.change(input, { target: { value: 'Sponsor Plan' } })
+    fireEvent.keyDown(input, { key: 'Enter' })
+
+    expect(screen.getAllByText('Sponsor Plan').length).toBeGreaterThan(0)
+    expect(onConversationSettingsChange).toHaveBeenLastCalledWith([
+      expect.objectContaining({ title: 'Sponsor Plan' }),
+    ])
+  })
+
+  it('collapses the workspace sidebar from the sidebar header', () => {
+    render(<AiWorkspace open mode="docked" aiAgentsStatus={installedStatuses()} aiModelProviders={providers} vaultPath="/tmp/vault" onClose={vi.fn()} />)
+
+    fireEvent.click(screen.getByRole('button', { name: 'Collapse AI chat list' }))
+
+    expect(screen.queryByText('AI workspace')).toBeNull()
+    expect(screen.getByRole('button', { name: 'Expand AI chat list' })).toBeTruthy()
+  })
 })
--- a/src/components/AiWorkspace.tsx
+++ b/src/components/AiWorkspace.tsx
@@ -1,12 +1,10 @@
-import { useCallback, useEffect, useMemo, useState } from 'react'
+import { useCallback, useEffect, useMemo, useRef, useState, type CSSProperties } from 'react'
 import {
  Archive,
  ArrowSquareIn,
  ArrowSquareOut,
  CaretDown,
  GearSix,
-  Plus,
-  Robot,
  WarningCircle,
  X,
 } from '@phosphor-icons/react'
@@ -47,19 +45,24 @@ import {
  type VaultAiGuidanceStatus,
 } from '../lib/vaultAiGuidance'
 import { translate, type AppLocale, type TranslationKey } from '../lib/i18n'
+import { trackAiWorkspaceChatTitled, trackAiWorkspaceSidebarToggled } from '../lib/productAnalytics'
 import type { AgentStatus } from '../hooks/useCliAiAgent'
+import type { AiWorkspaceConversationSetting } from '../types'
 import type { NoteListItem } from '../utils/ai-context'
 import type { VaultEntry } from '../types'
 import { NEW_AI_CHAT_EVENT } from '../utils/aiPromptBridge'
+import { generateAiConversationTitle } from '../utils/aiConversationTitle'
 import { AiPanelView } from './AiPanel'
+import { ConversationSidebar } from './AiWorkspaceSidebar'
 import { useAiPanelController } from './useAiPanelController'
 import { buildAiWorkspaceTargetGroups, type AiWorkspaceTargetGroups } from './aiWorkspaceTargetGroups'

-interface AiConversation {
+export interface AiConversation {
  archived: boolean
  id: string
  targetId: string
  title: string
+  usesDefaultTitle: boolean
  usesDefaultTarget: boolean
 }

@@ -68,6 +71,8 @@ interface AiWorkspaceProps {
  activeNoteContent?: string | null
  aiAgentsStatus: AiAgentsStatus
  aiModelProviders?: AiModelProvider[]
+  conversationSettings?: AiWorkspaceConversationSetting[] | null
+  conversationSettingsReady?: boolean
  defaultAiAgent?: AiAgentId
  defaultAiAgentReadiness?: AiAgentReadiness
  defaultAiAgentReady?: boolean
@@ -78,6 +83,7 @@ interface AiWorkspaceProps {
  noteList?: NoteListItem[]
  noteListFilter?: { type: string | null; query: string }
  onClose: () => void
+  onConversationSettingsChange?: (conversations: AiWorkspaceConversationSetting[]) => void
  onDock?: () => void
  onFileCreated?: (relativePath: string) => void
  onFileModified?: (relativePath: string) => void
@@ -94,22 +100,34 @@ interface AiWorkspaceProps {
  vaultPaths?: string[]
 }

+let fallbackConversationIdCounter = 0
+
+function randomConversationIdPart(): string {
+  const cryptoApi = globalThis.crypto
+  if (typeof cryptoApi?.randomUUID === 'function') return cryptoApi.randomUUID().slice(0, 8)
+
+  if (typeof cryptoApi?.getRandomValues === 'function') {
+    const values = new Uint32Array(2)
+    cryptoApi.getRandomValues(values)
+    return Array.from(values, (value) => value.toString(36)).join('').slice(0, 8)
+  }
+
+  fallbackConversationIdCounter += 1
+  return fallbackConversationIdCounter.toString(36).padStart(4, '0')
+}
+
 function nextConversationId(): string {
-  return `ai-chat-${Date.now()}-${Math.random().toString(36).slice(2, 8)}`
+  return `ai-chat-${Date.now()}-${randomConversationIdPart()}`
 }

 function statusLabelKey(status: AgentStatus): TranslationKey {
  if (status === 'thinking' || status === 'tool-executing') return 'ai.workspace.status.running'
  if (status === 'error') return 'ai.workspace.status.error'
-  if (status === 'done') return 'ai.workspace.status.done'
  return 'ai.workspace.status.idle'
 }

-function statusDotClassName(status: AgentStatus | undefined): string {
-  if (status === 'thinking' || status === 'tool-executing') return 'bg-blue-500'
-  if (status === 'error') return 'bg-destructive'
-  if (status === 'done') return 'bg-green-600'
-  return 'bg-muted-foreground'
+function isRunningStatus(status: AgentStatus | undefined): boolean {
+  return status === 'thinking' || status === 'tool-executing'
 }

 function agentReadinessForTarget(target: AiTarget, statuses: AiAgentsStatus): AiAgentReadiness {
@@ -142,189 +160,198 @@ function createConversation(locale: AppLocale, target: AiTarget, index: number):
    id: nextConversationId(),
    targetId: target.id,
    title: translate(locale, 'ai.workspace.chatTitle', { index }),
+    usesDefaultTitle: true,
    usesDefaultTarget: true,
  }
 }

-function useConversations(locale: AppLocale, fallbackTarget: AiTarget) {
-  const [conversations, setConversations] = useState<AiConversation[]>(() => [
-    createConversation(locale, fallbackTarget, 1),
-  ])
+function isDefaultConversationTitle(title: string): boolean {
+  return /^Chat\s+\d+$/i.test(title.trim())
+}
+
+function conversationFromSetting(setting: AiWorkspaceConversationSetting, fallbackTarget: AiTarget): AiConversation | null {
+  const id = setting.id.trim()
+  const title = setting.title.trim()
+  if (!id || !title) return null
+
+  return {
+    archived: setting.archived === true,
+    id,
+    targetId: setting.target_id?.trim() || fallbackTarget.id,
+    title,
+    usesDefaultTitle: isDefaultConversationTitle(title),
+    usesDefaultTarget: !setting.target_id,
+  }
+}
+
+function conversationsFromSettings(
+  settings: AiWorkspaceConversationSetting[] | null | undefined,
+  fallbackTarget: AiTarget,
+  locale: AppLocale,
+): AiConversation[] {
+  const stored = (settings ?? [])
+    .map((setting) => conversationFromSetting(setting, fallbackTarget))
+    .filter((conversation): conversation is AiConversation => conversation !== null)
+  return stored.length > 0 ? stored : [createConversation(locale, fallbackTarget, 1)]
+}
+
+function conversationsToSettings(conversations: AiConversation[]): AiWorkspaceConversationSetting[] {
+  return conversations.map((conversation) => ({
+    archived: conversation.archived,
+    id: conversation.id,
+    target_id: conversation.usesDefaultTarget ? null : conversation.targetId,
+    title: conversation.title,
+  }))
+}
+
+interface UseConversationsOptions {
+  fallbackTarget: AiTarget
+  locale: AppLocale
+  onSettingsChange?: (conversations: AiWorkspaceConversationSetting[]) => void
+  settings?: AiWorkspaceConversationSetting[] | null
+  settingsReady: boolean
+}
+
+function appendConversationState(
+  current: AiConversation[],
+  locale: AppLocale,
+  target: AiTarget,
+): { activeId: string; conversations: AiConversation[] } {
+  const next = createConversation(locale, target, current.length + 1)
+  return {
+    activeId: next.id,
+    conversations: [...current, next],
+  }
+}
+
+function archiveConversationState(
+  current: AiConversation[],
+  id: string,
+): { activeId?: string; conversations: AiConversation[] } {
+  const conversations = current.map((conversation) => (
+    conversation.id === id ? { ...conversation, archived: true } : conversation
+  ))
+  const fallback = conversations.find((conversation) => !conversation.archived && conversation.id !== id)
+  return { activeId: fallback?.id, conversations }
+}
+
+function restoreConversationState(current: AiConversation[], id: string): AiConversation[] {
+  return current.map((conversation) => (
+    conversation.id === id ? { ...conversation, archived: false } : conversation
+  ))
+}
+
+function retargetConversationState(current: AiConversation[], id: string, targetId: string): AiConversation[] {
+  return current.map((conversation) => (
+    conversation.id === id ? { ...conversation, targetId, usesDefaultTarget: false } : conversation
+  ))
+}
+
+function renameConversationState(current: AiConversation[], id: string, title: string): AiConversation[] {
+  const nextTitle = title.trim()
+  if (!nextTitle) return current
+
+  return current.map((conversation) => (
+    conversation.id === id ? { ...conversation, title: nextTitle, usesDefaultTitle: false } : conversation
+  ))
+}
+
+function titleConversationFromPromptState(current: AiConversation[], id: string, prompt: string): AiConversation[] {
+  const generatedTitle = generateAiConversationTitle(prompt)
+  if (!generatedTitle) return current
+
+  return current.map((conversation) => (
+    conversation.id === id && conversation.usesDefaultTitle
+      ? { ...conversation, title: generatedTitle, usesDefaultTitle: false }
+      : conversation
+  ))
+}
+
+function updateDefaultConversationTargetState(current: AiConversation[], targetId: string): AiConversation[] {
+  return current.map((conversation) => (
+    conversation.usesDefaultTarget && conversation.targetId !== targetId
+      ? { ...conversation, targetId }
+      : conversation
+  ))
+}
+
+function useConversations({
+  fallbackTarget,
+  locale,
+  onSettingsChange,
+  settings,
+  settingsReady,
+}: UseConversationsOptions) {
+  const [conversations, setConversations] = useState<AiConversation[]>(() => (
+    conversationsFromSettings(settings, fallbackTarget, locale)
+  ))
  const [activeId, setActiveId] = useState(() => conversations[0]?.id ?? '')
  const [showArchived, setShowArchived] = useState(false)
+  const onSettingsChangeRef = useRef(onSettingsChange)

  const addConversation = useCallback((target: AiTarget) => {
    setConversations((current) => {
-      const next = createConversation(locale, target, current.length + 1)
-      setActiveId(next.id)
-      return [...current, next]
+      const next = appendConversationState(current, locale, target)
+      setActiveId(next.activeId)
+      return next.conversations
    })
  }, [locale])

  const archiveConversation = useCallback((id: string) => {
    setConversations((current) => {
-      const next = current.map((conversation) => (
-        conversation.id === id ? { ...conversation, archived: true } : conversation
-      ))
-      const fallback = next.find((conversation) => !conversation.archived && conversation.id !== id)
-      if (fallback) setActiveId(fallback.id)
-      return next
+      const next = archiveConversationState(current, id)
+      if (next.activeId) setActiveId(next.activeId)
+      return next.conversations
    })
  }, [])

  const restoreConversation = useCallback((id: string) => {
-    setConversations((current) => current.map((conversation) => (
-      conversation.id === id ? { ...conversation, archived: false } : conversation
-    )))
+    setConversations((current) => restoreConversationState(current, id))
    setActiveId(id)
    setShowArchived(false)
  }, [])

  const setConversationTarget = useCallback((id: string, targetId: string) => {
-    setConversations((current) => current.map((conversation) => (
-      conversation.id === id ? { ...conversation, targetId, usesDefaultTarget: false } : conversation
-    )))
+    setConversations((current) => retargetConversationState(current, id, targetId))
+  }, [])
+
+  const renameConversation = useCallback((id: string, title: string) => {
+    setConversations((current) => renameConversationState(current, id, title))
+  }, [])
+
+  const titleConversationFromPrompt = useCallback((id: string, prompt: string) => {
+    setConversations((current) => titleConversationFromPromptState(current, id, prompt))
  }, [])

  const updateDefaultConversationTargets = useCallback((targetId: string) => {
-    setConversations((current) => current.map((conversation) => (
-      conversation.usesDefaultTarget && conversation.targetId !== targetId
-        ? { ...conversation, targetId }
-        : conversation
-    )))
+    setConversations((current) => updateDefaultConversationTargetState(current, targetId))
  }, [])

+  useEffect(() => {
+    onSettingsChangeRef.current = onSettingsChange
+  }, [onSettingsChange])
+
+  useEffect(() => {
+    if (!settingsReady) return
+    onSettingsChangeRef.current?.(conversationsToSettings(conversations))
+  }, [conversations, settingsReady])
+
  return {
    activeId,
    addConversation,
    archiveConversation,
    conversations,
+    renameConversation,
    restoreConversation,
    setActiveId,
    setConversationTarget,
    setShowArchived,
    showArchived,
+    titleConversationFromPrompt,
    updateDefaultConversationTargets,
  }
 }

-function SidebarHeader({ locale, onNewChat }: { locale: AppLocale; onNewChat: () => void }) {
-  const { dragRegionRef } = useDragRegion<HTMLDivElement>()
-
-  return (
-    <div
-      ref={dragRegionRef}
-      className="flex h-12 shrink-0 items-center justify-between border-b border-border px-3"
-      data-tauri-drag-region
-      data-testid="ai-workspace-sidebar-header"
-    >
-      <div className="flex min-w-0 items-center gap-2">
-        <Robot size={16} className="shrink-0 text-muted-foreground" />
-        <span className="truncate text-[13px] font-semibold text-foreground">
-          {translate(locale, 'ai.workspace.title')}
-        </span>
-      </div>
-      <Button
-        type="button"
-        variant="ghost"
-        size="icon-xs"
-        aria-label={translate(locale, 'ai.workspace.newChat')}
-        title={translate(locale, 'ai.workspace.newChat')}
-        data-testid="ai-workspace-sidebar-new-chat"
-        onClick={onNewChat}
-      >
-        <Plus size={15} />
-      </Button>
-    </div>
-  )
-}
-
-function ConversationSidebar({
-  activeId,
-  conversations,
-  locale,
-  onArchive,
-  onNewChat,
-  onRestore,
-  onSelect,
-  setShowArchived,
-  showArchived,
-  statuses,
-}: {
-  activeId: string
-  conversations: AiConversation[]
-  locale: AppLocale
-  onArchive: (id: string) => void
-  onNewChat: () => void
-  onRestore: (id: string) => void
-  onSelect: (id: string) => void
-  setShowArchived: (show: boolean) => void
-  showArchived: boolean
-  statuses: Record<string, AgentStatus>
-}) {
-  const visibleConversations = conversations.filter((conversation) => conversation.archived === showArchived)
-  const emptyLabel = showArchived
-    ? translate(locale, 'ai.workspace.noArchivedChats')
-    : translate(locale, 'ai.workspace.noActiveChats')
-
-  return (
-    <div className="flex w-[220px] shrink-0 flex-col border-r border-border bg-sidebar">
-      <SidebarHeader locale={locale} onNewChat={onNewChat} />
-      <div className="flex-1 overflow-y-auto p-2">
-        {visibleConversations.length === 0 ? (
-          <div className="px-2 py-4 text-[12px] text-muted-foreground">{emptyLabel}</div>
-        ) : visibleConversations.map((conversation) => {
-          const status = statuses[conversation.id] ?? 'idle'
-          const active = conversation.id === activeId
-          return (
-            <div key={conversation.id} className="group flex items-center gap-1">
-              <Button
-                type="button"
-                variant="ghost"
-                size="sm"
-                className={cn(
-                  'min-w-0 flex-1 justify-start rounded-md px-2 text-left text-[12px]',
-                  active ? 'bg-accent text-foreground' : 'text-muted-foreground hover:text-foreground',
-                )}
-                aria-pressed={active}
-                onClick={() => onSelect(conversation.id)}
-              >
-                <span className={cn('h-2 w-2 rounded-full', statusDotClassName(status))} />
-                <span className="truncate">{conversation.title}</span>
-                <span className="ml-auto truncate text-[10px] opacity-70">
-                  {translate(locale, statusLabelKey(status))}
-                </span>
-              </Button>
-              <Button
-                type="button"
-                variant="ghost"
-                size="icon-xs"
-                aria-label={translate(locale, showArchived ? 'ai.workspace.restore' : 'ai.workspace.archive')}
-                title={translate(locale, showArchived ? 'ai.workspace.restore' : 'ai.workspace.archive')}
-                onClick={() => showArchived ? onRestore(conversation.id) : onArchive(conversation.id)}
-              >
-                {showArchived ? <ArrowSquareIn size={14} /> : <Archive size={14} />}
-              </Button>
-            </div>
-          )
-        })}
-      </div>
-      <div className="border-t border-border p-2">
-        <Button
-          type="button"
-          variant="ghost"
-          size="sm"
-          className="w-full justify-start text-[12px] text-muted-foreground"
-          onClick={() => setShowArchived(!showArchived)}
-        >
-          <Archive size={14} />
-          {translate(locale, showArchived ? 'ai.workspace.hideArchived' : 'ai.workspace.showArchived')}
-        </Button>
-      </div>
-    </div>
-  )
-}
-
 function TargetGroup({ label, targets }: { label: string; targets: AiTarget[] }) {
  if (targets.length === 0) return null

@@ -340,13 +367,83 @@ function TargetGroup({ label, targets }: { label: string; targets: AiTarget[] })
  )
 }

+function TargetPickerTrigger({
+  compact,
+  disabled,
+  hasTargets,
+  locale,
+  selectedTarget,
+}: {
+  compact: boolean
+  disabled: boolean
+  hasTargets: boolean
+  locale: AppLocale
+  selectedTarget: AiTarget
+}) {
+  return (
+    <DropdownMenuTrigger asChild>
+      <Button
+        type="button"
+        variant={compact ? 'ghost' : 'outline'}
+        size={compact ? 'xs' : 'sm'}
+        className={cn(
+          'justify-between gap-1.5',
+          compact ? 'max-w-[150px] rounded-full px-2 text-[12px]' : 'max-w-[240px] gap-2',
+        )}
+        disabled={disabled || !hasTargets}
+        aria-label={translate(locale, 'ai.workspace.targetLabel')}
+        data-testid="ai-workspace-target-trigger"
+      >
+        <span className="truncate">{selectedTarget.shortLabel}</span>
+        <CaretDown size={compact ? 12 : 13} />
+      </Button>
+    </DropdownMenuTrigger>
+  )
+}
+
+function TargetPickerContent({
+  groups,
+  hasTargets,
+  locale,
+  onSelectTarget,
+  selectedTarget,
+}: {
+  groups: AiWorkspaceTargetGroups
+  hasTargets: boolean
+  locale: AppLocale
+  selectedTarget: AiTarget
+  onSelectTarget: (targetId: string) => void
+}) {
+  const hasLocalAgentsSeparator = groups.localAgents.length > 0
+    && (groups.localModels.length > 0 || groups.apiModels.length > 0)
+  const hasLocalModelsSeparator = groups.localModels.length > 0 && groups.apiModels.length > 0
+
+  return (
+    <DropdownMenuContent align="start" className="min-w-[280px]">
+      {hasTargets ? (
+        <DropdownMenuRadioGroup value={selectedTarget.id} onValueChange={onSelectTarget}>
+          <TargetGroup label={translate(locale, 'ai.workspace.targetLocalAgents')} targets={groups.localAgents} />
+          {hasLocalAgentsSeparator && <DropdownMenuSeparator />}
+          <TargetGroup label={translate(locale, 'ai.workspace.targetLocalModels')} targets={groups.localModels} />
+          {hasLocalModelsSeparator && <DropdownMenuSeparator />}
+          <TargetGroup label={translate(locale, 'ai.workspace.targetApiModels')} targets={groups.apiModels} />
+        </DropdownMenuRadioGroup>
+      ) : (
+        <DropdownMenuItem disabled>{translate(locale, 'ai.workspace.noTargets')}</DropdownMenuItem>
+      )}
+    </DropdownMenuContent>
+  )
+}
+
 function TargetPicker({
+  compact = false,
  disabled,
  groups,
  locale,
  selectedTarget,
  onSelectTarget,
 }: {
+  compact?: boolean
  disabled: boolean
  groups: AiWorkspaceTargetGroups
  locale: AppLocale
@@ -357,44 +454,33 @@ function TargetPicker({

  return (
    <DropdownMenu>
-      <DropdownMenuTrigger asChild>
-        <Button
-          type="button"
-          variant="outline"
-          size="sm"
-          className="max-w-[240px] justify-between gap-2"
-          disabled={disabled || !hasTargets}
-          aria-label={translate(locale, 'ai.workspace.targetLabel')}
-          data-testid="ai-workspace-target-trigger"
-        >
-          <span className="truncate">{selectedTarget.shortLabel}</span>
-          <CaretDown size={13} />
-        </Button>
-      </DropdownMenuTrigger>
-      <DropdownMenuContent align="start" className="min-w-[280px]">
-        {hasTargets ? (
-          <DropdownMenuRadioGroup value={selectedTarget.id} onValueChange={onSelectTarget}>
-            <TargetGroup label={translate(locale, 'ai.workspace.targetLocalAgents')} targets={groups.localAgents} />
-            {groups.localAgents.length > 0 && (groups.localModels.length > 0 || groups.apiModels.length > 0) && <DropdownMenuSeparator />}
-            <TargetGroup label={translate(locale, 'ai.workspace.targetLocalModels')} targets={groups.localModels} />
-            {groups.localModels.length > 0 && groups.apiModels.length > 0 && <DropdownMenuSeparator />}
-            <TargetGroup label={translate(locale, 'ai.workspace.targetApiModels')} targets={groups.apiModels} />
-          </DropdownMenuRadioGroup>
-        ) : (
-          <DropdownMenuItem disabled>{translate(locale, 'ai.workspace.noTargets')}</DropdownMenuItem>
-        )}
-      </DropdownMenuContent>
+      <TargetPickerTrigger
+        compact={compact}
+        disabled={disabled}
+        hasTargets={hasTargets}
+        locale={locale}
+        selectedTarget={selectedTarget}
+      />
+      <TargetPickerContent
+        groups={groups}
+        hasTargets={hasTargets}
+        locale={locale}
+        selectedTarget={selectedTarget}
+        onSelectTarget={onSelectTarget}
+      />
    </DropdownMenu>
  )
 }

 function PermissionPicker({
+  compact = false,
  disabled,
  locale,
  permissionMode,
  targetKind,
  onChange,
 }: {
+  compact?: boolean
  disabled: boolean
  locale: AppLocale
  permissionMode: AiAgentPermissionMode
@@ -403,7 +489,7 @@ function PermissionPicker({
 }) {
  if (targetKind === 'api_model') {
    return (
-      <Button type="button" variant="outline" size="sm" disabled className="text-muted-foreground">
+      <Button type="button" variant={compact ? 'ghost' : 'outline'} size={compact ? 'xs' : 'sm'} disabled className="rounded-full px-2 text-[12px] text-muted-foreground">
        {translate(locale, 'ai.panel.mode.chat')}
      </Button>
    )
@@ -414,15 +500,15 @@ function PermissionPicker({
      <DropdownMenuTrigger asChild>
        <Button
          type="button"
-          variant="outline"
-          size="sm"
-          className="justify-between gap-2"
+          variant={compact ? 'ghost' : 'outline'}
+          size={compact ? 'xs' : 'sm'}
+          className={cn('justify-between', compact ? 'rounded-full px-2 text-[12px]' : 'gap-2')}
          disabled={disabled}
          aria-label={translate(locale, 'ai.workspace.permissionMode')}
          data-testid="ai-workspace-permission-trigger"
        >
          {aiAgentPermissionModeLabels(permissionMode, locale).control}
-          <CaretDown size={13} />
+          <CaretDown size={compact ? 12 : 13} />
        </Button>
      </DropdownMenuTrigger>
      <DropdownMenuContent align="start" className="min-w-[180px]">
@@ -464,87 +550,61 @@ function GuidanceWarning({

 function WorkspaceHeader({
  conversation,
-  groups,
  locale,
  mode,
-  permissionMode,
-  selectedTarget,
  status,
  onArchive,
  onClose,
  onDock,
  onOpenAiSettings,
-  onPermissionModeChange,
  onPopOut,
-  onSelectTarget,
 }: {
  conversation: AiConversation
-  groups: AiWorkspaceTargetGroups
  locale: AppLocale
  mode: 'docked' | 'window'
-  permissionMode: AiAgentPermissionMode
-  selectedTarget: AiTarget
  status: AgentStatus
  onArchive: () => void
  onClose: () => void
  onDock?: () => void
  onOpenAiSettings?: () => void
-  onPermissionModeChange: (mode: AiAgentPermissionMode) => void
  onPopOut?: () => void
-  onSelectTarget: (targetId: string) => void
 }) {
  const { dragRegionRef } = useDragRegion<HTMLDivElement>()
-  const running = status === 'thinking' || status === 'tool-executing'

  return (
    <div
      ref={dragRegionRef}
      className="flex h-12 shrink-0 items-center justify-between gap-2 border-b border-border px-3"
-      data-tauri-drag-region
      data-testid="ai-workspace-chat-header"
    >
      <div className="flex min-w-0 flex-1 items-center gap-2">
-        <div className="min-w-[92px] max-w-[160px]">
+        <div className="min-w-0 max-w-[260px]">
          <div className="truncate text-[13px] font-semibold text-foreground">{conversation.title}</div>
          <div className="truncate text-[11px] text-muted-foreground">
            {translate(locale, statusLabelKey(status))}
          </div>
        </div>
-        <TargetPicker
-          disabled={running}
-          groups={groups}
-          locale={locale}
-          selectedTarget={selectedTarget}
-          onSelectTarget={onSelectTarget}
-        />
-        <PermissionPicker
-          disabled={running}
-          locale={locale}
-          permissionMode={permissionMode}
-          targetKind={selectedTarget.kind}
-          onChange={onPermissionModeChange}
-        />
      </div>
      <div className="flex items-center gap-1">
        {onOpenAiSettings && (
          <Button type="button" variant="ghost" size="icon-xs" aria-label={translate(locale, 'ai.workspace.settings')} title={translate(locale, 'ai.workspace.settings')} onClick={onOpenAiSettings}>
-            <GearSix size={15} />
+            <GearSix size={16} />
          </Button>
        )}
        <Button type="button" variant="ghost" size="icon-xs" aria-label={translate(locale, 'ai.workspace.archive')} title={translate(locale, 'ai.workspace.archive')} onClick={onArchive}>
-          <Archive size={15} />
+          <Archive size={16} />
        </Button>
        {mode === 'docked' ? (
          <Button type="button" variant="ghost" size="icon-xs" aria-label={translate(locale, 'ai.workspace.popOut')} title={translate(locale, 'ai.workspace.popOut')} onClick={onPopOut}>
-            <ArrowSquareOut size={15} />
+            <ArrowSquareOut size={16} />
          </Button>
        ) : (
          <Button type="button" variant="ghost" size="icon-xs" aria-label={translate(locale, 'ai.workspace.dock')} title={translate(locale, 'ai.workspace.dock')} onClick={onDock}>
-            <ArrowSquareIn size={15} />
+            <ArrowSquareIn size={16} />
          </Button>
        )}
        <Button type="button" variant="ghost" size="icon-xs" aria-label={translate(locale, 'ai.workspace.close')} title={translate(locale, 'ai.workspace.close')} onClick={onClose}>
-          <X size={15} />
+          <X size={16} />
        </Button>
      </div>
    </div>
@@ -575,6 +635,7 @@ function ConversationSession({
  onRestoreVaultAiGuidance,
  onSelectTarget,
  onStatusChange,
+  onTitleFromPrompt,
  onUnsupportedAiPaste,
  onVaultChanged,
  openTabs,
@@ -606,6 +667,7 @@ function ConversationSession({
  onRestoreVaultAiGuidance?: () => void
  onSelectTarget: (targetId: string) => void
  onStatusChange: (id: string, status: AgentStatus) => void
+  onTitleFromPrompt: (id: string, prompt: string) => void
  onUnsupportedAiPaste?: (message: string) => void
  onVaultChanged?: () => void
  openTabs?: VaultEntry[]
@@ -634,6 +696,27 @@ function ConversationSession({
    onFileModified,
    onVaultChanged,
  })
+  const running = isRunningStatus(controller.agent.status)
+  const composerControls = (
+    <>
+      <TargetPicker
+        compact
+        disabled={running}
+        groups={groups}
+        locale={locale}
+        selectedTarget={target}
+        onSelectTarget={onSelectTarget}
+      />
+      <PermissionPicker
+        compact
+        disabled={running}
+        locale={locale}
+        permissionMode={controller.permissionMode}
+        targetKind={target.kind}
+        onChange={controller.handlePermissionModeChange}
+      />
+    </>
+  )

  useEffect(() => {
    onStatusChange(conversation.id, controller.agent.status)
@@ -643,19 +726,14 @@ function ConversationSession({
    <div className={active ? 'flex min-h-0 flex-1 flex-col' : 'hidden'} data-testid={`ai-workspace-session-${conversation.id}`}>
      <WorkspaceHeader
        conversation={conversation}
-        groups={groups}
        locale={locale}
        mode={mode}
-        permissionMode={controller.permissionMode}
-        selectedTarget={target}
        status={controller.agent.status}
        onArchive={onArchive}
        onClose={onClose}
        onDock={onDock}
        onOpenAiSettings={onOpenAiSettings}
-        onPermissionModeChange={controller.handlePermissionModeChange}
        onPopOut={onPopOut}
-        onSelectTarget={onSelectTarget}
      />
      <GuidanceWarning locale={locale} onRestore={onRestoreVaultAiGuidance} status={vaultAiGuidanceStatus} />
      <div className="flex min-h-0 flex-1">
@@ -667,10 +745,12 @@ function ConversationSession({
          defaultAiTarget={target}
          entries={entries}
          activeEntry={activeEntry}
+          composerControls={composerControls}
          interactive={active}
          locale={locale}
          onClose={onClose}
          onOpenNote={onOpenNote}
+          onSendPrompt={(prompt) => onTitleFromPrompt(conversation.id, prompt)}
          onUnsupportedAiPaste={onUnsupportedAiPaste}
          showHeader={false}
        />
@@ -696,12 +776,16 @@ interface AiWorkspaceModel {
  fallbackTarget: AiTarget
  groups: AiWorkspaceTargetGroups
  handleStatusChange: (id: string, status: AgentStatus) => void
+  renameConversation: (id: string, title: string) => void
  restoreConversation: (id: string) => void
+  sidebarCollapsed: boolean
  setActiveId: (id: string) => void
  setConversationTarget: (id: string, targetId: string) => void
  setShowArchived: (show: boolean) => void
  showArchived: boolean
  statuses: Record<string, AgentStatus>
+  titleConversationFromPrompt: (id: string, prompt: string) => void
+  toggleSidebarCollapsed: () => void
  updateDefaultConversationTargets: (targetId: string) => void
 }

@@ -722,6 +806,18 @@ function workspaceClassName(mode: 'docked' | 'window'): string {
  return 'fixed bottom-10 right-4 z-[90] flex h-[min(680px,calc(100vh-88px))] w-[min(880px,calc(100vw-32px))] overflow-hidden rounded-lg border border-border bg-background text-foreground shadow-2xl'
 }

+function workspaceStyle(mode: 'docked' | 'window'): CSSProperties | undefined {
+  if (mode === 'window') return undefined
+
+  return {
+    maxHeight: 'calc(100vh - 88px)',
+    maxWidth: 'calc(100vw - 32px)',
+    minHeight: 420,
+    minWidth: 520,
+    resize: 'both',
+  }
+}
+
 function useAiWorkspaceModel(workspace: ResolvedAiWorkspaceProps): AiWorkspaceModel {
  const groups = useMemo(
    () => buildAiWorkspaceTargetGroups(workspace.aiAgentsStatus, workspace.aiModelProviders),
@@ -736,14 +832,23 @@ function useAiWorkspaceModel(workspace: ResolvedAiWorkspaceProps): AiWorkspaceMo
    addConversation,
    archiveConversation,
    conversations,
+    renameConversation,
    restoreConversation,
    setActiveId,
    setConversationTarget,
    setShowArchived,
    showArchived,
+    titleConversationFromPrompt,
    updateDefaultConversationTargets,
-  } = useConversations(workspace.locale, fallbackTarget)
+  } = useConversations({
+    fallbackTarget,
+    locale: workspace.locale,
+    onSettingsChange: workspace.onConversationSettingsChange,
+    settings: workspace.conversationSettings,
+    settingsReady: workspace.conversationSettingsReady ?? true,
+  })
  const [statuses, setStatuses] = useState<Record<string, AgentStatus>>({})
+  const [sidebarCollapsed, setSidebarCollapsed] = useState(false)
  const activeConversation = conversations.find((conversation) => conversation.id === activeId)
    ?? conversations.find((conversation) => !conversation.archived)
    ?? conversations[0]
@@ -761,6 +866,23 @@ function useAiWorkspaceModel(workspace: ResolvedAiWorkspaceProps): AiWorkspaceMo
  const handleStatusChange = useCallback((id: string, status: AgentStatus) => {
    setStatuses((current) => current[id] === status ? current : { ...current, [id]: status })
  }, [])
+  const trackedRenameConversation = useCallback((id: string, title: string) => {
+    if (!title.trim()) return
+    renameConversation(id, title)
+    trackAiWorkspaceChatTitled('manual')
+  }, [renameConversation])
+  const trackedTitleConversationFromPrompt = useCallback((id: string, prompt: string) => {
+    const conversation = conversations.find((candidate) => candidate.id === id)
+    titleConversationFromPrompt(id, prompt)
+    if (conversation?.usesDefaultTitle) trackAiWorkspaceChatTitled('generated')
+  }, [conversations, titleConversationFromPrompt])
+  const toggleSidebarCollapsed = useCallback(() => {
+    setSidebarCollapsed((current) => {
+      const next = !current
+      trackAiWorkspaceSidebarToggled(next, workspace.mode)
+      return next
+    })
+  }, [workspace.mode])

  useEffect(() => {
    if (!workspace.open) return
@@ -782,12 +904,16 @@ function useAiWorkspaceModel(workspace: ResolvedAiWorkspaceProps): AiWorkspaceMo
    fallbackTarget,
    groups,
    handleStatusChange,
+    renameConversation: trackedRenameConversation,
    restoreConversation,
+    sidebarCollapsed,
    setActiveId,
    setConversationTarget,
    setShowArchived,
    showArchived,
    statuses,
+    titleConversationFromPrompt: trackedTitleConversationFromPrompt,
+    toggleSidebarCollapsed,
    updateDefaultConversationTargets,
  }
 }
@@ -796,6 +922,7 @@ function AiWorkspaceLayout({ model, workspace }: { model: AiWorkspaceModel; work
  return (
    <section
      className={workspaceClassName(workspace.mode)}
+      style={workspaceStyle(workspace.mode)}
      data-testid="ai-workspace"
      data-ai-workspace-mode={workspace.mode}
      role="dialog"
@@ -803,12 +930,15 @@ function AiWorkspaceLayout({ model, workspace }: { model: AiWorkspaceModel; work
    >
      <ConversationSidebar
        activeId={model.activeId}
+        collapsed={model.sidebarCollapsed}
        conversations={model.conversations}
        locale={workspace.locale}
        onArchive={model.archiveConversationSafely}
        onNewChat={model.addDefaultConversation}
+        onRename={model.renameConversation}
        onRestore={model.restoreConversation}
        onSelect={model.setActiveId}
+        onToggleCollapsed={model.toggleSidebarCollapsed}
        setShowArchived={model.setShowArchived}
        showArchived={model.showArchived}
        statuses={model.statuses}
@@ -852,6 +982,7 @@ function ConversationSessions({ model, workspace }: { model: AiWorkspaceModel; w
            onRestoreVaultAiGuidance={workspace.onRestoreVaultAiGuidance}
            onSelectTarget={(targetId) => model.setConversationTarget(conversation.id, targetId)}
            onStatusChange={model.handleStatusChange}
+            onTitleFromPrompt={model.titleConversationFromPrompt}
            onUnsupportedAiPaste={workspace.onUnsupportedAiPaste}
            onVaultChanged={workspace.onVaultChanged}
            openTabs={workspace.openTabs}
--- a/src/components/AiWorkspaceSidebar.tsx
+++ b/src/components/AiWorkspaceSidebar.tsx
@@ -0,0 +1,426 @@
+import { useRef, useState } from 'react'
+import {
+  Archive,
+  ArrowSquareIn,
+  Check,
+  CircleNotch,
+  Plus,
+  Robot,
+  SidebarSimple,
+} from '@phosphor-icons/react'
+import { Button } from '@/components/ui/button'
+import { Input } from '@/components/ui/input'
+import { cn } from '@/lib/utils'
+import { useDragRegion } from '../hooks/useDragRegion'
+import { translate, type AppLocale } from '../lib/i18n'
+import type { AgentStatus } from '../hooks/useCliAiAgent'
+import type { AiConversation } from './AiWorkspace'
+
+interface ConversationSidebarProps {
+  activeId: string
+  collapsed: boolean
+  conversations: AiConversation[]
+  locale: AppLocale
+  onArchive: (id: string) => void
+  onNewChat: () => void
+  onRename: (id: string, title: string) => void
+  onRestore: (id: string) => void
+  onSelect: (id: string) => void
+  onToggleCollapsed: () => void
+  setShowArchived: (show: boolean) => void
+  showArchived: boolean
+  statuses: Record<string, AgentStatus>
+}
+
+function isRunningStatus(status: AgentStatus | undefined): boolean {
+  return status === 'thinking' || status === 'tool-executing'
+}
+
+function SidebarStatusIndicator({ status }: { status: AgentStatus | undefined }) {
+  if (isRunningStatus(status)) {
+    return <CircleNotch size={14} className="animate-spin text-muted-foreground" aria-hidden />
+  }
+
+  if (status === 'error') {
+    return <span className="h-2 w-2 rounded-full bg-destructive" aria-hidden />
+  }
+
+  return null
+}
+
+function SidebarHeader({
+  collapsed,
+  locale,
+  onNewChat,
+  onToggleCollapsed,
+}: {
+  collapsed: boolean
+  locale: AppLocale
+  onNewChat: () => void
+  onToggleCollapsed: () => void
+}) {
+  const { dragRegionRef } = useDragRegion<HTMLDivElement>()
+  const collapseLabel = translate(locale, collapsed ? 'ai.workspace.expandSidebar' : 'ai.workspace.collapseSidebar')
+
+  return (
+    <div
+      ref={dragRegionRef}
+      className={cn(
+        'flex h-12 shrink-0 items-center border-b border-border px-2',
+        collapsed ? 'justify-center' : 'justify-between',
+      )}
+      data-testid="ai-workspace-sidebar-header"
+    >
+      <div className="flex min-w-0 items-center gap-2" data-no-drag>
+        <Button
+          type="button"
+          variant="ghost"
+          size="icon-xs"
+          aria-label={collapseLabel}
+          title={collapseLabel}
+          onClick={onToggleCollapsed}
+        >
+          <SidebarSimple size={16} />
+        </Button>
+        {!collapsed && (
+          <>
+            <Robot size={16} className="shrink-0 text-muted-foreground" />
+            <span className="truncate text-[13px] font-semibold text-foreground">
+              {translate(locale, 'ai.workspace.title')}
+            </span>
+          </>
+        )}
+      </div>
+      {!collapsed && (
+        <Button
+          type="button"
+          variant="ghost"
+          size="icon-xs"
+          aria-label={translate(locale, 'ai.workspace.newChat')}
+          title={translate(locale, 'ai.workspace.newChat')}
+          data-testid="ai-workspace-sidebar-new-chat"
+          data-no-drag
+          onClick={onNewChat}
+        >
+          <Plus size={16} />
+        </Button>
+      )}
+    </div>
+  )
+}
+
+function ConversationTitleEditor({
+  conversation,
+  locale,
+  onCancel,
+  onRename,
+}: {
+  conversation: AiConversation
+  locale: AppLocale
+  onCancel: () => void
+  onRename: (title: string) => void
+}) {
+  const [draft, setDraft] = useState(conversation.title)
+  const finishedRef = useRef(false)
+  const submit = () => {
+    if (finishedRef.current) return
+    const nextTitle = draft.trim()
+    if (!nextTitle) {
+      finishedRef.current = true
+      onCancel()
+      return
+    }
+    finishedRef.current = true
+    onRename(nextTitle)
+    onCancel()
+  }
+  const cancel = () => {
+    finishedRef.current = true
+    onCancel()
+  }
+
+  return (
+    <div className="flex min-w-0 flex-1 items-center gap-1 pr-7">
+      <Input
+        value={draft}
+        onChange={(event) => setDraft(event.target.value)}
+        onBlur={submit}
+        onKeyDown={(event) => {
+          if (event.key === 'Enter') submit()
+          if (event.key === 'Escape') cancel()
+        }}
+        aria-label={translate(locale, 'ai.workspace.renameChat')}
+        className="h-7 min-w-0 flex-1 px-2 text-[12px]"
+        autoFocus
+      />
+      <Check size={14} className="shrink-0 text-muted-foreground" />
+    </div>
+  )
+}
+
+function CollapsedConversationSidebar({ locale, onNewChat }: { locale: AppLocale; onNewChat: () => void }) {
+  return (
+    <div className="flex flex-1 flex-col items-center gap-2 p-2">
+      <Button
+        type="button"
+        variant="ghost"
+        size="icon-xs"
+        aria-label={translate(locale, 'ai.workspace.newChat')}
+        title={translate(locale, 'ai.workspace.newChat')}
+        data-testid="ai-workspace-sidebar-new-chat"
+        onClick={onNewChat}
+      >
+        <Plus size={16} />
+      </Button>
+    </div>
+  )
+}
+
+function ConversationArchiveButton({
+  conversationId,
+  locale,
+  onArchive,
+  onRestore,
+  showArchived,
+}: {
+  conversationId: string
+  locale: AppLocale
+  onArchive: (id: string) => void
+  onRestore: (id: string) => void
+  showArchived: boolean
+}) {
+  const label = translate(locale, showArchived ? 'ai.workspace.restore' : 'ai.workspace.archive')
+
+  return (
+    <Button
+      type="button"
+      variant="ghost"
+      size="icon-xs"
+      className="absolute right-1 top-1/2 -translate-y-1/2 opacity-0 transition-opacity group-hover:opacity-100 focus:opacity-100"
+      aria-label={label}
+      title={label}
+      onClick={() => showArchived ? onRestore(conversationId) : onArchive(conversationId)}
+    >
+      {showArchived ? <ArrowSquareIn size={16} /> : <Archive size={16} />}
+    </Button>
+  )
+}
+
+function ConversationRow({
+  active,
+  conversation,
+  editing,
+  locale,
+  onArchive,
+  onRename,
+  onRestore,
+  onSelect,
+  onStartEditing,
+  showArchived,
+  status,
+  stopEditing,
+}: {
+  active: boolean
+  conversation: AiConversation
+  editing: boolean
+  locale: AppLocale
+  onArchive: (id: string) => void
+  onRename: (id: string, title: string) => void
+  onRestore: (id: string) => void
+  onSelect: (id: string) => void
+  onStartEditing: (id: string) => void
+  showArchived: boolean
+  status: AgentStatus
+  stopEditing: () => void
+}) {
+  return (
+    <div className="group relative flex min-w-0 items-center">
+      {editing ? (
+        <ConversationTitleEditor
+          conversation={conversation}
+          locale={locale}
+          onCancel={stopEditing}
+          onRename={(title) => onRename(conversation.id, title)}
+        />
+      ) : (
+        <Button
+          type="button"
+          variant="ghost"
+          size="sm"
+          className={cn(
+            'min-w-0 flex-1 justify-start gap-2 rounded-md px-2 pr-8 text-left text-[12px]',
+            active ? 'bg-accent text-foreground' : 'text-muted-foreground hover:text-foreground',
+          )}
+          aria-pressed={active}
+          onClick={() => onSelect(conversation.id)}
+          onDoubleClick={() => onStartEditing(conversation.id)}
+        >
+          <span className="truncate">{conversation.title}</span>
+          <span className="ml-auto flex shrink-0 items-center">
+            <SidebarStatusIndicator status={status} />
+          </span>
+        </Button>
+      )}
+      <ConversationArchiveButton
+        conversationId={conversation.id}
+        locale={locale}
+        onArchive={onArchive}
+        onRestore={onRestore}
+        showArchived={showArchived}
+      />
+    </div>
+  )
+}
+
+function ConversationList({
+  activeId,
+  conversations,
+  editingId,
+  locale,
+  onArchive,
+  onRename,
+  onRestore,
+  onSelect,
+  setEditingId,
+  showArchived,
+  statuses,
+}: Pick<ConversationSidebarProps,
+  'activeId' | 'conversations' | 'locale' | 'onArchive' | 'onRename' | 'onRestore' | 'onSelect' | 'showArchived' | 'statuses'
+> & {
+  editingId: string | null
+  setEditingId: (id: string | null) => void
+}) {
+  const visibleConversations = conversations.filter((conversation) => conversation.archived === showArchived)
+  const emptyLabel = showArchived
+    ? translate(locale, 'ai.workspace.noArchivedChats')
+    : translate(locale, 'ai.workspace.noActiveChats')
+
+  if (visibleConversations.length === 0) {
+    return <div className="px-2 py-4 text-[12px] text-muted-foreground">{emptyLabel}</div>
+  }
+
+  return visibleConversations.map((conversation) => (
+    <ConversationRow
+      key={conversation.id}
+      active={conversation.id === activeId}
+      conversation={conversation}
+      editing={editingId === conversation.id}
+      locale={locale}
+      onArchive={onArchive}
+      onRename={onRename}
+      onRestore={onRestore}
+      onSelect={onSelect}
+      onStartEditing={setEditingId}
+      showArchived={showArchived}
+      status={statuses[conversation.id] ?? 'idle'}
+      stopEditing={() => setEditingId(null)}
+    />
+  ))
+}
+
+function ArchivedConversationsToggle({
+  locale,
+  setShowArchived,
+  showArchived,
+}: Pick<ConversationSidebarProps, 'locale' | 'setShowArchived' | 'showArchived'>) {
+  return (
+    <div className="border-t border-border p-2">
+      <Button
+        type="button"
+        variant="ghost"
+        size="sm"
+        className="w-full justify-start text-[12px] text-muted-foreground"
+        onClick={() => setShowArchived(!showArchived)}
+      >
+        <Archive size={16} />
+        {translate(locale, showArchived ? 'ai.workspace.hideArchived' : 'ai.workspace.showArchived')}
+      </Button>
+    </div>
+  )
+}
+
+function ExpandedConversationSidebar({
+  activeId,
+  conversations,
+  locale,
+  onArchive,
+  onRename,
+  onRestore,
+  onSelect,
+  setShowArchived,
+  showArchived,
+  statuses,
+}: Omit<ConversationSidebarProps, 'collapsed' | 'onNewChat' | 'onToggleCollapsed'>) {
+  const [editingId, setEditingId] = useState<string | null>(null)
+
+  return (
+    <>
+      <div className="flex-1 overflow-y-auto p-2">
+        <ConversationList
+          activeId={activeId}
+          conversations={conversations}
+          editingId={editingId}
+          locale={locale}
+          onArchive={onArchive}
+          onRename={onRename}
+          onRestore={onRestore}
+          onSelect={onSelect}
+          setEditingId={setEditingId}
+          showArchived={showArchived}
+          statuses={statuses}
+        />
+      </div>
+      <ArchivedConversationsToggle
+        locale={locale}
+        setShowArchived={setShowArchived}
+        showArchived={showArchived}
+      />
+    </>
+  )
+}
+
+export function ConversationSidebar({
+  activeId,
+  collapsed,
+  conversations,
+  locale,
+  onArchive,
+  onNewChat,
+  onRename,
+  onRestore,
+  onSelect,
+  onToggleCollapsed,
+  setShowArchived,
+  showArchived,
+  statuses,
+}: ConversationSidebarProps) {
+  return (
+    <div className={cn(
+      'flex shrink-0 flex-col border-r border-border bg-sidebar transition-[width]',
+      collapsed ? 'w-12' : 'w-[220px]',
+    )}>
+      <SidebarHeader
+        collapsed={collapsed}
+        locale={locale}
+        onNewChat={onNewChat}
+        onToggleCollapsed={onToggleCollapsed}
+      />
+      {collapsed ? (
+        <CollapsedConversationSidebar locale={locale} onNewChat={onNewChat} />
+      ) : (
+        <ExpandedConversationSidebar
+          activeId={activeId}
+          conversations={conversations}
+          locale={locale}
+          onArchive={onArchive}
+          onRename={onRename}
+          onRestore={onRestore}
+          onSelect={onSelect}
+          setShowArchived={setShowArchived}
+          showArchived={showArchived}
+          statuses={statuses}
+        />
+      )}
+    </div>
+  )
+}
--- a/src/components/AiWorkspaceWindowApp.tsx
+++ b/src/components/AiWorkspaceWindowApp.tsx
@@ -0,0 +1,86 @@
+import { useCallback, useMemo, useState } from 'react'
+import { AppPreferencesProvider, useAppPreferences } from '../hooks/useAppPreferences'
+import { useAiAgentsStatus } from '../hooks/useAiAgentsStatus'
+import { useSettings } from '../hooks/useSettings'
+import { useVaultAiGuidanceStatus } from '../hooks/useVaultAiGuidanceStatus'
+import { areAiFeaturesEnabled } from '../lib/aiFeatures'
+import type { AiWorkspaceConversationSetting, Settings } from '../types'
+import { dockCurrentAiWorkspaceWindow, readAiWorkspaceWindowContext } from '../utils/openAiWorkspaceWindow'
+import { AppAiWorkspaceSurface } from './AppAiWorkspaceSurface'
+import { Toast } from './Toast'
+
+function useAiWorkspaceWindowContext() {
+  return useMemo(() => readAiWorkspaceWindowContext(), [])
+}
+
+function useAiWorkspaceSettingsSaver(
+  enabled: boolean,
+  settings: Settings,
+  saveSettings: (settings: Settings) => void | Promise<void>,
+) {
+  return useCallback((conversations: AiWorkspaceConversationSetting[]) => {
+    if (!enabled) return
+    void saveSettings({ ...settings, ai_workspace_conversations: conversations })
+  }, [enabled, saveSettings, settings])
+}
+
+export function AiWorkspaceWindowApp() {
+  const [toastMessage, setToastMessage] = useState<string | null>(null)
+  const context = useAiWorkspaceWindowContext()
+  const { settings, loaded: settingsLoaded, saveSettings } = useSettings()
+  const aiAgentsStatus = useAiAgentsStatus()
+  const aiFeaturesEnabled = areAiFeaturesEnabled(settings)
+  const preferences = useAppPreferences({
+    aiAgentsStatus,
+    onToast: setToastMessage,
+    saveSettings,
+    settings,
+    settingsLoaded,
+  })
+  const vaultPath = context.vaultPath ?? ''
+  const vaultPaths = context.vaultPaths ?? (vaultPath ? [vaultPath] : [])
+  const { status: vaultAiGuidanceStatus } = useVaultAiGuidanceStatus(
+    aiFeaturesEnabled && vaultPath ? vaultPath : null,
+    vaultPath,
+  )
+  const handleConversationSettingsChange = useAiWorkspaceSettingsSaver(settingsLoaded, settings, saveSettings)
+  const handleDock = useCallback(() => {
+    void dockCurrentAiWorkspaceWindow().catch((err) => {
+      console.warn('[ai] Failed to dock workspace window:', err)
+    })
+  }, [])
+
+  return (
+    <AppPreferencesProvider dateDisplayFormat={preferences.dateDisplayFormat}>
+      {settingsLoaded ? (
+        <AppAiWorkspaceSurface
+          mode="window"
+          open
+          aiAgentsStatus={aiAgentsStatus}
+          aiModelProviders={settings.ai_model_providers ?? []}
+          conversationSettings={settings.ai_workspace_conversations ?? null}
+          conversationSettingsReady={settingsLoaded}
+          defaultAiAgent={preferences.aiAgentPreferences.defaultAiAgent}
+          defaultAiTarget={preferences.aiAgentPreferences.defaultAiTarget}
+          defaultAiAgentReadiness={preferences.aiAgentPreferences.defaultAiAgentReadiness}
+          defaultAiAgentReady={preferences.aiAgentPreferences.defaultAiAgentReady}
+          entries={[]}
+          openTabs={[]}
+          noteList={[]}
+          noteListFilter={{ type: null, query: '' }}
+          onClose={handleDock}
+          onConversationSettingsChange={handleConversationSettingsChange}
+          onDock={handleDock}
+          onUnsupportedAiPaste={setToastMessage}
+          vaultAiGuidanceStatus={vaultAiGuidanceStatus}
+          vaultPath={vaultPath}
+          vaultPaths={vaultPaths}
+          locale={preferences.appLocale}
+        />
+      ) : (
+        <div className="fixed inset-0 bg-background" aria-hidden />
+      )}
+      <Toast message={toastMessage} onDismiss={() => setToastMessage(null)} />
+    </AppPreferencesProvider>
+  )
+}
--- a/src/components/AppAiWorkspaceSurface.tsx
+++ b/src/components/AppAiWorkspaceSurface.tsx
@@ -3,7 +3,7 @@ import type { AiModelProvider, AiTarget } from '../lib/aiTargets'
 import type { AppLocale } from '../lib/i18n'
 import type { NoteListItem } from '../utils/ai-context'
 import type { VaultAiGuidanceStatus } from '../lib/vaultAiGuidance'
-import type { VaultEntry } from '../types'
+import type { AiWorkspaceConversationSetting, VaultEntry } from '../types'
 import { AiWorkspace } from './AiWorkspace'

 interface AppAiWorkspaceSurfaceProps {
@@ -11,6 +11,8 @@ interface AppAiWorkspaceSurfaceProps {
  activeNoteContent?: string | null
  aiAgentsStatus: AiAgentsStatus
  aiModelProviders?: AiModelProvider[]
+  conversationSettings?: AiWorkspaceConversationSetting[] | null
+  conversationSettingsReady?: boolean
  defaultAiAgent: AiAgentId
  defaultAiAgentReadiness: AiAgentReadiness
  defaultAiAgentReady: boolean
@@ -21,6 +23,7 @@ interface AppAiWorkspaceSurfaceProps {
  noteList: NoteListItem[]
  noteListFilter: { type: string | null; query: string }
  onClose: () => void
+  onConversationSettingsChange?: (conversations: AiWorkspaceConversationSetting[]) => void
  onDock?: () => void
  onFileCreated?: (relativePath: string) => void
  onFileModified?: (relativePath: string) => void
@@ -42,6 +45,8 @@ export function AppAiWorkspaceSurface({
  activeNoteContent,
  aiAgentsStatus,
  aiModelProviders,
+  conversationSettings,
+  conversationSettingsReady,
  defaultAiAgent,
  defaultAiAgentReadiness,
  defaultAiAgentReady,
@@ -52,6 +57,7 @@ export function AppAiWorkspaceSurface({
  noteList,
  noteListFilter,
  onClose,
+  onConversationSettingsChange,
  onDock,
  onFileCreated,
  onFileModified,
@@ -73,6 +79,8 @@ export function AppAiWorkspaceSurface({
      open={open}
      aiAgentsStatus={aiAgentsStatus}
      aiModelProviders={aiModelProviders}
+      conversationSettings={conversationSettings}
+      conversationSettingsReady={conversationSettingsReady}
      defaultAiAgent={defaultAiAgent}
      defaultAiTarget={defaultAiTarget}
      defaultAiAgentReadiness={defaultAiAgentReadiness}
@@ -84,6 +92,7 @@ export function AppAiWorkspaceSurface({
      noteList={noteList}
      noteListFilter={noteListFilter}
      onClose={onClose}
+      onConversationSettingsChange={onConversationSettingsChange}
      onDock={onDock}
      onPopOut={onPopOut}
      onOpenAiSettings={onOpenAiSettings}
--- a/src/components/ui/button.tsx
+++ b/src/components/ui/button.tsx
@@ -26,7 +26,7 @@ const buttonVariants = cva(
        sm: "h-8 rounded-md gap-1.5 px-3 has-[>svg]:px-2.5",
        lg: "h-10 rounded-md px-6 has-[>svg]:px-4",
        icon: "size-9",
-        "icon-xs": "size-6 rounded-md [&_svg:not([class*='size-'])]:size-3",
+        "icon-xs": "size-6 rounded-md [&_svg:not([class*='size-'])]:size-4",
        "icon-sm": "size-8",
        "icon-lg": "size-10",
      },
--- a/src/hooks/useAppAiWorkspaceBridge.ts
+++ b/src/hooks/useAppAiWorkspaceBridge.ts
@@ -9,7 +9,7 @@ import {
 import {
  dockCurrentAiWorkspaceWindow,
  openAiWorkspaceWindow,
-  registerAiWorkspaceTrafficLightDocking,
+  type AiWorkspaceWindowContext,
 } from '../utils/openAiWorkspaceWindow'

 interface UseAppAiWorkspaceBridgeOptions {
@@ -20,6 +20,7 @@ interface UseAppAiWorkspaceBridgeOptions {
  openSettings: () => void
  setSettingsInitialSectionId: (sectionId: string | null) => void
  showAIChat: boolean
+  windowContext?: AiWorkspaceWindowContext
 }

 interface AppAiWorkspaceBridge {
@@ -79,13 +80,6 @@ function useCloseDisabledAiWorkspace(aiFeaturesEnabled: boolean, closeAIChat: ()
  }, [aiFeaturesEnabled, closeAIChat, showAIChat])
 }

-function useAiWorkspaceTrafficLights(aiWorkspaceWindow: boolean) {
-  useEffect(() => {
-    if (!aiWorkspaceWindow) return
-    return registerAiWorkspaceTrafficLightDocking()
-  }, [aiWorkspaceWindow])
-}
-
 export function useAppAiWorkspaceBridge({
  aiFeaturesEnabled,
  aiWorkspaceWindow,
@@ -94,11 +88,11 @@ export function useAppAiWorkspaceBridge({
  openSettings,
  setSettingsInitialSectionId,
  showAIChat,
+  windowContext,
 }: UseAppAiWorkspaceBridgeOptions): AppAiWorkspaceBridge {
  useOpenAiChatEvent(aiFeaturesEnabled, openAIChat)
  useCloseDisabledAiWorkspace(aiFeaturesEnabled, closeAIChat, showAIChat)
  useDockRequestEvent(aiFeaturesEnabled, aiWorkspaceWindow, openAIChat)
-  useAiWorkspaceTrafficLights(aiWorkspaceWindow)

  const handleOpenAiSettings = useCallback(() => {
    setSettingsInitialSectionId(SETTINGS_SECTION_IDS.ai)
@@ -113,7 +107,7 @@ export function useAppAiWorkspaceBridge({
  const handlePopOutAiWorkspace = useCallback(() => {
    closeAIChat()
    trackEvent('ai_workspace_pop_out')
-    void openAiWorkspaceWindow()
+    void openAiWorkspaceWindow(windowContext)
      .then((opened) => {
        if (!opened) openAIChat()
      })
@@ -121,7 +115,7 @@ export function useAppAiWorkspaceBridge({
        console.warn('[ai] Failed to open workspace window:', err)
        openAIChat()
      })
-  }, [closeAIChat, openAIChat])
+  }, [closeAIChat, openAIChat, windowContext])

  const handleDockCurrentAiWorkspaceWindow = useCallback(() => {
    trackEvent('ai_workspace_docked', { source: 'button' })
--- a/src/hooks/useSettings.test.ts
+++ b/src/hooks/useSettings.test.ts
@@ -33,6 +33,7 @@ const defaultSettings: Settings = {
  default_ai_agent: null,
  default_ai_target: null,
  ai_model_providers: null,
+  ai_workspace_conversations: null,
  hide_gitignored_files: null,
  multi_workspace_enabled: null,
  all_notes_show_pdfs: null,
@@ -61,6 +62,7 @@ const savedSettings: Settings = {
  default_ai_agent: null,
  default_ai_target: null,
  ai_model_providers: null,
+  ai_workspace_conversations: null,
  hide_gitignored_files: null,
  multi_workspace_enabled: null,
  all_notes_show_pdfs: null,
@@ -126,6 +128,7 @@ function changedSettings(): Settings {
    default_ai_agent: null,
    default_ai_target: null,
    ai_model_providers: null,
+    ai_workspace_conversations: null,
    hide_gitignored_files: false,
    multi_workspace_enabled: null,
    all_notes_show_pdfs: true,
--- a/src/hooks/useSettings.ts
+++ b/src/hooks/useSettings.ts
@@ -55,6 +55,7 @@ const EMPTY_SETTINGS: Settings = {
  ai_features_enabled: null,
  default_ai_target: null,
  ai_model_providers: null,
+  ai_workspace_conversations: null,
  hide_gitignored_files: null,
  all_notes_show_pdfs: null,
  all_notes_show_images: null,
@@ -80,6 +81,7 @@ function normalizeSettings(settings: Settings): Settings {
    default_ai_agent: normalizeStoredAiAgent(settings.default_ai_agent),
    default_ai_target: settings.default_ai_target?.trim() || null,
    ai_model_providers: aiModelProviders.length > 0 ? aiModelProviders : null,
+    ai_workspace_conversations: normalizeAiWorkspaceConversations(settings.ai_workspace_conversations),
    hide_gitignored_files: settings.hide_gitignored_files ?? null,
    all_notes_show_pdfs: settings.all_notes_show_pdfs ?? null,
    all_notes_show_images: settings.all_notes_show_images ?? null,
@@ -88,6 +90,17 @@ function normalizeSettings(settings: Settings): Settings {
  }
 }

+function normalizeAiWorkspaceConversations(settings: Settings['ai_workspace_conversations']) {
+  const conversations = (settings ?? []).map((conversation) => ({
+    archived: conversation.archived === true,
+    id: conversation.id.trim(),
+    target_id: conversation.target_id?.trim() || null,
+    title: conversation.title.trim(),
+  })).filter((conversation) => conversation.id && conversation.title)
+
+  return conversations.length > 0 ? conversations : null
+}
+
 function effectiveThemeMode(settings: Settings): ThemeMode {
  return normalizeThemeMode(settings.theme_mode) ?? DEFAULT_THEME_MODE
 }
--- a/src/lib/locales/be-BY.json
+++ b/src/lib/locales/be-BY.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Адправіць паведамленне",
  "ai.workspace.title": "Працоўная прастора ШІ",
  "ai.workspace.newChat": "Новы чат",
+  "ai.workspace.collapseSidebar": "Згарнуць спіс чатаў са ШІ",
+  "ai.workspace.expandSidebar": "Разгарнуць спіс чатаў са ШІ",
  "ai.workspace.close": "Зачыніць працоўную прастору ШІ",
  "ai.workspace.popOut": "Адкрыць у асобным акне",
  "ai.workspace.dock": "Закрыць працоўную прастору ШІ",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "Няма актыўных чатаў",
  "ai.workspace.noArchivedChats": "Няма архіваваных чатаў",
  "ai.workspace.chatTitle": "Чат {index}",
+  "ai.workspace.renameChat": "Перайменаваць чат",
  "ai.workspace.status.archived": "Архівавана",
  "ai.workspace.status.idle": "Бяздзейны",
  "ai.workspace.status.running": "Выконваецца",
--- a/src/lib/locales/be-Latn.json
+++ b/src/lib/locales/be-Latn.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Adpravić paviedamliennie",
  "ai.workspace.title": "ŠI prastora",
  "ai.workspace.newChat": "Novy čat",
+  "ai.workspace.collapseSidebar": "Zharnuć spis čataŭ sa ŠI",
+  "ai.workspace.expandSidebar": "Razhornuć spis čataŭ sa ŠI",
  "ai.workspace.close": "Zakryć ŠI prastoru",
  "ai.workspace.popOut": "Adkryć u asobnym aknie",
  "ai.workspace.dock": "Prymacavać ŠI prastoru",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "Niama aktyŭnych čataŭ",
  "ai.workspace.noArchivedChats": "Niama archivavanych čataŭ",
  "ai.workspace.chatTitle": "Čat {index}",
+  "ai.workspace.renameChat": "Pierajmienavać čat",
  "ai.workspace.status.archived": "Archivavany",
  "ai.workspace.status.idle": "Čakannie",
  "ai.workspace.status.running": "Pracuje",
--- a/src/lib/locales/de-DE.json
+++ b/src/lib/locales/de-DE.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Nachricht senden",
  "ai.workspace.title": "KI-Workspace",
  "ai.workspace.newChat": "Neuer Chat",
+  "ai.workspace.collapseSidebar": "AI-Chat-Liste einklappen",
+  "ai.workspace.expandSidebar": "KI-Chat-Liste erweitern",
  "ai.workspace.close": "AI-Workspace schließen",
  "ai.workspace.popOut": "In einem separaten Fenster öffnen",
  "ai.workspace.dock": "AI-Workspace andocken",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "Keine aktiven Chats",
  "ai.workspace.noArchivedChats": "Keine archivierten Chats",
  "ai.workspace.chatTitle": "Chat {index}",
+  "ai.workspace.renameChat": "Chat umbenennen",
  "ai.workspace.status.archived": "Archiviert",
  "ai.workspace.status.idle": "Inaktiv",
  "ai.workspace.status.running": "Wird ausgeführt",
--- a/src/lib/locales/en.json
+++ b/src/lib/locales/en.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Send message",
  "ai.workspace.title": "AI workspace",
  "ai.workspace.newChat": "New chat",
+  "ai.workspace.collapseSidebar": "Collapse AI chat list",
+  "ai.workspace.expandSidebar": "Expand AI chat list",
  "ai.workspace.close": "Close AI workspace",
  "ai.workspace.popOut": "Open in separate window",
  "ai.workspace.dock": "Dock AI workspace",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "No active chats",
  "ai.workspace.noArchivedChats": "No archived chats",
  "ai.workspace.chatTitle": "Chat {index}",
+  "ai.workspace.renameChat": "Rename chat",
  "ai.workspace.status.archived": "Archived",
  "ai.workspace.status.idle": "Idle",
  "ai.workspace.status.running": "Running",
--- a/src/lib/locales/es-419.json
+++ b/src/lib/locales/es-419.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Enviar mensaje",
  "ai.workspace.title": "Espacio de trabajo de IA",
  "ai.workspace.newChat": "Nuevo chat",
+  "ai.workspace.collapseSidebar": "Contraer la lista de chat de IA",
+  "ai.workspace.expandSidebar": "Expandir la lista de chat de IA",
  "ai.workspace.close": "Cerrar el espacio de trabajo de IA",
  "ai.workspace.popOut": "Abrir en una ventana separada",
  "ai.workspace.dock": "Acoplar el espacio de trabajo de IA",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "No hay chats activos",
  "ai.workspace.noArchivedChats": "No hay chats archivados",
  "ai.workspace.chatTitle": "Chat {index}",
+  "ai.workspace.renameChat": "Cambiar el nombre del chat",
  "ai.workspace.status.archived": "Archivado",
  "ai.workspace.status.idle": "Inactivo",
  "ai.workspace.status.running": "En ejecución",
--- a/src/lib/locales/es-ES.json
+++ b/src/lib/locales/es-ES.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Enviar mensaje",
  "ai.workspace.title": "Espacio de trabajo de IA",
  "ai.workspace.newChat": "Nuevo chat",
+  "ai.workspace.collapseSidebar": "Contraer la lista de chat de IA",
+  "ai.workspace.expandSidebar": "Expandir la lista de chat de IA",
  "ai.workspace.close": "Cerrar el espacio de trabajo de IA",
  "ai.workspace.popOut": "Abrir en una ventana separada",
  "ai.workspace.dock": "Acoplar el espacio de trabajo de IA",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "No hay chats activos",
  "ai.workspace.noArchivedChats": "No hay chats archivados",
  "ai.workspace.chatTitle": "Chat {index}",
+  "ai.workspace.renameChat": "Cambiar el nombre del chat",
  "ai.workspace.status.archived": "Archivado",
  "ai.workspace.status.idle": "Inactivo",
  "ai.workspace.status.running": "En ejecución",
--- a/src/lib/locales/fr-FR.json
+++ b/src/lib/locales/fr-FR.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Envoyer un message",
  "ai.workspace.title": "Espace de travail IA",
  "ai.workspace.newChat": "Nouveau chat",
+  "ai.workspace.collapseSidebar": "Réduire la liste de chat IA",
+  "ai.workspace.expandSidebar": "Développer la liste de chat IA",
  "ai.workspace.close": "Fermer l'espace de travail IA",
  "ai.workspace.popOut": "Ouvrir dans une fenêtre séparée",
  "ai.workspace.dock": "Ancrer l'espace de travail IA",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "Aucun chat actif",
  "ai.workspace.noArchivedChats": "Aucun chat archivé",
  "ai.workspace.chatTitle": "Chat {index}",
+  "ai.workspace.renameChat": "Renommer le chat",
  "ai.workspace.status.archived": "Archivé",
  "ai.workspace.status.idle": "Inactif",
  "ai.workspace.status.running": "En cours d'exécution",
--- a/src/lib/locales/it-IT.json
+++ b/src/lib/locales/it-IT.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Invia messaggio",
  "ai.workspace.title": "Area di lavoro IA",
  "ai.workspace.newChat": "Nuova chat",
+  "ai.workspace.collapseSidebar": "Comprimi l'elenco delle chat con l'IA",
+  "ai.workspace.expandSidebar": "Espandi l'elenco delle chat con l'IA",
  "ai.workspace.close": "Chiudi l'area di lavoro IA",
  "ai.workspace.popOut": "Apri in una finestra separata",
  "ai.workspace.dock": "Ancora l'area di lavoro IA",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "Nessuna chat attiva",
  "ai.workspace.noArchivedChats": "Nessuna chat archiviata",
  "ai.workspace.chatTitle": "Chat {index}",
+  "ai.workspace.renameChat": "Rinomina chat",
  "ai.workspace.status.archived": "Archiviate",
  "ai.workspace.status.idle": "Inattivo",
  "ai.workspace.status.running": "In esecuzione",
--- a/src/lib/locales/ja-JP.json
+++ b/src/lib/locales/ja-JP.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "メッセージを送信",
  "ai.workspace.title": "AIワークスペース",
  "ai.workspace.newChat": "新しいチャット",
+  "ai.workspace.collapseSidebar": "AIチャットリストを折りたたむ",
+  "ai.workspace.expandSidebar": "AIチャットリストを展開",
  "ai.workspace.close": "AIワークスペースを閉じる",
  "ai.workspace.popOut": "別のウィンドウで開く",
  "ai.workspace.dock": "AIワークスペースをドック",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "アクティブなチャットはありません",
  "ai.workspace.noArchivedChats": "アーカイブされたチャットはありません",
  "ai.workspace.chatTitle": "チャット {index}",
+  "ai.workspace.renameChat": "チャットの名前を変更",
  "ai.workspace.status.archived": "アーカイブ済み",
  "ai.workspace.status.idle": "アイドル",
  "ai.workspace.status.running": "実行中",
--- a/src/lib/locales/ko-KR.json
+++ b/src/lib/locales/ko-KR.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "메시지 보내기",
  "ai.workspace.title": "AI 작업 공간",
  "ai.workspace.newChat": "새 채팅",
+  "ai.workspace.collapseSidebar": "AI 채팅 목록 접기",
+  "ai.workspace.expandSidebar": "AI 채팅 목록 펼치기",
  "ai.workspace.close": "AI 작업 공간 닫기",
  "ai.workspace.popOut": "별도의 창에서 열기",
  "ai.workspace.dock": "AI 작업 공간 고정",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "진행 중인 채팅 없음",
  "ai.workspace.noArchivedChats": "보관된 채팅 없음",
  "ai.workspace.chatTitle": "채팅 {index}",
+  "ai.workspace.renameChat": "채팅 이름 변경",
  "ai.workspace.status.archived": "보관됨",
  "ai.workspace.status.idle": "유휴",
  "ai.workspace.status.running": "실행 중",
--- a/src/lib/locales/pl-PL.json
+++ b/src/lib/locales/pl-PL.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Wyślij wiadomość",
  "ai.workspace.title": "Obszar roboczy AI",
  "ai.workspace.newChat": "Nowy czat",
+  "ai.workspace.collapseSidebar": "Zwiń listę czatów AI",
+  "ai.workspace.expandSidebar": "Rozwiń listę czatów AI",
  "ai.workspace.close": "Zamknij obszar roboczy AI",
  "ai.workspace.popOut": "Otwórz w oddzielnym oknie",
  "ai.workspace.dock": "Zadokuj obszar roboczy AI",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "Brak aktywnych czatów",
  "ai.workspace.noArchivedChats": "Brak zarchiwizowanych czatów",
  "ai.workspace.chatTitle": "Czat {index}",
+  "ai.workspace.renameChat": "Zmień nazwę czatu",
  "ai.workspace.status.archived": "Zarchiwizowane",
  "ai.workspace.status.idle": "Bezczynny",
  "ai.workspace.status.running": "W toku",
--- a/src/lib/locales/pt-BR.json
+++ b/src/lib/locales/pt-BR.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Enviar mensagem",
  "ai.workspace.title": "Espaço de trabalho de IA",
  "ai.workspace.newChat": "Novo chat",
+  "ai.workspace.collapseSidebar": "Recolher lista de chat de IA",
+  "ai.workspace.expandSidebar": "Expandir lista de chat de IA",
  "ai.workspace.close": "Fechar o espaço de trabalho de IA",
  "ai.workspace.popOut": "Abrir em uma janela separada",
  "ai.workspace.dock": "Encaixar o espaço de trabalho de IA",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "Nenhum chat ativo",
  "ai.workspace.noArchivedChats": "Nenhum chat arquivado",
  "ai.workspace.chatTitle": "Chat {index}",
+  "ai.workspace.renameChat": "Renomear chat",
  "ai.workspace.status.archived": "Arquivado",
  "ai.workspace.status.idle": "Ocioso",
  "ai.workspace.status.running": "Em execução",
--- a/src/lib/locales/pt-PT.json
+++ b/src/lib/locales/pt-PT.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Enviar mensagem",
  "ai.workspace.title": "Espaço de trabalho de IA",
  "ai.workspace.newChat": "Novo chat",
+  "ai.workspace.collapseSidebar": "Recolher a lista de chat de IA",
+  "ai.workspace.expandSidebar": "Expandir a lista de chat de IA",
  "ai.workspace.close": "Fechar espaço de trabalho de IA",
  "ai.workspace.popOut": "Abrir numa janela separada",
  "ai.workspace.dock": "Afixar espaço de trabalho de IA",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "Sem chats ativos",
  "ai.workspace.noArchivedChats": "Sem chats arquivados",
  "ai.workspace.chatTitle": "Chat {index}",
+  "ai.workspace.renameChat": "Mudar o nome do chat",
  "ai.workspace.status.archived": "Arquivado",
  "ai.workspace.status.idle": "Inativo",
  "ai.workspace.status.running": "Em execução",
--- a/src/lib/locales/ru-RU.json
+++ b/src/lib/locales/ru-RU.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Отправить сообщение",
  "ai.workspace.title": "Рабочее пространство ИИ",
  "ai.workspace.newChat": "Новый чат",
+  "ai.workspace.collapseSidebar": "Свернуть список чатов с ИИ",
+  "ai.workspace.expandSidebar": "Развернуть список чатов с ИИ",
  "ai.workspace.close": "Закрыть рабочее пространство ИИ",
  "ai.workspace.popOut": "Открыть в отдельном окне",
  "ai.workspace.dock": "Закрепить рабочее пространство ИИ",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "Нет активных чатов",
  "ai.workspace.noArchivedChats": "Нет заархивированных чатов",
  "ai.workspace.chatTitle": "Чат {index}",
+  "ai.workspace.renameChat": "Переименовать чат",
  "ai.workspace.status.archived": "Архивировано",
  "ai.workspace.status.idle": "Бездействует",
  "ai.workspace.status.running": "Выполняется",
--- a/src/lib/locales/vi.json
+++ b/src/lib/locales/vi.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "Send message",
  "ai.workspace.title": "Không gian làm việc AI",
  "ai.workspace.newChat": "Trò chuyện mới",
+  "ai.workspace.collapseSidebar": "Thu gọn danh sách trò chuyện AI",
+  "ai.workspace.expandSidebar": "Mở rộng danh sách trò chuyện AI",
  "ai.workspace.close": "Đóng không gian làm việc AI",
  "ai.workspace.popOut": "Mở trong cửa sổ riêng",
  "ai.workspace.dock": "Gắn không gian làm việc AI vào màn hình",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "Không có cuộc trò chuyện đang hoạt động",
  "ai.workspace.noArchivedChats": "Không có cuộc trò chuyện nào được lưu trữ",
  "ai.workspace.chatTitle": "Trò chuyện {index}",
+  "ai.workspace.renameChat": "Đổi tên cuộc trò chuyện",
  "ai.workspace.status.archived": "Đã lưu trữ",
  "ai.workspace.status.idle": "Không hoạt động",
  "ai.workspace.status.running": "Đang chạy",
--- a/src/lib/locales/zh-CN.json
+++ b/src/lib/locales/zh-CN.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "发送消息",
  "ai.workspace.title": "AI 工作区",
  "ai.workspace.newChat": "新聊天",
+  "ai.workspace.collapseSidebar": "收起 AI 聊天列表",
+  "ai.workspace.expandSidebar": "展开 AI 聊天列表",
  "ai.workspace.close": "关闭 AI 工作区",
  "ai.workspace.popOut": "在单独窗口中打开",
  "ai.workspace.dock": "停靠 AI 工作区",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "没有活跃的聊天",
  "ai.workspace.noArchivedChats": "没有已归档的聊天",
  "ai.workspace.chatTitle": "聊天 {index}",
+  "ai.workspace.renameChat": "重命名聊天",
  "ai.workspace.status.archived": "已归档",
  "ai.workspace.status.idle": "空闲",
  "ai.workspace.status.running": "正在运行",
--- a/src/lib/locales/zh-TW.json
+++ b/src/lib/locales/zh-TW.json
@@ -312,6 +312,8 @@
  "ai.panel.send": "傳送訊息",
  "ai.workspace.title": "AI 工作區",
  "ai.workspace.newChat": "新對話",
+  "ai.workspace.collapseSidebar": "收合 AI 聊天清單",
+  "ai.workspace.expandSidebar": "展開 AI 聊天清單",
  "ai.workspace.close": "關閉 AI 工作區",
  "ai.workspace.popOut": "在單獨視窗中開啟",
  "ai.workspace.dock": "固定 AI 工作區",
@@ -323,6 +325,7 @@
  "ai.workspace.noActiveChats": "沒有進行中的聊天",
  "ai.workspace.noArchivedChats": "沒有已封存的聊天",
  "ai.workspace.chatTitle": "聊天 {index}",
+  "ai.workspace.renameChat": "重新命名聊天",
  "ai.workspace.status.archived": "已封存",
  "ai.workspace.status.idle": "閒置",
  "ai.workspace.status.running": "執行中",
--- a/src/lib/productAnalytics.ts
+++ b/src/lib/productAnalytics.ts
@@ -10,6 +10,8 @@ import type { ThemeMode } from './themeMode'
 type TrackedPreviewKind = FilePreviewKind | 'unsupported'
 type FilePreviewAction = 'copy_path' | 'open_external' | 'reveal'
 type AgentBlockedReason = 'agent_unavailable' | 'missing_vault'
+type AiWorkspaceMode = 'docked' | 'window'
+type AiWorkspaceTitleSource = 'generated' | 'manual'

 const ALL_NOTES_VISIBILITY_CATEGORIES: ReadonlyArray<keyof AllNotesFileVisibility> = [
  'pdfs',
@@ -144,3 +146,14 @@ export function trackAiAgentPermissionModeChanged(agent: AiAgentId, permissionMo
    permission_mode: permissionMode,
  })
 }
+
+export function trackAiWorkspaceSidebarToggled(collapsed: boolean, mode: AiWorkspaceMode): void {
+  trackEvent('ai_workspace_sidebar_toggled', {
+    collapsed: numericFlag(collapsed),
+    mode,
+  })
+}
+
+export function trackAiWorkspaceChatTitled(source: AiWorkspaceTitleSource): void {
+  trackEvent('ai_workspace_chat_titled', { source })
+}
--- a/src/types.ts
+++ b/src/types.ts
@@ -126,6 +126,7 @@ export interface Settings {
  default_ai_agent?: AiAgentId | null
  default_ai_target?: string | null
  ai_model_providers?: AiModelProvider[] | null
+  ai_workspace_conversations?: AiWorkspaceConversationSetting[] | null
  hide_gitignored_files?: boolean | null
  all_notes_show_pdfs?: boolean | null
  all_notes_show_images?: boolean | null
@@ -133,6 +134,13 @@ export interface Settings {
  multi_workspace_enabled?: boolean | null
 }

+export interface AiWorkspaceConversationSetting {
+  archived?: boolean | null
+  id: string
+  target_id?: string | null
+  title: string
+}
+
 export interface GitPullResult {
  status: 'up_to_date' | 'updated' | 'conflict' | 'no_remote' | 'error'
  message: string
--- a/src/utils/aiConversationTitle.test.ts
+++ b/src/utils/aiConversationTitle.test.ts
@@ -0,0 +1,16 @@
+import { describe, expect, it } from 'vitest'
+import { generateAiConversationTitle } from './aiConversationTitle'
+
+describe('generateAiConversationTitle', () => {
+  it('creates a compact title from the first prompt', () => {
+    expect(generateAiConversationTitle('please summarize quarterly sponsor outreach next steps')).toBe(
+      'Summarize Quarterly Sponsor Outreach',
+    )
+  })
+
+  it('strips wikilinks and urls before choosing title words', () => {
+    expect(generateAiConversationTitle('help with [[Sponsor Onboarding]] https://example.com plan')).toBe(
+      'Sponsor Onboarding Plan',
+    )
+  })
+})
--- a/src/utils/aiConversationTitle.ts
+++ b/src/utils/aiConversationTitle.ts
@@ -0,0 +1,49 @@
+const TITLE_WORD_LIMIT = 4
+
+const STOP_WORDS = new Set([
+  'a',
+  'an',
+  'and',
+  'are',
+  'can',
+  'could',
+  'for',
+  'from',
+  'help',
+  'how',
+  'into',
+  'make',
+  'please',
+  'the',
+  'this',
+  'that',
+  'with',
+  'you',
+])
+
+function cleanPrompt(prompt: string): string {
+  return prompt
+    .replace(/```[\s\S]*?```/g, ' ')
+    .replace(/\[\[([^\]]+)\]\]/g, '$1')
+    .replace(/https?:\/\/\S+/g, ' ')
+    .replace(/[^\p{L}\p{N}\s'-]/gu, ' ')
+    .replace(/\s+/g, ' ')
+    .trim()
+}
+
+function toTitleWord(word: string): string {
+  if (word.length <= 1) return word.toUpperCase()
+  return `${word[0].toUpperCase()}${word.slice(1)}`
+}
+
+export function generateAiConversationTitle(prompt: string): string | null {
+  const words = cleanPrompt(prompt)
+    .split(' ')
+    .map((word) => word.trim())
+    .filter(Boolean)
+  const meaningfulWords = words.filter((word) => !STOP_WORDS.has(word.toLowerCase()))
+  const titleWords = (meaningfulWords.length > 0 ? meaningfulWords : words).slice(0, TITLE_WORD_LIMIT)
+  if (titleWords.length === 0) return null
+
+  return titleWords.map(toTitleWord).join(' ')
+}
--- a/src/utils/openAiWorkspaceWindow.test.ts
+++ b/src/utils/openAiWorkspaceWindow.test.ts
@@ -5,9 +5,9 @@ import {
  buildRuntimeAiWorkspaceWindowUrl,
  dockCurrentAiWorkspaceWindow,
  openAiWorkspaceWindow,
+  readAiWorkspaceWindowContext,
 } from './openAiWorkspaceWindow'
 import { isTauri } from '../mock-tauri'
-import { shouldUseCustomWindowChrome } from './platform'
 import { AI_WORKSPACE_DOCK_REQUESTED_EVENT } from './aiPromptBridge'

 const webviewWindowCalls = vi.fn()
@@ -32,10 +32,6 @@ vi.mock('../mock-tauri', () => ({
  isTauri: vi.fn(),
 }))

-vi.mock('./platform', () => ({
-  shouldUseCustomWindowChrome: vi.fn(),
-}))
-
 vi.mock('@tauri-apps/api/webviewWindow', () => ({
  WebviewWindow: class MockWebviewWindow {
    static getByLabel = webviewGetByLabel
@@ -46,12 +42,6 @@ vi.mock('@tauri-apps/api/webviewWindow', () => ({
  },
 }))

-vi.mock('@tauri-apps/api/dpi', () => ({
-  LogicalPosition: class MockLogicalPosition {
-    constructor(public x: number, public y: number) {}
-  },
-}))
-
 vi.mock('@tauri-apps/api/event', () => ({
  emitTo,
 }))
@@ -64,18 +54,31 @@ describe('openAiWorkspaceWindow', () => {
  beforeEach(() => {
    vi.clearAllMocks()
    vi.mocked(isTauri).mockReturnValue(false)
-    vi.mocked(shouldUseCustomWindowChrome).mockReturnValue(false)
    webviewGetByLabel.mockResolvedValue(null)
    localStorage.clear()
  })

  it('builds the AI workspace route', () => {
-    const url = buildAiWorkspaceWindowUrl('ai-workspace')
+    const url = buildAiWorkspaceWindowUrl('ai-workspace', {
+      vaultPath: '/tmp/vault',
+      vaultPaths: ['/tmp/vault', '/tmp/other'],
+    })
    const parsed = new URL(url, 'https://tolaria.localhost')

    expect(parsed.pathname).toBe('/')
    expect(parsed.searchParams.get('window')).toBe('ai-workspace')
    expect(parsed.searchParams.get('windowLabel')).toBe('ai-workspace')
+    expect(parsed.searchParams.get('vault')).toBe('/tmp/vault')
+    expect(JSON.parse(parsed.searchParams.get('vaultPaths') ?? '[]')).toEqual(['/tmp/vault', '/tmp/other'])
+  })
+
+  it('reads the AI workspace route context', () => {
+    const search = '?window=ai-workspace&vault=%2Ftmp%2Fvault&vaultPaths=%5B%22%2Ftmp%2Fvault%22%5D'
+
+    expect(readAiWorkspaceWindowContext(search)).toEqual({
+      vaultPath: '/tmp/vault',
+      vaultPaths: ['/tmp/vault'],
+    })
  })

  it('resolves the runtime route against the current app origin', () => {
@@ -95,20 +98,19 @@ describe('openAiWorkspaceWindow', () => {
  it('opens one native Tauri AI workspace window', async () => {
    vi.mocked(isTauri).mockReturnValue(true)

-    await openAiWorkspaceWindow()
+    await openAiWorkspaceWindow({ vaultPath: '/tmp/vault' })

    expect(webviewWindowCalls).toHaveBeenCalledWith(
      AI_WORKSPACE_WINDOW_LABEL,
      expect.objectContaining({
+        url: expect.stringContaining('vault=%2Ftmp%2Fvault'),
        title: 'Tolaria AI',
        width: 940,
        height: 680,
        minWidth: 520,
        minHeight: 420,
-        titleBarStyle: 'overlay',
-        trafficLightPosition: expect.objectContaining({ x: 18, y: 22 }),
-        hiddenTitle: true,
-        decorations: true,
+        minimizable: false,
+        decorations: false,
      }),
    )
    expect(localStorage.getItem('tolaria:ai-workspace-window:ai-workspace')).toBe('true')
--- a/src/utils/openAiWorkspaceWindow.ts
+++ b/src/utils/openAiWorkspaceWindow.ts
@@ -1,26 +1,27 @@
 import { isTauri } from '../mock-tauri'
-import { shouldUseCustomWindowChrome } from './platform'
 import { rememberAiWorkspaceWindow } from './windowMode'
 import { AI_WORKSPACE_DOCK_REQUESTED_EVENT, requestDockAiWorkspace } from './aiPromptBridge'

 export const AI_WORKSPACE_WINDOW_LABEL = 'ai-workspace'

 const AI_WORKSPACE_WINDOW_TITLE = 'Tolaria AI'
-const MACOS_TRAFFIC_LIGHT_POSITION = { x: 18, y: 22 } as const
 const APP_ORIGIN_PROTOCOLS = new Set(['http:', 'https:'])
-const MINIMIZE_DOCK_POLL_MS = 250

-interface AiWorkspaceDockingState {
-  cancelled: boolean
-  minimizeTimer: number | null
-  unlistenClose: (() => void) | null
+export interface AiWorkspaceWindowContext {
+  vaultPath?: string
+  vaultPaths?: string[]
 }

-export function buildAiWorkspaceWindowUrl(windowLabel = AI_WORKSPACE_WINDOW_LABEL): string {
+export function buildAiWorkspaceWindowUrl(
+  windowLabel = AI_WORKSPACE_WINDOW_LABEL,
+  context: AiWorkspaceWindowContext = {},
+): string {
  const params = new URLSearchParams({
    window: 'ai-workspace',
    windowLabel,
  })
+  if (context.vaultPath) params.set('vault', context.vaultPath)
+  if (context.vaultPaths?.length) params.set('vaultPaths', JSON.stringify(context.vaultPaths))

  return `/?${params.toString()}`
 }
@@ -31,14 +32,39 @@ function resolveAiWorkspaceWindowUrlForRuntime(route: string): string {
  return new URL(route, window.location.origin).toString()
 }

-export function buildRuntimeAiWorkspaceWindowUrl(windowLabel = AI_WORKSPACE_WINDOW_LABEL): string {
-  return resolveAiWorkspaceWindowUrlForRuntime(buildAiWorkspaceWindowUrl(windowLabel))
+export function buildRuntimeAiWorkspaceWindowUrl(
+  windowLabel = AI_WORKSPACE_WINDOW_LABEL,
+  context: AiWorkspaceWindowContext = {},
+): string {
+  return resolveAiWorkspaceWindowUrlForRuntime(buildAiWorkspaceWindowUrl(windowLabel, context))
 }

-export async function openAiWorkspaceWindow(): Promise<boolean> {
+export function readAiWorkspaceWindowContext(search = window.location.search): AiWorkspaceWindowContext {
+  const params = new URLSearchParams(search)
+  const vaultPath = params.get('vault') ?? undefined
+  const vaultPaths = parseVaultPathsParam(params.get('vaultPaths'))
+  return { vaultPath, vaultPaths }
+}
+
+function parseVaultPathsParam(raw: string | null): string[] | undefined {
+  if (!raw) return undefined
+
+  try {
+    const parsed = JSON.parse(raw)
+    if (Array.isArray(parsed)) {
+      const paths = parsed.filter((item): item is string => typeof item === 'string' && item.trim().length > 0)
+      return paths.length > 0 ? paths : undefined
+    }
+  } catch {
+    return undefined
+  }
+
+  return undefined
+}
+
+export async function openAiWorkspaceWindow(context: AiWorkspaceWindowContext = {}): Promise<boolean> {
  if (!isTauri()) return false

-  const { LogicalPosition } = await import('@tauri-apps/api/dpi')
  const { WebviewWindow } = await import('@tauri-apps/api/webviewWindow')
  const existingWindow = await WebviewWindow.getByLabel(AI_WORKSPACE_WINDOW_LABEL)
  if (existingWindow) {
@@ -50,7 +76,7 @@ export async function openAiWorkspaceWindow(): Promise<boolean> {
  rememberAiWorkspaceWindow()

  new WebviewWindow(AI_WORKSPACE_WINDOW_LABEL, {
-    url: buildRuntimeAiWorkspaceWindowUrl(AI_WORKSPACE_WINDOW_LABEL),
+    url: buildRuntimeAiWorkspaceWindowUrl(AI_WORKSPACE_WINDOW_LABEL, context),
    title: AI_WORKSPACE_WINDOW_TITLE,
    width: 940,
    height: 680,
@@ -58,11 +84,8 @@ export async function openAiWorkspaceWindow(): Promise<boolean> {
    minHeight: 420,
    center: true,
    resizable: true,
-    minimizable: true,
-    titleBarStyle: 'overlay',
-    trafficLightPosition: new LogicalPosition(MACOS_TRAFFIC_LIGHT_POSITION.x, MACOS_TRAFFIC_LIGHT_POSITION.y),
-    hiddenTitle: true,
-    decorations: !shouldUseCustomWindowChrome(),
+    minimizable: false,
+    decorations: false,
  })

  return true
@@ -78,57 +101,3 @@ export async function dockCurrentAiWorkspaceWindow(): Promise<void> {
  await emitTo('main', AI_WORKSPACE_DOCK_REQUESTED_EVENT).catch(() => {})
  await getCurrentWindow().destroy().catch(() => {})
 }
-
-function dockOnCloseRequest(currentWindow: ReturnType<typeof import('@tauri-apps/api/window').getCurrentWindow>, state: AiWorkspaceDockingState) {
-  void currentWindow.onCloseRequested((event) => {
-    event.preventDefault()
-    void dockCurrentAiWorkspaceWindow()
-  }).then((unlisten) => {
-    if (state.cancelled) {
-      unlisten()
-      return
-    }
-
-    state.unlistenClose = unlisten
-  })
-}
-
-function dockOnMinimize(currentWindow: ReturnType<typeof import('@tauri-apps/api/window').getCurrentWindow>, state: AiWorkspaceDockingState) {
-  state.minimizeTimer = window.setInterval(() => {
-    void currentWindow.isMinimized()
-      .then((minimized) => {
-        if (!minimized || state.cancelled) return
-
-        void currentWindow.unminimize().catch(() => {})
-        void dockCurrentAiWorkspaceWindow()
-      })
-      .catch(() => {})
-  }, MINIMIZE_DOCK_POLL_MS)
-}
-
-function connectTrafficLightDocking(state: AiWorkspaceDockingState) {
-  void import('@tauri-apps/api/window').then(({ getCurrentWindow }) => {
-    if (state.cancelled) return
-
-    const currentWindow = getCurrentWindow()
-    dockOnCloseRequest(currentWindow, state)
-    dockOnMinimize(currentWindow, state)
-  })
-}
-
-export function registerAiWorkspaceTrafficLightDocking(): () => void {
-  if (!isTauri()) return () => {}
-
-  const state: AiWorkspaceDockingState = {
-    cancelled: false,
-    minimizeTimer: null,
-    unlistenClose: null,
-  }
-  connectTrafficLightDocking(state)
-
-  return () => {
-    state.cancelled = true
-    state.unlistenClose?.()
-    if (state.minimizeTimer !== null) window.clearInterval(state.minimizeTimer)
-  }
-}
--- a/src/utils/tauriWindowControlPermissions.test.ts
+++ b/src/utils/tauriWindowControlPermissions.test.ts
@@ -2,6 +2,7 @@ import { readFileSync } from 'node:fs'

 interface TauriCapability {
  permissions: string[]
+  windows: string[]
 }

 const LINUX_WINDOW_CHROME_PERMISSIONS = [
@@ -22,4 +23,12 @@ describe('Tauri window-control permissions', () => {
      expect.arrayContaining([...LINUX_WINDOW_CHROME_PERMISSIONS]),
    )
  })
+
+  it('allows the AI workspace pop-out window to use app APIs', () => {
+    const capability = JSON.parse(
+      readFileSync(`${process.cwd()}/src-tauri/capabilities/default.json`, 'utf8'),
+    ) as TauriCapability
+
+    expect(capability.windows).toEqual(expect.arrayContaining(['main', 'ai-workspace', 'note-*']))
+  })
 })
--- a/tests/smoke/fix-ai-chat-empty-body-v3.spec.ts
+++ b/tests/smoke/fix-ai-chat-empty-body-v3.spec.ts
@@ -49,7 +49,10 @@ test.describe('AI chat empty body fix — no regression', () => {

    // Open the AI panel from the editor toolbar
    await page.getByRole('button', { name: 'Open the AI panel' }).click()
+    await expect(page.getByTestId('ai-workspace')).toBeVisible({ timeout: 3000 })
    await expect(page.getByTestId('ai-panel')).toBeVisible({ timeout: 3000 })
+    await expect(page.getByTestId('ai-workspace-target-trigger')).toBeVisible()
+    await expect(page.getByTestId('ai-workspace-permission-trigger')).toBeVisible()

    // Send a message
    const input = page.getByTestId('agent-input')