feat(outline): opt-in conversation outline panel (#2124)

Adds an opt-in, default-off, desktop-only floating panel that lists the user's
questions in a conversation as a numbered jump-list (click to scroll + flash the
message). Gated behind a Settings → Preferences toggle (show_conversation_outline)
wired through the existing show_* preference boot/load/autosave/save paths.

Review follow-ups applied on absorb:
- Outline is now strictly chat-only: leaving the chat view (Settings, Tasks,
  Insights, …) hides the toggle button AND closes the panel; returning to chat
  restores the toggle (panel stays closed until re-opened). Implemented by gating
  _outlineAllowed() on the active panel and re-evaluating via a MutationObserver on
  the <main> showing-<panel> class (switchPanel is a global fn declaration that
  can't be reliably wrapped from this script).
- Fixed a latent visual bug: #outlinePanelWrapper{display:flex} (id selector)
  outranked the UA [hidden]{display:none}, so wrapper.hidden=true never actually
  hid the panel — the × close button and auto-close had no visual effect. Added
  #outlinePanelWrapper[hidden]{display:none;}.
- Regression tests for both.

Closes #2124.

Co-authored-by: Rod Boev <rod.boev@gmail.com>

api/config.py

@@ -5638,6 +5638,7 @@ _SETTINGS_DEFAULTS = {
     "send_key": "enter",  # 'enter' or 'ctrl+enter'
     "show_token_usage": False,  # show input/output token badge below assistant messages
     "show_quota_chip": False,  # show ambient provider quota chip in composer footer (default off; wide desktop only when enabled, see style.css @media)
+    "show_conversation_outline": False,  # show opt-in desktop jump-to-question outline panel
     "hide_empty_state_suggestions": False,  # hide the default new-chat suggestion buttons
     "show_tps": False,  # show tokens-per-second chip in assistant message headers
     "fade_text_effect": False,  # animate newly streamed words with a lightweight fade-in effect
@@ -5820,6 +5821,7 @@ _SETTINGS_BOOL_KEYS = {
     "onboarding_completed",
     "show_token_usage",
     "show_quota_chip",
+    "show_conversation_outline",
     "hide_empty_state_suggestions",
     "show_tps",
     "fade_text_effect",

static/boot.js

@@ -1779,8 +1779,14 @@ function applyBotName(){
     const s=await api('/api/settings');
     _bootSettings=s;
     window._sendKey=s.send_key||'enter';
+    // Persist default workspace so the blank new-chat page can show it
+    // and workspace actions (New file/folder) work before the first session (#804).
+    if(s.default_workspace) S._profileDefaultWorkspace=s.default_workspace;
     window._showTokenUsage=!!s.show_token_usage;
     window._showQuotaChip=s.show_quota_chip===true;
+    window._showConversationOutline=s.show_conversation_outline===true;
+    document.documentElement.dataset.conversationOutline=window._showConversationOutline?'enabled':'disabled';
+    if(typeof applyConversationOutlinePreference==='function') applyConversationOutlinePreference();
     window._hideEmptyStateSuggestions=s.hide_empty_state_suggestions===true;
     applyEmptyStateSuggestionPref();
     window._showTps=!!s.show_tps;
@@ -1789,9 +1795,6 @@ function applyBotName(){
     window._showPreviousMessagingSessions=!!s.show_previous_messaging_sessions;
     window._soundEnabled=!!s.sound_enabled;
     window._notificationsEnabled=!!s.notifications_enabled;
-    // Persist default workspace so the blank new-chat page can show it
-    // and workspace actions (New file/folder) work before the first session (#804).
-    if(s.default_workspace) S._profileDefaultWorkspace=s.default_workspace;
     window._whatsNewSummaryEnabled=!!s.whats_new_summary_enabled;
     window._showThinking=s.show_thinking!==false;
     window._simplifiedToolCalling=true;
@@ -1887,6 +1890,9 @@ function applyBotName(){
     window._sendKey='enter';
     window._showTokenUsage=false;
     window._showQuotaChip=false;
+    window._showConversationOutline=false;
+    document.documentElement.dataset.conversationOutline='disabled';
+    if(typeof applyConversationOutlinePreference==='function') applyConversationOutlinePreference();
     window._hideEmptyStateSuggestions=false;
     applyEmptyStateSuggestionPref();
     window._showTps=false;

static/i18n.js

@@ -630,6 +630,8 @@ const LOCALES = {
     settings_label_language: 'Language',
     settings_label_quota_chip: 'Show provider quota chip in composer',
     settings_desc_quota_chip: 'Displays an ambient remaining-quota indicator (e.g. OpenRouter credit balance) in the composer footer. Default off. Only visible on wide displays (≥1400px) when enabled, to keep the composer uncluttered on laptop and standard desktop widths.',
+    settings_label_conversation_outline: 'Show conversation outline',
+    settings_desc_conversation_outline: 'Show a desktop-only jump list for user questions in the current conversation. Off by default.',
     settings_label_hide_suggestions: 'Hide new-chat suggestions',
     settings_desc_hide_suggestions: 'Hide the three default suggestion buttons on the empty new-chat screen to avoid accidental taps.',
     settings_label_token_usage: 'Show token usage',
@@ -1406,6 +1408,10 @@ const LOCALES = {
     checkpoint_diff_title: 'Changes in checkpoint',
     checkpoint_diff_no_changes: 'No differences found between this checkpoint and the current workspace.',
     checkpoint_diff_files_changed: (n) => `${n} file${n === 1 ? '' : 's'} changed`,
+    // ── Conversation Outline (#2124) ──
+    outline_title: 'Outline',
+    outline_empty: 'No questions yet.',
+    outline_loading: 'Loading…',
   },
 
   it: {
@@ -2034,6 +2040,8 @@ const LOCALES = {
     settings_label_language: 'Lingua',
     settings_label_quota_chip: 'Mostra il chip della quota del provider nel compositore',
     settings_desc_quota_chip: "Mostra un indicatore di quota residua (es. saldo crediti OpenRouter) nel piè di pagina del compositore. Predefinito disattivato. Visibile solo su schermi larghi (≥1400px) quando attivato, per mantenere il compositore non affollato su laptop e desktop standard.",
+    settings_label_conversation_outline: 'Mostra struttura conversazione',
+    settings_desc_conversation_outline: 'Mostra un elenco di salto solo desktop per le domande utente nella conversazione corrente. Disattivato per impostazione predefinita.',
     settings_label_hide_suggestions: 'Hide new-chat suggestions',
     settings_desc_hide_suggestions: 'Hide the three default suggestion buttons on the empty new-chat screen to avoid accidental taps.',
     settings_label_token_usage: 'Mostra uso token',
@@ -2802,6 +2810,9 @@ const LOCALES = {
     checkpoint_diff_title: 'Modifiche nel checkpoint',
     checkpoint_diff_no_changes: 'Nessuna differenza trovata tra questo checkpoint e il workspace attuale.',
     checkpoint_diff_files_changed: (n) => `${n} file modificat${n === 1 ? 'o' : 'i'}`,
+    outline_title: 'Struttura',
+    outline_empty: 'Nessuna domanda ancora.',
+    outline_loading: 'Caricamento…',
   },
 
   ja: {
@@ -3430,6 +3441,8 @@ const LOCALES = {
     settings_label_language: '言語',
     settings_label_quota_chip: 'コンポーザーにプロバイダーのクォータチップを表示',
     settings_desc_quota_chip: 'コンポーザーのフッターに残りクォータインジケーター（例: OpenRouter のクレジット残高）を表示します。デフォルトはオフ。有効にした場合、ラップトップや標準デスクトップの幅でコンポーザーが混雑しないよう、ワイドディスプレイ（≥1400px）でのみ表示されます。',
+    settings_label_conversation_outline: '会話アウトラインを表示',
+    settings_desc_conversation_outline: '現在の会話内のユーザー質問へ移動するデスクトップ専用リストを表示します。デフォルトはオフです。',
     settings_label_hide_suggestions: '新規チャットの候補を非表示',
     settings_desc_hide_suggestions: '空の新規チャット画面に表示されるデフォルトの候補ボタン3つを非表示にして、誤タップを防ぎます。',
     settings_label_token_usage: 'トークン使用量を表示',
@@ -4203,6 +4216,9 @@ const LOCALES = {
     checkpoint_diff_title: 'チェックポイントの変更内容',
     checkpoint_diff_no_changes: 'このチェックポイントと現在のワークスペースの間に差分はありません。',
     checkpoint_diff_files_changed: (n) => `${n} 件のファイルが変更されました`,
+    outline_title: 'アウトライン',
+    outline_empty: 'まだ質問はありません。',
+    outline_loading: '読み込み中…',
   },
 
   ru: {
@@ -4618,6 +4634,8 @@ const LOCALES = {
     settings_label_language: 'Язык',
     settings_label_quota_chip: 'Показывать чип квоты провайдера в композиторе',
     settings_desc_quota_chip: 'Отображает фоновый индикатор остатка квоты (например, баланс кредитов OpenRouter) в подвале композитора. По умолчанию отключено. Виден только на широких экранах (≥1400px) при включении, чтобы не загромождать композитор на ноутбуках и стандартных мониторах.',
+    settings_label_conversation_outline: 'Показывать структуру беседы',
+    settings_desc_conversation_outline: 'Показывает на рабочем столе список переходов к вопросам пользователя в текущей беседе. По умолчанию отключено.',
     settings_label_hide_suggestions: 'Hide new-chat suggestions',
     settings_desc_hide_suggestions: 'Hide the three default suggestion buttons on the empty new-chat screen to avoid accidental taps.',
     settings_label_token_usage: 'Показывать использование токенов',
@@ -5541,6 +5559,9 @@ const LOCALES = {
     settings_desc_api_redact: 'Self-hosted users can disable for transparency (not recommended for shared instances).',  // TODO: translate
     settings_label_api_redact: 'Redact sensitive data in API responses',  // TODO: translate
     subagent_children: 'Subagent sessions',  // TODO: translate
+    outline_title: 'Outline',  // TODO: translate
+    outline_empty: 'No questions yet.',  // TODO: translate
+    outline_loading: 'Loading…',  // TODO: translate
   },
 
   es: {
@@ -5941,6 +5962,8 @@ const LOCALES = {
     settings_label_language: 'Idioma',
     settings_label_quota_chip: 'Mostrar el chip de cuota del proveedor en el compositor',
     settings_desc_quota_chip: 'Muestra un indicador ambiental de cuota restante (por ejemplo, saldo de crédito de OpenRouter) en el pie del compositor. Predeterminado: desactivado. Solo visible en pantallas anchas (≥1400px) cuando se activa, para mantener el compositor despejado en portátiles y monitores estándar.',
+    settings_label_conversation_outline: 'Mostrar esquema de conversación',
+    settings_desc_conversation_outline: 'Muestra una lista de salto solo en escritorio para las preguntas del usuario en la conversación actual. Desactivado de forma predeterminada.',
     settings_label_hide_suggestions: 'Hide new-chat suggestions',
     settings_desc_hide_suggestions: 'Hide the three default suggestion buttons on the empty new-chat screen to avoid accidental taps.',
     settings_label_token_usage: 'Mostrar uso de tokens',
@@ -6873,6 +6896,9 @@ const LOCALES = {
     voice_mode_toggle: 'Voice mode',  // TODO: translate
     voice_mode_toggle_active: 'Exit voice mode',  // TODO: translate
     subagent_children: 'Subagent sessions',  // TODO: translate
+    outline_title: 'Esquema',
+    outline_empty: 'Aún no hay preguntas.',
+    outline_loading: 'Cargando…',
   },
 
   de: {
@@ -7258,6 +7284,8 @@ const LOCALES = {
     settings_label_language: 'Sprache',
     settings_label_quota_chip: 'Anbieter-Kontingent-Chip im Editor anzeigen',
     settings_desc_quota_chip: 'Zeigt einen Hintergrund-Indikator des verbleibenden Kontingents (z. B. OpenRouter-Guthaben) in der Editor-Fußzeile an. Standardmäßig deaktiviert. Bei Aktivierung nur auf breiten Bildschirmen (≥1400px) sichtbar, damit der Editor auf Laptops und Standard-Desktops übersichtlich bleibt.',
+    settings_label_conversation_outline: 'Konversationsgliederung anzeigen',
+    settings_desc_conversation_outline: 'Zeigt eine Desktop-Sprungliste für Benutzerfragen in der aktuellen Konversation. Standardmäßig deaktiviert.',
     settings_label_hide_suggestions: 'Hide new-chat suggestions',
     settings_desc_hide_suggestions: 'Hide the three default suggestion buttons on the empty new-chat screen to avoid accidental taps.',
     settings_label_token_usage: 'Token-Verbrauch anzeigen',
@@ -8209,6 +8237,9 @@ const LOCALES = {
     voice_mode_toggle: 'Voice mode',  // TODO: translate
     voice_mode_toggle_active: 'Exit voice mode',  // TODO: translate
     subagent_children: 'Subagent sessions',  // TODO: translate
+    outline_title: 'Gliederung',
+    outline_empty: 'Noch keine Fragen.',
+    outline_loading: 'Laden…',
   },
 
   zh: {
@@ -8628,6 +8659,8 @@ const LOCALES = {
     settings_label_language: '语言',
     settings_label_quota_chip: '在编辑器中显示供应商配额标签',
     settings_desc_quota_chip: '在编辑器底部显示剩余配额指示器（如 OpenRouter 信用余额）。默认关闭。启用时仅在宽屏（≥1400px）显示，以保持笔记本和标准桌面屏幕上编辑器的整洁。',
+    settings_label_conversation_outline: '显示会话大纲',
+    settings_desc_conversation_outline: '显示仅限桌面的跳转列表，用于跳转到当前会话中的用户问题。默认关闭。',
     settings_label_hide_suggestions: 'Hide new-chat suggestions',
     settings_desc_hide_suggestions: 'Hide the three default suggestion buttons on the empty new-chat screen to avoid accidental taps.',
     settings_label_token_usage: '显示 token 用量',
@@ -9538,6 +9571,9 @@ const LOCALES = {
     voice_mode_toggle: '语音模式',
     voice_mode_toggle_active: '退出语音模式',
     subagent_children: '子代理会话',
+    outline_title: '大纲',
+    outline_empty: '暂无问题。',
+    outline_loading: '加载中…',
   },
 
   // Traditional Chinese (zh-Hant)
@@ -10159,6 +10195,8 @@ const LOCALES = {
     settings_label_language: '語言',
     settings_label_quota_chip: '在編輯器中顯示供應商配額標籤',
     settings_desc_quota_chip: '在編輯器底部顯示剩餘配額指示器（如 OpenRouter 點數餘額）。預設關閉。啟用時僅在寬螢幕（≥1400px）顯示，以保持筆記型電腦和標準桌面螢幕上編輯器的整潔。',
+    settings_label_conversation_outline: '顯示對話大綱',
+    settings_desc_conversation_outline: '顯示僅限桌面的跳轉清單，用於跳轉到目前對話中的使用者問題。預設關閉。',
     settings_label_hide_suggestions: '隱藏新聊天建議',
     settings_desc_hide_suggestions: '隱藏空白新聊天畫面上的三個預設建議按鈕，避免誤觸。',
     settings_label_token_usage: '顯示 token 用量',
@@ -10935,6 +10973,9 @@ const LOCALES = {
     checkpoint_diff_title: '檢查點中的變更',
     checkpoint_diff_no_changes: '這個檢查點與目前工作區沒有差異。',
     checkpoint_diff_files_changed: (n) => `已變更 ${n} 個檔案`,
+    outline_title: '大綱',
+    outline_empty: '尚無問題。',
+    outline_loading: '載入中…',
 
   },
 
@@ -11445,6 +11486,8 @@ const LOCALES = {
     settings_label_language: 'Idioma',
     settings_label_quota_chip: 'Mostrar o chip de cota do provedor no compositor',
     settings_desc_quota_chip: 'Exibe um indicador ambiente de cota restante (por exemplo, saldo de crédito do OpenRouter) no rodapé do compositor. Desativado por padrão. Visível apenas em telas largas (≥1400px) quando ativado, para manter o compositor livre em laptops e monitores padrão.',
+    settings_label_conversation_outline: 'Mostrar estrutura da conversa',
+    settings_desc_conversation_outline: 'Mostra uma lista de atalhos somente no desktop para as perguntas do usuário na conversa atual. Desativado por padrão.',
     settings_label_hide_suggestions: 'Hide new-chat suggestions',
     settings_desc_hide_suggestions: 'Hide the three default suggestion buttons on the empty new-chat screen to avoid accidental taps.',
     settings_label_token_usage: 'Mostrar uso de tokens',
@@ -12149,6 +12192,9 @@ const LOCALES = {
     sign_out_failed: 'Falha ao sair: ',
     auth_disabled: 'Autenticação desativada — proteção por senha removida',
     disable_auth_confirm_title: 'Desativar proteção por senha',
+    outline_title: 'Esboço',
+    outline_empty: 'Ainda não há perguntas.',
+    outline_loading: 'Carregando…',
   },
   ko: {
     offline_title: '연결이 끊겼습니다',
@@ -12742,6 +12788,8 @@ const LOCALES = {
     settings_label_language: '언어',
     settings_label_quota_chip: '작성기에 공급자 할당량 칩 표시',
     settings_desc_quota_chip: '작성기 푸터에 남은 할당량 표시기(예: OpenRouter 크레딧 잔액)를 표시합니다. 기본값은 끔. 활성화 시 노트북과 표준 데스크톱에서 작성기가 복잡해지지 않도록 와이드 디스플레이(≥1400px)에서만 표시됩니다.',
+    settings_label_conversation_outline: '대화 개요 표시',
+    settings_desc_conversation_outline: '현재 대화의 사용자 질문으로 이동하는 데스크톱 전용 목록을 표시합니다. 기본값은 꺼짐입니다.',
     settings_label_hide_suggestions: 'Hide new-chat suggestions',
     settings_desc_hide_suggestions: 'Hide the three default suggestion buttons on the empty new-chat screen to avoid accidental taps.',
     settings_label_token_usage: '토큰 사용량 표시',
@@ -13534,6 +13582,9 @@ const LOCALES = {
     voice_mode_toggle: 'Voice mode',  // TODO: translate
     voice_mode_toggle_active: 'Exit voice mode',  // TODO: translate
     subagent_children: 'Subagent sessions',  // TODO: translate
+    outline_title: '개요',
+    outline_empty: '아직 질문이 없습니다.',
+    outline_loading: '로딩 중…',
   },
 
   fr: {
@@ -14056,6 +14107,8 @@ const LOCALES = {
     settings_label_language: 'Langue',
     settings_label_quota_chip: 'Afficher la pastille de quota du fournisseur dans le compositeur',
     settings_desc_quota_chip: "Affiche un indicateur ambiant de quota restant (par ex. solde de crédit OpenRouter) dans le pied du compositeur. Désactivé par défaut. Visible uniquement sur les écrans larges (≥1400px) lorsqu'activé, pour garder le compositeur dégagé sur les ordinateurs portables et les bureaux standard.",
+    settings_label_conversation_outline: 'Afficher le plan de conversation',
+    settings_desc_conversation_outline: "Affiche une liste de saut réservée au bureau pour les questions utilisateur de la conversation actuelle. Désactivé par défaut.",
     settings_label_hide_suggestions: 'Hide new-chat suggestions',
     settings_desc_hide_suggestions: 'Hide the three default suggestion buttons on the empty new-chat screen to avoid accidental taps.',
     settings_label_token_usage: 'Afficher l\'utilisation du jeton',
@@ -14860,6 +14913,9 @@ const LOCALES = {
     usage_total: 'Total de tokens',
     usage_unknown: 'inconnu',
     workspace_auto_create_folder: 'Créer le dossier s\'il n\'existe pas',
+    outline_title: 'Plan',
+    outline_empty: 'Pas encore de questions.',
+    outline_loading: 'Chargement…',
   },
 
   tr: {
@@ -15471,6 +15527,8 @@ const LOCALES = {
     settings_label_language: 'Dil',
     settings_label_quota_chip: 'Bestecide sağlayıcı kota çipini göster',
     settings_desc_quota_chip: 'Besteci altbilgisinde bir ortam kalan kota göstergesini (örn. OpenRouter kredi bakiyesi) görüntüler. Varsayılan kapalı. Besteciyi dizüstü bilgisayar ve standart masaüstü genişliklerinde düzenli tutmak için yalnızca etkinleştirildiğinde geniş ekranlarda (≥1400 piksel) görünür.',
+    settings_label_conversation_outline: 'Konuşma ana hattını göster',
+    settings_desc_conversation_outline: 'Geçerli konuşmadaki kullanıcı soruları için yalnızca masaüstünde görünen bir atlama listesi gösterir. Varsayılan kapalıdır.',
     settings_label_hide_suggestions: 'Yeni sohbet önerilerini gizle',
     settings_desc_hide_suggestions: 'Yanlışlıkla dokunmayı önlemek için boş yeni sohbet ekranındaki üç varsayılan öneri düğmesini gizleyin.',
     settings_label_token_usage: 'Jeton kullanımını göster',
@@ -16249,6 +16307,9 @@ const LOCALES = {
     settings_desc_api_redact: 'Kendi sunucunuzda şeffaflık için devre dışı bırakılabilir (paylaşımlı örneklerde önerilmez).',
     settings_label_api_redact: 'API yanıtlarında hassas verileri gizle',
     subagent_children: 'Alt agent oturumları',
+    outline_title: 'Ana Hat',
+    outline_empty: 'Henüz soru yok.',
+    outline_loading: 'Yükleniyor…',
   
   
   
@@ -16878,6 +16939,8 @@ const LOCALES = {
     settings_label_language: 'Język',
     settings_label_quota_chip: 'Pokaż wskaźnik limitu dostawcy w polu wprowadzania',
     settings_desc_quota_chip: 'Wyświetla subtelny wskaźnik pozostałego limitu (np. saldo kredytów OpenRouter) w stopce pola wprowadzania. Domyślnie wyłączone. Widoczne tylko na szerokich ekranach (≥1400px), aby utrzymać pole wprowadzania czytelnym na laptopach i standardowych monitorach.',
+    settings_label_conversation_outline: 'Pokaż zarys konwersacji',
+    settings_desc_conversation_outline: 'Pokazuje desktopową listę skrótów do pytań użytkownika w bieżącej konwersacji. Domyślnie wyłączone.',
     settings_label_hide_suggestions: 'Ukryj sugestie nowej konwersacji',
     settings_desc_hide_suggestions: 'Ukryj trzy domyślne przyciski sugestii na pustym ekranie nowej konwersacji, aby zapobiec przypadkowym kliknięciom.',
     settings_label_token_usage: 'Pokaż zużycie tokenów',
@@ -17154,6 +17217,9 @@ const LOCALES = {
     settings_desc_token_usage: 'Wyświetla liczbę tokenów wejściowych/wyjściowych pod każdą odpowiedzią asystenta. Można też przełączyć za pomocą /usage.',
     settings_label_api_redact: 'Ukrywaj poufne dane w odpowiedziach API',
     settings_desc_api_redact: 'Użytkownicy korzystający z hostingu własnego mogą wyłączyć to dla przejrzystości (niezalecane dla współdzielonych instancji).',
+    outline_title: 'Zarys',
+    outline_empty: 'Nie ma jeszcze pytań.',
+    outline_loading: 'Ładowanie…',
     settings_sidebar_density_compact: 'Kompaktowa',
     settings_sidebar_density_detailed: 'Szczegółowa',
     settings_desc_sidebar_density: 'Kontroluje, ile metadanych wyświetla lista sesji na lewym pasku bocznym.',

static/index.html

@@ -1146,6 +1146,13 @@
               </label>
               <div style="font-size:11px;color:var(--muted);margin-top:4px" data-i18n="settings_desc_quota_chip">Displays an ambient remaining-quota indicator (e.g. OpenRouter credit balance) in the composer footer. Default off. Only visible on wide displays (≥1400px) when enabled, to keep the composer uncluttered on laptop and standard desktop widths.</div>
             </div>
+            <div class="settings-field">
+              <label style="display:flex;align-items:center;gap:8px;cursor:pointer">
+                <input type="checkbox" id="settingsShowConversationOutline" style="width:15px;height:15px;accent-color:var(--accent)">
+                <span data-i18n="settings_label_conversation_outline">Show conversation outline</span>
+              </label>
+              <div style="font-size:11px;color:var(--muted);margin-top:4px" data-i18n="settings_desc_conversation_outline">Show a desktop-only jump list for user questions in the current conversation. Off by default.</div>
+            </div>
             <div class="settings-field">
               <label style="display:flex;align-items:center;gap:8px;cursor:pointer">
                 <input type="checkbox" id="settingsShowTps" style="width:15px;height:15px;accent-color:var(--accent)">
@@ -1500,6 +1507,7 @@
 <script src="static/panels.js?v=__WEBUI_VERSION__" defer></script>
 <script src="static/onboarding.js?v=__WEBUI_VERSION__" defer></script>
 <script src="static/boot.js?v=__WEBUI_VERSION__" defer></script>
+<script src="static/outline.js?v=__WEBUI_VERSION__" defer></script>
 
 <!-- Kanban: create/rename board modal — used for both flows. -->
 <div class="kanban-modal-overlay" id="kanbanBoardModal" hidden onclick="if(event.target===this)closeKanbanBoardModal()">
@@ -1582,5 +1590,21 @@
     </div>
   </div>
 </div>
+<!-- Conversation Outline Panel (#2124): floating jump-to-question panel -->
+<button id="outlineToggleBtn" type="button" hidden
+  onclick="toggleOutlinePanel()"
+  title="Conversation outline"
+  aria-label="Toggle conversation outline"
+  aria-controls="outlinePanelWrapper">&#9776;</button>
+<div id="outlinePanelWrapper" hidden
+  role="navigation" aria-label="Conversation outline">
+  <div class="outline-header">
+    <span data-i18n="outline_title">Outline</span>
+    <button class="outline-close-btn" type="button"
+      onclick="toggleOutlinePanel()"
+      aria-label="Close outline">&#215;</button>
+  </div>
+  <div id="outlinePanel"></div>
+</div>
 </body>
 </html>

static/outline.js

@@ -0,0 +1,291 @@
+// ── Conversation Outline Panel (#2124) ───────────────────────────────────────
+// Floating panel listing user messages as jump targets.
+// _outlineSid guards against stale renders when the user switches sessions.
+
+'use strict';
+
+(function() {
+
+let _outlineSid = null;       // session id the panel was last built for
+let _panelOpen  = false;      // whether the panel is currently visible
+let _outlineResizeObserver = null;
+let _outlineWorkspaceObserver = null;
+
+// Returns the current session id, or null if no session is loaded.
+function _currentSid() {
+  return (S && S.session && S.session.session_id) || null;
+}
+
+function _outlineAllowed() {
+  const compact = window.matchMedia && window.matchMedia('(max-width:900px)').matches;
+  // The outline is a chat-view affordance only — never show the toggle or panel
+  // while another main panel (settings, tasks, insights, …) is active. _currentPanel
+  // is owned by panels.js; treat an undefined/absent value as the chat default.
+  const panel = (typeof _currentPanel === 'undefined') ? 'chat' : (_currentPanel || 'chat');
+  return window._showConversationOutline === true && !compact && panel === 'chat';
+}
+
+function _syncOutlinePosition() {
+  const root = document.documentElement;
+  const panel = document.querySelector('.rightpanel');
+  const open = root.dataset.workspacePanel === 'open';
+  const width = open && panel ? Math.max(0, Math.round(panel.offsetWidth || 0)) : 0;
+  root.style.setProperty('--outline-workspace-offset', width + 'px');
+}
+
+function applyConversationOutlinePreference() {
+  const toggle = document.getElementById('outlineToggleBtn');
+  const wrapper = document.getElementById('outlinePanelWrapper');
+  const enabled = _outlineAllowed();
+  document.documentElement.dataset.conversationOutline = enabled ? 'enabled' : 'disabled';
+  _syncOutlinePosition();
+  if (toggle) toggle.hidden = !enabled;
+  if (!enabled) {
+    _panelOpen = false;
+    if (wrapper) wrapper.hidden = true;
+  }
+}
+
+function _expandOutlineRenderWindow() {
+  if (typeof _currentMessageRenderWindowSize !== 'function' ||
+      typeof _messageRenderableMessageCount !== 'function' ||
+      typeof _messageRenderWindowSize === 'undefined') return;
+  _messageRenderWindowSize = Math.max(
+    _currentMessageRenderWindowSize(),
+    _messageRenderableMessageCount()
+  );
+}
+
+function _ensureOutlineMessagesLoaded(sid) {
+  if (!sid || S.busy || S.activeStreamId) return Promise.resolve(false);
+  if (typeof _messagesTruncated === 'undefined' || !_messagesTruncated) {
+    return Promise.resolve(false);
+  }
+  if (typeof _ensureAllMessagesLoaded !== 'function') return Promise.resolve(false);
+  return _ensureAllMessagesLoaded().then(function() {
+    if (!S.session || S.session.session_id !== sid) return false;
+    _expandOutlineRenderWindow();
+    return true;
+  }).catch(function() {
+    return false;
+  });
+}
+
+// Extracts the first 60 visible characters from a message content value.
+function _excerptText(content) {
+  let text = '';
+  if (Array.isArray(content)) {
+    text = content
+      .filter(p => p && p.type === 'text')
+      .map(p => p.text || p.content || '')
+      .join(' ');
+  } else {
+    text = String(content || '');
+  }
+  text = text.trim().replace(/\s+/g, ' ');
+  return text.length > 60 ? text.slice(0, 60) + '…' : text;
+}
+
+// Scrolls to a user message row identified by its rawIdx and flashes it.
+function _jumpToMessage(rawIdx) {
+  const sid = _currentSid();
+  if (!sid) return;
+
+  const rowId = 'msg-user-' + rawIdx;
+  const row   = document.getElementById(rowId);
+  if (row) {
+    row.scrollIntoView({ block: 'center', behavior: 'smooth' });
+    _flashRow(row);
+    return;
+  }
+
+  // Row is outside the render window — reload the full session and retry.
+  if (typeof api !== 'function') return;
+  if (S.busy || S.activeStreamId) return;
+  api('/api/session?session_id=' + encodeURIComponent(sid) +
+      '&messages=1&resolve_model=0&msg_limit=9999')
+    .then(function(data) {
+      if (!data || !data.session) return;
+      if (!S.session || S.session.session_id !== sid) return;  // session switched
+      S.messages = data.session.messages || [];                // populate S
+      _expandOutlineRenderWindow();
+      if (typeof renderMessages === 'function') renderMessages({ preserveScroll: true });
+      window.setTimeout(function() {
+        if (!S.session || S.session.session_id !== sid) return;
+        const r = document.getElementById('msg-user-' + rawIdx);
+        if (r) { r.scrollIntoView({ block: 'center', behavior: 'smooth' }); _flashRow(r); }
+      }, 120);
+    })
+    .catch(function() {});
+}
+
+// Brief highlight flash on a message row after jumping.
+function _flashRow(row) {
+  if (!row) return;
+  row.classList.remove('outline-jump-flash');
+  void row.offsetWidth;   // reflow to restart animation
+  row.classList.add('outline-jump-flash');
+  window.setTimeout(function() { row.classList.remove('outline-jump-flash'); }, 1200);
+}
+
+// Builds the list of user messages from S.messages.
+// Returns [{rawIdx, label, excerpt}, …] for every user message with content.
+function _buildEntries() {
+  const msgs = (S && S.messages) || [];
+  const entries = [];
+  let userN = 0;
+
+  for (let i = 0; i < msgs.length; i++) {
+    const m = msgs[i];
+    if (!m || m.role !== 'user') continue;
+    const text = _excerptText(m.content);
+    if (!text) continue;
+    userN++;
+    entries.push({ rawIdx: i, label: userN, excerpt: text });
+  }
+  return entries;
+}
+
+// Renders the panel body.  Called every time the panel opens or session changes.
+function _renderPanel() {
+  const panel = document.getElementById('outlinePanel');
+  if (!panel) return;
+
+  const sid = _currentSid();
+
+  // Session-scoped staleness guard.
+  if (!sid) {
+    panel.innerHTML = '<p class="outline-empty">' + t('outline_empty') + '</p>';
+    _outlineSid = null;
+    return;
+  }
+
+  if (!S.messages) {
+    panel.innerHTML = '<p class="outline-empty">' + t('outline_loading') + '</p>';
+    _outlineSid = sid;
+    return;
+  }
+
+  _outlineSid = sid;
+  const entries = _buildEntries();
+
+  if (!entries.length) {
+    panel.innerHTML = '<p class="outline-empty">' + t('outline_empty') + '</p>';
+    return;
+  }
+
+  const items = entries.map(function(e) {
+    return '<button class="outline-entry" type="button" ' +
+      'onclick="window._outlineJump(' + e.rawIdx + ')">' +
+      '<span class="outline-entry-num">' + e.label + '</span>' +
+      '<span class="outline-entry-text">' + _escHtml(e.excerpt) + '</span>' +
+      '</button>';
+  });
+
+  panel.innerHTML = items.join('');
+}
+
+// Simple HTML-escape for entry text.
+function _escHtml(str) {
+  return String(str)
+    .replace(/&/g, '&amp;')
+    .replace(/</g, '&lt;')
+    .replace(/>/g, '&gt;')
+    .replace(/"/g, '&quot;');
+}
+
+// Opens or closes the outline panel.
+function toggleOutlinePanel() {
+  if (!_outlineAllowed()) {
+    applyConversationOutlinePreference();
+    return;
+  }
+  _panelOpen = !_panelOpen;
+  const wrapper = document.getElementById('outlinePanelWrapper');
+  if (!wrapper) return;
+
+  if (_panelOpen) {
+    _syncOutlinePosition();
+    wrapper.hidden = false;
+    const sid = _currentSid();
+    const panel = document.getElementById('outlinePanel');
+    if (panel) panel.innerHTML = '<p class="outline-empty">' + t('outline_loading') + '</p>';
+    _ensureOutlineMessagesLoaded(sid).then(function() {
+      if (!_panelOpen || _currentSid() !== sid) return;
+      _renderPanel();
+      // Keep rendered data fresh after every renderMessages() call.
+      _outlineSid = _currentSid();
+    });
+  } else {
+    wrapper.hidden = true;
+  }
+}
+
+// Jump target exposed on window so inline onclick handlers can reach it.
+window._outlineJump = _jumpToMessage;
+window.applyConversationOutlinePreference = applyConversationOutlinePreference;
+
+// Re-render after renderMessages() if the panel is open and the session
+// changed or new messages arrived since the last render.
+(function _hookRenderMessages() {
+  if (typeof window._outlineRenderHooked !== 'undefined') return;
+
+  const _orig = window.renderMessages;
+  if (typeof _orig !== 'function') {
+    // renderMessages may not be defined yet — retry after DOMContentLoaded.
+    if (!window._outlineRenderHookPending) {
+      window._outlineRenderHookPending = true;
+      document.addEventListener('DOMContentLoaded', _hookRenderMessages, { once: true });
+    }
+    return;
+  }
+  window._outlineRenderHooked = true;
+  window._outlineRenderHookPending = false;
+  window.renderMessages = function() {
+    const result = _orig.apply(this, arguments);
+    if (_panelOpen) {
+      const sid = _currentSid();
+      if (sid && (sid !== _outlineSid || (S.messages || []).length > 0)) {
+        _renderPanel();
+      }
+    }
+    return result;
+  };
+})();
+
+// Expose public API.
+window.toggleOutlinePanel = toggleOutlinePanel;
+
+document.addEventListener('DOMContentLoaded', function() {
+  applyConversationOutlinePreference();
+  const root = document.documentElement;
+  const rightPanel = document.querySelector('.rightpanel');
+  if (rightPanel && typeof ResizeObserver !== 'undefined' && !_outlineResizeObserver) {
+    _outlineResizeObserver = new ResizeObserver(_syncOutlinePosition);
+    _outlineResizeObserver.observe(rightPanel);
+  }
+  if (!_outlineWorkspaceObserver) {
+    _outlineWorkspaceObserver = new MutationObserver(applyConversationOutlinePreference);
+    _outlineWorkspaceObserver.observe(root, {
+      attributes: true,
+      attributeFilter: ['data-workspace-panel']
+    });
+    // Also re-evaluate when the active main panel changes. switchPanel() is a
+    // global function declaration (called via inline onclick), so it can't be
+    // reliably wrapped from this script; instead we watch the `showing-<panel>`
+    // class it toggles on <main>. The outline is a chat-only affordance, so this
+    // hides the toggle + closes the panel when leaving chat (settings, tasks,
+    // insights, …) and restores the toggle on return to chat. _outlineAllowed()
+    // reads _currentPanel for the actual gate; this observer just triggers it.
+    const mainEl = document.querySelector('main.main');
+    if (mainEl) {
+      _outlineWorkspaceObserver.observe(mainEl, {
+        attributes: true,
+        attributeFilter: ['class']
+      });
+    }
+  }
+});
+window.addEventListener('resize', applyConversationOutlinePreference);
+
+})();

static/panels.js

@@ -6301,6 +6301,8 @@ function _preferencesPayloadFromUi(){
   if(showUsageCb) payload.show_token_usage=showUsageCb.checked;
   const showQuotaChipCb=$('settingsShowQuotaChip');
   if(showQuotaChipCb) payload.show_quota_chip=showQuotaChipCb.checked;
+  const showConversationOutlineCb=$('settingsShowConversationOutline');
+  if(showConversationOutlineCb) payload.show_conversation_outline=showConversationOutlineCb.checked;
   const hideSuggestionsCb=$('settingsHideSuggestions');
   if(hideSuggestionsCb) payload.hide_empty_state_suggestions=hideSuggestionsCb.checked;
   const showTpsCb=$('settingsShowTps');
@@ -6397,6 +6399,11 @@ async function _autosavePreferencesSettings(payload){
       window._hideEmptyStateSuggestions=!!(saved&&saved.hide_empty_state_suggestions);
       if(typeof applyEmptyStateSuggestionPref==='function') applyEmptyStateSuggestionPref();
     }
+    if(payload&&payload.show_conversation_outline!==undefined){
+      window._showConversationOutline=!!(saved&&saved.show_conversation_outline);
+      document.documentElement.dataset.conversationOutline=window._showConversationOutline?'enabled':'disabled';
+      if(typeof applyConversationOutlinePreference==='function') applyConversationOutlinePreference();
+    }
     _settingsPreferencesAutosaveRetryPayload=null;
     _setPreferencesAutosaveStatus('saved');
     // Only clear the global dirty flag and hide the unsaved-changes bar when
@@ -6618,6 +6625,19 @@ async function loadSettingsPanel(){
         _schedulePreferencesAutosave();
       },{once:false});
     }
+    const showConversationOutlineCb=$('settingsShowConversationOutline');
+    if(showConversationOutlineCb){
+      showConversationOutlineCb.checked=settings.show_conversation_outline===true;
+      window._showConversationOutline=showConversationOutlineCb.checked;
+      document.documentElement.dataset.conversationOutline=window._showConversationOutline?'enabled':'disabled';
+      if(typeof applyConversationOutlinePreference==='function') applyConversationOutlinePreference();
+      showConversationOutlineCb.addEventListener('change',()=>{
+        _schedulePreferencesAutosave();
+        window._showConversationOutline=showConversationOutlineCb.checked;
+        document.documentElement.dataset.conversationOutline=window._showConversationOutline?'enabled':'disabled';
+        if(typeof applyConversationOutlinePreference==='function') applyConversationOutlinePreference();
+      },{once:false});
+    }
     const showTpsCb=$('settingsShowTps');
     if(showTpsCb){showTpsCb.checked=!!settings.show_tps;showTpsCb.addEventListener('change',_schedulePreferencesAutosave,{once:false});}
     const pinnedLimitField=$('settingsPinnedSessionsLimit');
@@ -7727,10 +7747,13 @@ async function deletePasskey(id){
 }
 
 function _applySavedSettingsUi(saved, body, opts){
-  const {sendKey,showTokenUsage,showQuotaChip,showTps,fadeTextEffect,showCliSessions,theme,skin,language,sidebarDensity,fontSize}=opts;
+  const {sendKey,showTokenUsage,showQuotaChip,showConversationOutline,showTps,fadeTextEffect,showCliSessions,theme,skin,language,sidebarDensity,fontSize}=opts;
   window._sendKey=sendKey||'enter';
   window._showTokenUsage=showTokenUsage;
   window._showQuotaChip=showQuotaChip===true;
+  window._showConversationOutline=showConversationOutline===true;
+  document.documentElement.dataset.conversationOutline=window._showConversationOutline?'enabled':'disabled';
+  if(typeof applyConversationOutlinePreference==='function') applyConversationOutlinePreference();
   window._showTps=showTps;
   window._fadeTextEffect=!!fadeTextEffect;
   window._showCliSessions=showCliSessions;
@@ -8055,6 +8078,7 @@ async function saveSettings(andClose){
   const sendKey=($('settingsSendKey')||{}).value;
   const showTokenUsage=!!($('settingsShowTokenUsage')||{}).checked;
   const showQuotaChip=!!($('settingsShowQuotaChip')||{}).checked;
+  const showConversationOutline=!!($('settingsShowConversationOutline')||{}).checked;
   const showTps=!!($('settingsShowTps')||{}).checked;
   const fadeTextEffect=!!($('settingsFadeTextEffect')||{}).checked;
   const showCliSessions=!!($('settingsShowCliSessions')||{}).checked;
@@ -8079,6 +8103,7 @@ async function saveSettings(andClose){
   body.language=language;
   body.show_token_usage=showTokenUsage;
   body.show_quota_chip=showQuotaChip===true;
+  body.show_conversation_outline=showConversationOutline===true;
   body.show_tps=showTps;
   body.fade_text_effect=fadeTextEffect;
   body.terminal_auto_expand_on_output=!!($('settingsTerminalAutoExpand')||{}).checked;
@@ -8114,7 +8139,7 @@ async function saveSettings(andClose){
           if(typeof showToast==='function') showToast('Failed to update default model — settings saved');
         }
       }
-      _applySavedSettingsUi(saved, body, {sendKey,showTokenUsage,showQuotaChip,showTps,fadeTextEffect,showCliSessions,theme,skin,language,sidebarDensity,fontSize});
+      _applySavedSettingsUi(saved, body, {sendKey,showTokenUsage,showQuotaChip,showConversationOutline,showTps,fadeTextEffect,showCliSessions,theme,skin,language,sidebarDensity,fontSize});
       showToast(t(saved.auth_just_enabled?'settings_saved_pw':'settings_saved_pw_updated'));
       _settingsDirty=false;
       _resetSettingsPanelState();
@@ -8133,7 +8158,7 @@ async function saveSettings(andClose){
         if(typeof showToast==='function') showToast('Failed to update default model — settings saved');
       }
     }
-    _applySavedSettingsUi(saved, body, {sendKey,showTokenUsage,showQuotaChip,showTps,fadeTextEffect,showCliSessions,theme,skin,language,sidebarDensity,fontSize});
+    _applySavedSettingsUi(saved, body, {sendKey,showTokenUsage,showQuotaChip,showConversationOutline,showTps,fadeTextEffect,showCliSessions,theme,skin,language,sidebarDensity,fontSize});
     showToast(t('settings_saved'));
     _settingsDirty=false;
     _resetSettingsPanelState();

static/style.css

@@ -5366,3 +5366,65 @@ main.main.showing-logs > #mainLogs{display:flex;}
   display: block;
 }
 .interim-collapse-toggle:hover { text-decoration: underline; }
+
+/* ── Conversation Outline Panel (#2124) ─────────────────────────────────── */
+#outlineToggleBtn{
+  position:fixed;bottom:120px;right:calc(var(--outline-workspace-offset, 0px) + 20px);z-index:9999;
+  width:38px;height:38px;border-radius:50%;
+  background:var(--surface);border:1px solid var(--border2);
+  color:var(--text);cursor:pointer;
+  display:none;align-items:center;justify-content:center;
+  box-shadow:0 2px 8px rgba(0,0,0,.18);
+  font-size:16px;line-height:1;
+  transition:background .15s ease,border-color .15s ease,color .15s ease;
+}
+html[data-conversation-outline="enabled"] #outlineToggleBtn:not([hidden]){display:flex;}
+#outlineToggleBtn:hover{background:var(--accent-bg);border-color:var(--accent-bg-strong);color:var(--accent-text);}
+#outlinePanelWrapper{
+  position:fixed;right:calc(var(--outline-workspace-offset, 0px) + 20px);bottom:170px;width:320px;
+  max-height:50vh;z-index:9998;
+  background:var(--surface);border:1px solid var(--border2);
+  border-radius:10px;box-shadow:0 6px 24px rgba(0,0,0,.22);
+  display:flex;flex-direction:column;overflow:hidden;
+}
+/* The id selector's display:flex outranks the UA [hidden]{display:none}, so the
+   hidden attribute alone won't hide the panel — restore it explicitly. */
+#outlinePanelWrapper[hidden]{display:none;}
+.outline-header{
+  display:flex;align-items:center;justify-content:space-between;
+  padding:10px 12px 8px;border-bottom:1px solid var(--border2);
+  font-size:12px;font-weight:600;color:var(--muted);text-transform:uppercase;
+  letter-spacing:.04em;flex-shrink:0;
+}
+.outline-close-btn{
+  background:none;border:none;cursor:pointer;
+  color:var(--muted);font-size:16px;line-height:1;padding:0 2px;
+}
+.outline-close-btn:hover{color:var(--text);}
+#outlinePanel{overflow-y:auto;flex:1;}
+.outline-entry{
+  display:flex;align-items:baseline;gap:8px;
+  width:100%;padding:7px 12px;
+  background:none;border:none;border-bottom:1px solid var(--border-subtle);
+  cursor:pointer;text-align:left;color:var(--text);
+  transition:background .12s ease;
+}
+.outline-entry:last-child{border-bottom:none;}
+.outline-entry:hover{background:var(--accent-bg);}
+.outline-entry-num{
+  font-size:11px;font-weight:600;color:var(--muted);
+  min-width:18px;flex-shrink:0;
+}
+.outline-entry-text{font-size:13px;line-height:1.4;word-break:break-word;}
+.outline-empty{
+  padding:16px 12px;font-size:13px;color:var(--muted);text-align:center;
+}
+/* Flash animation when jumping to a message */
+@keyframes outline-flash{
+  0%{background:var(--accent-bg-strong);}
+  100%{background:transparent;}
+}
+.outline-jump-flash{animation:outline-flash 1.2s ease-out forwards;}
+@media(max-width:900px){
+  #outlineToggleBtn,#outlinePanelWrapper{display:none!important;}
+}

tests/test_1003_preferences_autosave.py

@@ -38,6 +38,7 @@ PREFERENCE_FIELDS_AUTOSAVE = [
     ("settingsSendKey", "send_key"),
     ("settingsLanguage", "language"),
     ("settingsShowTokenUsage", "show_token_usage"),
+    ("settingsShowConversationOutline", "show_conversation_outline"),
     ("settingsShowTps", "show_tps"),
     ("settingsShowCliSessions", "show_cli_sessions"),
     ("settingsShowPreviousMessagingSessions", "show_previous_messaging_sessions"),
@@ -53,8 +54,8 @@ PREFERENCE_FIELDS_AUTOSAVE = [
 ]
 
 
-def test_all_14_preference_fields_have_autosave_payload_entries():
-    """_preferencesPayloadFromUi must include all 14 preference fields."""
+def test_all_preference_fields_have_autosave_payload_entries():
+    """_preferencesPayloadFromUi must include every autosaved preference field."""
     block = _function_block(PANELS_JS, "_preferencesPayloadFromUi")
     for dom_id, field in PREFERENCE_FIELDS_AUTOSAVE:
         assert f"$('{dom_id}')" in block, \
@@ -64,7 +65,7 @@ def test_all_14_preference_fields_have_autosave_payload_entries():
 
 
 def test_preference_fields_use_schedule_autosave_not_mark_dirty():
-    """All 14 listener attachments (excluding bot_name's debounce wrapper) must
+    """All listener attachments (excluding bot_name's debounce wrapper) must
     use _schedulePreferencesAutosave. bot_name uses a wrapper but still
     eventually calls _schedulePreferencesAutosave."""
     panel = _load_settings_panel_block()

tests/test_issue2124_outline_panel.py

@@ -0,0 +1,117 @@
+"""Static-analysis tests for the conversation outline panel (issue #2124)."""
+
+from pathlib import Path
+import re
+
+ROOT        = Path(__file__).parent.parent
+STATIC      = ROOT / "static"
+INDEX_HTML  = (STATIC / "index.html").read_text(encoding="utf-8")
+I18N_JS     = (STATIC / "i18n.js").read_text(encoding="utf-8")
+OUTLINE_JS  = (STATIC / "outline.js").read_text(encoding="utf-8")
+STYLE_CSS   = (STATIC / "style.css").read_text(encoding="utf-8")
+BOOT_JS     = (STATIC / "boot.js").read_text(encoding="utf-8")
+PANELS_JS   = (STATIC / "panels.js").read_text(encoding="utf-8")
+CONFIG_PY   = (ROOT / "api" / "config.py").read_text(encoding="utf-8")
+
+# Number of locale blocks in i18n.js: en, it, ja, ru, es, de, zh, zh-Hant, pt, ko, fr, tr
+LOCALE_COUNT = 12
+
+
+def test_outline_panel_html_and_i18n_contract():
+    """The panel shell, script tag, and locale keys must be present."""
+    assert 'src="static/outline.js?v=__WEBUI_VERSION__"' in INDEX_HTML
+    assert "outline.js?v=__WEBUI_VERSION__" in INDEX_HTML
+    assert re.search(r'<script[^>]+outline\.js\?v=__WEBUI_VERSION__[^>]+defer', INDEX_HTML)
+    assert re.search(r'id="outlineToggleBtn"[^>]*hidden', INDEX_HTML)
+    assert re.search(r'id="outlinePanelWrapper"[^>]*hidden', INDEX_HTML)
+    assert 'id="outlinePanel"' in INDEX_HTML
+
+    for key in (
+        "outline_title:",
+        "outline_empty:",
+        "outline_loading:",
+        "settings_label_conversation_outline:",
+        "settings_desc_conversation_outline:",
+    ):
+        assert I18N_JS.count(key) >= LOCALE_COUNT
+
+
+def test_outline_setting_round_trip_contract():
+    """The outline preference must default off and use the normal settings path."""
+    assert '"show_conversation_outline": False' in CONFIG_PY
+    assert '"show_conversation_outline",' in CONFIG_PY
+    assert 'id="settingsShowConversationOutline"' in INDEX_HTML
+    assert "payload.show_conversation_outline=showConversationOutlineCb.checked;" in PANELS_JS
+    assert "settings.show_conversation_outline===true" in PANELS_JS
+    assert "body.show_conversation_outline=showConversationOutline===true;" in PANELS_JS
+    assert "window._showConversationOutline=s.show_conversation_outline===true" in BOOT_JS
+    assert "window._showConversationOutline=false" in BOOT_JS
+
+
+def test_outline_navigation_and_long_session_contract():
+    """Outline entries must come from session messages and recover off-window targets."""
+    for marker in (
+        "_outlineSid",
+        "window.toggleOutlinePanel",
+        "window._outlineJump",
+        "S.messages",
+        "'msg-user-'",
+        "/api/session",
+        "_ensureOutlineMessagesLoaded",
+        "_ensureAllMessagesLoaded()",
+        "_messagesTruncated",
+        "_expandOutlineRenderWindow()",
+        "_messageRenderWindowSize = Math.max(",
+        "renderMessages({ preserveScroll: true })",
+        "if (S.busy || S.activeStreamId) return;",
+    ):
+        assert marker in OUTLINE_JS
+
+
+def test_outline_opt_in_layout_and_render_state_contract():
+    """The enabled outline must stay desktop-only and avoid stale render states."""
+    for marker in (
+        "window._showConversationOutline === true",
+        "toggle.hidden = !enabled",
+        "wrapper.hidden = true",
+        "window.applyConversationOutlinePreference",
+        "matchMedia('(max-width:900px)')",
+        "--outline-workspace-offset",
+        "panel.offsetWidth",
+        "data-workspace-panel",
+        "window._outlineRenderHookPending",
+        "if (!S.messages) {",
+    ):
+        assert marker in OUTLINE_JS
+
+    assert "#outlineToggleBtn,#outlinePanelWrapper{display:none!important;}" in STYLE_CSS
+    assert "right:calc(var(--outline-workspace-offset, 0px) + 20px)" in STYLE_CSS
+    assert "if (!S.messages || !S.messages.length)" not in OUTLINE_JS
+
+    before_hooked = OUTLINE_JS.index("window._outlineRenderHooked = true")
+    before_wrapper = OUTLINE_JS.index("window.renderMessages = function")
+    missing_render_block = OUTLINE_JS.split("if (typeof _orig !== 'function')", 1)[1]
+    missing_render_block = missing_render_block.split("window._outlineRenderHooked = true", 1)[0]
+    assert before_hooked < before_wrapper
+    assert "window._outlineRenderHooked = true" not in missing_render_block
+
+
+def test_outline_is_chat_only_and_closes_on_panel_switch():
+    """The outline is a chat-view affordance: leaving chat must hide the toggle
+    AND close the panel, and returning to chat restores the toggle. (Auto-close
+    on panel switch — review follow-up.)"""
+    # _outlineAllowed() gates on the active panel, not just the setting + width.
+    assert "_currentPanel" in OUTLINE_JS
+    assert "panel === 'chat'" in OUTLINE_JS
+    # Re-evaluated on main-view changes: switchPanel() toggles `showing-<panel>`
+    # on <main>, and the MutationObserver watches that class to re-run the gate.
+    assert "main.main" in OUTLINE_JS
+    assert "attributeFilter: ['class']" in OUTLINE_JS
+
+
+def test_outline_wrapper_hidden_attr_actually_hides():
+    """The #outlinePanelWrapper id selector sets display:flex, which outranks the
+    UA [hidden]{display:none} rule — so the hidden attribute alone would NOT hide
+    the panel (the close button / auto-close set wrapper.hidden=true). An explicit
+    #outlinePanelWrapper[hidden]{display:none} rule restores the expected behavior."""
+    assert "#outlinePanelWrapper[hidden]{display:none;}" in STYLE_CSS