diff --git a/packages/client/src/components/hermes/chat/ChatPanel.vue b/packages/client/src/components/hermes/chat/ChatPanel.vue
index 697ec74..0e14839 100644
--- a/packages/client/src/components/hermes/chat/ChatPanel.vue
+++ b/packages/client/src/components/hermes/chat/ChatPanel.vue
@@ -24,6 +24,7 @@ import ConversationMonitorPane from "./ConversationMonitorPane.vue";
 import MessageList from "./MessageList.vue";
 import SessionListItem from "./SessionListItem.vue";
 import DrawerPanel from "./DrawerPanel.vue";
+import OutlinePanel from "./OutlinePanel.vue";
 
 const chatStore = useChatStore();
 const appStore = useAppStore();
@@ -33,6 +34,7 @@ const { t } = useI18n();
 
 const showDrawer = ref(false);
 const drawerActiveTab = ref<"terminal" | "files">("files");
+const showOutline = ref(false);
 
 const currentMode = ref<"chat" | "live">("chat");
 
@@ -988,6 +990,30 @@ async function handleSessionModelCustomSubmit() {
         <div class="header-actions">
           <!-- chat/live mode toggle hidden -->
           <template v-if="currentMode === 'chat'">
+            <NTooltip trigger="hover">
+              <template #trigger>
+                <NButton
+                  quaternary
+                  size="small"
+                  @click="showOutline = !showOutline"
+                  circle
+                >
+                  <template #icon>
+                    <svg
+                      width="14"
+                      height="14"
+                      viewBox="0 0 24 24"
+                      fill="none"
+                      stroke="currentColor"
+                      stroke-width="1.5"
+                    >
+                      <path d="M3 12h18M3 6h18M3 18h18" />
+                    </svg>
+                  </template>
+                </NButton>
+              </template>
+              {{ t("chat.outlineTitle") }}
+            </NTooltip>
             <NTooltip trigger="hover">
               <template #trigger>
                 <NButton
@@ -1042,7 +1068,12 @@ async function handleSessionModelCustomSubmit() {
       </header>
 
       <template v-if="currentMode === 'chat'">
-        <MessageList />
+        <div class="chat-content-wrapper">
+          <div class="chat-main-content">
+            <MessageList />
+          </div>
+          <OutlinePanel v-if="showOutline" :messages="chatStore.messages" />
+        </div>
         <div v-if="visibleApproval" class="approval-bar">
           <div class="approval-icon" aria-hidden="true">
             <svg
@@ -1637,6 +1668,21 @@ async function handleSessionModelCustomSubmit() {
   min-width: 0;
 }
 
+.chat-content-wrapper {
+  flex: 1;
+  display: flex;
+  overflow: hidden;
+  position: relative;
+}
+
+.chat-main-content {
+  flex: 1;
+  overflow: hidden;
+  display: flex;
+  flex-direction: column;
+  min-width: 0;
+}
+
 .chat-header {
   display: flex;
   align-items: center;
diff --git a/packages/client/src/components/hermes/chat/MarkdownRenderer.vue b/packages/client/src/components/hermes/chat/MarkdownRenderer.vue
index f30ef7f..6ce54c9 100644
--- a/packages/client/src/components/hermes/chat/MarkdownRenderer.vue
+++ b/packages/client/src/components/hermes/chat/MarkdownRenderer.vue
@@ -19,8 +19,10 @@ import { downloadFile, getDownloadUrl } from '@/api/hermes/download'
 const props = withDefaults(defineProps<{
     content: string
     mentionNames?: string[]
+    headingIdPrefix?: string
 }>(), {
     mentionNames: () => [],
+    headingIdPrefix: '',
 })
 
 const { t } = useI18n()
@@ -68,6 +70,27 @@ function normalizeLocalFilePath(path: string): string {
 const renderedHtml = computed(() => {
   let html = md.render(repairNestedMarkdownFences(props.content))
 
+  // Add IDs to headings for anchor links
+  const prefix = props.headingIdPrefix ? `${props.headingIdPrefix}-` : ''
+  let headingCounter = 0
+  // Match any h1-h6 tags, with or without attributes
+  html = html.replace(/<(h[1-6])([^>]*)>/g, (match, tag, attrs) => {
+    headingCounter++
+    const id = `${prefix}heading-${headingCounter}`
+    
+    // Check if id attribute already exists
+    if (attrs.includes('id=')) {
+      // Replace existing id
+      return match.replace(/id="[^"]*"/, `id="${id}"`).replace(/id='[^']*'/, `id="${id}"`)
+    }
+    
+    // Add new id
+    if (attrs.trim() === '') {
+      return `<${tag} id="${id}">`
+    }
+    return `<${tag} ${attrs.trim()} id="${id}">`
+  })
+
   // Replace image src paths with download URLs
   html = html.replace(/\bsrc=(["'])([^"']+)\1/g, (match, quote, path) => {
     if (!isLocalFilePath(path)) return match
diff --git a/packages/client/src/components/hermes/chat/MessageItem.vue b/packages/client/src/components/hermes/chat/MessageItem.vue
index efab97c..1daaee1 100644
--- a/packages/client/src/components/hermes/chat/MessageItem.vue
+++ b/packages/client/src/components/hermes/chat/MessageItem.vue
@@ -27,11 +27,13 @@ const JSON_MAX_KEYS_PER_OBJECT = 50;
 const JSON_MAX_ITEMS_PER_ARRAY = 50;
 const JSON_TRUNCATED_KEY = "__truncated__";
 
-const props = defineProps<{ message: Message; highlight?: boolean }>();
+const props = defineProps<{ message: Message; highlight?: boolean; headingIdPrefix?: string }>();
 const { t } = useI18n();
 const toast = useMessage();
 
 const isSystem = computed(() => props.message.role === "system");
+
+const effectiveHeadingIdPrefix = computed(() => props.headingIdPrefix || `msg-${props.message.id}`);
 const isCommandMessage = computed(() => props.message.role === "command" || props.message.systemType === "command");
 const isCommandError = computed(() => props.message.role === "command" && props.message.systemType === "error");
 const isStatusCommand = computed(() => isCommandMessage.value && props.message.commandAction === "status");
@@ -868,6 +870,7 @@ onBeforeUnmount(() => {
             <MarkdownRenderer
               v-if="parsedThinking.body && message.role === 'assistant'"
               :content="parsedThinking.body"
+              :heading-id-prefix="effectiveHeadingIdPrefix"
             />
 
             <!-- Render user message content -->
@@ -915,6 +918,7 @@ onBeforeUnmount(() => {
             <MarkdownRenderer
               v-if="message.role === 'assistant' && message.content && !parsedThinking.body"
               :content="message.content"
+              :heading-id-prefix="effectiveHeadingIdPrefix"
             />
 
             <!-- Render system message content -->
diff --git a/packages/client/src/components/hermes/chat/OutlinePanel.vue b/packages/client/src/components/hermes/chat/OutlinePanel.vue
new file mode 100644
index 0000000..60af8a1
--- /dev/null
+++ b/packages/client/src/components/hermes/chat/OutlinePanel.vue
@@ -0,0 +1,317 @@
+<script setup lang="ts">
+import { computed, nextTick } from 'vue'
+import { useI18n } from 'vue-i18n'
+import type { Message } from '@/stores/hermes/chat'
+
+interface OutlineItem {
+  id: string
+  type: 'user' | 'outline'
+  content: string
+  messageId: string
+  level: number
+  anchorId: string
+}
+
+const props = defineProps<{
+  messages: Message[]
+}>()
+
+const { t } = useI18n()
+
+function extractAllHeadings(text: string, messageId: string): OutlineItem[] {
+  const items: OutlineItem[] = []
+  let cleanedText = text.replace(/<think>[\s\S]*?<\/think>/g, '')
+  const lines = cleanedText.split('\n')
+  
+  let headingIndex = 0
+  for (const line of lines) {
+    const trimmed = line.trim()
+    const h1Match = trimmed.match(/^#\s+(.+)/)
+    const h2Match = trimmed.match(/^##\s+(.+)/)
+    const h3Match = trimmed.match(/^###\s+(.+)/)
+    
+    if (h1Match) {
+      headingIndex++
+      items.push({
+        id: `outline-${messageId}-h${headingIndex}`,
+        type: 'outline',
+        content: h1Match[1].trim(),
+        messageId,
+        level: 1,
+        anchorId: `msg-${messageId}-heading-${headingIndex}`
+      })
+    } else if (h2Match) {
+      headingIndex++
+      items.push({
+        id: `outline-${messageId}-h${headingIndex}`,
+        type: 'outline',
+        content: h2Match[1].trim(),
+        messageId,
+        level: 2,
+        anchorId: `msg-${messageId}-heading-${headingIndex}`
+      })
+    } else if (h3Match) {
+      headingIndex++
+      items.push({
+        id: `outline-${messageId}-h${headingIndex}`,
+        type: 'outline',
+        content: h3Match[1].trim(),
+        messageId,
+        level: 3,
+        anchorId: `msg-${messageId}-heading-${headingIndex}`
+      })
+    }
+  }
+  
+  return items
+}
+
+function extractUserQuestion(text: string): string {
+  const cleanedText = text.replace(/<think>[\s\S]*?<\/think>/g, '')
+  const firstLine = cleanedText.split('\n')[0] || ''
+  if (firstLine.length > 50) {
+    return firstLine.slice(0, 50) + '...'
+  }
+  return firstLine || t('chat.outlineUserQuestion')
+}
+
+const outlineItems = computed<OutlineItem[]>(() => {
+  const items: OutlineItem[] = []
+  let i = 0
+  const filteredMessages = props.messages.filter(m => m.role === 'user' || m.role === 'assistant')
+  
+  while (i < filteredMessages.length) {
+    const msg = filteredMessages[i]
+    if (msg.role === 'user') {
+      items.push({
+        id: `user-${msg.id}`,
+        type: 'user',
+        content: extractUserQuestion(msg.content || ''),
+        messageId: msg.id,
+        level: 0,
+        anchorId: `message-${msg.id}`
+      })
+      i++
+      while (i < filteredMessages.length && filteredMessages[i].role !== 'assistant') {
+        i++
+      }
+      if (i < filteredMessages.length) {
+        const assistantMsg = filteredMessages[i]
+        const headings = extractAllHeadings(assistantMsg.content || '', assistantMsg.id)
+        items.push(...headings)
+      }
+    }
+    i++
+  }
+  return items
+})
+
+function scrollToTarget(anchorId: string) {
+  console.log('Attempting to scroll to anchor:', anchorId)
+  nextTick(() => {
+    const el = document.getElementById(anchorId)
+    console.log('Found element:', el)
+    if (el) {
+      el.scrollIntoView({ behavior: 'smooth', block: 'start' })
+    } else {
+      // Debug: log all heading elements with IDs
+      console.log('All heading elements on page:')
+      document.querySelectorAll('h1, h2, h3, h4, h5, h6').forEach(el => {
+        console.log('  -', el.id, ':', el.textContent?.slice(0, 50))
+      })
+    }
+  })
+}
+</script>
+
+<template>
+  <div class="outline-panel">
+    <div class="outline-header">
+      <span class="outline-title">{{ t('chat.outlineTitle') }}</span>
+    </div>
+    <div class="outline-content">
+      <template v-if="outlineItems.length > 0">
+        <template v-for="item in outlineItems" :key="item.id">
+          <div
+            v-if="item.type === 'user'"
+            class="outline-item user-item"
+            @click="scrollToTarget(item.anchorId)"
+          >
+            <div class="user-question">
+              <span class="q-label">Q:</span>
+              <span class="q-text">{{ item.content }}</span>
+            </div>
+          </div>
+          <div
+            v-else
+            class="outline-item outline-heading-item"
+            :class="`level-${item.level}`"
+            @click="scrollToTarget(item.anchorId)"
+          >
+            <div class="heading-item">
+              <span class="heading-text">{{ item.content }}</span>
+            </div>
+          </div>
+        </template>
+      </template>
+      <div v-else class="outline-empty">{{ t('chat.outlineEmpty') }}</div>
+    </div>
+  </div>
+</template>
+
+<style scoped lang="scss">
+@use "@/styles/variables" as *;
+
+.outline-panel {
+  display: flex;
+  flex-direction: column;
+  height: 100%;
+  background-color: $bg-card;
+  border-left: 1px solid $border-color;
+  width: 280px;
+  flex-shrink: 0;
+
+  @media (max-width: $breakpoint-mobile) {
+    position: absolute;
+    top: 0;
+    right: 0;
+    bottom: 0;
+    width: min(280px, 86vw);
+    z-index: 8;
+    box-shadow: -4px 0 16px rgba(0, 0, 0, 0.12);
+  }
+}
+
+.outline-header {
+  padding: 16px;
+  border-bottom: 1px solid $border-color;
+  flex-shrink: 0;
+}
+
+.outline-title {
+  font-size: 14px;
+  font-weight: 600;
+  color: $text-primary;
+}
+
+.outline-content {
+  flex: 1;
+  overflow-y: auto;
+  padding: 12px;
+}
+
+.outline-item {
+  margin-bottom: 4px;
+  cursor: pointer;
+  transition: opacity 0.2s ease;
+
+  &:hover {
+    opacity: 0.8;
+  }
+}
+
+.user-item {
+  margin-bottom: 6px;
+}
+
+.user-question {
+  background-color: $bg-secondary;
+  color: $text-primary;
+  padding: 8px 12px;
+  border-radius: 8px;
+  display: flex;
+  align-items: flex-start;
+  gap: 6px;
+
+  .dark & {
+    background-color: $bg-input;
+  }
+
+  .q-label {
+    font-weight: 600;
+    flex-shrink: 0;
+    font-size: 13px;
+    line-height: 1.4;
+  }
+
+  .q-text {
+    font-size: 13px;
+    line-height: 1.4;
+    word-break: break-word;
+  }
+}
+
+.outline-heading-item {
+  &.level-1 {
+    padding-left: 0;
+  }
+
+  &.level-2 {
+    padding-left: 12px;
+  }
+
+  &.level-3 {
+    padding-left: 24px;
+  }
+}
+
+.heading-item {
+  display: flex;
+  align-items: flex-start;
+  gap: 6px;
+  padding: 4px 8px;
+  border-radius: 4px;
+  transition: background-color 0.15s ease;
+
+  &:hover {
+    background-color: rgba(0, 0, 0, 0.04);
+
+    .dark & {
+      background-color: rgba(255, 255, 255, 0.06);
+    }
+  }
+
+  .level-1 & {
+    .heading-marker {
+      color: $text-primary;
+      font-weight: 600;
+    }
+    .heading-text {
+      color: $text-primary;
+      font-weight: 500;
+    }
+  }
+
+  .level-2 & {
+    .heading-marker {
+      color: $text-secondary;
+    }
+    .heading-text {
+      color: $text-secondary;
+    }
+  }
+
+  .level-3 & {
+    .heading-marker {
+      color: $text-muted;
+    }
+    .heading-text {
+      color: $text-muted;
+      font-size: 12px;
+    }
+  }
+}
+
+.heading-text {
+  font-size: 13px;
+  line-height: 1.4;
+  word-break: break-word;
+}
+
+.outline-empty {
+  text-align: center;
+  color: $text-muted;
+  font-size: 13px;
+  padding: 20px 0;
+}
+</style>
diff --git a/packages/client/src/i18n/locales/de.ts b/packages/client/src/i18n/locales/de.ts
index 3c0e72c..152f499 100644
--- a/packages/client/src/i18n/locales/de.ts
+++ b/packages/client/src/i18n/locales/de.ts
@@ -120,6 +120,9 @@ export default {
     contextEditSuccess: 'Kontextlänge aktualisiert',
     contextEditFailed: 'Aktualisierung fehlgeschlagen',
     emptyState: 'Starten Sie eine Konversation mit Hermes Agent',
+    outlineTitle: 'Konversationsübersicht',
+    outlineEmpty: 'Kein Konversationsinhalt',
+    outlineUserQuestion: 'Benutzerfrage',
     inputPlaceholder: 'Nachricht eingeben... (Enter zum Senden, Shift+Enter fur neue Zeile)',
     slashCommandArgs: {
       message: '<Nachricht>',
diff --git a/packages/client/src/i18n/locales/en.ts b/packages/client/src/i18n/locales/en.ts
index 57627be..c3ad783 100644
--- a/packages/client/src/i18n/locales/en.ts
+++ b/packages/client/src/i18n/locales/en.ts
@@ -133,6 +133,9 @@ export default {
     contextEditFailed: 'Update failed',
     emptyState: 'Start a conversation with Hermes Agent',
     cliEmptyState: 'Start a CLI chat session',
+    outlineTitle: 'Conversation Outline',
+    outlineEmpty: 'No conversation content',
+    outlineUserQuestion: 'User question',
     inputPlaceholder: 'Type a message... (Enter to send, Shift+Enter for new line)',
     slashCommandArgs: {
       message: '<message>',
diff --git a/packages/client/src/i18n/locales/es.ts b/packages/client/src/i18n/locales/es.ts
index 170df80..726efe2 100644
--- a/packages/client/src/i18n/locales/es.ts
+++ b/packages/client/src/i18n/locales/es.ts
@@ -120,6 +120,9 @@ export default {
     contextEditSuccess: 'Longitud del contexto actualizada',
     contextEditFailed: 'Error en la actualización',
     emptyState: 'Inicia una conversacion con Hermes Agent',
+    outlineTitle: 'Esquema de la conversación',
+    outlineEmpty: 'Sin contenido de conversación',
+    outlineUserQuestion: 'Pregunta del usuario',
     inputPlaceholder: 'Escribe un mensaje... (Enter para enviar, Shift+Enter para nueva linea)',
     slashCommandArgs: {
       message: '<mensaje>',
diff --git a/packages/client/src/i18n/locales/fr.ts b/packages/client/src/i18n/locales/fr.ts
index bc760b2..d74f966 100644
--- a/packages/client/src/i18n/locales/fr.ts
+++ b/packages/client/src/i18n/locales/fr.ts
@@ -120,6 +120,9 @@ export default {
     contextEditSuccess: 'Longueur du contexte mise à jour',
     contextEditFailed: 'Échec de la mise à jour',
     emptyState: 'Demarrer une conversation avec Hermes Agent',
+    outlineTitle: 'Plan de la conversation',
+    outlineEmpty: 'Aucun contenu de conversation',
+    outlineUserQuestion: 'Question utilisateur',
     inputPlaceholder: 'Tapez un message... (Entree pour envoyer, Shift+Entree pour un saut de ligne)',
     slashCommandArgs: {
       message: '<message>',
diff --git a/packages/client/src/i18n/locales/ja.ts b/packages/client/src/i18n/locales/ja.ts
index 95c39ad..1857c4e 100644
--- a/packages/client/src/i18n/locales/ja.ts
+++ b/packages/client/src/i18n/locales/ja.ts
@@ -120,6 +120,9 @@ export default {
     contextEditSuccess: 'コンテキスト長を更新しました',
     contextEditFailed: '更新に失敗しました',
     emptyState: 'Hermes Agent と会話を開始しましょう',
+    outlineTitle: '会話アウトライン',
+    outlineEmpty: '会話内容はありません',
+    outlineUserQuestion: 'ユーザーの質問',
     inputPlaceholder: 'メッセージを入力... (Enter で送信、Shift+Enter で改行)',
     slashCommandArgs: {
       message: '<メッセージ>',
diff --git a/packages/client/src/i18n/locales/ko.ts b/packages/client/src/i18n/locales/ko.ts
index 103187c..e38c3ae 100644
--- a/packages/client/src/i18n/locales/ko.ts
+++ b/packages/client/src/i18n/locales/ko.ts
@@ -120,6 +120,9 @@ export default {
     contextEditSuccess: '컨텍스트 길이가 업데이트되었습니다',
     contextEditFailed: '업데이트 실패',
     emptyState: 'Hermes Agent와 대화를 시작하세요',
+    outlineTitle: '대화 개요',
+    outlineEmpty: '대화 내용이 없습니다',
+    outlineUserQuestion: '사용자 질문',
     inputPlaceholder: '메시지를 입력하세요... (Enter로 전송, Shift+Enter로 줄바꿈)',
     slashCommandArgs: {
       message: '<메시지>',
diff --git a/packages/client/src/i18n/locales/pt.ts b/packages/client/src/i18n/locales/pt.ts
index 7ccc65c..f1694b1 100644
--- a/packages/client/src/i18n/locales/pt.ts
+++ b/packages/client/src/i18n/locales/pt.ts
@@ -120,6 +120,9 @@ export default {
     contextEditSuccess: 'Tamanho do contexto atualizado',
     contextEditFailed: 'Falha na atualização',
     emptyState: 'Inicie uma conversa com o Hermes Agent',
+    outlineTitle: 'Esboço da conversa',
+    outlineEmpty: 'Nenhum conteúdo da conversa',
+    outlineUserQuestion: 'Pergunta do usuário',
     inputPlaceholder: 'Digite uma mensagem... (Enter para enviar, Shift+Enter para nova linha)',
     slashCommandArgs: {
       message: '<mensagem>',
diff --git a/packages/client/src/i18n/locales/zh-TW.ts b/packages/client/src/i18n/locales/zh-TW.ts
index 08ba02a..c68bd94 100644
--- a/packages/client/src/i18n/locales/zh-TW.ts
+++ b/packages/client/src/i18n/locales/zh-TW.ts
@@ -132,6 +132,9 @@ export default {
     contextEditSuccess: '上下文長度已更新',
     contextEditFailed: '更新失敗',
     emptyState: '開始與 Hermes Agent 對話',
+    outlineTitle: '會話大綱',
+    outlineEmpty: '暫無會話內容',
+    outlineUserQuestion: '使用者問題',
     inputPlaceholder: '輸入訊息... (Enter 發送，Shift+Enter 換行)',
     slashCommandArgs: {
       message: '<訊息>',
diff --git a/packages/client/src/i18n/locales/zh.ts b/packages/client/src/i18n/locales/zh.ts
index 5ca7272..77ffeee 100644
--- a/packages/client/src/i18n/locales/zh.ts
+++ b/packages/client/src/i18n/locales/zh.ts
@@ -133,6 +133,9 @@ export default {
     contextEditFailed: '更新失败',
     emptyState: '开始与 Hermes Agent 对话',
     cliEmptyState: '开始 CLI 对话',
+    outlineTitle: '会话大纲',
+    outlineEmpty: '暂无会话内容',
+    outlineUserQuestion: '用户问题',
     inputPlaceholder: '输入消息... (Enter 发送，Shift+Enter 换行)',
     slashCommandArgs: {
       message: '<消息>',
diff --git a/packages/client/src/views/hermes/HistoryView.vue b/packages/client/src/views/hermes/HistoryView.vue
index 720ec02..a108ae2 100644
--- a/packages/client/src/views/hermes/HistoryView.vue
+++ b/packages/client/src/views/hermes/HistoryView.vue
@@ -10,6 +10,7 @@ import { getSourceLabel } from '@/shared/session-display'
 import { copyToClipboard } from '@/utils/clipboard'
 import HistoryMessageList from '@/components/hermes/chat/HistoryMessageList.vue'
 import SessionListItem from '@/components/hermes/chat/SessionListItem.vue'
+import OutlinePanel from '@/components/hermes/chat/OutlinePanel.vue'
 import { fetchHermesSessions, fetchHermesSession, type SessionSummary } from '@/api/hermes/sessions'
 
 const chatStore = useChatStore()
@@ -26,6 +27,7 @@ const hermesSessionsLoaded = ref(false)
 // History page's own selected session (independent from chatStore)
 const historySessionId = ref<string | null>(null)
 const historySession = ref<Session | null>(null)
+const showOutline = ref(false)
 
 async function loadHermesSessions() {
   if (hermesSessionsLoading.value) return
@@ -340,6 +342,16 @@ async function copySessionId(id?: string) {
           <span v-if="historySession?.workspace" class="workspace-badge" :title="historySession.workspace">📁 {{ historySession.workspace.split('/').pop() || historySession.workspace }}</span>
         </div>
         <div class="header-actions">
+          <NTooltip trigger="hover">
+            <template #trigger>
+              <NButton quaternary size="small" @click="showOutline = !showOutline" circle>
+                <template #icon>
+                  <svg width="14" height="14" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="1.5"><path d="M3 12h18M3 6h18M3 18h18"/></svg>
+                </template>
+              </NButton>
+            </template>
+            {{ t('chat.outlineTitle') }}
+          </NTooltip>
           <NTooltip trigger="hover">
             <template #trigger>
               <NButton quaternary size="small" @click="copySessionId()" circle>
@@ -353,7 +365,12 @@ async function copySessionId(id?: string) {
         </div>
       </header>
 
-      <HistoryMessageList :session="historySession" />
+      <div class="history-content-wrapper">
+        <div class="history-main-content">
+          <HistoryMessageList :session="historySession" />
+        </div>
+        <OutlinePanel v-if="showOutline && historySession" :messages="historySession.messages || []" />
+      </div>
     </div>
   </div>
 </template>
@@ -367,6 +384,21 @@ async function copySessionId(id?: string) {
   position: relative;
 }
 
+.history-content-wrapper {
+  flex: 1;
+  display: flex;
+  overflow: hidden;
+  position: relative;
+}
+
+.history-main-content {
+  flex: 1;
+  overflow: hidden;
+  display: flex;
+  flex-direction: column;
+  min-width: 0;
+}
+
 .session-list {
   width: 220px;
   border-right: 1px solid $border-color;