diff --git a/packages/client/src/components/hermes/chat/ChatPanel.vue b/packages/client/src/components/hermes/chat/ChatPanel.vue
index e171511..77dade5 100644
--- a/packages/client/src/components/hermes/chat/ChatPanel.vue
+++ b/packages/client/src/components/hermes/chat/ChatPanel.vue
@@ -38,6 +38,7 @@ const { t } = useI18n();
 const showDrawer = ref(false);
 const drawerActiveTab = ref<"terminal" | "files">("files");
 const showOutline = ref(false);
+const messageListRef = ref<InstanceType<typeof MessageList> | null>(null);
 
 const currentMode = ref<"chat" | "live">("chat");
 
@@ -72,6 +73,10 @@ function openSessionInNewTab(sessionId: string) {
   window.open(sessionHref(sessionId), "_blank", "noopener,noreferrer");
 }
 
+function handleOutlineNavigate(target: { messageId: string; anchorId: string }) {
+  messageListRef.value?.scrollToAnchor(target.messageId, target.anchorId);
+}
+
 async function handleSessionClick(sessionId: string) {
   await router.push({
     name: "hermes.session",
@@ -1201,9 +1206,13 @@ async function handleSessionModelCustomSubmit() {
       <template v-if="currentMode === 'chat'">
         <div class="chat-content-wrapper">
           <div class="chat-main-content">
-            <MessageList />
+            <MessageList ref="messageListRef" />
           </div>
-          <OutlinePanel v-if="showOutline" :messages="chatStore.messages" />
+          <OutlinePanel
+            v-if="showOutline"
+            :messages="chatStore.messages"
+            @navigate="handleOutlineNavigate"
+          />
         </div>
         <div v-if="visibleApproval" class="approval-bar">
           <div class="approval-icon" aria-hidden="true">
diff --git a/packages/client/src/components/hermes/chat/HistoryMessageList.vue b/packages/client/src/components/hermes/chat/HistoryMessageList.vue
index bfc18d7..3395b6c 100644
--- a/packages/client/src/components/hermes/chat/HistoryMessageList.vue
+++ b/packages/client/src/components/hermes/chat/HistoryMessageList.vue
@@ -41,6 +41,10 @@ function scrollToMessage(messageId: string) {
   listRef.value?.scrollToMessage(messageId);
 }
 
+function scrollToAnchor(messageId: string, anchorId: string) {
+  listRef.value?.scrollToAnchor(messageId, anchorId);
+}
+
 // Scroll to bottom on session switch
 watch(
   () => activeSession.value?.id,
@@ -81,6 +85,12 @@ watch(
     scrollToBottom();
   },
 );
+
+defineExpose({
+  scrollToBottom,
+  scrollToMessage,
+  scrollToAnchor,
+});
 </script>
 
 <template>
diff --git a/packages/client/src/components/hermes/chat/MessageList.vue b/packages/client/src/components/hermes/chat/MessageList.vue
index ad374b3..27eb22d 100644
--- a/packages/client/src/components/hermes/chat/MessageList.vue
+++ b/packages/client/src/components/hermes/chat/MessageList.vue
@@ -96,6 +96,10 @@ function scrollToMessage(messageId: string) {
   listRef.value?.scrollToMessage(messageId);
 }
 
+function scrollToAnchor(messageId: string, anchorId: string) {
+  listRef.value?.scrollToAnchor(messageId, anchorId);
+}
+
 async function handleTopReach() {
   const session = chatStore.activeSession;
   if (!session?.hasMoreBefore || session.isLoadingOlderMessages) return;
@@ -156,6 +160,12 @@ watch(currentToolCalls, () => {
   if (!isNearBottom()) return;
   scrollToBottom();
 });
+
+defineExpose({
+  scrollToBottom,
+  scrollToMessage,
+  scrollToAnchor,
+});
 </script>
 
 <template>
diff --git a/packages/client/src/components/hermes/chat/OutlinePanel.vue b/packages/client/src/components/hermes/chat/OutlinePanel.vue
index 60af8a1..301d7af 100644
--- a/packages/client/src/components/hermes/chat/OutlinePanel.vue
+++ b/packages/client/src/components/hermes/chat/OutlinePanel.vue
@@ -1,5 +1,5 @@
 <script setup lang="ts">
-import { computed, nextTick } from 'vue'
+import { computed } from 'vue'
 import { useI18n } from 'vue-i18n'
 import type { Message } from '@/stores/hermes/chat'
 
@@ -16,6 +16,10 @@ const props = defineProps<{
   messages: Message[]
 }>()
 
+const emit = defineEmits<{
+  navigate: [target: { messageId: string; anchorId: string }]
+}>()
+
 const { t } = useI18n()
 
 function extractAllHeadings(text: string, messageId: string): OutlineItem[] {
@@ -106,20 +110,10 @@ const outlineItems = computed<OutlineItem[]>(() => {
   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))
-      })
-    }
+function scrollToTarget(item: OutlineItem) {
+  emit('navigate', {
+    messageId: item.messageId,
+    anchorId: item.anchorId,
   })
 }
 </script>
@@ -135,7 +129,7 @@ function scrollToTarget(anchorId: string) {
           <div
             v-if="item.type === 'user'"
             class="outline-item user-item"
-            @click="scrollToTarget(item.anchorId)"
+            @click="scrollToTarget(item)"
           >
             <div class="user-question">
               <span class="q-label">Q:</span>
@@ -146,7 +140,7 @@ function scrollToTarget(anchorId: string) {
             v-else
             class="outline-item outline-heading-item"
             :class="`level-${item.level}`"
-            @click="scrollToTarget(item.anchorId)"
+            @click="scrollToTarget(item)"
           >
             <div class="heading-item">
               <span class="heading-text">{{ item.content }}</span>
diff --git a/packages/client/src/components/hermes/chat/VirtualMessageList.vue b/packages/client/src/components/hermes/chat/VirtualMessageList.vue
index 3c10278..4db1361 100644
--- a/packages/client/src/components/hermes/chat/VirtualMessageList.vue
+++ b/packages/client/src/components/hermes/chat/VirtualMessageList.vue
@@ -50,6 +50,29 @@ function itemHeight(key: string): number {
   return measuredHeights.get(key) || props.estimatedItemHeight;
 }
 
+function measuredRowHeight(el: HTMLElement): number {
+  return Math.ceil(el.getBoundingClientRect().height || props.estimatedItemHeight);
+}
+
+function setMeasuredHeight(key: string, height: number) {
+  const oldHeight = itemHeight(key);
+  if (oldHeight === height) return;
+
+  const index = messageKeys.value.indexOf(key);
+  if (index >= 0) {
+    const el = scrollerRef.value;
+    const rowTop = layout.value.offsets[index] || 0;
+    const delta = height - oldHeight;
+    if (el && rowTop < scrollTop.value && delta !== 0) {
+      el.scrollTop = Math.max(0, el.scrollTop + delta);
+      syncViewport();
+    }
+  }
+
+  measuredHeights.set(key, height);
+  heightVersion.value += 1;
+}
+
 const layout = computed(() => {
   heightVersion.value;
   const offsets: number[] = [];
@@ -115,18 +138,11 @@ function setItemRef(key: string, el: Element | ComponentPublicInstance | null) {
 
   observedElements.set(key, el);
   if (typeof ResizeObserver === "undefined") {
-    const height = Math.ceil(el.getBoundingClientRect().height || props.estimatedItemHeight);
-    measuredHeights.set(key, height);
-    heightVersion.value += 1;
+    setMeasuredHeight(key, measuredRowHeight(el));
     return;
   }
 
-  const observer = new ResizeObserver(entries => {
-    const height = Math.ceil(entries[0]?.contentRect.height || props.estimatedItemHeight);
-    if (measuredHeights.get(key) === height) return;
-    measuredHeights.set(key, height);
-    heightVersion.value += 1;
-  });
+  const observer = new ResizeObserver(() => setMeasuredHeight(key, measuredRowHeight(el)));
   observer.observe(el);
   observers.set(key, observer);
 }
@@ -174,6 +190,23 @@ function scrollToMessage(messageId: string) {
   });
 }
 
+function scrollToAnchor(messageId: string, anchorId: string) {
+  const index = props.messages.findIndex(message => String(message.id) === messageId);
+  if (index < 0) return;
+
+  nextTick(() => {
+    const el = scrollerRef.value;
+    if (!el) return;
+    el.scrollTop = Math.max(0, (layout.value.offsets[index] || 0) - 24);
+    syncViewport();
+    nextTick(() => {
+      const target = document.getElementById(anchorId) || document.getElementById(`message-${messageId}`);
+      target?.scrollIntoView({ behavior: "smooth", block: "start" });
+      syncViewport();
+    });
+  });
+}
+
 function captureScrollPosition() {
   const el = scrollerRef.value;
   if (!el) return null;
@@ -218,6 +251,13 @@ watch(messageKeys, keys => {
     observers.delete(key);
     observedElements.delete(key);
   }
+  let droppedHeights = false;
+  for (const key of [...measuredHeights.keys()]) {
+    if (activeKeys.has(key)) continue;
+    measuredHeights.delete(key);
+    droppedHeights = true;
+  }
+  if (droppedHeights) heightVersion.value += 1;
   nextTick(syncViewport);
 });
 
@@ -225,6 +265,7 @@ defineExpose({
   isNearBottom,
   scrollToBottom,
   scrollToMessage,
+  scrollToAnchor,
   captureScrollPosition,
   restoreScrollPosition,
 });
diff --git a/packages/client/src/views/hermes/HistoryView.vue b/packages/client/src/views/hermes/HistoryView.vue
index 1995abc..3997e48 100644
--- a/packages/client/src/views/hermes/HistoryView.vue
+++ b/packages/client/src/views/hermes/HistoryView.vue
@@ -42,6 +42,7 @@ const hermesSessionsLoaded = ref(false)
 const historySessionId = ref<string | null>(null)
 const historySession = ref<Session | null>(null)
 const showOutline = ref(false)
+const historyMessageListRef = ref<InstanceType<typeof HistoryMessageList> | null>(null)
 const isBatchMode = ref(false)
 const isBatchDeleting = ref(false)
 const showBatchDeleteConfirm = ref(false)
@@ -52,6 +53,10 @@ const contextMenuX = ref(0)
 const contextMenuY = ref(0)
 let hermesSessionsRequestId = 0
 
+function handleOutlineNavigate(target: { messageId: string; anchorId: string }) {
+  historyMessageListRef.value?.scrollToAnchor(target.messageId, target.anchorId)
+}
+
 async function loadHermesSessions() {
   const requestId = ++hermesSessionsRequestId
   hermesSessionsLoading.value = true
@@ -759,9 +764,13 @@ function handleBatchDeleteConfirm() {
 
       <div class="history-content-wrapper">
         <div class="history-main-content">
-          <HistoryMessageList :session="historySession" />
+          <HistoryMessageList ref="historyMessageListRef" :session="historySession" />
         </div>
-        <OutlinePanel v-if="showOutline && historySession" :messages="historySession.messages || []" />
+        <OutlinePanel
+          v-if="showOutline && historySession"
+          :messages="historySession.messages || []"
+          @navigate="handleOutlineNavigate"
+        />
       </div>
     </div>
   </div>