diff --git a/packages/app/src/components/chat/ChatHeader.vue b/packages/app/src/components/chat/ChatHeader.vue
index 98a769a9..b4f2f3be 100644
--- a/packages/app/src/components/chat/ChatHeader.vue
+++ b/packages/app/src/components/chat/ChatHeader.vue
@@ -33,6 +33,25 @@
         </svg>
       </button>
 
+      <button
+        class="w-9 h-9 rounded-xl path-glass-icon flex items-center justify-center transition-colors"
+        :class="chatStore.chatCollapsed
+          ? 'text-accent'
+          : isDark
+            ? 'text-white/70 hover:text-white'
+            : 'text-gray-500 hover:text-gray-900'"
+        :title="chatStore.chatCollapsed ? 'Expand chat' : 'Collapse to prompts'"
+        aria-label="Toggle prompt index"
+        @click="chatStore.toggleChatCollapse()"
+      >
+        <svg v-if="!chatStore.chatCollapsed" class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24">
+          <path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M4 6h16M4 12h10M4 18h16" />
+        </svg>
+        <svg v-else class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24">
+          <path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M8 12h.01M12 12h.01M16 12h.01M21 12c0 4.418-4.03 8-9 8a9.863 9.863 0 01-4.255-.949L3 20l1.395-3.72C3.512 15.042 3 13.574 3 12c0-4.418 4.03-8 9-8s9 3.582 9 8z" />
+        </svg>
+      </button>
+
       <button
         class="w-9 h-9 rounded-xl path-glass-icon flex items-center justify-center transition-colors"
         :class="isDark
diff --git a/packages/app/src/components/chat/ChatWindow.vue b/packages/app/src/components/chat/ChatWindow.vue
index 20873ccf..9b4aba55 100644
--- a/packages/app/src/components/chat/ChatWindow.vue
+++ b/packages/app/src/components/chat/ChatWindow.vue
@@ -10,7 +10,16 @@
       @close="$emit('close')"
     />
 
+    <!-- Collapsed: prompt index -->
+    <PromptIndex
+      v-if="chatCollapsed"
+      :messages="messages"
+      @select="handlePromptSelect"
+    />
+
+    <!-- Expanded: full message list -->
     <div
+      v-else
       ref="messageListRef"
       class="relative z-0 flex-1 min-h-0 overflow-y-auto scrollbar-hide p-4 space-y-3"
     >
@@ -54,6 +63,8 @@ import ChatHeader from './ChatHeader.vue'
 import ChatMessage from './ChatMessage.vue'
 import ChatInput from './ChatInput.vue'
 import StreamingDots from './StreamingDots.vue'
+import PromptIndex from './PromptIndex.vue'
+import type { Message } from '@aiui/core/types/message'
 
 withDefaults(
   defineProps<{
@@ -81,6 +92,7 @@ const messageListRef = ref<HTMLElement | null>(null)
 
 const messages = computed(() => chatStore.messages)
 const isStreaming = computed(() => chatStore.isStreaming)
+const chatCollapsed = computed(() => chatStore.chatCollapsed)
 
 const title = computed(
   () => chatStore.activeConversation?.title ?? 'New Chat'
@@ -112,6 +124,12 @@ async function handleSend(text: string) {
   await sendMessage(text)
 }
 
+function handlePromptSelect(_userMsg: Message, assistantMsg: Message | null) {
+  if (assistantMsg?.content) {
+    updatePanelFromText(assistantMsg.content, _userMsg.content, assistantMsg.webResults ?? [])
+  }
+}
+
 watch(
   () => messages.value.length,
   () => {
diff --git a/packages/app/src/components/chat/PromptIndex.vue b/packages/app/src/components/chat/PromptIndex.vue
new file mode 100644
index 00000000..ba93c899
--- /dev/null
+++ b/packages/app/src/components/chat/PromptIndex.vue
@@ -0,0 +1,111 @@
+<template>
+  <div class="flex-1 min-h-0 overflow-y-auto scrollbar-hide p-3 space-y-1">
+    <div v-if="promptPairs.length === 0" class="flex items-center justify-center h-full">
+      <p class="text-xs" :class="isDark ? 'text-white/30' : 'text-gray-400'">
+        No prompts yet
+      </p>
+    </div>
+
+    <button
+      v-for="(pair, i) in promptPairs"
+      :key="pair.userMsg.id"
+      class="w-full text-left px-3 py-2.5 rounded-xl transition-all duration-150 group"
+      :class="[
+        activeIndex === i
+          ? 'path-glass-bubble-user'
+          : isDark
+            ? 'hover:bg-white/5'
+            : 'hover:bg-black/3'
+      ]"
+      @click="selectPrompt(pair, i)"
+    >
+      <p class="text-sm leading-snug truncate"
+         :class="isDark ? 'text-white/90' : 'text-gray-800'">
+        {{ pair.userMsg.content }}
+      </p>
+      <div class="flex items-center gap-1.5 mt-1">
+        <span class="text-[10px]"
+              :class="isDark ? 'text-white/30' : 'text-gray-400'">
+          {{ formatTime(pair.userMsg.timestamp) }}
+        </span>
+        <span
+          v-for="badge in pair.badges"
+          :key="badge"
+          class="text-[9px] px-1.5 py-0.5 rounded-md"
+          :class="isDark
+            ? 'bg-white/8 text-white/40'
+            : 'bg-black/5 text-gray-500'"
+        >
+          {{ badge }}
+        </span>
+      </div>
+    </button>
+  </div>
+</template>
+
+<script setup lang="ts">
+import { computed, ref } from 'vue'
+import type { Message } from '@aiui/core/types/message'
+import { useTheme } from '@/composables/useTheme'
+import { useContentPanel } from '@/composables/useContentPanel'
+
+interface PromptPair {
+  userMsg: Message
+  assistantMsg: Message | null
+  badges: string[]
+}
+
+const props = defineProps<{
+  messages: Message[]
+}>()
+
+const emit = defineEmits<{
+  select: [userMsg: Message, assistantMsg: Message | null]
+}>()
+
+const { isDark } = useTheme()
+const { getContextualInlineContent } = useContentPanel()
+const activeIndex = ref<number | null>(null)
+
+const promptPairs = computed<PromptPair[]>(() => {
+  const pairs: PromptPair[] = []
+  const msgs = props.messages
+
+  for (let i = 0; i < msgs.length; i++) {
+    if (msgs[i].role !== 'user') continue
+
+    const userMsg = msgs[i]
+    const assistantMsg = (i + 1 < msgs.length && msgs[i + 1].role === 'assistant')
+      ? msgs[i + 1]
+      : null
+
+    const badges: string[] = []
+    if (assistantMsg && assistantMsg.content) {
+      const content = getContextualInlineContent(
+        assistantMsg.content,
+        userMsg.content,
+        assistantMsg.webResults ?? [],
+      )
+      if (content.films.length > 0) badges.push('Films')
+      if (content.songs.length > 0) badges.push('Music')
+      if (content.podcasts.length > 0) badges.push('Podcasts')
+      if (content.magazineSections.length > 0) badges.push('Magazine')
+      if ((content.newsLinks?.length ?? 0) > 0) badges.push('News')
+      if ((content.websitesLinks?.length ?? 0) > 0) badges.push('Web')
+    }
+
+    pairs.push({ userMsg, assistantMsg, badges })
+  }
+
+  return pairs
+})
+
+function selectPrompt(pair: PromptPair, index: number) {
+  activeIndex.value = index
+  emit('select', pair.userMsg, pair.assistantMsg)
+}
+
+function formatTime(ts: number): string {
+  return new Date(ts).toLocaleTimeString([], { hour: '2-digit', minute: '2-digit' })
+}
+</script>
diff --git a/packages/app/src/components/content/MagazineGrid.vue b/packages/app/src/components/content/MagazineGrid.vue
index 82f605b9..32de9fe5 100644
--- a/packages/app/src/components/content/MagazineGrid.vue
+++ b/packages/app/src/components/content/MagazineGrid.vue
@@ -15,7 +15,7 @@
 
     <div class="flex-1 overflow-y-auto custom-scrollbar">
       <!-- Query context -->
-      <div v-if="headlineText" class="px-5 pt-4 pb-1">
+      <div v-if="headlineText" class="px-5 pt-4 pb-3">
         <p class="text-[9px] uppercase tracking-[0.3em] font-medium"
            :class="isDark ? 'text-white/30' : 'text-black/40'">
           In response to
@@ -24,18 +24,19 @@
            :class="isDark ? 'text-white/60' : 'text-black/50'">
           {{ headlineText }}
         </p>
+        <div class="mt-3 h-px" :class="isDark ? 'bg-white/8' : 'bg-black/6'" />
       </div>
 
       <!-- Tile grid -->
-      <div class="px-3 py-3">
-        <div class="grid grid-cols-2 gap-[1px]"
-             :class="isDark ? 'bg-white/8' : 'bg-black/8'">
+      <div class="px-3 pt-2 pb-8">
+        <div class="grid grid-cols-2 gap-px"
+             :class="isDark ? 'bg-white/12' : 'bg-black/10'">
           <template v-for="(tile, i) in tiles" :key="i">
             <!-- Banner tile: full width with icon -->
             <div v-if="tile.type === 'banner'"
-                 class="col-span-2 flex flex-col items-center justify-center py-6 px-5"
+                 class="col-span-2 flex flex-col items-center justify-center py-8 px-5"
                  :class="isDark ? 'bg-[#0a0a0a]' : 'bg-[#faf9f6]'">
-              <svg class="w-6 h-6 mb-2" :class="isDark ? 'text-white/20' : 'text-black/15'"
+              <svg class="w-5 h-5 mb-2.5" :class="isDark ? 'text-white/20' : 'text-black/15'"
                    viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="1.5">
                 <path v-if="tile.icon === 'compass'" stroke-linecap="round" stroke-linejoin="round"
                       d="M12 2a10 10 0 100 20 10 10 0 000-20zm0 0v2m0 16v2m10-10h-2M4 12H2m15.07-5.07l-1.41 1.41M8.34 15.66l-1.41 1.41m0-11.14l1.41 1.41m7.32 7.32l1.41 1.41" />
@@ -96,12 +97,16 @@
                  :class="isDark ? 'text-white/25' : 'text-black/30'">
                 {{ tile.label }}
               </p>
-              <h3 class="font-serif text-sm font-bold leading-snug mb-1"
+              <h3 v-if="tile.title"
+                  class="font-serif text-sm font-bold leading-snug mb-1"
                   :class="isDark ? 'text-white/90' : 'text-black/85'">
                 {{ tile.title }}
               </h3>
               <p class="font-serif text-xs leading-relaxed flex-1"
-                 :class="isDark ? 'text-white/55' : 'text-black/50'">
+                 :class="[
+                   isDark ? 'text-white/55' : 'text-black/50',
+                   !tile.title ? 'italic' : ''
+                 ]">
                 {{ tile.text }}
               </p>
             </button>
@@ -186,6 +191,10 @@ const tiles = computed<Tile[]>(() => {
   for (const c of (props.query || 'brief')) seed = ((seed << 5) - seed + c.charCodeAt(0)) | 0
   const rand = () => { seed = (seed * 16807 + 0) % 2147483647; return (seed & 0x7fffffff) / 2147483647 }
 
+  // Layout rhythm: wide → half pair → banner → wide → half pair → ...
+  // This creates the New Yorker editorial cadence
+  let layoutPhase = 0 // 0=wide, 1=half-pair, 2=banner
+
   secs.forEach((section, i) => {
     const bullets = splitIntoBullets(section.content)
 
@@ -199,11 +208,12 @@ const tiles = computed<Tile[]>(() => {
         author: section.author,
         section,
       })
+      layoutPhase = 1
       return
     }
 
-    // Insert a banner between groups to break up content
-    if (i % 3 === 0 && i > 0) {
+    // Insert banner to break up content
+    if (layoutPhase === 2) {
       const bIdx = Math.floor(rand() * bannerIcons.length)
       result.push({
         type: 'banner',
@@ -212,11 +222,11 @@ const tiles = computed<Tile[]>(() => {
         icon: bannerIcons[bIdx],
         label: bannerLabels[bIdx],
       })
+      layoutPhase = 0
     }
 
-    // If the section has multiple bullets, split into individual tiles
-    if (bullets.length >= 2) {
-      // Section header as wide tile
+    if (bullets.length >= 3) {
+      // Multi-bullet section: wide header + half tiles for bullets
       result.push({
         type: 'wide',
         title: section.title,
@@ -224,35 +234,79 @@ const tiles = computed<Tile[]>(() => {
         label: section.author ? `By ${section.author}` : undefined,
         section,
       })
-      // Remaining bullets as half-width tiles in pairs
       for (let b = 1; b < bullets.length; b++) {
-        const isOdd = rand() > 0.7
+        const variant = rand() > 0.6 ? 'dark' : 'half'
         result.push({
-          type: isOdd ? 'dark' : 'half',
+          type: variant,
           title: extractBulletTitle(bullets[b]) || section.title,
           text: truncate(cleanBulletTitle(bullets[b]), 100),
           section,
         })
       }
-    } else {
-      // Single-content section: alternate between wide and half
-      const useWide = rand() > 0.5 || section.content.length > 200
+      layoutPhase = 2
+    } else if (layoutPhase === 0) {
+      // Wide tile phase
       result.push({
-        type: useWide ? 'wide' : 'half',
+        type: 'wide',
         title: section.title,
-        text: truncate(section.content, useWide ? 200 : 100),
+        text: truncate(section.content, 180),
         author: section.author,
         section,
       })
-      // If half, add a companion dark tile for visual pairing
-      if (!useWide) {
+      layoutPhase = 1
+    } else {
+      // Half-width tile phase: split content at a sentence boundary
+      const cleaned = cleanText(section.content)
+
+      // Only split if content is long enough for two meaningful tiles
+      if (cleaned.length < 120) {
+        // Too short to split — use as a half tile with a decorative companion
+        result.push({
+          type: 'half',
+          title: section.title,
+          text: truncate(section.content, 120),
+          section,
+        })
         result.push({
           type: 'dark',
+          title: '',
+          text: '',
+        })
+      } else {
+        // Find a sentence boundary (. or — or ;) after first ~40% of content
+        const target = Math.floor(cleaned.length * 0.4)
+        let splitAt = -1
+        for (const sep of ['. ', ' — ', '; ']) {
+          const idx = cleaned.indexOf(sep, target)
+          if (idx > 0 && idx < cleaned.length * 0.7) {
+            splitAt = idx + sep.length
+            break
+          }
+        }
+        // Fallback: find a word boundary near the middle
+        if (splitAt < 0) {
+          const mid = Math.floor(cleaned.length / 2)
+          const spaceIdx = cleaned.indexOf(' ', mid)
+          splitAt = spaceIdx > 0 ? spaceIdx + 1 : mid
+        }
+
+        const firstHalf = cleaned.slice(0, splitAt).trim()
+        const secondHalf = cleaned.slice(splitAt).trim()
+
+        result.push({
+          type: 'half',
           title: section.title,
-          text: truncate(section.content.slice(100), 80),
+          text: firstHalf.length > 110 ? firstHalf.slice(0, 107) + '\u2009...' : firstHalf,
+          section,
+        })
+        result.push({
+          type: 'dark',
+          title: '',
+          text: secondHalf.length > 110 ? secondHalf.slice(0, 107) + '\u2009...' : secondHalf,
           section,
         })
       }
+      layoutPhase = 2
     }
   })
 
diff --git a/packages/app/src/composables/useContentPanel.ts b/packages/app/src/composables/useContentPanel.ts
index 90e6f7aa..2b943af2 100644
--- a/packages/app/src/composables/useContentPanel.ts
+++ b/packages/app/src/composables/useContentPanel.ts
@@ -79,16 +79,16 @@ function extractUrlFromText(text: string): string | undefined {
 
 function extractAuthorFromText(text: string): string | undefined {
   const patterns = [
-    /(?:analyst|according to)\s+\*{0,2}([^*\n]+?)\*{0,2}(?:\s+(?:is|calls?|says?|cited)|\.|,)/i,
-    /\bby\s+\*{0,2}([^*\n]+?)\*{0,2}(?:\s|$|\.|,)/i,
-    /(?:source|—)\s*:?\s*\*{0,2}([^*\n]+?)\*{0,2}(?:\s|$|\.|,)/i,
-    /\*\*([^*]+)\*\*(?:\s+(?:is|calls?|says?|cited|predicts?))/,
+    /(?:analyst|according to)\s+\*{0,2}([A-Z][^*\n]+?)\*{0,2}(?:\s+(?:is|calls?|says?|cited)|\.|,)/,
+    /\bby\s+\*{0,2}([A-Z][a-zA-Z]+(?:\s+[A-Z][a-zA-Z]+)+)\*{0,2}/,
+    /(?:source|—)\s*:?\s*\*{0,2}([A-Z][^*\n]+?)\*{0,2}(?:\s|$|\.|,)/,
+    /\*\*([A-Z][^*]+)\*\*(?:\s+(?:is|calls?|says?|cited|predicts?))/,
   ]
   for (const re of patterns) {
     const m = re.exec(text)
     if (m) {
       const name = m[1].trim().slice(0, 60)
-      if (name.length > 2 && name.length < 50) return name
+      if (name.length > 3 && name.length < 50) return name
     }
   }
   return undefined
diff --git a/packages/app/src/stores/chat.ts b/packages/app/src/stores/chat.ts
index 2a862acd..3da7d51d 100644
--- a/packages/app/src/stores/chat.ts
+++ b/packages/app/src/stores/chat.ts
@@ -53,6 +53,7 @@ export const useChatStore = defineStore('chat', () => {
   const panelSide = ref<'left' | 'right'>(savedSide ?? 'left')
 
   const webSearchEnabled = ref(localStorage.getItem('aiui-web-search') !== 'false')
+  const chatCollapsed = ref(localStorage.getItem('aiui-chat-collapsed') === 'true')
 
   // Load chats from server on startup — _loaded gate prevents the watcher
   // from overwriting the file with empty data before the load completes
@@ -81,6 +82,10 @@ export const useChatStore = defineStore('chat', () => {
     localStorage.setItem('aiui-web-search', String(val))
   })
 
+  watch(chatCollapsed, (val) => {
+    localStorage.setItem('aiui-chat-collapsed', String(val))
+  })
+
   watch(
     [conversations, activeConversationId],
     ([conv, active]) => {
@@ -151,6 +156,10 @@ export const useChatStore = defineStore('chat', () => {
     panelSide.value = panelSide.value === 'right' ? 'left' : 'right'
   }
 
+  function toggleChatCollapse() {
+    chatCollapsed.value = !chatCollapsed.value
+  }
+
   function setActiveConversation(id: string) {
     if (conversations.value.has(id)) {
       activeConversationId.value = id
@@ -175,11 +184,13 @@ export const useChatStore = defineStore('chat', () => {
     loaded,
     panelSide,
     webSearchEnabled,
+    chatCollapsed,
     createConversation,
     addMessage,
     appendToLastMessage,
     setMessageWebResults,
     switchSide,
+    toggleChatCollapse,
     setActiveConversation,
     deleteConversation,
   }