diff --git a/frontend/src/components/ChatPanel.vue b/frontend/src/components/ChatPanel.vue
index 3be41ef..48c05e2 100644
--- a/frontend/src/components/ChatPanel.vue
+++ b/frontend/src/components/ChatPanel.vue
@@ -299,12 +299,22 @@ defineExpose({ focus, prefill, send })
       <!-- Message list -->
       <div ref="messagesEl" class="messages-container">
         <div class="messages-inner">
-          <ChatMessage
-            v-for="msg in store.currentConversation?.messages ?? []"
+          <template
+            v-for="(msg, index) in store.currentConversation?.messages ?? []"
             :key="msg.id"
-            :message="msg"
-            @save-as-note="handleSaveAsNote"
-          />
+          >
+            <!-- Briefing slot separator: shown before a 2nd+ briefing slot message -->
+            <div
+              v-if="briefingMode && index > 0 && msg.role === 'assistant' && msg.metadata?.rss_item_ids"
+              class="briefing-slot-separator"
+            >
+              <span>New Briefing Update</span>
+            </div>
+            <ChatMessage
+              :message="msg"
+              @save-as-note="handleSaveAsNote"
+            />
+          </template>
           <!-- Streaming bubble -->
           <ChatStreamingBubble v-if="store.streaming" />
           <!-- Queued messages -->
@@ -523,6 +533,28 @@ defineExpose({ focus, prefill, send })
   justify-content: flex-end;
 }
 
+/* Briefing slot separator */
+.briefing-slot-separator {
+  display: flex;
+  align-items: center;
+  gap: 0.75rem;
+  margin: 1.25rem 0 0.5rem;
+  color: var(--color-text-muted, #888);
+  font-size: 0.7rem;
+  font-weight: 600;
+  letter-spacing: 0.08em;
+  text-transform: uppercase;
+  opacity: 0.7;
+}
+.briefing-slot-separator::before,
+.briefing-slot-separator::after {
+  content: '';
+  flex: 1;
+  height: 1px;
+  background: var(--color-border, #333);
+  opacity: 0.5;
+}
+
 /* Context sidebar */
 .context-sidebar {
   width: 200px;
diff --git a/frontend/src/types/chat.ts b/frontend/src/types/chat.ts
index 9d97812..162dd99 100644
--- a/frontend/src/types/chat.ts
+++ b/frontend/src/types/chat.ts
@@ -28,6 +28,7 @@ export interface Message {
   context_note_id: number | null;
   context_note_title?: string | null;
   tool_calls?: ToolCallRecord[] | null;
+  metadata?: Record<string, unknown> | null;
   created_at: string;
   timing?: GenerationTiming;
   thinking?: string;
diff --git a/src/fabledassistant/services/llm.py b/src/fabledassistant/services/llm.py
index 67abd71..178e501 100644
--- a/src/fabledassistant/services/llm.py
+++ b/src/fabledassistant/services/llm.py
@@ -607,6 +607,25 @@ async def build_context(
             f"\n\n--- Earlier Conversation ---\n{history_summary}\n--- End Earlier Conversation ---"
         )
 
+    # Detect briefing conversation — used for both system prompt instruction and article injection
+    _is_briefing_conv = False
+    if conv_id is not None:
+        from fabledassistant.models import async_session as _async_session
+        from fabledassistant.models.conversation import Conversation as _Conversation
+        async with _async_session() as _sess:
+            _conv = await _sess.get(_Conversation, conv_id)
+        if _conv and getattr(_conv, "conversation_type", None) == "briefing":
+            _is_briefing_conv = True
+
+    if _is_briefing_conv:
+        system_content += (
+            "\n\nYou are in a briefing conversation. "
+            "The conversation history contains today's briefing — news stories, weather, and tasks. "
+            "When the user asks about a topic, person, or event from the briefing, answer directly "
+            "from the conversation history and the article context that follows. "
+            "Do NOT search the web for information that is already present in the briefing."
+        )
+
     context_meta: dict = {
         "context_note_id": None,
         "context_note_title": None,
@@ -769,16 +788,10 @@ async def build_context(
             )
 
     # Briefing article context for follow-up Q&A
-    if conv_id is not None:
-        from fabledassistant.models import async_session as _async_session
-        from fabledassistant.models.conversation import Conversation
-
-        async with _async_session() as _sess:
-            _conv = await _sess.get(Conversation, conv_id)
-        if _conv and getattr(_conv, "conversation_type", None) == "briefing":
-            article_context = await _build_briefing_article_context(conv_id)
-            if article_context:
-                user_context_parts.append(article_context.strip())
+    if _is_briefing_conv:
+        article_context = await _build_briefing_article_context(conv_id)  # type: ignore[arg-type]
+        if article_context:
+            user_context_parts.append(article_context.strip())
 
     # Build final user message — context prefix (if any) followed by the actual message
     if user_context_parts: