fix(messaging): make persistence and delivery explicit

src/bus/dispatcher.rs

@@ -56,10 +56,14 @@ impl OutboundDispatcher {
             if sender.as_ref().is_none_or(mpsc::Sender::is_closed) {
                 let Some(channel) = self.channel_manager.get_channel(&msg.channel).await else {
                     tracing::warn!(channel = %msg.channel, "No channel found for message");
+                    msg.complete_delivery(Err(format!("channel not found: {}", msg.channel)));
                     continue;
                 };
                 let (new_sender, receiver) = mpsc::channel(LANE_CAPACITY);
-                self.spawn_lane(channel, receiver, msg.channel.clone(), msg.chat_id.clone());
+                if !self.spawn_lane(channel, receiver, msg.channel.clone(), msg.chat_id.clone()) {
+                    msg.complete_delivery(Err("dispatcher is shutting down".to_string()));
+                    continue;
+                }
                 lanes.insert(lane_key.clone(), new_sender.clone());
                 sender = Some(new_sender);
             }
@@ -77,6 +81,7 @@ impl OutboundDispatcher {
                         capacity = LANE_CAPACITY,
                         "Outbound lane full; rejecting message instead of blocking other destinations"
                     );
+                    msg.complete_delivery(Err("outbound lane is full".to_string()));
                 }
                 Err(mpsc::error::TrySendError::Closed(msg)) => {
                     // The lane may have expired between the closed check and
@@ -84,13 +89,25 @@ impl OutboundDispatcher {
                     lanes.remove(&lane_key);
                     let Some(channel) = self.channel_manager.get_channel(&msg.channel).await else {
                         tracing::warn!(channel = %msg.channel, "No channel found for message");
+                        msg.complete_delivery(Err(format!("channel not found: {}", msg.channel)));
                         continue;
                     };
                     let (new_sender, receiver) = mpsc::channel(LANE_CAPACITY);
-                    self.spawn_lane(channel, receiver, msg.channel.clone(), msg.chat_id.clone());
+                    if !self.spawn_lane(channel, receiver, msg.channel.clone(), msg.chat_id.clone())
-                    if new_sender.try_send(msg).is_ok() {
+                    {
+                        msg.complete_delivery(Err("dispatcher is shutting down".to_string()));
+                        continue;
+                    }
+                    match new_sender.try_send(msg) {
+                        Ok(()) => {
                             lanes.insert(lane_key, new_sender);
                         }
+                        Err(error) => {
+                            error.into_inner().complete_delivery(Err(
+                                "outbound lane could not be restarted during shutdown".to_string(),
+                            ));
+                        }
+                    }
                 }
             }
         }
@@ -102,7 +119,7 @@ impl OutboundDispatcher {
         mut receiver: mpsc::Receiver<OutboundMessage>,
         channel_name: String,
         chat_id: String,
-    ) {
+    ) -> bool {
         self.task_supervisor.spawn(
             format!("outbound-lane:{channel_name}:{chat_id}"),
             async move {
@@ -111,7 +128,8 @@ impl OutboundDispatcher {
                         Ok(Some(msg)) => msg,
                         Ok(None) | Err(_) => break,
                     };
-                    if let Err(error) = Self::send_with_retry(&*channel, msg).await {
+                    let result = Self::send_with_retry(&*channel, &msg).await;
+                    if let Err(error) = &result {
                         tracing::error!(
                             channel = %channel_name,
                             chat_id = %chat_id,
@@ -119,14 +137,15 @@ impl OutboundDispatcher {
                             "Failed to send message after retries"
                         );
                     }
+                    msg.complete_delivery(result.map_err(|error| error.to_string()));
                 }
             },
-        );
+        )
     }
 
     async fn send_with_retry(
         channel: &dyn Channel,
-        msg: OutboundMessage,
+        msg: &OutboundMessage,
     ) -> Result<(), ChannelError> {
         const DELAYS: &[u64] = &[1, 2, 4];
 
@@ -201,6 +220,7 @@ mod tests {
             reply_to: None,
             media: vec![],
             metadata: HashMap::new(),
+            delivery: None,
         }
     }
 
@@ -247,4 +267,49 @@ mod tests {
         task.abort();
         supervisor.shutdown(Duration::from_secs(1)).await;
     }
+
+    #[tokio::test]
+    async fn confirmed_delivery_reports_missing_channel() {
+        let bus = MessageBus::new(8);
+        let manager = ChannelManager::with_bus(
+            Arc::new(crate::channels::CliChatChannel::new()),
+            bus.clone(),
+        );
+        let supervisor = TaskSupervisor::new();
+        let dispatcher = OutboundDispatcher::new(bus.clone(), manager, supervisor.clone());
+        let task = tokio::spawn(async move { dispatcher.run().await });
+
+        let mut message = outbound("missing", "not delivered");
+        message.channel = "missing".to_string();
+        let error = bus.deliver_outbound(message).await.unwrap_err();
+
+        assert!(matches!(error, crate::bus::BusError::DeliveryFailed(_)));
+        task.abort();
+        supervisor.shutdown(Duration::from_secs(1)).await;
+    }
+
+    #[tokio::test]
+    async fn confirmed_delivery_waits_for_channel_send() {
+        let bus = MessageBus::new(8);
+        let manager = ChannelManager::with_bus(
+            Arc::new(crate::channels::CliChatChannel::new()),
+            bus.clone(),
+        );
+        let channel = Arc::new(RecordingChannel {
+            sent: Mutex::new(Vec::new()),
+            notify: Notify::new(),
+        });
+        manager.register_channel("recording", channel.clone()).await;
+        let supervisor = TaskSupervisor::new();
+        let dispatcher = OutboundDispatcher::new(bus.clone(), manager, supervisor.clone());
+        let task = tokio::spawn(async move { dispatcher.run().await });
+
+        bus.deliver_outbound(outbound("confirmed", "delivered"))
+            .await
+            .unwrap();
+
+        assert_eq!(channel.sent.lock().await.as_slice(), &["delivered"]);
+        task.abort();
+        supervisor.shutdown(Duration::from_secs(1)).await;
+    }
 }

src/bus/message.rs

@@ -276,6 +276,15 @@ pub struct OutboundMessage {
     pub reply_to: Option<String>,
     pub media: Vec<MediaItem>,
     pub metadata: HashMap<String, String>,
+    pub(crate) delivery: Option<tokio::sync::watch::Sender<Option<Result<(), String>>>>,
+}
+
+impl OutboundMessage {
+    pub(crate) fn complete_delivery(&self, result: Result<(), String>) {
+        if let Some(delivery) = &self.delivery {
+            delivery.send_replace(Some(result));
+        }
+    }
 }
 
 // ============================================================================

src/bus/mod.rs

@@ -68,6 +68,25 @@ impl MessageBus {
             .map_err(|_| BusError::Closed)
     }
 
+    /// Publish an outbound message and wait for the dispatcher to report the
+    /// actual channel delivery result.
+    pub async fn deliver_outbound(&self, mut msg: OutboundMessage) -> Result<(), BusError> {
+        let (delivery_tx, mut delivery_rx) = tokio::sync::watch::channel(None);
+        msg.delivery = Some(delivery_tx);
+        self.publish_outbound(msg).await?;
+
+        tokio::time::timeout(std::time::Duration::from_secs(120), async {
+            loop {
+                delivery_rx.changed().await.map_err(|_| BusError::Closed)?;
+                if let Some(result) = delivery_rx.borrow().clone() {
+                    return result.map_err(BusError::DeliveryFailed);
+                }
+            }
+        })
+        .await
+        .map_err(|_| BusError::DeliveryTimedOut)?
+    }
+
     /// Consume an outbound message (Dispatcher -> Bus)
     pub async fn consume_outbound(&self) -> Option<OutboundMessage> {
         self.outbound_rx.lock().await.recv().await
@@ -95,12 +114,16 @@ impl MessageBus {
 #[derive(Debug)]
 pub enum BusError {
     Closed,
+    DeliveryFailed(String),
+    DeliveryTimedOut,
 }
 
 impl std::fmt::Display for BusError {
     fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
         match self {
             BusError::Closed => write!(f, "Bus channel closed"),
+            BusError::DeliveryFailed(error) => write!(f, "Outbound delivery failed: {error}"),
+            BusError::DeliveryTimedOut => write!(f, "Outbound delivery confirmation timed out"),
         }
     }
 }

src/channels/cli_chat.rs

@@ -650,6 +650,7 @@ mod tests {
                 reply_to: None,
                 media: Vec::new(),
                 metadata: Default::default(),
+                delivery: None,
             })
             .await
             .unwrap();

src/gateway/mod.rs

@@ -226,6 +226,7 @@ impl GatewayState {
                                     reply_to: None,
                                     media: vec![],
                                     metadata: inbound.forwarded_metadata,
+                                    delivery: None,
                                 };
                                 if let Err(e) = bus.publish_outbound(outbound).await {
                                     tracing::error!(error = %e, "Failed to publish outbound");
@@ -239,6 +240,7 @@ impl GatewayState {
                                     reply_to: None,
                                     media: vec![],
                                     metadata: inbound.forwarded_metadata,
+                                    delivery: None,
                                 };
                                 if let Err(e) = bus.publish_outbound(outbound).await {
                                     tracing::error!(error = %e, "Failed to publish outbound");

src/session/session.rs

@@ -98,6 +98,9 @@ pub struct Session {
     /// not overwrite a session that was changed by a command such as /clear or
     /// /delete while the slow work was in flight.
     state_version: u64,
+    /// Serializes durable mutations while allowing the session state mutex to
+    /// be released during SQLite I/O.
+    persistence_lock: Arc<Mutex<()>>,
 }
 
 /// A task to be processed by the per-session agent worker
@@ -171,6 +174,7 @@ impl Session {
             current_cancel: None,
             worker_generation: 0,
             state_version: 0,
+            persistence_lock: Arc::new(Mutex::new(())),
         })
     }
 
@@ -346,6 +350,7 @@ impl Session {
             current_cancel: None,
             worker_generation: 0,
             state_version: 0,
+            persistence_lock: Arc::new(Mutex::new(())),
         })
     }
 
@@ -354,22 +359,6 @@ impl Session {
         self.id.to_string()
     }
 
-    /// 添加消息到历史并持久化到 Storage
-    /// 如果 `persist` 为 false，只更新内存（用于 compaction 场景）
-    pub async fn add_message(
-        &mut self,
-        message: ChatMessage,
-        persist: bool,
-    ) -> Result<(), StorageError> {
-        let message_id = message.id.clone();
-        let snapshot = self.add_message_in_memory(message, persist);
-        if let Err(error) = persist_added_message(snapshot).await {
-            self.rollback_message_suffix(std::slice::from_ref(&message_id));
-            return Err(error);
-        }
-        Ok(())
-    }
-
     fn add_message_in_memory(
         &mut self,
         message: ChatMessage,
@@ -480,30 +469,6 @@ impl Session {
         &self.messages
     }
 
-    /// 清除历史消息
-    pub fn clear_history(&mut self) {
-        let len = self.messages.len();
-        self.messages.clear();
-        self.seq_counter = 1;
-        self.total_message_count = 0;
-        self.message_count = 0;
-        self.state_version = self.state_version.wrapping_add(1);
-        #[cfg(debug_assertions)]
-        tracing::debug!(session_id = %self.id, previous_len = len, "Chat history cleared");
-    }
-
-    /// 重置对话上下文
-    pub fn reset_context(&mut self) {
-        let len = self.messages.len();
-        self.messages.clear();
-        self.seq_counter = 1;
-        self.total_message_count = 0;
-        self.message_count = 0;
-        self.state_version = self.state_version.wrapping_add(1);
-        #[cfg(debug_assertions)]
-        tracing::debug!(session_id = %self.id, previous_len = len, "Chat context reset in memory");
-    }
-
     pub fn create_user_message(&self, content: &str, media_refs: Vec<MediaRef>) -> ChatMessage {
         if media_refs.is_empty() {
             ChatMessage::user(content)
@@ -535,14 +500,6 @@ impl Session {
         message
     }
 
-    /// 将 session 元数据写回 Storage
-    pub async fn persist_session_meta(&self) -> Result<(), StorageError> {
-        if let Some((storage, meta)) = self.session_meta_snapshot() {
-            storage.upsert_session(&meta).await?;
-        }
-        Ok(())
-    }
-
     fn session_meta_snapshot(
         &self,
     ) -> Option<(StdArc<Storage>, crate::storage::session::SessionMeta)> {
@@ -1079,6 +1036,7 @@ impl SessionManager {
                     reply_to: None,
                     media: vec![],
                     metadata: std::collections::HashMap::new(),
+                    delivery: None,
                 };
                 let _ = sm_bus.publish_outbound(outbound).await;
             }
@@ -1701,17 +1659,28 @@ impl SessionManager {
     ) -> Result<(), AgentError> {
         // Update in-memory session
         let session = self.get_or_create_session(session_id).await?;
+        let persistence_lock = { session.lock().await.persistence_lock.clone() };
+        let _persistence_guard = persistence_lock.lock().await;
+        let meta_snapshot = {
             let mut session_guard = session.lock().await;
             session_guard.title = title.to_string();
-        session_guard
+            session_guard.state_version = session_guard.state_version.wrapping_add(1);
-            .persist_session_meta()
+            session_guard.session_meta_snapshot()
+        };
+        if let Some((storage, meta)) = meta_snapshot {
+            storage
+                .upsert_session(&meta)
                 .await
                 .map_err(|e| AgentError::Other(format!("failed to rename dialog: {}", e)))?;
+        }
         Ok(())
     }
 
     pub async fn delete_dialog(&self, session_id: &UnifiedSessionId) -> Result<(), AgentError> {
         let session_id_str = session_id.to_string();
+        let session = self.get_or_create_session(session_id).await?;
+        let persistence_lock = { session.lock().await.persistence_lock.clone() };
+        let _persistence_guard = persistence_lock.lock().await;
 
         // Soft delete from Storage
         self.storage
@@ -1730,6 +1699,9 @@ impl SessionManager {
 
     pub async fn archive_dialog(&self, session_id: &UnifiedSessionId) -> Result<(), AgentError> {
         let session_id_str = session_id.to_string();
+        let session = self.get_or_create_session(session_id).await?;
+        let persistence_lock = { session.lock().await.persistence_lock.clone() };
+        let _persistence_guard = persistence_lock.lock().await;
         self.storage
             .archive_session(&session_id_str)
             .await
@@ -1842,8 +1814,6 @@ impl SessionManager {
     ) -> Result<(), AgentError> {
         let unified_id = self.resolve_dialog_id(channel, chat_id).await?;
         let session = self.get_or_create_session(&unified_id).await?;
-        {
-            let mut guard = session.lock().await;
         let source = MessageSource {
             kind: SourceKind::SystemNotification,
             from_channel: None,
@@ -1853,11 +1823,9 @@ impl SessionManager {
             task_id: task_id.map(|s| s.to_string()),
         };
         let msg = ChatMessage::assistant_with_source(content, source);
-            guard
+        append_persisted_messages(&session, vec![msg])
-                .add_message(msg, true)
             .await
             .map_err(|e| AgentError::Other(format!("persist error: {}", e)))?;
-        }
 
         let outbound = OutboundMessage {
             channel: channel.to_string(),
@@ -1866,9 +1834,10 @@ impl SessionManager {
             reply_to: None,
             media: vec![],
             metadata: HashMap::new(),
+            delivery: None,
         };
         self.bus
-            .publish_outbound(outbound)
+            .deliver_outbound(outbound)
             .await
             .map_err(|e| AgentError::Other(format!("bus publish error: {}", e)))?;
 
@@ -2014,6 +1983,8 @@ async fn maybe_generate_title_outside_lock(session: Arc<Mutex<Session>>) -> Resu
         .map_err(|e| AgentError::Other(format!("LLM call failed: {}", e)))?;
     let title = response.content.trim().to_string();
 
+    let persistence_lock = { session.lock().await.persistence_lock.clone() };
+    let _persistence_guard = persistence_lock.lock().await;
     let meta_snapshot = {
         let mut guard = session.lock().await;
         if guard.apply_generated_title(title) {
@@ -2033,22 +2004,6 @@ async fn maybe_generate_title_outside_lock(session: Arc<Mutex<Session>>) -> Resu
     Ok(())
 }
 
-async fn persist_added_message(
-    snapshot: Option<MessagePersistSnapshot>,
-) -> Result<(), StorageError> {
-    let Some((storage, session_id, msg_meta, session_meta)) = snapshot else {
-        return Ok(());
-    };
-
-    storage
-        .persist_message_batch_with_retry(
-            &session_id,
-            std::slice::from_ref(&msg_meta),
-            &session_meta,
-        )
-        .await
-}
-
 async fn persist_added_messages(
     snapshots: Vec<Option<MessagePersistSnapshot>>,
 ) -> Result<(), StorageError> {
@@ -2081,6 +2036,32 @@ async fn persist_added_messages(
         .await
 }
 
+async fn append_persisted_messages(
+    session: &Arc<Mutex<Session>>,
+    messages: Vec<ChatMessage>,
+) -> Result<(), StorageError> {
+    if messages.is_empty() {
+        return Ok(());
+    }
+
+    let persistence_lock = { session.lock().await.persistence_lock.clone() };
+    let _persistence_guard = persistence_lock.lock().await;
+    let message_ids: Vec<_> = messages.iter().map(|message| message.id.clone()).collect();
+    let snapshots = {
+        let mut guard = session.lock().await;
+        messages
+            .into_iter()
+            .map(|message| guard.add_message_in_memory(message, true))
+            .collect()
+    };
+
+    if let Err(error) = persist_added_messages(snapshots).await {
+        session.lock().await.rollback_message_suffix(&message_ids);
+        return Err(error);
+    }
+    Ok(())
+}
+
 fn spawn_agent_worker(
     mut task_rx: mpsc::Receiver<AgentTask>,
     session: Arc<Mutex<Session>>,
@@ -2122,6 +2103,7 @@ fn spawn_agent_worker(
                                     reply_to: None,
                                     media: vec![],
                                     metadata,
+                                    delivery: None,
                                 };
                                 let _ = bus.publish_outbound(outbound).await;
                             }
@@ -2134,6 +2116,30 @@ fn spawn_agent_worker(
                 // /stop and other commands are not blocked behind slow I/O or
                 // LLM-backed compaction.
                 let skills_prompt = skills_loader.build_skills_prompt();
+                let user_message = {
+                    let guard = session.lock().await;
+                    if guard.worker_generation != worker_gen {
+                        return;
+                    }
+                    let media_refs: Vec<MediaRef> =
+                        task.media.iter().map(MediaItem::to_media_ref).collect();
+                    guard.create_user_message(&task.content, media_refs)
+                };
+                if let Err(e) = append_persisted_messages(&session, vec![user_message]).await {
+                    tracing::error!(error = %e, "Failed to persist user message");
+                    let err_outbound = OutboundMessage {
+                        channel: task_chan.clone(),
+                        chat_id: task_cid.clone(),
+                        content: "Failed to save your message, please try again.".to_string(),
+                        reply_to: None,
+                        media: vec![],
+                        metadata: HashMap::new(),
+                        delivery: None,
+                    };
+                    let _ = bus.publish_outbound(err_outbound).await;
+                    continue 'tasks;
+                }
+
                 let (agent, history_raw, mut compressor, base_version, cancel_rx) = {
                     let mut guard = session.lock().await;
 
@@ -2141,31 +2147,6 @@ fn spawn_agent_worker(
                         return; // stale worker
                     }
 
-                    let media_refs: Vec<MediaRef> =
-                        task.media.iter().map(|m| m.to_media_ref()).collect();
-                    let user_message = guard.create_user_message(&task.content, media_refs);
-                    let user_message_id = user_message.id.clone();
-                    let user_persist = guard.add_message_in_memory(user_message, true);
-                    if let Err(e) = persist_added_message(user_persist).await {
-                        guard.rollback_message_suffix(std::slice::from_ref(&user_message_id));
-                        drop(guard);
-                        tracing::error!(error = %e, "Failed to persist user message");
-                        let err_outbound = OutboundMessage {
-                            channel: task_chan.clone(),
-                            chat_id: task_cid.clone(),
-                            content: "Failed to save your message, please try again."
-                                .to_string(),
-                            reply_to: None,
-                            media: vec![],
-                            metadata: HashMap::new(),
-                        };
-                        let _ = bus.publish_outbound(err_outbound).await;
-                        continue 'tasks;
-                    }
-                    if guard.worker_generation != worker_gen {
-                        return;
-                    }
-
                     let history_raw = guard.get_history().to_vec();
 
                     let agent = match guard.create_agent_with_notify(notify_tx) {
@@ -2180,6 +2161,7 @@ fn spawn_agent_worker(
                                 reply_to: None,
                                 media: vec![],
                                 metadata: HashMap::new(),
+                                delivery: None,
                             };
                             let _ = bus.publish_outbound(err_outbound).await;
                             continue 'tasks;
@@ -2332,6 +2314,7 @@ fn spawn_agent_worker(
                                             reply_to: None,
                                             media: vec![],
                                             metadata: HashMap::new(),
+                                            delivery: None,
                                         };
                                         let _ = bus2.publish_outbound(err_outbound).await;
                                         return;
@@ -2390,6 +2373,7 @@ fn spawn_agent_worker(
                                         reply_to: None,
                                         media: vec![],
                                         metadata: HashMap::new(),
+                                        delivery: None,
                                     };
                                     let _ = bus2.publish_outbound(err_outbound).await;
                                     return;
@@ -2405,29 +2389,24 @@ fn spawn_agent_worker(
                                 reply_to: None,
                                 media: vec![],
                                 metadata: HashMap::new(),
+                                delivery: None,
                             };
                             let _ = bus2.publish_outbound(err_outbound).await;
                             return;
                         }
                     };
 
-                    let response = {
+                    let response_content = result.final_response.content;
-                        let mut guard = session2.lock().await;
+                    let total_tokens = result.total_tokens;
-                        let mut persist_snapshots = Vec::new();
+                    let response =
-                        let mut message_ids = Vec::new();
+                        if let Err(e) = append_persisted_messages(&session2, result.emitted_messages).await {
-                        for msg in result.emitted_messages {
-                            message_ids.push(msg.id.clone());
-                            persist_snapshots.push(guard.add_message_in_memory(msg, true));
-                        }
-                        let sent_count = guard.messages.len();
-                        guard.compressor.set_last_api_info(sent_count, result.total_tokens);
-                        if let Err(e) = persist_added_messages(persist_snapshots).await {
-                            guard.rollback_message_suffix(&message_ids);
                             tracing::error!(error = %e, "Failed to atomically persist agent turn");
                             None
                         } else {
-                            Some(result.final_response.content)
+                            let mut guard = session2.lock().await;
-                        }
+                            let sent_count = guard.messages.len();
+                            guard.compressor.set_last_api_info(sent_count, total_tokens);
+                            Some(response_content)
                         };
 
                     let Some(response) = response else {
@@ -2439,6 +2418,7 @@ fn spawn_agent_worker(
                             reply_to: None,
                             media: vec![],
                             metadata: HashMap::new(),
+                            delivery: None,
                         };
                         let _ = bus2.publish_outbound(err_outbound).await;
                         return;
@@ -2455,6 +2435,7 @@ fn spawn_agent_worker(
                         reply_to: None,
                         media: vec![],
                         metadata: HashMap::new(),
+                        delivery: None,
                     };
                     let _ = bus2.publish_outbound(outbound).await;
                 };
@@ -2533,6 +2514,8 @@ impl SessionManager {
         unified_id: &UnifiedSessionId,
     ) -> Result<(), AgentError> {
         let session = self.get_or_create_session(unified_id).await?;
+        let persistence_lock = { session.lock().await.persistence_lock.clone() };
+        let _persistence_guard = persistence_lock.lock().await;
         let (storage, session_id, meta_snapshot) = {
             let mut session_guard = session.lock().await;
             // Clear in-memory
@@ -2618,15 +2601,11 @@ impl OutboundMessenger for SessionManager {
             format!("[message from {}] \n{}", origin, content)
         };
 
-        // Write source-tagged assistant message to target session history
+        // Write the same text and media delivered to the target into history.
-        {
+        let msg = outbound_history_message(marked_content.clone(), source, &media);
-            let mut guard = session.lock().await;
+        append_persisted_messages(&session, vec![msg])
-            let msg = ChatMessage::assistant_with_source(marked_content.clone(), source);
-            guard
-                .add_message(msg, true)
             .await
             .map_err(|e| e.to_string())?;
-        }
 
         // Restore active dialog if source and target share channel:chat_id but differ in dialog_id
         if let Some(ref origin_id) = origin_id {
@@ -2653,9 +2632,10 @@ impl OutboundMessenger for SessionManager {
             reply_to: None,
             media,
             metadata: HashMap::new(),
+            delivery: None,
         };
         self.bus
-            .publish_outbound(outbound)
+            .deliver_outbound(outbound)
             .await
             .map_err(|e| e.to_string())?;
 
@@ -2663,6 +2643,16 @@ impl OutboundMessenger for SessionManager {
     }
 }
 
+fn outbound_history_message(
+    content: impl Into<String>,
+    source: MessageSource,
+    media: &[MediaItem],
+) -> ChatMessage {
+    let mut message = ChatMessage::assistant_with_source(content, source);
+    message.media_refs = media.iter().map(MediaItem::to_media_ref).collect();
+    message
+}
+
 fn format_task_notification(
     task_id: &str,
     status: &crate::agent::TaskStatus,
@@ -2680,3 +2670,27 @@ fn format_task_notification(
         crate::agent::TaskStatus::TimedOut => format!("📋 后台任务超时\n\n任务 ID: {}", task_id),
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn outbound_history_preserves_delivered_media() {
+        let source = MessageSource {
+            kind: SourceKind::CrossChannel,
+            from_channel: Some("cli_chat".into()),
+            from_session: Some("cli_chat:source:dialog".into()),
+            from_user_id: None,
+            system_name: None,
+            task_id: None,
+        };
+        let media = vec![MediaItem::new("/tmp/report.pdf", "file")];
+
+        let message = outbound_history_message("report", source, &media);
+
+        assert_eq!(message.media_refs.len(), 1);
+        assert_eq!(message.media_refs[0].path, "/tmp/report.pdf");
+        assert_eq!(message.media_refs[0].media_type, "file");
+    }
+}