diff --git a/crates-tauri/yaak-app/src/lib.rs b/crates-tauri/yaak-app/src/lib.rs
index 7b0311d7..d176f9bc 100644
--- a/crates-tauri/yaak-app/src/lib.rs
+++ b/crates-tauri/yaak-app/src/lib.rs
@@ -360,10 +360,8 @@ async fn cmd_grpc_go<R: Runtime>(
 
     let cb = {
         let cancelled_rx = cancelled_rx.clone();
-        let app_handle = app_handle.clone();
         let environment_chain = environment_chain.clone();
         let window = window.clone();
-        let base_msg = base_msg.clone();
         let plugin_manager = plugin_manager.clone();
         let encryption_manager = encryption_manager.clone();
 
@@ -385,8 +383,6 @@ async fn cmd_grpc_go<R: Runtime>(
             match serde_json::from_str::<IncomingMsg>(ev.payload()) {
                 Ok(IncomingMsg::Message(msg)) => {
                     let window = window.clone();
-                    let app_handle = app_handle.clone();
-                    let base_msg = base_msg.clone();
                     let environment_chain = environment_chain.clone();
                     let plugin_manager = plugin_manager.clone();
                     let encryption_manager = encryption_manager.clone();
@@ -411,19 +407,6 @@ async fn cmd_grpc_go<R: Runtime>(
                         })
                     });
                     in_msg_tx.try_send(msg.clone()).unwrap();
-                    tauri::async_runtime::spawn(async move {
-                        app_handle
-                            .db()
-                            .upsert_grpc_event(
-                                &GrpcEvent {
-                                    content: msg,
-                                    event_type: GrpcEventType::ClientMessage,
-                                    ..base_msg.clone()
-                                },
-                                &UpdateSource::from_window_label(window.label()),
-                            )
-                            .unwrap();
-                    });
                 }
                 Ok(IncomingMsg::Commit) => {
                     maybe_in_msg_tx.take();
@@ -470,12 +453,48 @@ async fn cmd_grpc_go<R: Runtime>(
         )?;
 
         async move {
+            // Create callback for streaming methods that handles both success and error
+            let on_message = {
+                let app_handle = app_handle.clone();
+                let base_event = base_event.clone();
+                let window_label = window.label().to_string();
+                move |result: std::result::Result<String, String>| match result {
+                    Ok(msg) => {
+                        let _ = app_handle.db().upsert_grpc_event(
+                            &GrpcEvent {
+                                content: msg,
+                                event_type: GrpcEventType::ClientMessage,
+                                ..base_event.clone()
+                            },
+                            &UpdateSource::from_window_label(&window_label),
+                        );
+                    }
+                    Err(error) => {
+                        let _ = app_handle.db().upsert_grpc_event(
+                            &GrpcEvent {
+                                content: format!("Failed to send message: {}", error),
+                                event_type: GrpcEventType::Error,
+                                ..base_event.clone()
+                            },
+                            &UpdateSource::from_window_label(&window_label),
+                        );
+                    }
+                }
+            };
+
             let (maybe_stream, maybe_msg) =
                 match (method_desc.is_client_streaming(), method_desc.is_server_streaming()) {
                     (true, true) => (
                         Some(
                             connection
-                                .streaming(&service, &method, in_msg_stream, &metadata, client_cert)
+                                .streaming(
+                                    &service,
+                                    &method,
+                                    in_msg_stream,
+                                    &metadata,
+                                    client_cert,
+                                    on_message.clone(),
+                                )
                                 .await,
                         ),
                         None,
@@ -490,6 +509,7 @@ async fn cmd_grpc_go<R: Runtime>(
                                     in_msg_stream,
                                     &metadata,
                                     client_cert,
+                                    on_message.clone(),
                                 )
                                 .await,
                         ),
diff --git a/crates/yaak-grpc/src/manager.rs b/crates/yaak-grpc/src/manager.rs
index 48294e7f..bd1dd17a 100644
--- a/crates/yaak-grpc/src/manager.rs
+++ b/crates/yaak-grpc/src/manager.rs
@@ -115,14 +115,18 @@ impl GrpcConnection {
         Ok(client.unary(req, path, codec).await?)
     }
 
-    pub async fn streaming(
+    pub async fn streaming<F>(
         &self,
         service: &str,
         method: &str,
         stream: ReceiverStream<String>,
         metadata: &BTreeMap<String, String>,
         client_cert: Option<ClientCertificateConfig>,
-    ) -> Result<Response<Streaming<DynamicMessage>>> {
+        on_message: F,
+    ) -> Result<Response<Streaming<DynamicMessage>>>
+    where
+        F: Fn(std::result::Result<String, String>) + Send + Sync + Clone + 'static,
+    {
         let method = &self.method(&service, &method).await?;
         let mapped_stream = {
             let input_message = method.input();
@@ -139,6 +143,8 @@ impl GrpcConnection {
                     let md = md.clone();
                     let use_reflection = use_reflection.clone();
                     let client_cert = client_cert.clone();
+                    let on_message = on_message.clone();
+                    let json_clone = json.clone();
                     async move {
                         if use_reflection {
                             if let Err(e) =
@@ -149,9 +155,13 @@ impl GrpcConnection {
                         }
                         let mut de = Deserializer::from_str(&json);
                         match DynamicMessage::deserialize(input_message, &mut de) {
-                            Ok(m) => Some(m),
+                            Ok(m) => {
+                                on_message(Ok(json_clone));
+                                Some(m)
+                            }
                             Err(e) => {
                                 warn!("Failed to deserialize message: {e}");
+                                on_message(Err(e.to_string()));
                                 None
                             }
                         }
@@ -171,14 +181,18 @@ impl GrpcConnection {
         Ok(client.streaming(req, path, codec).await?)
     }
 
-    pub async fn client_streaming(
+    pub async fn client_streaming<F>(
         &self,
         service: &str,
         method: &str,
         stream: ReceiverStream<String>,
         metadata: &BTreeMap<String, String>,
         client_cert: Option<ClientCertificateConfig>,
-    ) -> Result<Response<DynamicMessage>> {
+        on_message: F,
+    ) -> Result<Response<DynamicMessage>>
+    where
+        F: Fn(std::result::Result<String, String>) + Send + Sync + Clone + 'static,
+    {
         let method = &self.method(&service, &method).await?;
         let mapped_stream = {
             let input_message = method.input();
@@ -195,6 +209,8 @@ impl GrpcConnection {
                     let md = md.clone();
                     let use_reflection = use_reflection.clone();
                     let client_cert = client_cert.clone();
+                    let on_message = on_message.clone();
+                    let json_clone = json.clone();
                     async move {
                         if use_reflection {
                             if let Err(e) =
@@ -205,9 +221,13 @@ impl GrpcConnection {
                         }
                         let mut de = Deserializer::from_str(&json);
                         match DynamicMessage::deserialize(input_message, &mut de) {
-                            Ok(m) => Some(m),
+                            Ok(m) => {
+                                on_message(Ok(json_clone));
+                                Some(m)
+                            }
                             Err(e) => {
                                 warn!("Failed to deserialize message: {e}");
+                                on_message(Err(e.to_string()));
                                 None
                             }
                         }