diff --git a/src-tauri/src/core/setup.rs b/src-tauri/src/core/setup.rs
index ef372ec43..6883b2a3b 100644
--- a/src-tauri/src/core/setup.rs
+++ b/src-tauri/src/core/setup.rs
@@ -10,9 +10,9 @@ use tauri::{App, Emitter, Listener, Manager};
 use tauri_plugin_shell::process::{CommandChild, CommandEvent};
 use tauri_plugin_shell::ShellExt;
 use tauri_plugin_store::StoreExt;
-use tokio::time::{sleep, Duration};
-use tokio::{sync::Mutex}; // Using tokio::sync::Mutex
-                                            // MCP
+use tokio::sync::Mutex;
+use tokio::time::{sleep, Duration}; // Using tokio::sync::Mutex
+                                    // MCP
 use super::{
     cmd::{get_jan_data_folder_path, get_jan_extensions_path},
     mcp::run_mcp_commands,
@@ -220,6 +220,7 @@ pub fn setup_sidecar(app: &App) -> Result<(), String> {
 
         let app_state = app_handle_for_spawn.state::<AppState>();
         let cortex_restart_count_state = app_state.cortex_restart_count.clone();
+        let cortex_killed_intentionally_state = app_state.cortex_killed_intentionally.clone();
         let app_data_dir = get_jan_data_folder_path(app_handle_for_spawn.clone());
 
         let sidecar_command_builder = || {
@@ -274,9 +275,11 @@ pub fn setup_sidecar(app: &App) -> Result<(), String> {
             let child_to_kill_arc = child_process_clone_for_kill.clone();
             tauri::async_runtime::spawn(async move {
                 let app_state = app_handle.state::<AppState>();
-                let mut count = app_state.cortex_restart_count.lock().await;
-                *count = 5;
-                drop(count);
+                // Mark as intentionally killed to prevent restart
+                let mut killed_intentionally = app_state.cortex_killed_intentionally.lock().await;
+                *killed_intentionally = true;
+                drop(killed_intentionally);
+
                 log::info!("Received kill-sidecar event (processing async).");
                 if let Some(child) = child_to_kill_arc.lock().await.take() {
                     log::info!("Attempting to kill sidecar process...");
@@ -329,6 +332,19 @@ pub fn setup_sidecar(app: &App) -> Result<(), String> {
                             );
                             *count = 0;
                         }
+                        drop(count);
+
+                        // Only reset the intentionally killed flag if it wasn't set during spawn
+                        // This prevents overriding a concurrent kill event
+                        let mut killed_intentionally =
+                            cortex_killed_intentionally_state.lock().await;
+                        if !*killed_intentionally {
+                            // Flag wasn't set during spawn, safe to reset for future cycles
+                            *killed_intentionally = false;
+                        } else {
+                            log::info!("Kill intent detected during spawn, preserving kill flag");
+                        }
+                        drop(killed_intentionally);
                     }
 
                     let mut process_terminated_unexpectedly = false;
@@ -373,7 +389,13 @@ pub fn setup_sidecar(app: &App) -> Result<(), String> {
                         log::info!("Cleared child process lock after termination.");
                     }
 
-                    if process_terminated_unexpectedly {
+                    // Check if the process was killed intentionally
+                    let killed_intentionally = *cortex_killed_intentionally_state.lock().await;
+
+                    if killed_intentionally {
+                        log::info!("Cortex server was killed intentionally. Not restarting.");
+                        break;
+                    } else if process_terminated_unexpectedly {
                         log::warn!("Cortex server terminated unexpectedly.");
                         let mut count = cortex_restart_count_state.lock().await;
                         *count += 1;
@@ -387,9 +409,7 @@ pub fn setup_sidecar(app: &App) -> Result<(), String> {
                         sleep(Duration::from_millis(RESTART_DELAY_MS)).await;
                         continue;
                     } else {
-                        log::info!(
-                            "Cortex server terminated normally or was killed. Not restarting."
-                        );
+                        log::info!("Cortex server terminated normally. Not restarting.");
                         break;
                     }
                 }
diff --git a/src-tauri/src/core/state.rs b/src-tauri/src/core/state.rs
index 7ce3db443..cb6a5d3fa 100644
--- a/src-tauri/src/core/state.rs
+++ b/src-tauri/src/core/state.rs
@@ -11,6 +11,7 @@ pub struct AppState {
     pub mcp_servers: Arc<Mutex<HashMap<String, RunningService<RoleClient, ()>>>>,
     pub download_manager: Arc<Mutex<DownloadManagerState>>,
     pub cortex_restart_count: Arc<Mutex<u32>>,
+    pub cortex_killed_intentionally: Arc<Mutex<bool>>,
 }
 pub fn generate_app_token() -> String {
     rand::thread_rng()
diff --git a/src-tauri/src/lib.rs b/src-tauri/src/lib.rs
index 635e307c3..076984106 100644
--- a/src-tauri/src/lib.rs
+++ b/src-tauri/src/lib.rs
@@ -91,6 +91,7 @@ pub fn run() {
             mcp_servers: Arc::new(Mutex::new(HashMap::new())),
             download_manager: Arc::new(Mutex::new(DownloadManagerState::default())),
             cortex_restart_count: Arc::new(Mutex::new(0)),
+            cortex_killed_intentionally: Arc::new(Mutex::new(false)),
         })
         .setup(|app| {
             app.handle().plugin(