diff --git a/CHANGELOG.md b/CHANGELOG.md
index a1f6990f..8f87f31d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -116,8 +116,12 @@ Status of the `main` branch. Changes prior to the next official version change w
 
 * Dashboard:
   - Fix: Serena PyPI version check triggered by callback on main thread could delay agent startup #1774
-  - Fix: on macOS, the `tray_manager` interface put an icon in the Dock and in the app switcher
-    (should only use menu bar icon)
+  - Improvements in `tray_manager` interface mode:
+    - Fix: on macOS, the `tray_manager` interface put an icon in the Dock and in the app switcher
+      (should only use menu bar icon)
+    - On Serena shutdown, message the tray manager before lengthy project shutdowns
+    - Fix: When dead ports are detected (Serena instance gone), explicitly update the tray menu 
+      immediately (may not update automatically)
   - Use `tray_manager` interface as new default on macOS
 
 * Hooks:
diff --git a/src/serena/agent.py b/src/serena/agent.py
index 898bfcab..175f338b 100644
--- a/src/serena/agent.py
+++ b/src/serena/agent.py
@@ -1472,10 +1472,7 @@ class SerenaAgent:
         Shutdown handler of the agent, freeing resources and stopping background tasks.
         """
         log.info("SerenaAgent is shutting down ...")
-        if self._active_project is not None:
-            log.info(f"Shutting down active project '{self._active_project.project_name}' ...")
-            self._active_project.shutdown(timeout=timeout)
-            self._active_project = None
+        # apply shutdown depending on allocated resources, handling quick ones first (dashboard manager & GUI viewer)
         if self._gui_log_viewer:
             log.info("Stopping the GUI log window ...")
             self._gui_log_viewer.stop()
@@ -1483,6 +1480,10 @@ class SerenaAgent:
         if self._dashboard_manager:
             self._dashboard_manager.shutdown()
             self._dashboard_manager = None
+        if self._active_project is not None:
+            log.info(f"Shutting down active project '{self._active_project.project_name}' ...")
+            self._active_project.shutdown(timeout=timeout)
+            self._active_project = None
 
     def shutdown(self) -> None:
         """
diff --git a/src/serena/dashboard.py b/src/serena/dashboard.py
index b92fcb51..1a1718a2 100644
--- a/src/serena/dashboard.py
+++ b/src/serena/dashboard.py
@@ -1155,6 +1155,7 @@ class SerenaDashboardTrayManager:
                         for port in dead_ports:
                             self._instances.pop(port, None)
                             log.info("Removed unreachable instance on port %d", port)
+                    self._update_menu()
 
                 # terminate if no instances remain
                 with self._lock: