diff --git a/main/src/core/MonoDevelop.Ide/MonoDevelop.Components.Commands/CommandManager.cs b/main/src/core/MonoDevelop.Ide/MonoDevelop.Components.Commands/CommandManager.cs
index f2bafbd9225..1f3792e0c06 100644
--- a/main/src/core/MonoDevelop.Ide/MonoDevelop.Components.Commands/CommandManager.cs
+++ b/main/src/core/MonoDevelop.Ide/MonoDevelop.Components.Commands/CommandManager.cs
@@ -97,6 +97,7 @@ enum JIS_VKS {
 
 #if MAC
 		Foundation.NSObject keyMonitor;
+		Foundation.NSObject closeWindowMonitor;
 		uint throttleLastEventTime = 0;
 #endif
 
@@ -124,6 +125,12 @@ public CommandManager (Window root)
 			ActionCommand c = new ActionCommand (CommandSystemCommands.ToolbarList, "Toolbar List", null, null, ActionType.Check);
 			c.CommandArray = true;
 			RegisterCommand (c);
+
+			closeWindowMonitor = Foundation.NSNotificationCenter.DefaultCenter.AddObserver (AppKit.NSWindow.WillCloseNotification, (s) => {
+				if (topLevelWindows.Any (h => h.nativeWidget == s.Object)) {
+					TopLevelDestroyed (s.Object, EventArgs.Empty);
+				}
+			});
 		}
 
 		/// <summary>
@@ -869,13 +876,18 @@ void TopLevelDestroyed (object o, EventArgs args)
 		{
 			RegisterUserInteraction ();
 
-			Gtk.Window w = (Gtk.Window)o;
-			w.Destroyed -= TopLevelDestroyed;
-			w.KeyPressEvent -= OnKeyPressed;
-			w.KeyReleaseEvent -= OnKeyReleased;
-			w.ButtonPressEvent -= HandleButtonPressEvent;
-			topLevelWindows.Remove (w);
+			if (o is Gtk.Window w) {
+				w.Destroyed -= TopLevelDestroyed;
+				w.KeyPressEvent -= OnKeyPressed;
+				w.KeyReleaseEvent -= OnKeyReleased;
+				w.ButtonPressEvent -= HandleButtonPressEvent;
+				topLevelWindows.Remove (w);
+			}
 #if MAC
+			else if (o is AppKit.NSWindow nsWindow) {
+				topLevelWindows.Remove (nsWindow);
+			}
+
 			if (topLevelWindows.Count == 0) {
 				if (keyMonitor != null) {
 					AppKit.NSEvent.RemoveMonitor (keyMonitor);
@@ -884,7 +896,7 @@ void TopLevelDestroyed (object o, EventArgs args)
 			}
 #endif
 
-			if (w == lastFocused?.nativeWidget)
+			if (o == lastFocused?.nativeWidget)
 				lastFocused = null;
 		}
 		
@@ -898,6 +910,11 @@ public void Dispose ()
 				AppKit.NSEvent.RemoveMonitor (keyMonitor);
 				keyMonitor = null;
 			}
+
+			if (closeWindowMonitor != null) {
+				AppKit.NSEvent.RemoveMonitor (closeWindowMonitor);
+				closeWindowMonitor = null;
+			}
 #endif
 
 			if (bindings != null) {
diff --git a/main/src/core/MonoDevelop.Ide/MonoDevelop.Ide.Commands/WindowCommands.cs b/main/src/core/MonoDevelop.Ide/MonoDevelop.Ide.Commands/WindowCommands.cs
index 230a36b320c..24c46b9fbab 100644
--- a/main/src/core/MonoDevelop.Ide/MonoDevelop.Ide.Commands/WindowCommands.cs
+++ b/main/src/core/MonoDevelop.Ide/MonoDevelop.Ide.Commands/WindowCommands.cs
@@ -253,26 +253,39 @@ internal class OpenWindowListHandler : CommandHandler
 		protected override void Update (CommandArrayInfo info)
 		{
 			foreach (Components.Window window in IdeApp.CommandService.TopLevelWindowStack) {
+
+				string title = null;
+				bool hasTopLevel = false;
+
+				try {
+					title = window.Title;
+					hasTopLevel = window.HasTopLevelFocus;
 #if !WINDOWS
-				//we don't want include hidden windows
-				if (!window.IsRealized || !window.IsVisible || Components.Mac.GtkMacInterop.IsGdkQuartzWindow (window))
-					continue;
+					//we don't want include hidden windows
+					if (!window.IsRealized || !window.IsVisible || Components.Mac.GtkMacInterop.IsGdkQuartzWindow (window))
+						continue;
 #endif
+				} catch (System.Exception ex) {
+					LoggingService.LogInternalError (ex);
+					//we log the issue
+					continue;
+				}
+
 
 				//Create CommandInfo object
 				var commandInfo = new CommandInfo ();
-				commandInfo.Text = window.Title.Replace ("_", "__").Replace ("-", "\u2013").Replace (" \u2013 " + BrandingService.ApplicationName, "");
+				commandInfo.Text = title.Replace ("_", "__").Replace ("-", "\u2013").Replace (" \u2013 " + BrandingService.ApplicationName, "");
 
 				if (string.IsNullOrEmpty (commandInfo.Text)) {
 					commandInfo.Text = GettextCatalog.GetString ("No description");
 				}
 
-				if (window.HasTopLevelFocus) 
+				if (hasTopLevel) 
 					commandInfo.Checked = true;
 				commandInfo.Description = GettextCatalog.GetString ("Activate window '{0}'", commandInfo.Text);
 
 				//Add menu item
-				info.Add (commandInfo, window.Title);
+				info.Add (commandInfo, title);
 			}
 		}