diff --git a/src/BizHawk.Client.EmuHawk/MainForm.Events.cs b/src/BizHawk.Client.EmuHawk/MainForm.Events.cs
index b4c8ddc990..c14fb8f228 100644
--- a/src/BizHawk.Client.EmuHawk/MainForm.Events.cs
+++ b/src/BizHawk.Client.EmuHawk/MainForm.Events.cs
@@ -1205,18 +1205,10 @@ namespace BizHawk.Client.EmuHawk
 
 			foreach (var item in ExtToolManager.ToolStripMenu)
 			{
-				if (item.Tag is ValueTuple<string, string> tuple)
+				if (item.Enabled && item.Tag is ValueTuple<string, string> tuple)
 				{
-					if (item.Enabled)
-					{
-						item.Click += (clickEventSender, clickEventArgs) => Tools.LoadExternalToolForm(tuple.Item1, tuple.Item2);
-					}
+					item.Click += (_, _) => Tools.LoadExternalToolForm(tuple.Item1, tuple.Item2);
 				}
-				else
-				{
-					item.Image = Properties.Resources.ExclamationRed;
-				}
-
 				ExternalToolMenuItem.DropDownItems.Add(item);
 			}
 
diff --git a/src/BizHawk.Client.EmuHawk/tools/ExternalToolManager.cs b/src/BizHawk.Client.EmuHawk/tools/ExternalToolManager.cs
index 2edfc16f8a..2394478c0e 100644
--- a/src/BizHawk.Client.EmuHawk/tools/ExternalToolManager.cs
+++ b/src/BizHawk.Client.EmuHawk/tools/ExternalToolManager.cs
@@ -71,7 +71,11 @@ namespace BizHawk.Client.EmuHawk
 		private ToolStripMenuItem GenerateToolTipFromFileName(string fileName)
 		{
 			if (fileName == null) throw new Exception();
-			var item = new ToolStripMenuItem(Path.GetFileName(fileName)) { Enabled = false };
+			var item = new ToolStripMenuItem(Path.GetFileName(fileName))
+			{
+				Enabled = false,
+				Image = Properties.Resources.ExclamationRed,
+			};
 			try
 			{
 				if (!OSTailoredCode.IsUnixHost) MotWHack.RemoveMOTW(fileName);
@@ -89,6 +93,8 @@ namespace BizHawk.Client.EmuHawk
 				{
 					foreach (var depFilename in toolAttribute.LoadAssemblyFiles) Assembly.LoadFrom($"{_paths[PathEntryCollection.GLOBAL, "External Tools"].Path}/{depFilename}");
 				}
+
+				item.Image = null; // no errors, remove error icon
 				var embeddedIconAttr = allAttrs.OfType<ExternalToolEmbeddedIconAttribute>().FirstOrDefault();
 				if (embeddedIconAttr != null)
 				{