diff --git a/Wabbajack.Common/ExtensionManager.cs b/Wabbajack.Common/ExtensionManager.cs
index 98aeb8c9..76afdd6d 100644
--- a/Wabbajack.Common/ExtensionManager.cs
+++ b/Wabbajack.Common/ExtensionManager.cs
@@ -28,6 +28,14 @@ namespace Wabbajack.Common
             {"PerceivedType", "Compressed"}
         };
 
+        public static bool NeedsUpdating(string appPath)
+        {
+            var progIDKey = Registry.CurrentUser.OpenSubKey(ProgIDPath);
+            var tempKey = progIDKey?.OpenSubKey("shell\\open\\command");
+            if (progIDKey == null || tempKey == null) return true;
+            return tempKey.GetValue("").ToString().Equals($"\"{appPath}\" -i \"%1\"");
+        }
+
         public static bool IsAssociated(string appPath)
         {
             var progIDKey = Registry.CurrentUser.OpenSubKey(ProgIDPath);
diff --git a/Wabbajack/AppState.cs b/Wabbajack/AppState.cs
index bf7c649a..fcc8f9ba 100644
--- a/Wabbajack/AppState.cs
+++ b/Wabbajack/AppState.cs
@@ -86,17 +86,7 @@ namespace Wabbajack
             }
 
             var appPath = Assembly.GetExecutingAssembly().Location;
-            var iconPath = Path.Combine(Path.GetDirectoryName(appPath), "wabbajack.ico");
-            if(!File.Exists(iconPath))
-            {
-                using (var s = Utils.GetResourceStream("Wabbajack.UI.Icons.icon-embedded.ico"))
-                using (var fs = new FileStream(iconPath, FileMode.Create))
-                {
-                    s.CopyTo(fs);
-                }
-            }
-
-            if (!ExtensionManager.IsAssociated(appPath))
+            if (!(ExtensionManager.IsAssociated(appPath) || ExtensionManager.NeedsUpdating(appPath)))
             {
                 ExtensionManager.Associate(appPath);
             }