diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI/Helpers/IconCacheService.cs b/src/modules/cmdpal/Microsoft.CmdPal.UI/Helpers/IconCacheService.cs
index 3b4bc56ffd..59a6d04ca4 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI/Helpers/IconCacheService.cs
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI/Helpers/IconCacheService.cs
@@ -34,9 +34,9 @@ public sealed class IconCacheService(DispatcherQueue dispatcherQueue)
                 {
                     return await StreamToIconSource(icon.Data.Unsafe!);
                 }
-                catch
+                catch (Exception ex)
                 {
-                    Debug.WriteLine("Failed to load icon from stream");
+                    Debug.WriteLine("Failed to load icon from stream: " + ex);
                 }
             }
         }
@@ -63,17 +63,37 @@ public sealed class IconCacheService(DispatcherQueue dispatcherQueue)
     {
         // Return the bitmap image via TaskCompletionSource. Using WCT's EnqueueAsync does not suffice here, since if
         // we're already on the thread of the DispatcherQueue then it just directly calls the function, with no async involved.
-        var completionSource = new TaskCompletionSource<BitmapImage>();
-        dispatcherQueue.TryEnqueue(async () =>
+        return await TryEnqueueAsync(dispatcherQueue, async () =>
         {
             using var bitmapStream = await iconStreamRef.OpenReadAsync();
             var itemImage = new BitmapImage();
             await itemImage.SetSourceAsync(bitmapStream);
-            completionSource.TrySetResult(itemImage);
+            return itemImage;
+        });
+    }
+
+    private static Task<T> TryEnqueueAsync<T>(DispatcherQueue dispatcher, Func<Task<T>> function)
+    {
+        var completionSource = new TaskCompletionSource<T>();
+
+        var enqueued = dispatcher.TryEnqueue(DispatcherQueuePriority.Normal, async void () =>
+        {
+            try
+            {
+                var result = await function();
+                completionSource.SetResult(result);
+            }
+            catch (Exception ex)
+            {
+                completionSource.SetException(ex);
+            }
         });
 
-        var bitmapImage = await completionSource.Task;
+        if (!enqueued)
+        {
+            completionSource.SetException(new InvalidOperationException("Failed to enqueue the operation on the UI dispatcher"));
+        }
 
-        return bitmapImage;
+        return completionSource.Task;
     }
 }