Audio / USB adapter problems

[anon(9785393)]

I hope someone can help. I'm having trouble getting consistent audio through the USB to headphone jack adapter. If I restart the phone and plug in the adapter the sound will work if I stop my music app then start again the sound cuts out and there's no further sound that will come out of the output unless I restart the phone. As you can see in the picture below there appears to be some issue with the USB adapter that was supplied by HTC. I'm getting an error message saying that it's not supported. Has anyone else seen this Behavior.?