Can't completely upload a playlist to my Thunderbolt

[androiddad]

EDIT: I've noticed I can get the whole playlist on my phone if I transfer 10-15 songs at a time. If I try 20 it just shows "Connecting".

I started off just fine transferring music to my HTC Thunderbolt.

For some reason it starts uploading only every other track.

The results shows staggered Completed and Failed upload status but it still goes through the motions of showing the uploading % increasing per track.

I've removed all the music from my phone about three or four times and started the process all over again only to have the same results each time.

I've also re-installed Winamp. That allowed me to get my phone to show under devices again after Winamp crashed.

Each time I try to upload again it gets about 70-80% through the play list and then just shows "Connecting" for the next track and nothing else happens.

Any idea why this is happening?

Thanks for reading. This is driving me nuts.