Syncing between Windows 7 and Android Jellybean with Winamp
I know this is an old thread and you may have already found an answer, but I had the same problem after installing Winamp 5 pro on an Android device. I had previously had no problems with Winamp standard on both Android &amp; PC

I upgraded the PC version to Winamp Pro and now it all works as expected again. So I suspect you need the same version of Winamp on both platforms ie. either standard or Pro