I have used Winamp, Media Monkey, Windows Media Player, and Rhapsody 4. All of them work with the Connect. If you use subscription music with DRM, Windows Media Player is the only one that will properly transfer licenses. Also, WMA files have embedded album art, not supported by Winamp and many others. WMP11 has its flaws, but has proven to be the most reliable at syncing and transferring album art for me, and across numerous devices, including the Connect, and my phone (which is a Windows Mobile device).