I have wondows vista and all my daughter does when she puts my music on is use windows media player and at the top click sync and then just drag and drop your music to the playlist and then when your finished click start sync at the bottom of the list and it will put your music on their for you. I hope it works for you!!!
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I would have to say that vista is the problem. Many people are happy with there vista, mainly becuse they only have programs that fit it. But i definitely think that microsoft could have done better. So i would have to say that because you have XP, you should use it. And if there is a button that says sync or connect, try it. I am happy that i could help:)
I know that sometimes certain USB ports don't give the information that the installer is looking for. Try a different USB port on the PC and see if that works. Make sure you have the latest version of easyRip from:
Uninstall all zune software and download and install it again. Possibly a bad download.
Or run error check on your computer then try it again.
Go to my computer, right-click on C: - go to properties- then go to TOOLS tab. Click on Error check - make sure you have both boxe(s) checked to fix errors as they are found then hit start. You will have to restart your computer for this check to happen. Usually takes a a few hours, but recommended to do at least once every few months.