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Are you using Rhapsody or other subscription service?

If not, I’m guessing you ripped your own CD’s with Windows Media Player, leaving it at the default setting of ripping to .wma format and adding “copy protection”.

If this is the case, you’ll need to change your Rip settings in WMP and re-rip your files. You can still rip to .wma format if you want to (although .mp3 is more universal), but you’ll need to un-tick the “Add copy protection” option.

If you’re using a subscription service like Rhapsody, you’ll need to authorize, or re-authorize the device with that service.