The zune software only supports a few audio files such as WMA, WMA 9.2 lossless, WMA 10 Professional, AAC, Mp3 etc. It doesn't support lossless files such as apple lossess, FLAC etc. Zune software also doesnt' support DRMed songs such as songs you bought from Apple store. Those songs only work on apple Ipod. So you have to either burn it on a cd or get a DRM stripper to get rid of the DRM or you have to convert it to another format.
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