itunes files only work with the ipod but you could burn a cd with your itunes music then rip it with Windows Media Player into WMA files the transfer the ripped files to the player. The Rio Music Manager probbly can't use DRM protected files but the Rio Carbon can. Use Musicmatch Jukebox or Windows Media Player to transfer the music files to the Carbon. If you still have problems contact Musicmatch tec support.
I have downloaded from Musicmatch, itunes, and WalMart and when I try to transfer those songs to my Rio Carbon I get the message, "One or more files will not be downloaded to Carbon (H) because the file does not have the proper download to portable device right."
When I move the files to Rio Music Manager and then try to transfer them to the Carbon it says, "Failed to transfer 'name of song' to player: The player is no longer connected." I know I am still connected.
In the file info it says, "DRM Protected Audio (cannot convert). Does anyone know what my problem is?

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