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Hey JodGamer, Two of the most likely reasons why this may be occurring would be if the files you are attempting to play are in formats that the PS3 does not currently recognize, or if they are "locked" by iTunes' DRM protection. Unfortunately, until Sony or another third-party developer chooses to provide support for such files, you may not be able to play them through your PS3. Please keep in mind that DRM protection generally only applies to files that were purchased and downloaded through a music service, such as iTunes. iTunes Plus files however, do not normally carry DRM protection. As such, they should be able to be played by any MP3-complaint device, much like songs copied directly from a CD. Hope this helps you out. Sincerely, Aaron Go Ahead. Use Us.
And when you run it, click the checkbox for "Format Data Area." When the message comes up saying you want to delete all the files, click "yes-" it's worth deleting all your songs if it works properly afterwards. You'll have to re-sync your songs and the downloads take forever, but it works.