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So basically, if I convert the files to mp3 or whatever, it might lose the protection and iTunes'll play it? I've tried it with Switch and it worked, but it lost all information (artist, album, genre, etc.). Is there anyway to convert without losing the attached information?

Are there any programs that will play all files that can run on a mac os x, then?

It's is all music from online, and I didn't create any. I just find it extraordinarily odd that on my PC I can run Zune and it'll play everything, yet on my Mac I have these issues...

How would I check to see whether or not it does, and if so, how would I go about either changing it?

I have about 65 gigs of music, and only 51 transfered over, I've tried clicking and dragging the specific bands that didn't transfer, but it's still a no go. They're both wma files and mp3 that didn't work, so I'm not sure why it's not flowing. Any tips?