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Mar 6, 2015 7:47 AM in response to JasonAYby joe_7399,Hi JasonAY,
Welcome to the Apple Support Communities!
I understand that you are repeatedly prompted to authorize your computer to play your iTunes purchases, but are still unable to play them. There could be a few different steps I would suggest to troubleshoot and resolve this situation. Please read over and work through the steps located in the attached article.
iTunes repeatedly prompts to authorize computer to play iTunes Store purchases - Apple Support
Best regards,
Joe
