4535 Views 3 Replies Latest reply: Oct 15, 2009 6:02 PM by sydneymo17
And welcome to Apple Discussions!
First, a couple of questions. Are you positive all these songs were purchased under the same iTunes account? Have you tried deauthorizing the computer, logging out of your iTunes account, closing iTunes, then reopening it, signing back in and re-authorizing to see if that helps.
Lastly, it may be a good idea to take a look at this article. Hope this helps.
[iTunes repeatedly prompts to authorize computer to play iTunes Store purchases|http://support.apple.com/kb/TS1389]