Imported iTunes will not let me play or authorize my purchased music!

Question

Hi,
I upgraded the hard drive in my trusty MacBook Pro, and then put my old HD in a usb enclosure and used Migration Assistant to transfer over my old stuff. The music I had from my CDs transferred over without issue.
The problem is, the music I had purchased from the iTunes store. When I go to play these songs, I get the authorization window with the option to enter my Apple ID to authorize this computer. Well, I had already authorized this computer right after I transferred these songs to it.
I originally had used my old AOL account for purchases etc. I tried that username and password. No luck, it tells me I have to update my account. (I have, before I had swapped my hard drive, updated my account when I bought an iPhone 4 and MobilMe, but we will get to that in a minute).
So, I clicked 'update,' figuring I will simply enter my new information and this will all be over with, but no! I get a screen that says "Your Request Cannot be Completed. Make sure your computer's date is set correctly and that it accepts cookies from the iTunes Music Store. For detailed solutions to resolve this issue, click More Info."
I clicked 'More Info,' which is of no help, as it takes me to a iTunes for Windows XP Windows 2000 support page with no solution that works. I set my Safari preferences to accept all cookies (something I don't want long term, but figured would do for this and then switch once I got MY music back.) Also, my date and time are set correctly. I scoured the help for a solution, but cannot find one.
So, I repeated this process, clicked on a purchased song, and tried entering my updated ID and PW. I get a message window saying "This Computer is Already Authorized. Including this one, you have authorized 3 computers out of your available 5." And, the purchased music still will not play!
So, I next de-authorized my computer and reauthorized it again. Which had no effect, as what I described above still occurs the same way and I cannot play some of my favorite songs which I did the right thing and paid for and now can only look at their titles wistfully.
So, I am hoping there is someone out there who can help me get my groove back with a solution to this problem. Help please!
Thanks,
Grugi
Message was edited by: Grugi

Answer 1

this was a know problem with older ipods, I had to go to the apple store and they traded me up to a new nano
I had the exact same problem, interesting, sometimes when you completely re-load the device, it wouold work for a couple of days, and then not play purchased songs.
Go to an apple store and let them know about this, it is their problem to fix.
I would guess, if you connected a nano, this would not happen