Protected AAC files won't play on authorized computer

I have a two year old computer with iTunes 10 that plays both Purchased AAC and Protected AAC songs fine.
I just moved my iTunes files to a new computer with iTunes 10 and authorized the computer. It will play Purchased AAC songs fine, but when I try to play a Protected AAC file it says I have to authorize the computer. When I do that again, it says that the computer is already authorized and that I have authorized 4 of my possible 5 computers. But when I try again to play the Protected AAC song, it does the same thing all over again.
Why can't I play music I have already paid for on one of my "authorized" computers?

Your post is more informative than any of the punks at the apple store and the email-only (!!!) itunes support they refered me to. Basically, my wife is having the same issue with her old library. She has an old @aol.com as the "user name". When I try to play one of these old songs (that I copied from her old laptop onto my desktop for a consolidated, shared library) I get that pop up, "This computer is not authorized to play "[song title]". Would you like to authorize it?" The 'Apple ID' auto populates with [heremail]@aol.com. You mentioned that you used your name and also your apple ID. What is the difference, and how can I enter it differently in the pop-up? I have tried manually typing in her (maiden) name, with and without a space, also the [heremail] without the @aol.com, then entering the password that we know of, and still nothing.
Sorry to bring up old issues, but I could really use the help. She has over 2000 purchased songs and they can't be played on anything but the ipod that hasn't been synced in years.
Also, when I log into her old iTunes account in the iTunes store, there are only about a dozen songs in the Purchased section. ***??? This makes me think there is a real issue with the iTunes system.
Like I said, apple was ZERO help with this. The emails that we received were sent to us by a person who probably bangs her head against brick walls for fun.
Also, I have set all the permissions to the folders and files so both her and my login have read/write.
Thanks in advance.

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Since ten days ago both my iPods (Video 60GB and Photo 40GB) are not capable anymore to play iTMS purchased music. The music plays fine on iTunes (Windows, last version), is correctly copied on both the iPods (both updated to the last version of iPod software) but when I try to play any of the Protected AAC file kind the iPods just shows the Cover and skips to the next songs.
The bad thing is that is happening on any Protected AAC file i try to play on any of the iPods and we are talking about 527 songs, for a total more than 500 euros. THAT'S BAD!!!
I've tryed everything, re-flashed the iPods with the last iPod Updater (any hint on where to find the 2005 version?), reinstalled iTunes on both the PCs I've at home, deauthorized and re-authorized the iTMS account, deleted all the music from the iPod and loaded back again, no light at all...
I've contacted the iTMS support, they have deauthorized all my PCs, I've authorized them back but nothing. After four email they passed me to the Tech iPod support.
I've called them, on the Video I've also the AppleCare, we tryed everything, also formatting the iPod via the Operating System, but no luck.
At the end they have said that is a problem with the FairPlay authorization and brought me back to the iTMS support.
I wrote them again, explaining all the situation and giving them the SR number and this is what I got as an answer:
"have escalated the issue you reported, and you will receive an email message once we have a resolution. Thank you for your patience as we work to make your experience with the iTunes Music Store more enjoyable."
No timeline, no explanation at all.
Obviusly all the other functionalities of the iPods are working fine and all the Protected AAC files plays fine on iTunes, but nothing on the iPods.
I've also tryed to buy a couple on new songs from iTunes but also these do not play on any of the iPods.
From the tech support side, seems I'm the only one to have this problem in the world. From my point of view this could be a FairPlay keys problem but the result is that I cannot play any of the music I've bought.
Does anybody had this kind of problem or some hints to save the day?
One bottle of italian wine (Brunello di Montalcino, very fine red wine) to who finds a solution.
Have an happy life.
MB from Italy

Nobody replyed to my message but I think that knowing the solution can be helpful for someone in the future.
I've made some extensive testing.
To me the problem has appeared when I've update both the iPod to the last iPod software version, 1.1.1 for the Video and 1.2.1 for the Photo.
At that time I was using the iTunes for Windows version 6.0.4
Thanks to the hint of a user on the iLounge forum (www.ilounge.com), the problem was related to the versions combination between iTunes for Windows and the iPod Software.
Today I've tried all the version of iTunes form the 6.0.0 to the 6.0.4 (thanks to File Hippo) and the only one that works is the 6.0.0
The problem seems solved on both the iPods, obviously I've notified Apple of the temporary solution and I really hope that someone will take care of this one.

My shuffle will NOT play protected AAC files but will play ripped AAC files

When I download a playlist to my Ipod Shuffle all files appear to transfer OK, but only the regular AAC files (the ones from my CD's) will play (i.e. the protectet AAC files will NOT play). If I create a playlist with only protected AAC files purchased from Itunes, NOTHING will play.
Yes, I've run updater (latest version).
Yes, I've reset to factory defaults.
Yes, I'm using the latest version of Itunes
Yes, These songs play fine on my Windows XP PC.
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Yes, I've deleted all my music files and restored them.
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Hi,
Check the iPod hardware properties. Make sure that the iPod shuffle is connected to computer.
1. Right-click My Computer and click Manage.
2. Select Device manager.
3. Then select Universal Serial Bus controllers.
4. Right-click USB Mass Storage devices and click Properties.
5. Click the Details tab.
Check for the string of numbers if it is 000a.2700.FFFFFFF then send the iPod shuffle for service. http://depot.info.apple.com/ipodshuffle/
http://docs.info.apple.com/article.html?artnum=302110
or take it back to the place from were you brought and ask for a replacement.

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Click here and follow the instructions.
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Protected AAC files won't play on authorized computer

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