Purchased songs no longer play and unable to authorise PC

Songs that I have purchased from the iTunes store have suddenly ceased playing and have been removed from my iPod.
Whenever I try to play one, I get presented with the authorisation window and enter my password. I then get the message that authorisation was successful quickly followed by a message that an unkown error has occurred.
If I look under iTunes > Advanced the Deauthorize Computer option is available, inferring that the computer is authorized.
This is starting to annoy me now as I cannot play music I have purchased.
What on earth is wrong?

I then get the message that authorisation was successful quickly followed by a message that an unkown error has occurred.
are you getting a -208 error message number with that, Demonic?
what version of itunes are you currently running? to check, in itunes go "help > about itunes" and wait for the version number to scroll up from the bottom of the screen. for example, mine says "itunes 7.0.1.8".

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Try:
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Reset iOS device: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
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Go to Settings > General > Reset and tap Reset All Settings.
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- Restore from backup. See:
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You are in that awful authorization loop.
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Any help greatly appreciated. Years ago I downloaded some music and have been playing it for some time. Car, computer everywhere.
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Anyone else had this problem?
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I completely agree with you on it not being easy to get a list of purchases from account info. It's completely ridiculous that one can't cut/paste from that list. If you happen to have saved the confirmation emails, you can at least cut/paste from those.
itunes menu > help > provide itunes feedback
If enough people ask for it, maybe they'll change it on the account info page.
let's back up, though...are you putting these songs back into itunes after a PC reformat?
One thing to do, create a smart playlist with criteria "kind contains protected". Select all items in that smart playlist, and drag it to the green purchased playlist. Press the Skip button if you see it, so you won't get duplicates. That will add all newer itunes-plus purchased songs.
Then change that smart playlist criteria to "kind contains protected". That will add older non-plus songs.

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Dreading he is out a few hundred bucks,
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THeres really no tellin what happened, could of been windows restored itself, antivirus interfering with itunes ect ect
What you need to do is go here and follow steps for searching your system for purchased songs http://docs.info.apple.com/article.html?artnum=301749
If you can't find it you need to go here, overlook the page and contact the music store where it says to http://www.apple.com/support/itunes/musicstore/lostmusic/

Purchased songs no longer play and unable to authorise PC

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