Bought song won't play, stuck in re-authorization loop

Usually if the song shows up as (purchased AAC file) you've probably bought it from the iTunes store. The songs that show up as (ACC file) are usually ones that you've converted yourself using iTunes and not necessarily purchased from iTunes and ones you've converted yourself.

At least that's how it works in my book.

There is no reason to "purchase" the song again. Or to download it from somewhere on the internet, which is what you really mean.

If you are in a country that allows re-downloading of content simply delete the transfered track from the iTunes library and download it from your purchase history.

Unless I'm misunderstanding you, you are looking in the wrong "purchase history." The "Purchased" playlist in iTunes is not a history, it merely a static playlist in iTunes that may or may not contain all your purchases, and of course, if you delete anything from the iTunes library that will also delete it from that playlist.

Delete the track from the iTunes library and the HDD. Go to the iTunes Store and on the right side, under Quick Links, click "purchased." Select Music > All Songs then "not on this computer." This will show you all your purchases that are not currently on the computer. Find the tracks that have been giving you trouble and download them. This ought to clear up the problem.

Ok, good. That information is helpful.

Delete the track from the iTunes library, if you have not already, sign out of the iTunes Store. Quit iTunes, wait a few seconds and open it again. Sign back into the store and see if the purchases now show up in your online purchase history. They ought to be there now.

At this time I believe you need to contact iTunes Store support for more help, or make an appointment at your nearest Genius Bar. Everything we have done should have worked. At this point there is no apparent reason why this track isn't showing up in your purchase history.

I had this happen when I bought my new computer this December. After a *lot* of work, I finally got ahold of the correct Apple Support which re-authorized 4 of my protected songs again. And that appeared to work for a few weeks.

Now they don't play and give errors when I synchronize with my iPad.

If I click on them, to play within iTunes, I get a window saying 'This computer is not authorized to play "House of the Rising Sun". Would you like to authorize it?'. I enter my password and am told 'This computer is already authorized. Including this one, you have authorized 3 out of your available 5.'.

Same problem I had a month ago, which I thought they fixed after talking to a *bunch* of apple support people, and making two fruitless genius bar appointments.

I agree with you, you shouldn't have to "legally buy" the song again if you've already purchased it. I simply deleted it from iTunes and re-downloaded it and it worked! Thanks!