Problems downloading purchased items - please help!

Question

I keep getting error 37 when I try to download music.  The songs I have purchased are in my "downloads" list, but they will not download.
The error message on my screen says, "There was a problem downloading some of your purchased items."  When I expand this message the list of songs appears, alongside each song it says that the file name may be invalid or too long.
I have been emailing Apple back and forth for days, I get a different advisor replying every time, they obviously don't read the email trail and therefore aren't aware of the troubleshooting steps I've tried so far - basically all of them!  They keep sending me duplicate information and I'm now very fed up and frustrated with Apple.
I tried to phone them, was put on hold for 40 mins before speaking to a less than helpful man for a few moments before the call was cut off.
I have tried: Itunes diagnostics (connections are fine), turning off Windows Firewall, ensuring I have the latest version of Itunes, msconfig.  They said they had removed the pending downloads from my account and added fresh copies, but this did not work either.
They also said that if I go to the new "Purchased" sections of the Itunes store, I would be able to dowload my previously purchased items, however, this didn't work because the songs had "dowloaded" next to them, so downloading wasn't an option.
Any help would be greatly appreciated.

Answer 1

I'd take iTune's word for it and assume the file somehow has become corrupted.  I would suggest two things.
(1) try to play the song on the computer where it is stored locally (where you uploaded it to the cloud from)  Just want to be certain that your copy will play.
(2) delete the song from your library and the cloud (just highlight it, hit the delete key)  When asked if you want to put it in the trash, say no.  When you are asked if you want to delete from the cloud, say yes.
(3) go to the store menu and select Update iTunes Match.
(4) go to another computer or iOS device and confirm that the song no longer appears (you shouldn't even see the title, not grayed out, just not there).
(5) go back and add the track back in to your library, hit update iTunes match and watch the progress bar to be certain you see the track title appear - this will help you confirm that the file is actually uploading.  Sometimes iTunes match just re-links to the old file in the cloud and that's sure not what you want!
(6) see if the track will play now.
"check for available downloads" only has to do with purchases you made.  I don't think it's relevant to the issue you're describing.
Sorry I should have mentioned that the previous suggestion to take the slash out of the title still applies.  I would rename it by doing a get info. on it in iTunes before I turned Match back on and uploaded a fresh copy.
Message was edited by: JiminMissouri