Currently Being ModeratedJan 1, 2013 10:47 PM (in response to zak123)
This is an ongoing issue. I've found that if you're just patient it will eventually finish. I've sometimes had to leave it overnight.
Currently Being ModeratedJan 2, 2013 10:25 AM (in response to zak123)
I've had the same issue, for almost a month now. I can't find any pattern to indicate which songs it fails on and why. Once I made it through nearly 2000 tracks before it failed. More often than not it won't even upload one before it dies. Very frustrating.
Currently Being ModeratedJan 23, 2013 8:33 PM (in response to zak123)
I was having similiar problems uploading songs to iTunes match. It turned out to be my internet connection. I happened to take my laptop to my parents' house, and iTunes Match worked perfectly, uploading all the songs that hadn't uploaded yet. My internet connection at home doesn't seem to be problematic, but I'm almost certain it was the issue. Try taking your computer to a friend's house and using their internet connection to upload your music.
Currently Being ModeratedJan 24, 2013 2:24 PM (in response to zak123)
Had it just as bad and just got it working. I had some corrupt sound capture and recordings files like .wav, .aiff, that iTunes didn't like, or 2 hour long mp3 files it just choked on. The Apple store told me to start gdragging out songs to a folder on the desktop, deleting them from the libary and the cloud, make it work - it has - then reload songs.