Itunes Match upload keeps failing

Hey there,
I signed up for iTunes Match yesterday and it's matched up most of my library but it's just started running the Step 3 "Uploading Artwork And Remaning Songs" FOR THE THIRD TIME - it gets all the way through the process then I turn around ten minutes later and the **** thing has started the whole process again. Any ideas?
Cheers
Rob

Rob,
I posted on a similar topic, you are lucky if it takes 10 minutes to get to the point where it crashes, due to the size of my library mine takes around 2 hours, and I have had to restart it hundreds of time and been at it for 4 months now I think. Each time an update for itunes is available I hopefully install it, problem not fixed as yet, I live in hope. itunes 11 was in my opinion a downgrade, features removed, can't see where apple are going with this, downhill mostly.
Only solution I have found so far is sheer persistence, just keep on restarting it, until eventually you get all your songs uploaded. There are some songs at the top of the list which dont have an itunes match/cloud status but I will deal with those once uploads have finished.
From what I've read elsewhere the crashing *may* be related to the size of the files (seems iTunes match doesn't like large files). If you have lossless or WAV files, consider converting to AAC 256kb which I think is what iTunes match wants to put into the cloud, so might help. The conspiracy theorists would probably say the bug intentional and in order to get you to purchase apple hardware.
Last time I asked iTunes about a refund a very partronising lady replied and in essence told me that iTunes store policy is "All sales are final", in other words, no refunds. I guess if it happened on the internet then it didn't really happen, not same as the store where you can get no questions asked refund.
Hope you get it sort, good luck

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