The problem may be with a slow internet speed the download, "times out".
Go to the iTunes menu bar top of your screen, click Store > Check for Availalble Downloads. Or follow the directions for re downloading past purchases > Downloading past purchases from the App Store, iBookstore, and iTunes Store
Try iTunes Store Connection Issues here > http://www.apple.com/support/itunes/troubleshooting/
Read here also > iTunes Store: Download times will vary
You can resume the download with the little button right next to the individual item in the list (it's the pause/resume button. If you click it while downloading it pauses the download). It will usually pick the download up somewhere not too far from the point at which the error occured, but you have to click the button manually every time there's an error, which prohibits its use overnight (bacause I am sleeping and don't click many buttons while asleep).
I was hoping there was some way to have it auto-resume the download without having to interact with it, sort of the way that the app store on my iPad works. I purchase the app, and if there's a minor problem with the internet it keeps trying to download.
Point of interest: The instructions for redownloading purchases don't apply to movies. With movies, you purchase exactly one download and you have to contact customer support if you accidentally delete the download and need to ask for it again (By the way, they're really nice at customer service and will almost always reactivate your order for download). I know because I did that once like a silly person.
I believe the "little button" start progrss on 0KB although my files is bigger than 600 Megs.
I download it for hours for a single file (4 - 5 hours) and there are 25 files, so how patient am I !?!?!?!?
why a mature app, iTune, developed over than decade by professional engineer can not provide a simple tthing, autoresume ?
Ever wondered how people get to "Level 9" status on this forum? They come to your problem, post a response that does not help at all, click "This Helped Me" and earn themselves 5 points. Sorry you got affected by this.
I am in Malaysia for the moment and I am having the same problem. I have no solution unfortunately. I wanted to let you know that you are not alone. My only advice is to use the feedback option on the Apple website and make a suggestion. Apple generally builds their software process for people with perfect super fast internet connections.