I've had an annoying problem with my iTunes library lately. The trouble starts when I sync my iPod the night before a trip. I select the movies I want to sync from my movie section; but they don't all sync, one or two stubbornly stay back. I waste precious time trying to troubleshoot my way through iTunes help archives with serious tension. Then I end up giving up on the whole idea in favor of getting finished packing and sleeping. A few weeks later I find myself in the same cycle. And again today.
Apple Tech Support Pool with a phone call for help. At first my Applet didn't seem to know any more than I did, but soon enough we had chatted our way around the account and found a way to correct the problem.
So, if you find yourself needing this, or shall I ask, when you find yourself needing this, it is a very easy fix.
The first thing you need to do is stop trying to sync the movie from your account. Start by clicking the iTunes Store "home" button. Now click "Movies" from the header. Click "purchased" from the bottom of the Movies Quick Links column on the right side of the page. This should open your list of all purchased movies in your iTunes account. Notice: the small check-box at the bottom right of page, "Download HD When Available", make sure it is NOT checked.
Next, select the movie you are having the problem moving to your iPod. It probably has a little cloud next to it which means that you never actually downloaded it to your computer, you've been watching it from the cloud. Click to download. This will take approximately ten minutes for the average movie...
After downloading is complete you may click the iPod from your Devices on the left page menu bar. Make the movie selection now and "sync" as usual. You will have your movie on your iPod.