Currently Being ModeratedNov 28, 2012 7:53 AM (in response to perkidanman)
To be sure there are no errors, right->click your iPod under Devices in the left hand pane of iTunes and select Reset Warnings. Then resync your iPod and make note of any error messages that may or may not appear.
Currently Being ModeratedDec 4, 2012 10:05 PM (in response to perkidanman)
If it's a newer movie, I fear we aren't going to be able to download anymore. I sent Apple an inquiry, I think any movie that will be available in the cloud will not sync on an iPod Classic. Two recent movies I purchased, one through iTunes, an HD version, and one at a store with a digital download code, will no longer sync to my Classic, but it will to the phone or iPad. Not a happy camper with Apple at this time!
Currently Being ModeratedFeb 19, 2013 9:31 AM (in response to heidi noel)
That's frustrating! Did you ever hear back from Apple. I have an iPod Classic too and the James Bond Skyfall is not synching with it! Not happy.