HT1363: Putting iPod into Disk Mode
Learn about Putting iPod into Disk Mode
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Helpful answers
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Sep 11, 2012 8:50 AM in response to wjmansonby planb77,Are these downloads from the iTunes Store? If so, it sounds like you are trying to sync the HD version of the video. You should try to download the Standard Definition copy instead and sync that to your device as HD content is not compatible with the Nano. See here for more information:
iTunes: May be unable to transfer videos to iPhone, iPad, or iPod
To prevent HD versions from being downloaded in the future head to the iTunes Store, click the Purchased link, and then select Movies/TV Shows and remove the tick mark next to Download HD when available. You should be able to download the SD version now from under this same page.
B-rock