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Helpful answers
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Aug 27, 2012 2:45 PM in response to chris2729by lllaass,See:
iTunes: May be unable to transfer videos to iPhone, iPad, or iPod
iTunes: Frequently asked questions about viewing and syncing videos
You may need a third-party program . I use HandBrake, it is free and has presets for the iPad.
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Aug 27, 2012 2:54 PM in response to chris2729by Texas Mac Man,Another way. You can use a USB flash drive & the camera connection kit.
Plug the USB flash drive into your computer & create a new folder titled DCIM. Then put your movie/photo files into the folder. The files must have a filename with exactly 8 characters long (no spaces) plus the file extension (i.e., my-movie.mov; DSCN0164.jpg).
Now plug the flash drive into the iPad using the camera connection kit. Open the Photos app, the movie/photo files should appear & you can import. (You can not export using the camera connection kit.)
Secrets of the iPad Camera Connection Kit
http://howto.cnet.com/8301-11310_39-57401068-285/secrets-of-the-ipad-camera-conn ection-kit/
Cheers, Tom