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Helpful answers
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Feb 5, 2015 8:15 AM in response to VWeismanby Phil0124,★HelpfulIts possible yes. As long as the movies are not bought by your Apple Id on iTunes.
i.e Movies form iTunes are licensed to the Apple Id that buys them/ downloads them. And can only be played by devices/software authorized by that Apple ID.
You would need to use her Apple ID on iTunes to download movies for her.
If the movies are obtained form other sources, it will depend on whether they are DRM protected or not.
All in all there's nothing directly stopping playback form an external flash drive, its whether the movies are protected and authorized for a device or user and not another.
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Feb 5, 2015 8:32 AM in response to Phil0124by VWeisman,If I used her Apple ID, she would get billed for the purchases, I suppose. Plus, I doubt she would want me to have that information. How can you find out if a movie is DRM protected?
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Feb 5, 2015 8:54 AM in response to VWeismanby Limnos,While a kind thought technically it is skirting legality.
If you give her DVDs she is in ownership of the rights to watch the movie as long as she has the DVDs. DVDs are almost all with DRM protection and cannot be legally converted.
Your movies from the iTunes Store can only be played on devices authorized to your iTunes account. You could authorize her computer to your account so your purchases can be played on that computer though I don't think it is intended that sharing be between friends, only family members or people in the same household (at least all the other sharing methods are set up to be that way). If you authorize her computer to your media she can continue to make purchases from the iTunes Store with her account but will not be able to re-download anything from her account for 90 days (a kind of discouragement for exactly this kind of sharing).
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Feb 5, 2015 9:19 AM in response to VWeismanby Phil0124,By default all or nearly all commercial movies bought from iTunes are DRM protected. If bought from somewhere else, it depends on the source. The only way to know is to try to play them on a different device.
Your best bet, to make it easy on her and you, and avoid any legal entanglements, is to buy her an iTunes Gift Card, or simply gift her the movies through the iTunes store. They will be billed to you, but will be authorized for playback on her account when she redeems them on her computer.
Send iTunes Gifts - Apple Support
Scroll down to the section titled: Gift an item on Mac or PC