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I have videos on iTunes that I've purchased that I'd like to watch on my big screen TV. I'm wondering if there's a way I can send them to the XBox?

I also have PlayOn but I'm not sure if/how to do it through that.

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up vote 1 down vote accepted

You can't, as the Xbox doesn't work with FairPlay, the protection system that iTunes uses. You can't view them outside of Quicktime and iTunes. You'll have to buy, or "buy" it again.

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True, from what I understand the xbox can receive videos from: Zune, Netflix, and it can act as a media extender for Windows. – Not Kyle stop stalking me Feb 6 '11 at 22:41
This is correct. iTunes protected content does not work outside of Apple's ecosystem. You can use an AppleTV or connect a computer's HDMI output to your TV (and playback via iTunes on the computer) – Bala Sivakumar Jun 19 '13 at 18:41

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