DRM striping - Removing FairPlay from iTunes purchased videos
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Getting iTunes purchased video into XBMC is not possible since iTunes embeds FairPlay DRM into videos purchased from iTunes. There are a few DRM removal commercial software packages that essentially "Play" a video and re-encode it. I hate trans-coding as it strips quality from your content.

There is a Free and Open Source application that strips DRM from iTunes purchased video called Requiem and does it without any trans-coding. Apple has aggressively pursued all references to Requiem with DMCA takedown notices so I will not post any URL's, you're going to be responsible for finding that on your own.

The author has gone "underground" so to get to his website, you will have to use "Tor" https://www.torproject.org/, an internet protocol that protects your anonymity. Tor has "Browser bundles" available to make using Tor simple.

Requiem only strips the DRM and encryption. Your videos retain all of the information and tags that can identify you as the purchaser so it is not about file sharing.

After Requiem has stripped the DRM from your iTunes purchased videos, they can be played just fine by XBMC.

Currently Requiem only works with content that has been downloaded with iTunes 10.5.3 http://www.oldversion.com/iTunes.html or earlier so 720P content can have DRM stripped but 1080 content can not. You can purchase new content but Requiem can only strip DRM from files downloaded on a machine that has never had an iTunes version higher than 10.5.3 installed.

This can get complicated fast. I suggest running a Windows VM dedicated to DRM stripping. Install iTunes 10.5.3 and Download Requiem. Authorize your VM to Play iTunes videos (required for Requiem to work). Strip the DRM from your iTunes library and then move the unlocked files to your XMBC library.

Remember that your personally identifiable information remains in the files so this is NOT a licence to pirate, rather a tool for you to exercise your Fair Use rights under copyright law.
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