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It's not particularly difficult technology to pull off. The actual TSA agents are clearly dumb as rocks, but if you give them a machine that just sucks up data and sends it off to some central repository, they'll have no problem plugging it in.

From my understanding, they already can make sort of "notes" on your file - including books you have in your luggage, that sort of thing. It's not that crazy to imagine that they'd distribute some simple juice-jacking equipment if people are very frequently wanting to plug in.