If TSA agents knew anything about technology, they wouldn't be working for the TSA. I'd check it. If not, be prepared to answer questions about it and give a demonstration. Also, there's a small chance that you'll be asked to throw it away or miss your flight.

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I try extremely hard not to check bags, especially if I'm only going away for a few days. But that is also good to know.

Perhaps ship the bags to your destination?