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I have to do the "TSA" dance (or the equivalent international agency) 3-4 times a week...a hazard of the job.
It really does vary from agent to agent, there is almost no standardization whatsoever. I've even had the same agent tell me different things on different days! BTW Amsterdam is one of the worst for getting in to your business...they asked to see my frequent flyer card as a means of identification...apparently my passport, flight crew ID, and drivers license weren't enough!!
I don't think the size matters, just how uptight the agent feels on that day...
Anyway, I have my iPad and my surface in individual nylon sleeves - no cables in the sleeve. I just automatically take them both out and put them side by side in the same bin, but they stay in the sleeve. I have never been asked to remove the sleeves, so it ends up going fairly quickly and my devices stay protected.
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