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I've never tried that, and can't verify what happens, but I can tell you that if you bring too large a bottle of liquid they will let you put it into checked baggage to retrieve at your destination. Clearly the same offer is not on the table with cash.

Furthermore, nothing in the TSA rules says "no cash exceeding X dollars". If they don't want you to bring it, they should explicitly disallow it.

Interesting. They do say that in Aus and NZ. No cash over a few thousand IIRC. Then you have to declare it to customs

My dad walked through with a Leatherman accidentally, set off the metal detector.

He got let through eventually. I seem to remember someone escorting him out to let him put in in his parked car, which to my mind seems unusually accommodating but I'm pretty sure that's what happened.

Right, if you attempt to smuggle a listed banned item through. If you get there and say, "crap it says no ulus (knives)" no problem. Happens at ANC all day long.