I went through TSA, with the boot on, at a very small airport (MFR, probably less than 500' from the UA counter though security to the jetway for my flight). It was such a short distance through security that I had no problem on crutches. TSA was actually extremely polite, offering me a hand or a shoulder to lean on as I hobbled through and standing by on either side to catch me if I wobbled in the scanner.
UA insisted on gate checking my crutches and bent one of them rather alarmingly. Unfortunately I didn't see this until we were out of the airport. My husband tried to bend it back into shape, and even using two hard surfaces and his knee to push, could not unbend it. Given that a new set was $27, it wasn't a huge loss, but the last thing I need is for a crutch to crumple out from under me and I'd fall again.
Landing at DEN, out at B84, I was very grateful for the wheelchair ride all the way to baggage, I'd never have made it on my own.
I asked the wheelchair attendant if he'd seen "miracle flights" and he said not a day goes by that he doesn't get a call for a wheelchair at an arriving plane and when the plane lands, doesn't have a taker - whoever needed a wheelchair on the other end has declined one at DEN. He also said his most amusing passenger of the week was a tiny elderly lady with a whistle, a cane and a tight connection - he pushed the chair and she used her whistle to alert people they were coming and when a clot of people would not move, used a few judicious cane pokes to clear the way.