I've flown over 50 segments this year, not once have I been checked.
I "tested" WJ on a flight to San Diego, and they didn't bat an eye on my questionable bag. Skipped the baggage fee, gate checked it, no problem at all.
I don't think I've EVER seen the size get enforced, and I've seen some pretty hilarious carry-ons. We're talking suitcases that aren't even CLOSE to the required limit.
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