I’m A-List and have flown Southwest a ton without issues, but this week was different.
Gate agent pulled me aside while boarding and made me measure my bag. It fit on width and length, just a bit thicker. I even said I could move stuff into my personal item (had a wetsuit in there), but she wouldn’t hear it.
Every time I tried to explain, she just shut me down and said I was being disruptive.
Ended up having to check it anyway. Honestly felt like a total power trip.

