True story , about 2 years ago.
DW is handicapped. I carry her bags. I had a rolling carry on and another bag on top of it, much smaller but bigger than a personal item. she had her small purse . I always check in with the GA for her pre-board. I wait in line, she sits.

Flight is slightly delayed and there is an additional GA. full flight DW is sitting in the handicap area. New GA demands that I put my bags in the sizer . I put in the roller, fits nicely, pull it out and put in the other bag in the large sizer. GA goes ballistic and he insists loudly that I must put it in the smaller sizer. I say "no I don't it's my wife's bag" he bellows I don't care who owns it you have to put it in the smaller sizer. At this point original GA has reached the man, pulls him aside and talks to him. He grumps at me "why didn't you say your wife was a passenger?" I said I have two boarding cards in my hand, I thought it was your job to ask.

He quickly finds other things to do and the original GA is apologizing and laughing at the same time