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If it doesn’t fit under the seat they will open the door and throw it out
They don’t care at all. The only thing I ever got lip for was having the extender zipper open on my carryon once lol
American is by far the worst and most strict on the size of your carry on. If it doesn’t fit into the sizer they will make you check it. Speaking from someone who has traveled consistently for years with the same bag and only been asked to put my bag into the sizer before boarding with American. Can count on one hand the # of times I wasn’t asked.
Only speaking about the personal item
If it actually fits in the sizer than you’re fine.
Totally depends on the airport and who’s working the gate
They will visually size it up. Then if they think that it's too big they will ask you to put in a the baggage sizer. I experienced it once. I have this beige-colored roller luggage. It looks big but it 's actually not. I used it for travelling several times already and for the first time I was asked to be accompanied by the attendant to check my luggage's size. I understand though, they are just doing their jobs.
Especially if you are also carrying on something large it may be an issue.