Just flew United to Maui last week ... 2 planes ... Airbus 320 and Boeing 777.
Our carry-on is a 15.5 x 9 x 22.5 hard-sided roller ... no issues stowing it overhead on the 320 ... but on the 777 they were really hounding passengers about gate-checking roller bags. Turns out once we boarded I understood why - roller bags that were within the size requirements actually didn't fit properly in the overhead bins over the middle seating section.
You know they always tell you to put your bags in rollers first? If you did that in the overheads on the outside rows, it was fine - but in the middle overheads the bags were mostly too long, and had to go in sideways, which the flight attendants then ***** at you about.
So they was a lot of moving smaller bags and backpacks from the sides to the middle overheads to make room for the larger bags on the sides.
I didn't see anyone's carry-on get denied due to size, but they were really pushing the gate-check. For what it's worth, we did gate-check our roller on the 777 both times - it was free and we had no issues.