and overhead bin space (or lack thereof) is completely besides the point - bringing a regular roller and garment bag is clearly not within the carry on allowance for any passenger on UA. A regular size roller is also allowed as ‘carry on’ if you’re flying a CR7, but obviously, it’s not getting in the bin and will be green tagged and checked. As I said, bin size or fullness and what you are allowed to bring as a carry on are two different things.

I would never recommend anyone, including myself, trying this, though OP or other pax may do it, and may even get away with it. Or get away with checking the second bag for free if they are caught. Which should never happen.

IMO, anyone caught trying to bring on more carry on bags then allowed should be forced to check at the gate, and pay the bag fee, with no waiver for elite at that point. I’d also be open to an additional charge, like is supposed to happen for (non-elite) BE pax trying to bring a roller on.