I travel regularly for work, mostly on regional airplanes due to my location. One thing that frustrates me is having to valet-check my carry-on, especially when making tighter connections. For several months now I have been obsessively trying to find a carry-on that rolls (not a duffel, because I hate that it can't sit upright) and also fits into the overhead bin, with enough room for my luggage.

I finally found my perfect bag last month (Eastpak Tranverz S - in case you're interested). It's well under carry-on size limits (approx. 20Lx12Wx7D) and fits with room to spare in the overhead bin (2x2 rows and also 1x2 rows).

HOWEVER, I continue to get confronted and in many cases forced to gate check my bag anyway, despite attempting to explain and show that the bag WILL fit in the overhead bin. The most popular excuse is, "it's policy." And yet, anyone with a roller bag that looks small-ish gets on without issue.

Does anyone deal with this regularly, and have a method that usually works to get their bag on the plane?

I understand that flight attendants deal with this every day with people whose bags don't actually fit and then have to bring back to the front, but the inflexibility on this is just incredibly frustrating.

AA.com policy snippet below:
"There may be more restrictions on carry-on baggage at certain airports and on certain airplanes due to their storage capacity. If your belongings don’t fit in the overhead bin or under the seat, when you’re traveling on an American Eagle airplane, you’ll have to check personal items such as:

Roller board bags
Duffle bags
Larger backpacks"