As a diabetic, I carry a blood glucose monitor with me always. One time I flew, I had my roll-aboard bag, my laptop computer bag, and a small camera bag. The camera bag also held my glucose meter in it. When stopped at boarding, I quickly said that the small bag contained medical supplies, and they let me on board, no further questions.

I do this most of the time, and usually before I'm questioned, I volunteer the information that the small bag contains medical supplies. No further questions. BTW, it doesn't take up any more space on the plane, since I put both the laptop bag, AND the small camera bag UNDER my seat.

OK, not that I am suggesting that anyone should lie, but if you honestly have to get to get that extra piece of carry-on luggage aboard, you could use the above mentioned information.

And just as soon as everyone does that, you will have to check that rollaboard!

Typically, if you make even a half hearted attempt to put one bag inside the other i.e. unzip the top of the bigger one and set the small one on top whle walking onto the plane, nobody says anything.

Actually, no. Medical supplies are EXEMPT from the 2 bag limit. Interesting, the term "medical supplies/equipment" is never defined. Therefore, if you had an extra bag with Tums in it, that could possibly be medical supplies.

As this is not about US Airways and is basically promoting behavior to skirt airline rules, it's closed.