Normally, I'm a rule-follower. My bags are all the right dimensions and I roll my eyes at people "trying to get away with stuff." However, I'm flying with my dog in-cabin coming up soon, on an airline I don't have status with. I'm debating whether to go ahead and pack three days worth of clothes in my wheeled laptop back, AND STUFF MY PURSE IN THE LAPTOP BAG SO I ONLY HAVE TWO TOTAL BAGS, and try to board with that and the dog to avoid the baggage fee. My wheeled laptop bag is very much smaller than the carry-on suitcase maximum, and I could always whip my purse out of it, put my Macbook Air in my purse, and check the laptop bag/board with just my purse and his carrier if the counter agent objected or the gate agent told me I had to gate-check the small wheelie. Anyone have experience with this? To me, it's crazy that he counts as my *bigger* carry on, since he is *required* to go under the seat in front of me, but I've only flown with him on airlines I have status with up to this point, so I've always just checked my actual luggage and boarded with him and a medium-size purse (which contained my laptop and went in the overhead since my under-seat space was occupied).

Relax, follow the rules and just make sure your pet is traveling comfortably.