We've traveled several times with our Frog and never had an issue with security. You'll need to take the kid out of the stroller and carry him/her through the WTMD and you'll need to fold up the stroller and put it through the x-ray machine (it fits in every machine I've tried).

Note that if you're using the standard Bugaboo seat on the stroller, you'll need to ask for two gate check tags (one for the seat and one for the wheels) unless you're also bringing the enormous Bugaboo travel bag to gate check (we never bought one--just checked it bare).

If you're using an infant car seat (like a Graco Snugride) with an infant seat adapter instead of the standard Bugaboo seat, you should be able to use it on the plane as long as you've paid for a seat and the car seat is FAA approved. gobluetwo, does AA have a specific restriction on infant seats?