If I'm taking a normal size carry on bag, would a daypack with my computer and ipad in it be considered a personal item or briefcase?
Thanks in advance!

I carried a normal carry on and my hunting backpack crammed with my optics, laptop and other electrnoics, books, travel docs, etc. Neither the gate agents or flight attendants gave it a second look. I think as long as it fits overhead or under a seat, they dont much care.

I've had the same experience as Adamhunter traveling domestically over the last few years.

I fly over 200,000 miles a year. You will have no problem unless the flight is sold out and everyone on the flight is doing the same (has 2 carry ons). Since airlines started charging for bags, no one wants to check a bag and overhead space runs out quick.

My favorite is the mom, dad, 2+ kids family that each have a large back pack and maximum size carry on per person. Then of course now days, any child under 5' tall is incapable of walking so they require a stroller the size of a Prius and a car seat that meets the specs of a pilot's seat for an A-10 Warthog.

A lot of flights are making people check their "max capacity" carry on bags at the gate for free. Word of advice, have the items you do not want to check in a bag that will go under the seat.

I've also seen the airline personnel weighing the carry on bags. Over a certain amount and in the cargo hold it goes!