I have a power chair and have made 6 round trips (with layovers it has been on and off the plane more than 22 times). All of those were on Southwest and I have never had a problem and my chair has never been damaged. I do take off the headrest, foot plate and joy stick, put in bag and take onto plane. Southwest will have you board first, let you take the chair all the way down the walkway to the door of the plane. If needed they will meet you with an aisle chair for you to transfer to and wheel you to a seat.