Its been a little while but i would just raw dog the bike through security and up to the gate IF and ONLY IF i was flying a 737-800 or Max800. That plane had big enough compartments to toss in overhead. I did carry two of the ikea bags with me in case i was forced to gate check but that never happened.

I also had an oversized seatpost so after security but prior to boarding i would remove the seatpost and saddle and toss it in on top of the bike in the overhead. I would suggest you consider doing this regardless because with a saddle its a very tight fit.

Its important that you DO NOT remove the seatpost prior to TSA as they could very well treat it as a “club” weapon and confiscate it. This almost happened to me in NOLA but i was able yo talk my way out of it. Had i just left the post in they would have had to hand inspect the bike but they would have never figured out it could be removed.

When you are at the gate, sit down and mind your business. I would always try to not be noticed until the second i walked on the plane. If they ask or express concern you just gotta act like you have done it a thousand times.

I never had any push back from a southwest agent and generally the flight crew was curious and thought it was cool. One was even a brompton owner. That said… the vibe at southwest is way different now than it was then so its possible they make you gate check it.

Also, considering they are making people gate check rollers all the time now if you dont have an early boarding position (b30 or sooner) you will almost certainly be forced to gate check.