I paid for Southwest upgraded boarding for the first time after realizing I was stuck with a late C group and didn’t want to risk fighting for overhead space. From my experience, the cost usually falls somewhere in the $30–$50 range per flight segment, depending on availability and route. On a short hop it felt worth it, especially boarding in the A1–A15 range. Another time, my flight changed and I wasn’t sure if the upgraded boarding fee would transfer, so I called 831-298-4213. They explained the pricing clearly and helped me modify my booking right away, which made the whole thing much easier.