Southwest Airlines will give you 90 days of status and an expedited challenge to keep that status (3 roundtrips or 6 one ways) if you have status with a competitor airline.
However I learned that when you fly enough to keep the status you don’t get it for the next full membership year, you get it for 12 months. Since my challenge ended September 30, 2018 I kept my status through September 30, 2019. So when I went to check in for my flight on October 4 I had no status – and didn’t realize it – and a C-11 boarding pass.
Fortunately Southwest will let you status match over and over. It isn’t once in a lifetime. You have to wait 12 months between challenges, so you can challenge and meet the challenge, use the status and when it expires you can challenge again. They may not keep those rules, but for now that’s pretty lucrative. The only thing you cannot do is get 90 days of status over and over (without flying the 6 one ways to keep status), since you have to go 12 months between challenges.
I submitted a new status challenge request around 4 p.m. on Sunday and then before 8 a.m. on Monday I had already been approved for another status challenge. They’ve added a quirk I don’t recall from the challenge last time. “Please note that any previously booked reservations will not qualify towards the promotion.”
I assumed the three Southwest flights I already had booked would count towards the challenge. They won’t. Fortunately Southwest has no change fees. I can cancel and rebook my existing itineraries so that they count (in one case the fare has gone up a bit).