Success: Back-to-Back Southwest Airlines Status Matches (With a New Twist)

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).

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. […] I signed up for a status challenge in 2018, met the terms of the challenge, and extended status for a year. I assumed I’d have all of 2019 to requalify, but Southwest’s challenges are weird, they provide exactly 12 months of status when you meet the terms of the challenge. So my status did expire in 2019 before I could requalify. However I rectified that with… another challenge. Once status expires from a successful challenge you can do another challenge. […]


  1. There are worse things than boarding C11 on a Southwest flight to a destination you enjoy for a week or more (particularly if you have a companion pass and don’t travel at least monthly). I would enjoy more conversation about the amount of work vs reward for each travel hack you do- for the busy professionals, or non-professionals. That is what I frequently find myself wondering. Awesome site.

  2. Could you elaborate on “status with another airline”? Like, any status at all? Even that “Silver Status” or whatever it is you get automatically for being a Marriott Platinum?

    Thanks in advance, this could dramatically change my flying habits as I heavily value A-List status with Southwest for Business Travel but would be WAY more inclined to chase status on another airline if I only needed 6 one-ways next year to re-establish A-List.

  3. Good information, Gary. Could you please clear up a little bit of confusion. You wrote, “Southwest Airlines will give you 90 days of status and an expedited CHALLENGE…” and ” Southwest will let you status MATCH over and over….” Am I right to assume that the way this would work is (1) request the challenge, (2) fly 6 segments, (3) start the 12 month clock ticking on status, (4) wait 12 months, then rinse and repeat? And, as Jeff asked, does any status count or must that status be of a certain level and above?

  4. Speaking of C11, I had C-10 recently and took a middle seat in the first row. I love the extra legroom. This works 75% of the time. Everyone hates the bulkhead, except this solo flyer.

  5. They are very strict about the prior reservations. I blew a challenge a few years ago when I used 2 one-way trips that were booked before my challenge was approved. Idiotic (like all the other promos that don’t count prior bookings which makes customers angry) but that’s the rule.

  6. Jeff, I did this last year using my United Silver status I got through Marriott…and I’ve never even flown on United. I also cancelled a previously booked flight and rebooked and the fare had gone down, so it was a total win.

  7. Blackpond,

    Thanks so much for sharing that makes total sense and is hilarious about United. I’m in exactly the same position with the Marriott-Silver United Status and I think it’s time for me to shift my strategy. My company prefers for me to fly Delta or AA anyway, so bundling business flights with a CC I could probably get to a decent status level. Thanks!

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