Reminder: Don’t book multiple Southwest reservations on the same day

Southwest has the best cancellation policy in the business: cancel up to 10 minutes before your flight takes off and get all of your points back and the taxes refunded or get a Southwest credit good for 1 year from the date you booked your flight if you bought a cash ticket. That creates awesome flexibility. It creates so much flexibility that it is tempting to book yourself on multiple flights on the same date with the goal of letting yourself solidify your plans at a later date while taking advantage of a cheap ticket when booking in advance. I strongly recommend you do not do this. Southwest has been known to cancel your tickets when you book multiples on the same day / route or that put you in the sky at the same time. See this Flyertalk thread for more and the email below from reader Frank as a caution.


Reader Frank reached out with a recent story illustrating what can happen with multiple reservations. Here’s the full text of Frank’s email:

Hi Greg, you may want to publish this.

One of the best things about Southwest Airlines, perhaps second only to the companion pass, is the ability to cancel a reservation made on their site up until just before departure and get either a full refund or a credit to be used within a year, depending on how you paid for the ticket. This feature has been of great value to me and, I am sure, many others. It allows one to make multiple reservations at the lowest prices, say 3 weeks in advance, and then still be able to cancel the ones you don’t want up until the last minute (10 minutes actually). Southwest’s site even allows for multiple reservations for the same route on the same day – but here comes the word of caution:

Recently I made multiple reservations including two on the same day for myself and my wife because we weren’t sure which would suit us best. These were just fine … until a day and a half before the flights were taking place when I received two emails from Southwest showing two reservations cancelled, one for each of us. Now imagine the reservation codes were:

Flight 1: My wife’s reservation code was, say, AAAAAA and mine as a companion was BBBBBB.

Flight 2: My wife’s reservation code was, say, CCCCCC and mine as a companion was DDDDDD.

What did Southwest do? They cancelled AAAAAA and DDDDDD, leaving us on different flights (BBBBBB and CCCCCC) making both reservations useless to us as we always travel together. To make matters worse, because we were using a companion certificate, my reservation BBBBBB could not even get a boarding pass as Southwest does not allow me to fly without my wife being on the same flight. I couldn’t even cancel mine, leaving a total mess.

The cancellation emails came late at night and I immediately called Southwest and was told the wait was 15 minutes on hold or I could leave my number and would be called back. I left my number and was told I would get a call back in 49 minutes! Not good, so I called again and was given a 45 minute hold time. While on hold I sent an email complaint to which I received a call back the next day, when I was unable to see the call, and was told it was because of the duplicate reservations (which was obvious to me anyway) but no explanation of why they messed up both reservations rather than picking one. It took 2 additional phone calls to get the reservations somewhat corrected by Southwest’s sympathetic and very helpful staff but by the time this was done all done I was all done and decided to fly the following day, partly because I was not sure the boarding passes would be valid – my account still showed no ticket.

I don’t think this was done maliciously as punishment for my double booking (at least I hope not), rather I think it was just their computer system not being able to handle this very well. So, be warned or you could find yourself stranded.

I am not sure what you would do if you really wanted to fly the same route on the same day twice.


Bottom line

Don’t book multiple Southwest reservations at the same time. According to the Flyertalk thread, Southwest’s system generally auto-cancels duplicate bookings sometime between 24-48 hours after making the duplicate reservation and they cancel just after midnight central time (explaining the late night email Frank received). It is unpredictable as to whether they will cancel the first booking you made or the second, so you can’t count on one or the other to be cancelled (which is presumably how Frank’s got so mixed up). Furthermore, making bookings that you don’t intend to fly is against Southwest’s program terms, so there is also the risk of shut down if Southwest perceives you to be abusing its system. I’ve personally cancelled plenty of Southwest bookings without issue, but it’s worth a note of caution.

About Nick Reyes

Nick Reyes is a (fairly) regular guy with an animalistic passion for maximizing the value of miles and money to travel the world in comfort and style. There is little in life that he loves more than finding a fantastic deal and helping you shop smarter & harder to achieve your travel dreams.

More articles by Nick Reyes »

Leave a Reply

13 Comments on "Reminder: Don’t book multiple Southwest reservations on the same day"

Notify of

I had a similar scenario happen last year around the time their new system rolled out. I was in the habit of booking multiple reservations like this (guess that wasn’t my best choice, but didn’t give it much thought) and when the new system rolled out (their website/backend system) I experience this first hand on multiple trips I had planned. It was a huge, huge mess, and without flyer talk I concluded the same things you make note of Nick. Just after midnight the cancels come in, and it’s unpredictable. In fact, I believe I had both trips canceled on some of them, and it was clearly an automatic thing, not a human being doing this cancelling, so I don’t think it was to spite anyone, that’s for sure. Either way, point being, I think this rolled out about a year ago, because before that, I could book in this fashion, without issue.

Thanks for the reminder! Good for readers to watch out. 🙂

Michael Karpiel

WN (SouthWest) had the most antiquated Res and Inventory management systems in the business. Finally last year they converted to the Amadeus platform which also allowed them to schedule flights further in advance and allowing bookings up to I think 330 days in the future like most carriers.

Anyone that books multiple flights on the same day is gaming the system and taking advantage of a feature that is pretty unique to WN with their flexible cancellation policy. It hurts their bottom line and if allowed to continue would eventually force them to abandon this flexible policy.

I’m all for saving money but also understand that the companies that I do business with are for profit organizations and need to make money to continue to operate. As long as they are ethical and not gouging it’s up to us as consumers to pick the service and price point we are willing to pay.


This will happen to you even if you CAN and WILL fly twice on the same day. I was in Oakland for business and my husband and I planned to go to Lake Tahoe for the weekend. I was flying from Oakland to Reno and he would be coming from BWI. Because there were no direct flights from BWI to Reno, I booked him BWI to Oakland where we planned to meet up, have dinner, then fly together Oakland to Reno. But Southwest cancelled his reservation as a “duplicate.” I had to call to get it reinstated. The system must automatically look for two bookings on the same day in the same name, regardless of details. Beware!


If you do this as a matter of habit, you are taking away seats from other travelers that you will not use. I find that to be a bad habit.


Agreed! This is a pretty DICK move to leave two open reservations a day before a flight knowing you will only fly one flight. Things like this drive up travel costs for everyone. And then You’ll complain when they stop allowing last minute reservations to be fully cancelled


I would Cancel 48 hrs out but in Dec.because of the weather @ MDW i would book 4 in the morning and use two .No I don’t care I was going to see my Doc as in huge costs if I don’t get there.
Thanks SW and my Chase I’ve not used $$$ for a SW ticket I bet in 6 years .


Points Adventure

Two comments.

1. You can use this restriction to your advantage in certain situations. Example:

2. Points bookings don’t have to be cancelled before departure. You get the points back even if cancel after takeoff (that you’re not on, obviously). This is stated in the T&C.


As a former travel agent, the policy of cancelling double bookings has been around for a long time with all the airlines, not just Southwest.


Southwest did the right thing. It’s abusive behavior on the part of the customer to keep multiple bookings up to the last minute. A few weeks out, I get it. That close to flight time, it’s wrong.

Lee @ BaldThoughts

I’ve had this happen to me once when I booked extra flights because I wasn’t sure when my meetings would be over. Not cool when they cancel your extra reservations.


Serves you right!! Not feeling sorry for you at all! It’s selfish behavior. Making duplicate reservation blocks seats for other travelers and causes revenue loss for the airline.

David Benkof

Life Hack:

Whenever there’s a 45-minute wait for anything, call back and “opprima el numero nueve” for Spanish speakers. Sometimes (only sometimes) there’s a much shorter wait for the Spanish line, and the operators ALWAYS speak English. It’s not like using a handicapped parking space; Spanish speaking is not a disability.