It is no secret that the Southwest “allows” a ton of flexibility for a passenger. In the past, you could have multiple flights booked on the same day if you were unsure about the time you wanted to fly or the destination you wanted to fly to. And when you make these speculative reservations with points, as long as you cancel 10 minutes prior to the flights departure time, the points go straight back to your account and the taxes/fees paid back to your credit card. While doing this has always explicitly been against the terms, Southwest’s IT system is so outdated that they never caught on and reservations were 99.99% kept.
This is all about to change though. According to this FlyerTalk thread, there are many reports of reservations being canceled for reservations made May 8th or later. It seems like if you have two reservations that put you in the air at the same time or two reservations with the same two city pairs on the same day, 24 hours after the 2nd reservation is made, one of the two reservations will be auto canceled. Based on the thread, it seems like we are still unsure if it is the first or second reservation that will be canceled. Reports show it both ways. It seems as though Southwest’s new IT system that is being implemented is able to pick up these double bookings.
So for those looking to make future reservations, be cautious. For those that are currently holding two reservations for flights previously booked, you are probably in the clear, but keep these new IT enhancements in mind for the future!
I am personally a big Southwest flier. And I will be 100% honest with you. There are times when I have had two flights booked on the same day. Not often, but I have done it. This was always the beauty of using points on Southwest flights. I am perfectly okay with the system now cracking down on it though. At the end of the day, this will help all travelers. Extra flights will no longer be booked meaning other fliers should be able to book flights at a lower fare class for the same flight.
Feel free to report any data points you have in the comments section below!