I have a group of friends I travel with every year and there is always indecision on if we will arrive on a Wednesday or a Thursday. Since I have enough points I have always booked the Wednesday and the Thursday one way flight early and then just canceled the one I didn’t need when the decision was finally made. I have done this for many years. No malicious intent, just trying to make sure I get the Flight times and prices I want.

last night, in the middle of the night, Southwest canceled my Wednesday flight. This is the first time this ever happened. I am assuming there is some new algorithm in place that noticed I had two flights that were unrealistically close and the computer decided I could only have one of them. Just wondering if there is some new policy in place as this never happened to me before. Further, even though I received the email stating my points were refunded I’m actually Not quite sure they were so now I need to deal with that as well.

Just wanted to check if what I was doing was unscrupulous and I’ve just been getting lucky or if there is a new policy in place where I can no longer hold two reservations like this anymore. I was just sort of shocked to see Southwest cancel something without permission like that. In all my years, this is the first time.