I'm a high mile flyer on Southwest (earned CP) who routinely books multiple reservations and rearranges them as my schedule changes. I've read that Southwest has started aggressively cancelling same day reservations but haven't had a problem with it until now. They auto cancelled a reservation for a flight 16 days out. One flight was heading east, the other west at about the same time. I planned to figure which place I needed to be next week and cancel the unneeded ticket about a week out. In the past, I've routinely booked multiple tickets for the same day and cancel them as needed a few days in advance without issue, sometimes at 24 hours out. I guess what's surprising to me about this is how far in advance they cancelled it, given that it's currently not anywhere close to a full flight. I'll submit this as a data point for people who triage tickets like I do. It doesn't bold well for my relationship with Southwest as I value the flexibility.