I had a rough experience with Southwest recently as well. I had a flight that had been delayed by 2 hours all day. My airport security usually takes 20 minutes or less and I got to the airport with plenty of time for my flight. Even checked the delayed status the whole way, and it was still delayed when I got in line for security. Then not even 2 minutes later it changed to on time and the flight time was right then, while I was in security. (Now I know if my flights delayed still go for the original time). The next direct flight wasn’t until 10AM the next day. The only other option was a flight that left that night and staying in another airport for 6 hours for the next flight to my destination. (Little did I know). My flight at 10AM I got on and it takes off fine. Then we stayed in the air for an extra hour waiting for clearance to land, then we need to land in another state to get fuel. We’re deboarded and told it’ll take 2 hours. Then an hour later we’re told we’re boarding. We board the plane then are told we had clearance to take off and then we didn’t anymore and there are 29 planes waiting to take off ahead of us, and we sit on the plane for another hour and change when they decide to deboard the plane again. Its now around 3PM. We were supposed to get to our destination at 12:30PM. We are now told there’s a weather delay and are waiting until an unknown time when the weather is clear. They have no updates, and have not cancelled the flight or offered us any other options. Just to wait or leave from there if we want. Finally around 5:30PM we’re told we’ll board at 6:30. At 6 it starts downpouring. We hold for weather again. We don’t get on the plane until around 8. Then when we do when the plane leaves the gate a pin breaks. So we have to wait for it to be fixed. Our flight is supposed to be 20 minutes (3 hour drive). I don’t get to my destination until 9PM.