For the second week in a row, my Sunday flight home to NYC after work was cancelled. I'm a PM/MM and it still took me almost two full days to get out of Tampa. Now I'm in Charlotte and my JFK flight yesterday (Sunday 7/16/23) was also cancelled after everyone was on the plane. But this time I was more prepared, knowing that getting a Monday flight was going to be challenging. As soon as we were delayed even ten minutes, I booked a paid one-way for today just so I had a seat. When the flight was eventually cancelled, I immediately rebooked (on the app while still sitting on the plane) and got another Monday flight. Of course, it's later than the backup flight I had already booked. Within 5 minutes, the only other options left are for Tuesday connections to NYC.

After last week's experience, I'd rather take the earlier flight because of concerns over more issues / cancellations. But obviously I'd rather not spend the extra money since I already have a paid round trip (this is the return flight FYI). Last week, when discussing this potential scenario with a phone agent, she said I should ask for the Global Reissue Team and they may be able to switch my tickets to get me "rebooked" on the earlier flight and make my paid ticket the later flight. Assuming I get on the early one, I could then cancel the later one either for a 24-hour refund or credit, which is fine.

I just called and the agent put me on hold to talk to global reissue. She wouldn't connect me. Came back and said they couldn't do it. Before I call back and wait on hold another 30 minutes (what happened to the callback option?), has anyone ever had success doing this? Worst case is I can just take the flight and then try after the fact to get refunded, but not sure that will be fruitful either.

Hope that all makes sense! Thanks in advance.