Had a marginally frustrating GS experience on Wednesday. Was at RSW trying to get to ORD as the snow storm started there. On the 3PM departure and was pretty tight to that with work meetings so wasn't being particularly vigilant on my flight options given that I assumed this one would be delayed if not cancelled. Get to RSW and see that the 12:30 ORD departure is still there but that it's making moves to board. Check the app and see that 12:30 flight is pretty open. The line for the GA was very long so I call GS.

I'm on a OW D Fare on the 3PM. Ask if I can be moved to the 12:30. She tells me only in coach. The UG WL shows 4 seats available in F at the gate screen (as in 16/20 booked with 16 checked in). I tell this to the GS agent and she tells me that she would have to oversell it to put me in F. I ask if she'll do that given my D fare and she says no, she can't but if I go talk to the GA they can probably get me on standby and have me pop to the top of the list. Wait in line for 25 minutes to get to the GA while they start boarding and by the time I get up there they're booked full not just in F but in Y so I stick with the 3PM which ends up going but got me in ~2.5 hours later than the other flight would have. RSW GA was super chatty after they closed the flight, told me I should have called GS because they actually processed 2 Y upgrades to fill F.

I get it was WX IRROPs and I was asking for an exception but 10 years ago when I first made GS I have a very strong sense that I would have been oversold onto that flight and home before my kids went to bed instead of after. Smallest violin moment for sure but was a reminder to me of what GS really means to UA in 2025.