Update:

Called again yesterday. Our flight yesterday (entirely different trip) on DL was delayed by 1 hr. Called to see if could be rebooked on an earlier flight. Was all sold out. Asked if could the change to SWF be made for September as a courtesy due to the delay. No.

Friends still took us to the airport, called again asking if they could overbook us on the flight they said no. Asked if could the change to SWF be made for September as a courtesy due to the delay. No. Asked if I could speak with supervisor. Kindly asked if she had the ability to put us on earlier flight and she said completely full. Asked same thing of consideration could be made for September due to us now arriving at almost 1a instead of 11:30 (flight had additional delay by this time). She said absolutely not. I tried to reason with her that I understand schedule changes but this is two changes that I’m being inconvenienced on, could a bit of flexibility be made. Yes, I’ll give you $25 e-cert or allow you to change your time for September flights for no fee collected. I asked if that was actually something she would be doing because my understanding is as the flight is under MCT it has to be changed. That’s not a customer service gesture but an illegal connection. She conceded that yes I would no longer be able to be on my scheduled flights. I politely declined the $25 as I saw this was going no where.

We arrive at airport. Get through security with HBO. Go to the earlier flight and agent said completely full no seats left. As closing a flight can be busy, went to the next gate over which was empty and the GA was just sitting there. Asked if she could help just with rebooking and she said call the number on the red card. (At this point I can’t believe how far DL customer service has declined.)

call the number. Got an amazing agent. She put us on the earlier flight, connecting via atl rather than direct. I asked if she could at all possible look into our pnr for September. She was more than happy to do it. I explained that I called earlier and did not have a good experience, therefore there may be notes in the file. She confirmed this saying that notes indicated do not change the flight to SWF without collecting increase in miles. The agent said my request was perfectly reasonable, apologized for the delay, gave us the exact flights we wanted, and thanked us for being a loyal customer.

Resolved!!!!

p.s. sorry for the long story.

P.p.s. So happy we rebooked thru ATL as our original flight was eventually cancelled. They said was due to mechanical issues.