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Are upgrade offers available after flight change?

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Hi All! I am based in ATL but booked two roundtrip flights from JFK to MAD in May in miles. As many of you know, flights out of Atlanta to Europe are typically more costly so flying out of JFK was significantly cheaper at the time I booked. Since the plan was to start in Madrid and end in Barcelona, I later changed the return flight to Barcelona (so, JFK to MAD and BCN to JFK). The BCN to JFK route ended up having a flight change - Delta essentially cancelled the 2 PM flight we were booked on and booked us on the 9 AM instead. I saw this as an opportunity to see if I could change the return flight from BCN to JFK to BCN to ATL. I knew it was a longshot, but I called the DM line, and the representative changed it! So to me, I am getting a pretty great deal at 56K miles/person for a double open jaw flight. However, ever since this change was made, my entire seat map (outside of Delta Comfort) has been greyed out so I am concerned that I will never be presented with the opportunity to upgrade since the representative that initially made the change made an exception which wasn't technically allowed. Of course, I can't make any changes to the flight in the app without getting errors. I tried calling a few times to see if there was an issue with my itinerary and if they could see upgrade offers on their end, but the representatives didn't see an issue with the flight precluding me from being presented upgrade offers in the app and said that offers would still be generated as they become available.....so to test this, I booked two dummy RT JFK to MAD flights to see if I would get an offer to upgrade on the JFK to MAD leg, and the seat map showed upgrade options for both PS and D1 so I'm convinced there's something going on with my itinerary due to the inbound flight change.

Has anyone had a similar fact pattern but received upgrade offers in the app? I think I'm going to have to re-book, but I'm trying to avoid doing so. I really want my mother to get the full D1 experience including a visit to the JFK D1 lounge (although it would have been nice had Delta been flying something other than the A330-300 on this route :-)). I know that many would advise that I book D1 outright, but I don't want the experience bad enough to warrant $10,000 lol. I've had pretty good luck in the past getting reasonable offers through the app.

What would you do in this situation? Wait it out or re-book a "normal" non multi-city route?

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