So I recently booked a JFK-SEA rt on DL via Kayak.com. I used Kayak because it actually got me the fare that is published for the T bucket ($402 rt ai) rather than DL.dumb that wanted to charge me $417 for the exact same flights. Using Kayak, you choose the flights, and then it transfer you to DL.dumb to complete the sale. Well, I logged in to SM, and my info came up, but it did not request the UG (it just said UG eligible).

Concerned, I called CSR, and was told "Your upgrade request processes automatically, you have nothing to worry about." When it came time for OLCI, I find out I'm not on the UG list! OLCI asked if I wanted to add my name and try for a BF UG, so I did that. Missed the UG by 4 spots, they were using a 73H instead of the usual 752, oh well.

Now, I got to SEA this morning, went to SC, and asked the desk agent to request the UG for the return trip. A (rather new) desk agent said FO's weren't eligible for clearing at the 24-hour window, and that I could only try for a BF UG!! I politely told her that this is not the policy, I know it is not because I have cleared on the 24 hour sweep before, and she said, "Okay, I've marked it for upgrade." Get back home, check DL.dumb, still shows "Upgrade Eligible"

Finally, decided to try tweeting @DeltaAssist, and they got it done in 2 minutes! Now DL.dumb shows "Upgrade Requested" It's just amazing that two different CSR's botched this, and the twitter team took care of it so fast. I'm using twitter from now on.

Stating the obvious here, but make sure that your settings are such that it does automatically request your upgrade or else you'll see upgrade eligible instead.

Glad to hear that DL Assist got it done. I've had excellent luck with them resolving issues that seemingly don't get fixed by anyone else. That service is one of the best things, in my opinion, that DL has done in a long time!

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Settings don't matter when you use kayak to start the reservation. I use Kayak each time so I always have to tweet DL assist immediately following to request my UG.

Almost seems they're making you earn that $15.

Good to know. I've never used Kayak. I assumed it could've been a settings issue. Thanks, I learned something new!

I honestly believe that DL has their best CSRs on Twitter. Those folks are awesome and they are quick.

I've run into the same issue ..... Kayak does not carry forward your "upgrade requested" check-mark.

Sometimes this approach works ... go through the motions of booking your trip with Kayak, however before clicking the "Enter Passenger Info" button (after being refered back to Delta.com), click on "Start Over".

Make sure the "upgrade requested" block is checked, then re-enter the same itinerary (if available on Delta.com). You may or may not be able to get the same routing as Kayak and you may or may not get the same price as Kayak; but at least your upgrade will be requested.

This is also a DL.dumb issue (although it could also be related to Kayak.com). I had all of my reservations revert back to "Upgrade Eligible" in early March. It took a quick tweet to DeltaAssist to get it all sorted out. Not sure if our events are related, but just wanted to point out that it isn't strictly a kayak.com issue.

These are 2 seperate issues.

1) Deltamatic will drop upgrade requests at random times.
2) Booking 3rd party, dl.com drops the upgrade request at booking.

Same solution to both though, check your ITNs often.