Diamond Medallion upgrade... how does it work?
 

I read from Delta site that Diamond medallion starts to clear 120 hours (5 days) prior to departure, but my LAX-LIH flight departs 6/8, which is about 3 days prior to departure. There are still 6 open seats in first class, and there hasn't been change in first class seating from T120 until now. I am just wondering if Delta holds specific flight from upgrading medallion members or they won't start clearing upgrade on certain routes based on popularity...

I put a lot of spending on AmEx card to earn the diamond status, so I am just wondering what's the value of it if what's said on the Delta site isn't what's in reality....

DL may upgrade you as early as five days beforehand, but often holds seats for buyups to first class. In this case, I suspect they think they can convince some folks to buy LAX-LIH upgrades. I don't know where you're seeing six open seats in first, but if it's from the seat map, keep in mind that there may be people who have booked seats in first class but who haven't yet selected seats.

"Open seats" do not mean you can upgraded into them for 2 reasons.

One is that some pax already in BE might not have selected seats. The other is that DL will hold back BE inventory in case people want to buy expensive tickets.

The open seats might be an indication you have good odds of getting upgraded in the next few days or at the gate. But that is all.

Upgrades are capacity controlled. All airlines hold seats hoping they sell. If they dont you'll get seat at the gate.

Being a HNL based flyer, most of the time, Hawaii based flight upgrades will happen at the day of departure or gate. As a Diamond, you have the opportunity to clear 5 days prior if upgrade space is available. We all have been there, assuming once the 5 day hits, we automatically get upgraded. This is not the case, as only if automatically upgradeable inventory is available once your window hits. Your upgrade will depends on when the inventory becomes available within that 5 day time frame.

when i was a platinum medallion, i almost always got upgraded more than 5 days prior to departure on routes like LAX-SJC, LAX-SFO, LAX-SLC, LAX-LAS. So I had good upgrade experience as Plat so I was under impression that Delta treats its elite members well. I understand they are short-haul compared to LAX-LIH, but I was thinking if got upgraded easily as Platinum on those routes, I would have even better chance as Diamond on longer-haul routes.

Really depends on the routes of when they release upgrade inventory. For example, my SEA to MFR, 9 out of 10 times upgrade within 5 days as a Diamond. My XXX-HNL, HNL-XXX usually upgrades at the gate (T-60 minutes or so). However, as a Diamond, you will be higher on the upgrade list versus being a Platinum, so yes, you have a higher chance on upgrades.

I don't think short haul west coast flights are a fair comparison to mainland to Hawaii when it seems like everybody and their dog wants to go there this summer.

As mentioned above their capacity controlled based off what rev management things they'll sell. My trip last weekend I cleared 3 of the 4 flights at the window and the last one day of. Is what it is

Doubt you see this upgrade earlier than day of. Your value as Diamond will be that you will be at the top of the upgrade list when the time comes.

(as a side note, per expertflyer this flight has 4 seats left for sale)

Unless someone has used an “upgrade cert” (GUC or RUC), then you will be below them.

FWIW LAX-SFO is one of the easiest upgrades in the DL system. Trying to compare that to a hawaii route where they actually sell lots of premium cabin inventory is just setting yourself up for disappointment.

True -- provided the agent applied it properly (sadly, not a given)

Just FYI, my upgrade was cleared a 1.5 days prior to departure in later part of 6/6 evening