Diamond Medallion Status & upgrade certificates

I have been flying Delta Airlines and have been a frequent flyer with them for 40 years.  I have achieved Silver, Gold and Platinum status numerous times, but I've never reached Diamond Medallion status....until this year. 

Often the perks you get by achieving a status level are not as great as they sound.  For instance, as a solo traveler, getting a companion ticket isn't of great benefit to me.  So, when I reached Diamond level this year, I looked into all the benefits to see how usable they were for me.  Some of them were great, such as ride share credits.  Since I use Uber and Lyft often, it was valuable to get a $10 statement credit each time I used the service.   Some of the benefits weren't as valuable to me, such as Resy rewards, where you'd have to eat at 10 specific restaurants to get the $200 value. 

When I reached Diamond level, I received some automatic benefits, as well as "Choice Benefits."  I could pick three "Choice Benefits," which included perks, such as Starbucks rewards, gifting status to a friend, and getting lounge access.  I chose what I thought were the most usable and concrete choices: a $700 credit on my American Express Card, 35000 bonus miles to my Delta mileage account, and upgrade certificates (4 regional and 2 global).  These upgrade certificates were the most valuable perks for me. Let me explain why.

The way the upgrade works is that you pay for a seat class and immediately get upgraded to the class above.  Of course, I wanted to use them to fly first class. Sounds great; however, it has been a little tricky to use them. 

When you go to the website to search for flights, the upgrade availability is listed below the flight.  I discovered they are only available on some flights, which are usually those that are less desirable times.  It's necessary to book fairly early to nab them since they only offer limited certificates for any one flight. A certificate is good for a destination, even if it requires more than one flight leg.  However, sometimes the upgrade would be available for one leg of a flight but not the other.  They will add you to a waitlist if this is the case, but, personally, I don't like the idea of using up one of my certificates without being assured I'd have the upgrade for both legs of a flight.  I tried to book these on the Delta website, but it wasn't a clear process. 

To get some clarity, I called and spoke with a Delta agent. She told me it was actually best to call rather than try to book online.  She helped me through the process and gave me options for flights that had no waitlists. Later, when I called an agent to book an upgrade for another flight, the agent informed me that they were revamping the website to make booking certificates online easier.  I'll be looking forward to a simpler system. 

So far, I have used one regional certificate from Ft Lauderdale to Phoenix and an international upgrade certificate round trip from Phoenix to Peru.  I paid for whatever the class below first class was, either Delta Comfort Plus or Delta Premium Select and was immediately upgraded to first-class or Delta One.  On one flight the Premium Select was sold out, so I was able to book Delta Comfort Plus and be upgraded two classes to Delta One.  Using these certificates for the Delta One lie flat seats is definitely the best benefit!  I achieved Diamond Medallion status in 2024 and the upgrades expire in 2026.  I'm determined to use all of them before they expire!