What are your chances of getting upgraded on Delta?

I am currently a Platinum Medallion flyer on Delta.  I barely made 100 segments last year, and I hope to get to 100 this year to continue the status.  I get upgraded on my flights about 50% of the time.  When I don't, I don't really mind, though it is nice to have the extra room, and not worry that a Yeti will sit next to you and blop over into your space.

Getting that upgrade has to mostly do with 3 factors:

1. Your Status (Silver, Gold, Platinum or Diamond)
2. Your travel woes (flight cancelled?)
3. Price of your ticket.

I had one manager that was Gold Medallion and got upgraded over myself as a platinum because she always bought an expensive ticket.  Not very nice to the client, but that may be one of the reasons she no longer works for the company.  This same manager would also go to dinner with me, get several expensive drinks and then have us split the ticket.  Even though the client paid for the meal, my meal looked $15 more expensive than it ordinarily would.  I was not amused.

Most travel warriors (the Plats and the Diamonds) like to travel Monday morning through Thursday night.  Therefore, you are competing with high status folks if you choose to travel during those periods.  I've seen one flight that had about 15 diamond tags (you see them on their bags) that didn't get into first class.  If you choose to fly Sunday night instead, your chance of getting upgraded is more likely.

Shmoozing with the red coat (the Delta managers) doesn't help, though you might get a free drink ticket or two.