Trip summary page (first page you see after selecting the flights) shows "Not Upgrade Eligible" even while properly logged in.
After filling out my personal information (all while logged in)
It then switches to Upgrade eligible on the Review and Purchase page before submitting final payment.
I think it's an error with their search system not pulling in the SM info to show upgrade eligibility on the flight searches, but once you start filling in pax info it properly pulls in the eligibility info at that time. It might be an error with the fields and the search platform... without knowing more about how their software works though it's just a guess. However, I DO know that I don't worry about the upgrade eligibility issue until I get all the way through to the Review before purchase screen. As long as I show Up Elig. at that point I know I'm good to hit the payment submission button.
Hope this helps clarify for people. I know it's not completely satisfying, but it's a relatively minor issue that I don't consider mission critical (yet) for dl.com either.