Originally Posted by
MSPeconomist
If you booked when logged in on delta.dumb, the request upgrade box normally is automatically pre-checked unless you have a bunch of others on your PNR. If you book through another channel, you must actively request the upgrade.
This has become a significant problem of late. Flying with my SO (who until 29Dec12 was non-status) led to about half of our itineraries being "Eligible" and not "requested". Adding insult to injury, if you don't get to it quickly (tweet DeltaAssist), you lose some priority on the UP6 list as you wait
Of note, this occurred because I failed to enter her SM# at the time of booking. Without this, it will not automatically request upgrades, even once her info was entered.
Best of luck with your upgrades!