Was this booked on your errorplan account or a non-status members?
The only explanation I have is that if it was a non-status account, erroplan's IT can't deal with a status member on a non-status account for some transactions. Has worked great for my family members the other way (non-status member on status member errorplan award resulting in non-existent upgrades being moved to the front of the cue and eventually the plane).
If it wasn't offered at OLCI and it was on your account, I can't figure out why not--would be interesting to get a read from others if they have been able to do this easily with OLCI and whether the reward was from a status or non-status account.
Maddening either way though--you still didn't get your upgrade!