The automated upgrade system kind of got in the way. I called and asked for an upgrade 2 days out (gold elite) and was told that the agent upgraded me. It turned out day of the flight I was not upgraded. Everything worked out ok, after a few tries I got a helpful agent on the phone who upgraded me. They tell me the problem was that I was silver at the time I made the reservation. It seems not all of the agents know how to grant elite upgrades now that the automated system is in place.

Just keep calling until someone says yes, thats my advice.