I was able to upgrade hours after OLCI!
 

Here is some info I would like to relate. Yesterday I flew AS 30 PDX to BOS. I had went to check in online Sunday morning 24 hours or so prior to departure. the F cabin was full so I went ahead and checked in. Early yesterday morning before going to the airport I clicked on my res to see if there were any flight delays. Much to my delight the "upgrade to first class" icon was now showing! This is after I had been checked in for several hours. I had to reprint my boarding pass at the airport. I could not do it at a kiosk. I saw an agent and he looked a bit puzzled at what he was seeing on his screen but made no mention why and I got my boarding pass. I am flying as a DL gold btw. At the gate there were about 10 or so on the list. Was I just rely lucky and snuck one by?

You were very lucky... this is a known issue with AS, that within 24 hours, if U class is released, someone with elite status can upgrade, or pay to upgrade the route if on a high enough value ticket, w/o status.

I've had a similar experience. I checked in for AS 2 once the afternoon before departure (SEA-DCA), and misplaced my boarding pass, and went back in and the icon was there. yay. I was comfortably seated and saw 3 or 4 colleagues from the office shuffle by on the way to the back.