On September 1st, the day the program to auto upgrade began there was a computer problem. There were a lot more silver elites to be upgraded than anyone anticipated. It took a few days to resolve but I've been reassured that as of this Sunday, (9/10) the problem will be completely solved. They've upgraded the capacity a lot.
Re your question on if there are 3 silvers and 1 seat...who gets it? The criteria is whoever booked their reservation first.
Hope this helps! Honestly, it's a great program. You won't have to stay up til midnight anymore to call in to upgrade.