@GamerNerd_i The "Simulated ladder games" achievement is updated in-game sometimes when making requests to the server. The quickest way to update it is to tweak the game volume a few times.
As a suggestion/feature request, perhaps an "Update achievements" or "Recalculate achievements" button in the achievements modal could be useful. Or, perhaps, automatically update the achievements when (re)loading the game. Maybe @nick already has a plan to make this more intuitive.