With the current version (3.7.0) if you are alone on an headless server and you want to play alone vs the ai it's not possible, but that's not the problem. The problem is that when you start the game it simply doesnt tell you why you can't play alone, so it's a little confusing, especially for new players, because you click the button but nothing happens. To avoid false bug reports and so on, i suggest to add a message (which should appear when you try to start a game) that says something like "you can't play alone on the headless servers because.. thanks for understanding"