Can't Undo Several Times

So me and my buddy are making D&D dungeons and let's say he makes two mistakes, he undos twice and it puts the first mistake back rather than undos the two mistakes. Is there anything where we DON'T undo the undo?

This is a bit ambiguous question, could you give a more concrete example of what/where you mean this would happen? I'm going to assume you're referring to the "Undo"-action you can do to tokens on the map. AFAIK, this can be done to object/tokens on the map, but don't know the extent of it's capabilities, apart from it seems to be able to Undo at least 4 token movements. Considering there isn't a "Redo" option, I think you have to just manually do the action again in most cases.