If you click on that boolean it will show you what is wrong.
I tried to replicate your issue, and it did same result. I think is that, when you move with your bodies, you did without boolean. But than you change them with boolean action.
And if you change history, that you put that boolean before move/rotation. The shape which was moved, isn’t same as before (now its already booleantificated but history remember just normal bodies, if it make any sense)