Supervisors often prefer rule breakers, up to a point

A more palatable phrasing, "supervisors prefer people that engage with the rules with purpose." That is, choosing to break a rule because you are making a cost call based on what you were able to achieve is not, necessarily, a bad thing.

The "point" where this fails, of course, is where the "cost" call above is such that the supervisor can't agree.

Sometimes, the goal is to create an environment where people must break certain rules to get anything done, which everyone (including supervisors) understands, but by way of imposing those rules responsibility and liability is transferred to subordinates.

I think those environments are bad, most likely? Why would it be a goal to make it so that people break rules?

Making people think about the rules? That is fine and good. Setting them to be broken, though? That just sounds broken.