Supervisors often prefer rule breakers, up to a point

Fundamentally, rules almost always come with compromises — for the sake of making rules understandable by humans, they have to be relatively simple. Simple rules for complex situations will always forbid some amount of good behaviour, and allow some bad behaviour. Many of society's parasites live in the space of "allowable bad behaviour", but there is a lot of value to knowing how to exploit the "forbidden good behaviour" space.

The worst of all worlds is when a blind application of the rules results in bad behavior.

This situation seems to come up frequently, and I'm very often appalled at how readily otherwise normal people will "follow the rules" even when it's clearly and objectively bad, and there may even be existing pathways to seek exceptions.

AKA "perverse incentive"[0]

[0]: https://en.wikipedia.org/wiki/Perverse_incentive