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.

Example?

For which side?

Most examples boil down to common sense. Nobody is going to arrest a 14 year old for driving their dying parent to the hospital.

Similarly, it is reprehensible but legal to pull up a chair and watch a child drown in a pool.

There is a difference between law and morality, and humans will use the second to selectively enforce the former.

> Similarly, it is reprehensible but legal to pull up a chair and watch a child drown in a pool.

In which country? Even for the US I don't believe the law system is that crappy.