Breaking a rule means having to make an exception.
An exception means an edge case that the rule did not cover.
Making an exception means that the rule was not specific enough, that it was too general and too broad, and that the rule’s criteria matched against situations that the rule does not apply to.
On the one hand, good rules must be specific not over-generalized, but on the other hand, lies another question:
How detailed should they be?
Rules are maps, and a map is not the territory. If a map has every detail of reality, then it becomes an exact copy; it becomes the reality.
Maps, which rules are a derivative of, are made to abstract unnecessary details, simplify the intricacies and complexities of reality, and make it processable for our feeble human brains.
So here’s another question.

What is unnecessary? What can be left out? What has to be included?

Note: In rare situations, thoughtfully challenging a clearly outdated or unjust rule may be warranted - and ironically right here, I just made an exception.