I think it's pretty common for guards to be persuaded by prisoners to give them extra privileges based on built-up friendship, empathy, or attraction. Another example would be whistleblowers or ideological spies, who are persuaded by the contents of secret documents to leak those documents against obviously their official instructions. On a day to day level humans ignore instructions constantly, for eg I've almost never seen people enforce a 'no tailgating' policy at a doorway, despite constantly being told. The people observe their environment and the non-effects of others breaking that rule, as well as reason about common sense situations like people they know well, then simply ignore the tailgating rule.