This chapter reviews that human nature to get frustrated when teachers repeatedly deal with the same students who misbehave or with parents who never support the school, even when it should be obvious that their child is in the wrong. During these difficult times, it is essential that they do not lose professional and empathetic stance. There is no way of knowing what the students and parents lives are like away from school. This should not have to bear the brunt of their unhappiness, sometimes that just goes with the job. There are certain things can do even in these most predefined circumstances that can assist in working with challenging parents. Difficult parents already know how to behave inappropriately, and sadly, their children, regardless of their ages, have years to use this as a role model. This chapter shows concern for students' success even if school has a zero tolerance policy.