A novice principal's decision not to intervene on an ill-conceived policy prompts a parent to pursue a line of questioning administrators are not prepared for. In this case, a young man working through a high school transition while preparing for college is met with unexpected challenges in motivation. What the principal initially perceives as inconsequential becomes a Wicked Problem when the parent questions the ethics and legalities of the policy, teachers' intent, and potential civil rights violations. Underscored are nuances in communication, decision making, motivation, and ethics. As the elements of the case unfold, matters pertaining to school and community relations, policy, law, race, and gender present themselves useful for discussing a variety of key issues related to school leadership.