School leaders are under constant pressure to ensure that schools are safe and to demonstrate that student safety and discipline are priorities. In many districts, schools rely on local law enforcement, school police, or security personnel to assist with promoting and maintaining safe schools. To encourage school leaders to think critically about the role of law enforcement and security personnel in schools, we present a school-level case where a principal is arrested for intervening to stop the arrest of a student. The case is appropriate for school- and district-level leadership courses that examine social, political, and cultural contexts that shape decision making.