Courtney and Dennis, two African American male students at McDowell High, were arrested at school for throwing water balloons during senior prank week. The principal assigned two police officers to the magnet school to oversee the implementation of a new discipline protocol. However, several members of the school staff were ill-informed about the policy, and the use of security officers in disciplining students. This case considers the punitive consequences two Black male students encountered at an urban high school by examining how an administrator, teachers, and two police officers observed, interpreted, and instituted a discipline protocol on the front lines.