The school-to-prison pipeline (STPP) describes in shorthand the problematic relationship between some students' school experiences and their subsequent incarceration. One summer, in response to vocal concerned parents, a suburban school board adopted a zero-tolerance policy for smoking and vaping. Through the combined effects of the zero-tolerance approach, exclusionary punishments, the presence of SROs (school resource officers), racially disproportionate disciplinary practices, and a culturally nonresponsive school setting, 90 students were introduced to the criminal justice system in one school year. This case helps school leaders examine the elements of the STPP and how they work together to damaging effect. The questions and activities will guide readers to develop multiple ways to forestall and/or repair STPP supporting policies and practices.