The theory of a “school to prison pipeline” posits that harsh disciplinary practices in schools may heighten the risk that youth are involved with the carceral system. We examine one part of that pipeline, analyzing the links between two different types of school staff – school police officers and school social workers - and students’ experiences with law enforcement. Using data from a large and diverse national sample of 15-year-olds from the Fragile Families and Child Wellbeing Study, we find that students in schools with greater numbers of school police officers are more likely to experience police stops, are stopped more frequently, and are more likely to be arrested, whereas students in schools with greater numbers of school social workers are less likely to experience police stops and are stopped less frequently. These results are robust to controlling for student demographics, past student behavior, and other school context characteristics.