This chapter focuses on the role of schools in the pathway to crime. It highlights research that points to the importance of relationships in development, reviews theoretical perspectives of relationships and the development of delinquency, and considers school violence. Next, the chapter focuses on the importance of school connections and relationships, with a consideration of engagement and bonding with school, failing academic performance, and dropout rates. School and classroom organization as well as relationships with teachers and with peers are identified as potential risk factors that further alienate troubled youth. Conversely, if these systemic and relationship processes are positive, they can mitigate the risk of moving along the pathway to crime. To conclude, the chapter revisits the theory and research, with a call to identify and intervene with the most vulnerable youth and leading to a discussion of implications for programming and policy.