This chapter begins by posing the similarities of the alleged educational mission of state-regulated compulsory schooling and JJCs through historical, political, and emancipatory lenses. It argues that compulsory schooling emerges less from a commitment to children’s flourishing than from projects of social control and capitalist discipline, thus highlighting the still ongoing structural continuities between schools and JJCs. It then explores the inevitable tensions between coercion and care, emphasizing youth agency and the potential of a relationally-based education. Special attention is given to the place of vulnerability, especially the educator’s, in building educational relationships, and to the role that (toxic) masculinity plays in tampering with those relationships.