This article examines the dynamics of youth identity formation at a boarding school for “at-risk” children. The school prepares its young boarders for adulthood through systematic intervention in their everyday cultural practices. By inducing a state of social liminality, or felt in-betweenness, the school seeks to guide its students—mainly youth of color—towards particular social roles, norms, and beliefs. However, children respond and adapt to this ambivalence, which leads to lasting effects as they transition into young adulthood. Utilizing extensive fieldwork and longitudinal data, the analysis employs an interpretive approach to provide context-specific insights into these dynamics. The study details the cultural interventions observed in 2013-14 and revisits the children, now young adults, a decade later, to understand the policy and ethical implications of those interventions. In so doing, this study contributes to understanding the complex interaction between authority, conformity, and identity management within institutions devoted to transforming the lives of children at the social margins.