This paper deals with the discourses of power and gender that influence the way in which at-risk adolescent boys think and solve problems within a specific educational context. The focus is on how some adolescent boys perceive their masculinities, identity, and support networks after they have completed an alternative education program. The position being presented in this paper is that for recovery from adversity, at-risk boys must be provided with protective processes that address masculinities and the impact of power relations within masculinities. In doing so, the research connects gender and protective processes and the role that gender construction plays in successful educational outcomes. It is also argued that for successful reintegration of at-risk adolescent males into an educational setting requires opportunity to be provided within the environment to challenge the legitimacy of traditional masculine performances.