This ethnographic case study examined the experiences and perceptions of young adolescent male alternative school students who are at-risk for delinquency. Through the use of participant observation and interviews with students, parents/grandparents, and school staff, I examined as a primary research question, What are the experiences of young male adolescents who are placed at alternative school settings? Secondary research questions were as follows: How do young adolescent males perceive their traditional school experiences? How do young adolescent males perceive their alternative school experiences? In what ways do young adolescent males make connections between their schooling experiences and their involvement in delinquent activities? How do young adolescent males view race as a factor in their successes and failures as students? Findings from this study describe student experiences and perceptions based upon the context of the school, and include the philosophy, the culture of transience, inadequacies in the teaching and learning environments, the role of discipline, and the patterns of interactions noted among students and among students and teachers. Additionally I describe ways in which teachers and students resist the school context. This study also examines school as a contributor and deterrent of delinquency, and looks specifically at the role of race in student schooling experiences. I discuss implications for classroom practices, the structures of school, teacher education, and future research.