Research on the intersection of racial and gender identities is important in understanding the processes of school engagement. This article focuses on how African-American male adolescents move in and out of schooling and make sense of those experiences. By examining how they construct meanings of masculinity a textured and complex trajectory of schooling is captured. Using qualitative data from a group of African-American male high-school dropouts who participated in a national alternative high school program, the author highlights the nuances of racial and gendered identities and their consequences for schooling experiences and outcomes. The results uniquely highlight and map the social mobility between contested traditional and alternative schooling spaces by uncovering these young men's personal pathways of reflection, regret and social redemption.