Although schools themselves cannot address resegregation, they can mitigate some of the detrimental effects of racial inequalities. Students of color internalize racial inequalities in educational environments at critical times in their identity formation. This internalization can lead to attitudes and behaviors that contribute to academic underperformance, most notably in boys and young men of color (BYMOC; Noguera, 2009; Tatum, 2005). As educators search for ways to close academic achievement gaps, they need to consider the role of both schools and out-of-school time (OST) programs in developing healthy racial identities in BYMOC. This case study explores the group mentoring program Natural Circles of Support (NCOS), which combines school-based and community-based support to mitigate the risks faced by BYMOC in urban school districts. As a classroom teacher at a NCOS school, author Kevin Pribnow taught several program participants. After seeing the impact NCOS had on participants' lives, he conducted this qualitative case study into NCOS to discover how its community circle of support met the needs of BYMOC.