One segment of the student population that is regularly and systematically ignored is Black male students labeled "overage, under-credited" (OA/UC) based on their age and credits earned towards graduation. These young men are typically educated in alternative settings such as transfer high schools and adult learning centers. A critical race theory (CRT) analysis calls into question expanding alternative school options while limiting the exploration of how and to what extent Black male students benefit. The purpose of this study is to highlight how, if at all, OA/UC Black male students at an alternative school in New York City experience culturally relevant caring. We add to literature on culturally relevant caring by considering its importance in schooling experiences of three OA/UC Black male students in relation to tenets of CRT and examine two questions: (1) How, if at all, do OA/UC Black male students in a transfer high school experience culturally relevant care? (2) In what ways are students' experiences of culturally relevant care shaped by structural determinism and intersectionality? Our analysis indicates that the school itself is reflective of a structural determinism that prevents transformative alternatives from fully emerging, particularly in relation to culturally relevant caring.