The current study examined the potential of relational closeness in the natural mentoring relationships (NMRs) of Black students to counter and protect against the noxious effects of school-based discrimination on academic engagement. The study sample included 663 Black students between the ages of 12 and 19 (M = 14.96 years, SD = 1.81 years), all reporting a natural mentor. Approximately half of participants were female (53%). Participants were recruited from three different school districts in a Midwestern metropolitan area. Findings indicated that perceived school-based discrimination was negatively associated with academic engagement. Relational closeness in NMRs countered, but did not protect against, the negative effects of perceived school-based discrimination on students’ academic engagement. Additional analyses indicated that one mechanism through which relational closeness in NMRs may promote greater academic engagement among Black students is via increased racial pride. Results highlight the potential of NMRs to counter messages of inferiority communicated through discriminatory experiences in the school. Fostering relational closeness between Black students and supportive non-parental adults in their lives may be an effective strategy to boost academic achievement among Black youth experiencing discrimination in the school environment. In addition to fostering stronger bonds with natural mentors, strategic efforts to reduce school-based discrimination are needed to truly bolster the academic success of Black youth.