Background: Urban Black adolescents' wellbeing in the early high school years can be negatively impacted by exposure to racial discrimination. These impacts may be buffered by supportive relationships with adults at school. We considered both the protective and promotive effects of culturally responsive teachers and caring school police on school engagement for students exposed to racial discrimination across settings. Method: This study leveraged baseline student report from a sample of urban, predominantly Black high school students with elevated teacher-rated levels of aggressive behavior (N = 397 9th graders; 91.2% Black; 50.4% male; J = 10 schools). Using a path model with full-information maximum likelihood estimation, we examined the associations of racial discrimination, teacher cultural responsiveness, and school police caring in relation to school engagement and school disconnection, adjusting for covariates and family racial socialization. Results: Frequency of racial discrimination was significantly associated with lower school engagement and greater school disconnection. Teacher cultural responsiveness was significantly, favorably associated with all outcomes. Police caring had no significant direct associations; however, there were moderation effects. When police caring was below average, increased racial discrimination was associated with significantly poorer attitudes toward school. Conclusions: Findings suggested that students' perceptions of school police caring may buffer some negative school-related impacts of racial discrimination. Moreover, students who perceive that their teachers are culturally responsive may feel more engaged at school. Interventions to promote teachers' and school police officers' cultural responsiveness and caring may improve engagement among at-risk urban youth who experience racial discrimination. [This paper was published in "Journal of School Health" (EJ1274287).]