We explore Black male high school students’ perceptions of racial oppression, their internalization of racial oppression, and the impact of these experiences on their academic lives. Using constructivist grounded theory, 10 semi-structured interviews were conducted with Black adolescent boys. Results identified five core categories: (a) racial socialization, (b) understandings of and experiences with racism, (c) emotional and behavioral responses to racism, (d) internalization of racial oppression, and (e) school resistance and support needed. Based on these categories, we developed an ecological model of Black male students’ experiences with racism and internalized racial oppression to elucidate existing interactional dynamics within students’ ecological contexts. We discuss how schools and counselors can better support Black adolescent boys’ positive development and ability to cope with racism and internalized racial oppression.