We conducted four focus group interviews with 24 high school youth to examine facilitators and barriers to African American high school students' expression of various self-determination skills (e.g., choice/decision making, self-advocacy, goal setting, and attainment etc.). The majority of our research participants were African American, with one student identifying as multiracial (African American and White). Key findings revealed that personal (e.g., desire to graduate from school) and contextual factors (e.g., school counselor and teacher support) influenced the participants' expression of multiple self-determination skills. We also found that some of the participants' motives for utilizing or not utilizing specific skills were influenced by what they perceived as racist, punitive, and restrictive school practices (e.g., teachers holding negative perceptions about African American students and school counselors restricting their access to advanced courses). Findings from this study support ongoing calls for educators to consider students' cultural backgrounds and lived experiences when promoting their expression of self-determination skills.