The study discussed in this article examined the relationships between support from parents, teachers, and peers; contextual risks; and select achievement outcomes in a representative sample of African American female high school seniors enrolled in an urban school district in southeastern Virginia. Quantitative analysis revealed that some support variables were predictive of better achievement outcomes and others were associated with poorer outcomes. Qualitative analysis identified significant similarities and differences within the study sample with respect to the types and sources of support reported to have had an impact on the participants' success in school. The study's findings increase our knowledge about and highlight the complex nature of the context-linked experiences of African American female adolescents who underachieve relative to white adolescents in spite of educational reform.