The state of African American education is complex. Beginning in the 17th century, African Americans fought for an education that allowed them to read and write. During the 21st century, African Americans value on education extends beyond only reading and writing to using these skills and other skills to maintain strong academic and leadership backgrounds for a higher education. The purpose of this study was to understand the college preparation process of high-achieving, middle-class, African American students at a large research institution in the mid-Atlantic United States. This study was important because despite high-achieving, middle-class, African American students' success, there still exists an achievement gap between African American students and their White and Asian peers. Three theoretical frameworks and models were used as a guide for this study, critical race theory (Delgado & Stefancic, 2001), Perna and Titus' (2005) integrated conceptual model on college enrollment, and the predisposition stage of the college choice research (Hossler & Gallagher, 1987; Hossler, Braxton, & Coppersmith, 1989). Utilizing a constructivist case study methodology, data was collected using personal interviews, a focus group, and personal documents (college admissions statement and/or resumes). Through a within-case and cross-case analysis, school, family, and community contexts that influence the college preparation process were explored.