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This qualitative case study explores the career and educational aspirations, college choice process, and college barriers and opportunities of 26 rural, African American high school students. Data included interviews with 26 students and 11 school staff members. Findings suggest that the students’ rural context shapes aspirations. In addition, students have emotional support and motivation to attend college from their family members and schools, but the students did not always have the “know how” to prepare for college. Finally, students described financial and academic preparedness barriers for college, but they also mentioned grades and teenage pregnancy as potential barriers for college.