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This paper examines the postsecondary planning and decision-making processes for high-achieving high school seniors and their families in an urban high school. The study aims to increase our understanding of the postsecondary planning process for high-achieving, African American students with financial need who may be the first in their families to attend higher education. A qualitative case method was employed for data collection; case analysis allows for an in-depth presentation of individual student case data and also for a cross-case descriptive comparison of the experiences and perceptions of students and families in the study. Preliminary study findings are centered on the role of family support and the perceived and real costs of postsecondary education.