Purpose: The purpose of this interpretive case study is to examine the assumptions underpinning one Upward Bound program to understand how the program attempts to increase educational opportunity for poor urban youth and how this approach plays out in the lived experiences of three young men who participate in the program. Research Design: This study of an Upward Bound program was conducted at a large urban university in the Northeast. Based on the methodological framework of interpretive interactionism by Norman Denzin (1989), this interpretive case study was conducted over an entire academic year. Formal and informal interviews, observations, and document analysis were used to gather data to understand the phenomena being studied in-depth. The conceptual lenses of Amartya Sen and Martha Nussbaum frame the analysis of this study, revealing the logic and limits of focusing on achievement alone to increase educational opportunity for impoverished youth. Findings: The director of "College Access Initiative" believes that this program can increase educational equity and opportunity for impoverished youth by: a) emphasizing an ethic of rugged individualism, b) insisting that the young men focus on the future, and c) immersing students in an intense academic and test preparation program. The findings of this study reveal that this academic approach to expanding educational opportunity for the young men was not sufficient for increasing their freedom to focus on academic achievement or to stay in the program. Conclusions: These findings suggest an urgent need for coordinating academic support programs with other social, economic, and human service agencies serving poor communities if we are to enhance real opportunities to achieve for impoverished youth. (Contains 3 notes.)