Facilitating economically disadvantaged students’ access to higher education is an important goal of educational policy. However, some practices toward this goal are based on theories and assumptions not informed by the students’ conditions or needs. The purpose of this study was to understand the challenges faced by students from high poverty, urban high schools in their yearning for a college education. Analyses of interview and observation data from a yearlong study in six high-poverty schools revealed that economically disadvantaged students face contextual challenges that necessitate additional efforts and resources not required by others, including money, time, knowledge, courage, sacrifice, and taking risks. The findings are discussed in light of Bourdieu’s theory of capital in education. Implications for educational policy and practice are outlined, including increased attention to non-psychological, structural factors impacting college attainment such as systemic and cumulative disadvantage resulting from lack of various forms of capital.