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College degrees have increasingly become prerequisites for employment. While college enrollment numbers have risen accordingly, low-income and first-generation students enroll and complete college at lower rates than their counterparts. To provide insights into persisting inequalities in educational attainment, this study focused on potentially college-bound high-poverty urban high school students’ educational aspirations, perceptions of the educational landscape, and post-graduation educational plans. Data were collected through interviews with students and observations of their classes during an academic year, and analyzed using grounded theory. Our findings suggest that higher education was seen as promise for economic security but a rocky road to take, and accordingly students’ plans for higher education were based on a confluence of their aspirations and limited resources.