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This study examines the high school-to-college pathways of first generation students of color from a high-poverty urban neighborhood. I draw data from a two-year ethnographic study of college preparation in an urban high school and follow-up interviews with two cohorts of graduates who entered postsecondary institutions. Drawing on Bronfenbrenner’s (1979) ecological framework, I explore how social, cultural, and institutional contexts shape urban students’ experiences preparing for and transitioning to college. The purpose is to inform a culturally relevant, context-based conception of college readiness that is attentive to the particular challenges underrepresented students face.