Policy efforts to enhance postsecondary access and completion often emphasize the construct of college readiness (CR). While most research has focused on defining and measuring CR, less has examined the perspectives of first generation students and the urban high school contexts in which many prepare for college. This study utilizes data from an ethnography of college preparation in a low-performing urban high school. Drawing on sensemaking theory, I explore how high-achieving college-bound seniors make sense of CR and what factors shape their sensemaking. Findings offer insight into how CR discourses manifest at the local level to shape opportunity for urban youth.