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Although strong academic preparation is critical to support college-going, many first generation students attend low-performing schools with minimal access to challenging coursework. These school environments, in turn, position students to approach postsecondary academics in particular ways. This study employs narrative inquiry to investigate the academic identity development of four college-bound, high-achieving, first generation seniors attending a low-performing, urban high school. Findings suggest that students’ academic identities were complex and, to varying degrees, conflicted; participants struggled to reconcile the positive signals of achievement they received from their school with their sense of under-preparedness relative to their perceptions of college. These narratives offer insight into the challenges of postsecondary transition among first generation youth and suggest pathways for improving college readiness policy.