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As school choice policy gains prominence, and scholars and policymakers debate choice’s merits and drawbacks, knowledge about how youth experience school choice remains limited. In particular, we know little about youth experience of competing to access schools under choice policies. This comparative, longitudinal case study followed 36 Chicago youth through the high school application process to address these gaps. Framed by stage-environment fit theory (Eccles & Midgley 1989), our study investigates how early adolescents encountered and navigated this policy within in local and national contexts of unequal educational opportunities. While participants’ developmental characteristics were constant, parent resources mediated their policy experiences and led to different admissions outcomes and senses of academic identity. School choice policy and theoretical implications are addressed.