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This piece explores the complex role of College Preparatory School Programs (CPSPs) in preparing economically disadvantaged Black and Brown students for prestigious independent schools while precipitating habitus clivé, a Bourdieusian concept referring to the internal division felt when conditions of existence change dramatically. Based on a year-long ethnographic study with 150 semi-structured interviews at Uplift Academy (UA), I argue these programs can both mitigate and exacerbate habitus clivé. While UA instills human, social, and cultural capital to ease habitus clivé, some unintended consequences arise, exacerbating it. The findings highlight the dual role of CPSPs and the challenges in preparing marginalized youth to thrive in markedly different elite environments.