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In the United States, there are 6.7 million young people between the ages of 16-24 who are “disconnected” from education and employment (WHCCS, 2012). While researchers have documented demographic characteristics of this population, few empirical studies examine how youth become disconnected and the role context plays in this process. This paper draws on ethnographic data to show how features of educational and community settings were used as resources to categorize young people. I explore the implications of these categories on youth participation in academic and community life and identity development. I argue services and programs designed for youth reinforced rather than interrupted pathways to disconnection and advocate for researchers and educators to expand our thinking about how youth become disconnected.