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Given the long-standing policy of residentially-based school assignment, prior researchers have focused less on the emotional investment required for parents to manage application enrollment in urban areas. This article brings attention to application challenges by studying the behavior of parents within New York City’s open enrollment elementary system. Drawing on interviews with 100 parents from working-class and middle-class backgrounds, I find that parents express high levels of emotional investment when navigating school application procedures. Parents struggle to manage application materials, are challenged by the uncertainty of admissions timelines, and have difficulty interpreting school data and discerning differences across schools. As parents face obstacles within the application process, I find that middle-class parents are better equipped to overcome enrollment challenges. Middle-class parents rely on insider knowledge, online support groups and exmission assistance to ease the application process. These findings may help explain inequality in school choice outcomes at the elementary level and broader feelings of insecurity that extend to parents’ experiences with educational systems.