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Financial aid administrators serve as critical gatekeepers for U.S. college students who are estranged from their parents. Federal policy allows institutions to implement their own process to decide on whether a “dependency override” is warranted to exempt students from the expectation of parental financial support. Drawing on 31 in-depth interviews with financial aid directors at U.S. higher education institutions, I utilize an inhabited institutions framework to examine how these street-level bureaucrats enact federal and institutional policy in dependency override appeals across institution types. I find that financial aid directors vary in how they choose to apply policy from their institutions and the Department of Education, with directors demonstrating significant variation across institution type: community colleges, public universities, and private universities. Financial aid director decisions are shaped by competing logics of student equity and stewardship within the financial aid office and the ever-present concern of audits by the Department of Education. They are also influenced by directors’ awareness of potential fraudulent practices, personal biases, and generalizations about the circumstances of students who attend their type of institution.