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This longitudinal multiple case study of the parents of first-generation college students and staff members from nine institutions focuses on the ways in which institutions and families encourage development related to students’ independence. The results revealed four major themes, including: 1) the importance of parents and staff working together to better serve students, 2) the process of independence development, 3) the balance of involvement as being influential in fostering students’ independence, and 4) frustrations in the parent and university relationship, in terms of gaps in support and resources, and parents taking on students’ frustrations. The results deepen our understanding of how higher education can better partner with the parents of first-generation college students.