Disparities in college attainment among racially and economically marginalized students have persisted for more than forty years despite concurrent gains in college access. In response, a field of college success nonprofits has emerged and diffused across states. I conducted a multilevel, longitudinal, qualitative study situated within one such program and found that administrative burdens from need-based financial aid, along with the associated learning and compliance costs, cause delays that stratify campus life and drive cumulative disadvantage for students during this critical developmental transition. Finally, I contribute theoretically to the burgeoning literature on administrative burdens in three ways: 1) I empirically demonstrate the compounding costs of burdens associated with need-based financial aid redemption, 2) I provide a rich case study on the role of nongovernmental third parties in reducing burdens in a specific policy area, and 3) I add to the theory by linking administrative burdens and their costs to the life course of service users. Together, my findings raise questions about nonprofits, their capacity to address the problem of administrative burdens, their underexplored but necessary role in policy feedback loops, and their unintended role in replicating institutional inequality. This study offers insight not only into the problems inherent in the use of need-based financial aid among first-generation, low-income college students, but also into pragmatic solutions for policy and practice.