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This paper explores the struggles and experiences that first generation, low-income (FG/LI) students are having with financial aid at a residential liberal arts college in the northeast. Our objective is to recommend what financial aid offices can do to support FG/LI students. Given how often respondents noted that the financial aid package offered to them by the college was a determining factor in their decision to attend, our analysis focuses on how students’ expectations and concerns regarding financial aid are addressed once they matriculate. Despite a generous financial aid policy, FG/LI students continue to struggle. In an effort to create educational environments rooted in equity, it is essential to address the shortcomings of even the most generous financial aid policies.