This study explores and examines the differences in financial resources and access to college between transgender and cisgender students. Using a quantitative criticalist lens, the authors analyzed data from the U.S. Department of Education High School Longitudinal Study (HSLS:09) and found that while trans and cisgender students attend college at similar rates, trans students were more likely to experience discrimination in and drop out of high school. Further, trans students were more likely to take out loans, have lower incomes, and be less able to pay an unexpected $500 expense compared to their cisgender peers. The article closes with recommendations to researchers, policymakers, and leaders in education.