In the United States there are significant gaps in college-going between high-income and low-income students and between White students and African American and Latino/a students. A number of factors contribute to this persistent gap. Among these factors are the rising cost of college attendance and the complexity of the financial aid process. The present study describes how a group of low-income students of color at a New York City high school learned about the costs associated with college attendance and participated in the financial aid process. Drawing on data collected during a one-year ethnographic study, this article examines what students initially believed about the cost of college and the availability of financial aid, how the students’ high school supported them through the financial aid process, and challenges students faced. Results from the study suggest that the textual complexity of the financial aid process, uneven support from counselors, and the high cost of college posed challenges for many students. However, those students who formed relationships with trusted advisors or “literacy sponsors” were more likely to successfully complete the financial aid process and enroll in college. The article ends with a discussion of implications for theory and practice.