With the US recovering from a recession, a college diploma has become more valuable to avoid unemployment. Despite a college degree’s importance, the access to higher education is a challenge for lower income Pell-Eligible Vermont students. For the past three decades, higher education continues to rise in cost faster than family income. Cost is not only an inhibitor for Pell-Eligible Vermont students. The complexities of navigating the financial systems of higher education to acquire aid in order to make college obtainable is also an issue for Pell-Eligible students. In order to successfully navigate these systems, a Pell-Eligible student’s habitus, cultural capital, and social capital, greatly influence their decisions about applying to college and being able to successfully participate once accepted. To help understand the experience of Pell-Eligible Vermont students as they navigate the financial system of higher education institutions, I utilized a qualitative case-study phenomenological approach. The study was guided by the following research questions: (1) What are the specific challenges for Pell-Eligible students during their navigation of the financial systems of college? (2) What messages/information/support and from where do Pell-Eligible students receive about financing a college education? (3) How does cultural and social capital, and habitus influence a Pell-Eligible student in navigating the financial systems of higher education? (4) What are the implications for high schools, states, and colleges in providing information for Pell-Eligible students in navigating the college process? The study looked at the experiences of Pell-Eligible students who applied to and were accepted at Green Mountain University (GMU), a public four-year university in the Northeast region of the US. I interviewed undergraduates of GMU, the financial-aid officers of GMU, and professionals from the Vermont Higher Education Agency (VHEA). The goal of the study was to find areas where higher education institutions, high schools, and government agencies, can provide better support, more transparency, and ease the navigation process for Pell-Eligible Vermont students as they make decision and navigate the financial aid process in order to enroll into college after high school graduation.