Students from underrepresented groups who seek to become the first in their family to attend college confront economically and racially stratified education systems. This article reports findings from an evaluation of First Graduate, an organization that offers college advising, mentoring, tutoring, and case management to first-generation students starting in seventh grade. We highlight three systems that youth say they encountered on their pathway to college: open enrollment, course taking, and college admissions. We describe how youth navigated these systems and the roles that adults played in support. Our conclusion discusses implications for how after-school programs can support first-generation students.