Students from racially minoritized groups attending Title I high schools need support preparing, applying, enrolling, financing, and transitioning into college. Previous research has demonstrated that (a) skills in time-management, (b) ability to apply oneself and focus on a goal, and (c) skills for advocating for oneself as a learner are essential for college readiness. The current study explored 35 Georgia high school students’ experiences of locally created and delivered college readiness programming. Guided by a social capital theoretical framework and informed by grounded theory developed by Glaser and Strauss (1967), investigators discovered hypotheses and concepts through constant comparative analysis. Students’ preparation for college began well before they started their post-secondary education journey and was shaped by their environmental, familial, cultural, academic, and socio-economic context, which served as a framework that either supported or challenged their post-secondary education experience. When examining the intersections of social capital supports of and obstacles to college readiness, students’ preexisting frameworks provided a unique variation to their experience. Findings showed that college readiness is comprised of social capital and obstacles that are multilayered and are further complicated by an interaction with each student’s personal strengths and challenges before beginning college readiness programing.