Upward Bound (UB) projects provide educational support services to high school students in order to address inequalities in college access for low-income (LI) and first-generation students (FGS). However, access alone does not eradicate systemic barriers to positive collegiate experiences and degree attainment. As a federally funded program, UB regularly collects mandated outcome data; however, little is known about the specific academic, social, and emotional supports these programs provide. Especially lacking are in-depth qualitative studies that follow students into college and focus on students’ own stories. To address this gap in research, this study used in-depth interviews to capture the stories of LI, FGS first-year college experiences. Thematic analysis was used to identify challenges, successes, and commonalities in how participants described impacts of their UB participation. The research questions included: 1) What are the academic and social experiences of Upward Bound alumni in their first year at a four-year postsecondary institution, and 2) What is the perceived relationship between Upward Bound participation and the first-year college experience of Program alumni? This research leveraged Yosso’s (2005) Community Cultural Wealth framework to elevate diverse forms of capital involved in students’ UB participation and college experiences. Analysis revealed significant themes related to expectations, belonging, the pressure to succeed, mental health, the impact of the UB experience, and the power of voice, concluding that, through UB participation, students’ existing capital/cultural wealth is honored, leveraged, and ultimately multiplied. Recommendations for addressing pervasive obstacles to success in college are provided for Upward Bound projects and higher education.