Low-income, first-generation college students face a host of obstacles on their journeys toward degree completion. Providing effective supports for these students as they navigate their postsecondary experiences is an important determinant of success, the implications of which can be far-reaching. The purpose of the current study discussed in this article was to examine the impact of Wyman’s Teen Leadership Program (TLP) on positive college outcomes for low-income, first-generation students pursuing higher education at Missouri State University (MSU). TLP is a community-based, postsecondary access and success program comprising three developmentally progressive phases that begin when teens are ninth graders and ends after their second year of postsecondary education. During the postsecondary phase of the program, TLP works in close partnership with higher education institutions like MSU to effectively support students through caring relationships and coordinated services. Using a mixed-methods approach, the authors analyzed the college retention rates and grade point averages (GPAs) of 39 TLP participants attending MSU and 82 comparison students with similar background characteristics. Findings revealed statistically higher retention rates and GPAs for TLP participants compared to non-participants. Focus groups were also conducted to better understand the perceptions of TLP participants (n = 15) and TLP staff members (n = 6). Using Schlossberg’s (1989) theory of marginality and mattering as a framework, the authors analyzed focus group responses, from which three overarching themes emerged: relationships, intentional experiences, and self-efficacy. The study findings suggest that postsecondary access and success programs are most effective when their curricula and program experiences are supported by strong and consistent student-adult relationships.