San José's public schools provide a quality education, enhanced by programs and services that advance students' educational outcomes. Yet it is estimated that less than 4 of 10 students starting 9th grade will successfully navigate a path to and through postsecondary education. Many of these students lack clear guidance, financial resources, and/or adequate access to academic counseling to support their journey to a college degree or career. These supports are especially critical for students who are the first in their family to attend college and for those who are from low- or moderate-income backgrounds. To address this need, in 2018, former San José Mayor Sam Liccardo launched the San Jose Aspires (SJ Aspires) program in partnership with the San José Public Library and the San José Public Library Foundation to enable youth in underserved neighborhoods to chart a path toward a postsecondary education and to reduce the financial and informational barriers preventing them from attending college. The current study examines SJ Aspires students' post-secondary outcomes and the relationship between their participation in SJ Aspires and their readiness for and persistence in higher education.