The majority of postsecondary students in the United States today do not have a postsecondary experience that matches the archetype of the “traditional” college student (i.e., financially dependent on parents, enrolled full time with no interruption, with no one else depending on them) (Zerguera, Ziskin, & Torres, 2018). Even among those who are categorized as “traditional” in age, many students are contributing members of their home communities as they work long-hours, take breaks in their education and transfer between institutions - all while pursuing their postsecondary goals. This dissertation draws on longitudinal qualitative data from the Milwaukee College Access Project (MCAP) to contribute three articles on the impact of social support on college access and persistence for a cohort of students who graduated from the same urban high school. Findings from this study underscore that the support of siblings and adult “advocates” is key for these students as they navigate a complex postsecondary system. Understanding how social support helps students on their postsecondary path is vital in order to institutionalize measures that lead to postsecondary success.