The transition out of adolescence signals a period of increasing personal and social responsibility. For many this means entering postsecondary or the labor market. Previous research has demonstrated that youth who do not finish high school in four years have less favorable postsecondary and labor outcomes. However, few studies compare the postsecondary and labor market outcomes within the group of students who do not finish high school in four years. The current study uses 12 years of linked-administrative data from Maryland to present the first statewide analyses comparing postsecondary and labor market outcomes for on-time graduates, GED earners, non-completers, and late graduates. The results describe an under-researched and underserved group of vulnerable students, with implications for supporting students during high school to improve the postsecondary and labor market transition.