Educational interventions typically center on youth displaying early academic risk, potentially overlooking those falling off track academically later in their educational careers. The current study investigated the extent to which life course transitions experienced during adolescence were linked to falling off-track academically in high school. Data from the National Longitudinal Study of Adolescent to Adult Health (N = 4284; 53% female; Mage = 14.88) documented that 1516 students displayed no educational risk in early high school, yet 14% did not pursue 4-year college by age 24. Analyses revealed the unique life course transitions predictive of falling off-track academically (i.e., sexual intercourse, alcohol use, family transitions, residential mobility). The study’s findings highlight important intervention avenues to promote adolescents’ continued educational persistence.