This study utilized life history theory to test a developmental cascade model linking harsh parenting to low educational attainment. Multigroup models were examined to test for potential gender differences. The sample consisted of 1,482 adolescents followed up for 9 years starting in seventh grade (Mage = 12.74). Results supported indirect links between harsh parenting and low educational attainment through the development of extreme peer orientations, early sexual behavior, and delinquency. Among male adolescents, harsh parenting was related to the development of an extreme peer orientation, which further led to increased delinquency, and subsequently lower educational attainment. Among female adolescents, harsh parenting predicted extreme peer orientations, which increased both delinquency and early sexual behavior. Early sexual behavior further predicted lower educational attainment in female adolescents.