Growing evidence suggests that maltreatment is reproduced across generations as victims of maltreatment are at an increased risk for maltreatment perpetration. Unfortunately, little information about mediating pathways exists to provide an explanation for why maltreatment begets maltreatment. We use the number of types of maltreatment experienced to predict later maltreatment perpetration and then examine two developmental pathways that may serve as bridges between maltreatment victimization and perpetration: adolescent problem behaviors and precocious transitions to adulthood. With prospective, longitudinal data from the Rochester Youth Development Study, we assess the relevance of these pathways for the number of maltreatment experiences as well as the number of maltreatment victimization experiences by developmental period (i.e., childhood and adolescence). Our results demonstrate a significant relationship between maltreatment victimization and maltreatment perpetration. Adolescent delinquency and two precocious transitions, dropping out of school and independent living, as well as the accumulation of precocious transitions and problem behaviors, serve as mediators of this intergenerational relationship. Furthermore, the relationship between the number of types of maltreatment and subsequent perpetration is primarily driven by experiences of maltreatment during adolescence. We discuss the implications of these results and set an agenda for the development of programs and policies to interrupt the cycle of maltreatment.