The purpose of the present study was to examine longitudinal associations among maternal responsiveness, self-regulation, and behavioral adjustment in adolescents. The authors used structural equation modeling to test a model that demonstrates that the effects of early cumulative risk on behavioral problems is mediated by maternal responsiveness and self-regulation. Furthermore, the authors examine the contributions of cumulative risk and maternal responsiveness on children's self-regulatory abilities. The study uses a 3-wave longitudinal design with multiple measures of risk and self-regulation from multiple observers. Data were collected from adolescents (N = 265, male = 140) and their parents at age 9, 13, and 17. Results suggest that the mediation hypothesis held true for externalizing, but not internalizing problems. Furthermore, cumulative risk and maternal responsiveness contributed uniquely to children's self-regulation abilities. (Contains 1 table and 4 figures.)