Background: This study examined relations among cumulative risk, nurturant and involved parenting, and behavior problems across early childhood. Methods: Cumulative risk, parenting, and behavior problems were measured in a sample of low-income toddlers participating in a family-centered program to prevent conduct problems. Results: Path analysis was utilized to examine longitudinal relations among these constructs, with results supporting an indirect effect of cumulative risk on externalizing and internalizing problems through nurturant and involved parenting. Conclusion: Results highlight the importance of cumulative risk during early childhood, and particularly the effect that the level of contextual risk can have on the parenting context during this developmental period.