Coercion theory posits a cyclical relationship between harsh and coercive parent–child interactions and problem behavior beginning in early childhood. As coercive interactions have been theorized and found to facilitate the development and growth of early conduct problems, early interventions often target parenting to prevent or reduce early disruptive problem behavior. This study utilizes direct observations of parent–child interactions from the Early Steps Multisite study (N = 731; 369 boys) to examine the effect of the Family Check-Up, a family-centered intervention program, on measures of parent–child positive engagement and coercion from age 2 through 5, as well as on childhood problem behavior at age 5. Results indicate that high levels of parent–child positive engagement were associated with less parent–child coercion the following year, but dyadic coercion was unrelated to future levels of positive engagement. In addition, families assigned to the Family Check-Up showed increased levels of positive engagement at ages 3 and 5, and the association between positive engagement at age 3 and child problem behavior at age 5 was mediated by reductions in parent–child coercion at age 4. These findings provide longitudinal confirmation that increasing positive engagement in parent–child interaction can reduce the likelihood of coercive family dynamics in early childhood and growth in problem behavior.