This prospective, intergenerational study investigated the influences of maternal histories of childhood aggression and social withdrawal on maternal request strategies and child compliance and noncompliance. Seventy-four women from the Concordia Longitudinal Risk Project, who were rated during childhood using peer nomination measures of aggression and social withdrawal, played with their 2-6 year-old children in three naturalistic conditions. Videotaped interactions were coded for mothers' requests and children's compliance/noncompliance. The results revealed that mothers who were socially withdrawn during childhood were more likely to employ intrusive requests (i.e., physical interventions, repetitions, and requests without opportunity to comply), which subsequently predicted children's noncompliant behaviour. In addition, mothers who were aggressive during childhood were more likely to repeat their requests, which also predicted children's noncompliance. Furthermore, the findings replicated previous research indicating that children demonstrate more sophisticated forms of noncompliance with age. Taken together, results from this study elucidate the trajectories of childhood aggression and social withdrawal, and provide evidence for possible pathways by which problematic behaviour is transferred from mother to child in vulnerable populations. This research has implications for the design of preventative interventions for at-risk families. (Contains 5 tables.)