The objectives of this study were to examine whether a maternal history of maltreatment in childhood has a detrimental impact on young children's mental health and to test theoretically and empirically informed pathways by which maternal history may influence child mental health. Mother-child dyads (N = 187) were evaluated between birth and 64 months of age via home and laboratory observations, medical and child protection record reviews, and maternal interviews to assess maternal history of childhood maltreatment and microsystem and exosystem measures of the caregiving context, including child maltreatment, maternal caregiving quality, stress exposures, and social support. When the children were 7 years of age, mothers and teachers reported on child emotional and behavioral problems. Analyses examined whether the caregiving context variables linked maternal maltreatment history with child emotional and behavioral problems, controlling for child sex (54% male), race/ethnicity (63% White), and family sociodemographic risk at birth. Maltreated mothers experienced greater stress and diminished social support, and their children were more likely to be maltreated across early childhood. By age 7, children of maltreated mothers were at increased risk for clinically significant emotional and behavioral problems. A path analysis model showed mediation of the effects of maternal childhood maltreatment history on child symptoms, with specific effects significant for child maltreatment. Interventions that reduce child maltreatment risk and stress exposures and increase family social support may prevent deleterious effects of maternal childhood maltreatment history on child mental health.