Research documents that African American children, relative to White peers, are disproportionally at-risk for being unready for kindergarten. However, research finds that parental involvement can promote positive educational outcomes, and that parental involvement is influenced by parents' own histories of involvement. The authors use qualitative interviews with a sample of low-income, African American mothers of preschoolers in Head Start to explore parental engagement (or lack of) over three generations. Various types and levels of parental engagement were identified. Patterns of intergenerational continuity and discontinuity in parental engagement were found. Findings from the study provide substantive insights on parental involvement during the preschool years. They also suggest ways that preschool programs can further strengthen families as they promote the development of young children.