The present research examined how family psychosocial risk may be associated with emotional availability (EA) across age and time in two longitudinal, intergenerational studies with high-risk, disadvantaged mother–child dyads. Study 1 examined dyads during preschool and middle childhood. Study 2 examined a different sample of dyads, tested intensively at five time points (6, 12, and 18 months; preschool; and school age). Across studies, maternal childhood histories of aggression and social withdrawal predicted negative EA (higher levels of maternal hostility) during mother–child interactions at preschool age. In Study 1, mothers with higher levels of social withdrawal during childhood had preschoolers who were less appropriately responsive to and involving of their mothers during interactions. In Study 2, higher levels of observed appropriate maternal structuring predicted child responsiveness while observed maternal sensitivity (and structuring) predicted observed child involvement. More maternal social support and better home environment combined with lower stress predicted better mother–child relationship quality. Findings contribute to the burgeoning literature on EA by focusing on a high-risk community sample across time and generations. Results are interpreted in light of the developmental psychopathology framework, and have implications for a broader understanding of how EA is related to parental history and personal characteristics, as well as ongoing family and environmental context.