The current longitudinal study examined whether attachment states of mind and childhood maltreatment predict sensitive caregiving during infancy, early childhood, and middle childhood among a sample of 178 parents who were involved with Child Protective Services. Nearly all the parents had themselves experienced childhood maltreatment based on their reports on the Childhood Trauma Questionnaire—Short Form (Bernstein et al., 2003) when their children were infants. Adult Attachment Interviews (George, Kaplan, & Main, 1985) were administered to parents when their children were infants (M = 10.92 months, SD = 8.66). Parental sensitivity was rated based on observations of parent–child interactions at three time points: infancy, early childhood, and middle childhood. During infancy, dismissing states of mind of parents predicted marginally lower sensitivity scores than autonomous states of mind. In early and middle childhood, dismissing states of mind of parents predicted significantly lower sensitivity ratings than autonomous states of mind. Unresolved states of mind of parents predicted significantly lower sensitivity scores than autonomous states of mind only during early childhood. Childhood maltreatment was not significantly associated with parents’ sensitivity ratings at all three time points. Findings suggest that among parents with Child Protective Services involvement, most of whom had themselves experienced maltreatment, parents’ unresolved states of mind predict insensitive caregiving in early childhood, and parents’ dismissing states of mind predict insensitive caregiving from infancy through middle childhood.