Data from a large prospective longitudinal study (n = 1,239) was used to investigate the association between observed sensitive parenting in early childhood and children's representations of family relationships as measured by the Family Drawing Paradigm (FDP) in first grade as well as the extent to which these representations partially mediate the influences of early caregiving experiences on later conduct problems and callous-unemotional behaviors. A structural equation modeling approach revealed that less sensitive parenting at 24, 36, and 58 months predicts higher levels of conduct problems (CP) and callous-unemotional (CU) behaviors in first grade controlling for earlier measures of CP and CU behaviors. Results also indicated that greater dysfunctional family representations, as assessed with the FDP, are significantly associated with higher CU behaviors in the first grade, but not CP. Finally, a test of the indirect pathway suggests that children's dysfunctional family representations may, in part, account for the association between sensitive parenting and CU behaviors.