This study examined detached parenting among Early Head Start mothers, and associated maternal characteristics and child behavior. Participants included 81 mother-child dyads. Data were collected in participants' homes during two visits. Mothers reported on demographic factors, parenting stress, and children's problem behaviors. Children's neurodevelopment was assessed, and videotaped parent-child play interactions were coded. Path analyses indicated that demographic risk factors and parenting stress were associated with higher levels of detached parenting. As a mediator, detached parenting significantly predicted children's later problem behavior. There was a direct effect of parenting stress on children's behavior problems, but no direct effect of children's neurodevelopmental risk. Detached parenting partially mediated the influence of parenting stress on children's problem behavior. The final model moderately accounted for the variance in detached parenting and children's problem behaviors. The results suggest that parents who experience multiple risks and high levels of parenting stress are more likely to demonstrate detached parenting. In addition, detached parenting leads to higher levels of toddler problem behavior, and may increase the problem behavior displayed by toddlers of parents experiencing multiple risks and parenting stress. These findings are discussed in the context of infant mental health practice.