Research suggests that adults who have developed a coherent perspective on their negative, early attachment relationships (i.e., earned secures) do not reenact poor parenting practices with their own children. However, no studies have addressed whether earned secures maintain positive parenting under the pressures of aversive environmental conditions. This study tested five alternative models that predict how earned secures parent under low and high stress in comparison to adults who had a positive upbringing (i.e., continuous secures) and adults who have an incoherent perspective on a troubled childhood (i.e., insecures). Only if earned secures exhibit effective caregiving under high stress, in comparison to the other security groups, can it be assumed that they have broken the intergenerational cycle of poor parenting. The Adult Attachment Interview was used to classify 97 mothers as earned secure, continuous secure, and insecure. Home observations of parenting and maternal self-reports of daily hassles (our stress measure) were obtained when children were 27 months old. Planned comparisons revealed that the diathesis-stress/incoherent present state of mind model most accurately predicted parenting. Thus, under high stress, the earned secures parented equivalently to the continuous secures and more positively than the insecures; under low stress no group differences were obtained. These findings indicate that in a normative sample earned secures break the intergenerational cycle and exhibit resilient parenting even under high stress conditions.