The ways in which parents appraise and experience stress related to parenting and the amount of compassion or criticism they hold towards the self during instances of pain or failure have been associated with their attachment orientations, which are thought to significantly influence socioemotional adjustment in children. This study explored the links between parenting stress and self-compassion and the mediating effects of parenting stress and self-compassion in the association between parental attachment and child adjustment. A total of 165 mothers of elementary school-aged children participated in the study. Mothers completed self-report measures of attachment orientation (ECR-R), self-compassion (SCS-SF), and parenting stress (PSS), as well as a proxy report of child adjustment (CBCL). The current study showed that mothers’ attachment-related anxiety was directly and indirectly associated with their children’s level of adjustment through the mechanisms of self-compassion and parenting stress. Specifically, higher levels of maternal attachment-related anxiety were related to poorer child adjustment through lower levels of maternal self-compassion and higher levels of parenting stress. No significant direct or indirect effects of maternal attachment-related avoidance on maternal self-compassion, parenting stress, or child adjustment, were observed. These results highlight the importance of parental developmental histories in child adjustment and the utility of parenting interventions focused on decreasing stress and cultivating compassion towards the self in the promotion of adaptive child outcomes.