Although stepmothering is a common undertaking in American families, little research has investigated the mental health consequences, and their correlates, associated with adopting a stepmother role. To help fill this gap, the current study examines parenting stress and participants’ perceptions of their (step)children’s regard toward them and the family as mediators in the relation between parenting role (stepmother or biological mother) and depressive symptoms. Participants included 60 biological mothers and 75 stepmothers living in the United States. Stepmothers reported more depressive symptoms and parenting stress and lower perceptions of child regard than did biological mothers. Further, the relation between parenting role and depressive symptoms was mediated by parenting stress and perceptions of child regard. Results suggest that stepmothers are at risk for depressive symptoms and illuminate possible contributors to this risk, providing important directions for research and intervention.