This study examined (a) whether retrospective reports of specific parent responses to sadness (i.e., reward, punishment, neglect, override, magnification) were related to deliberate self-harm (DSH) and (b) whether difficulties regulating emotions (i.e., difficulties monitoring, evaluating, and modifying emotions) mediated those relations. One hundred eighteen college students completed measures of parental emotion socialization, emotion regulation difficulties, and DSH. Parental reward and override of sadness were directly related to lower DSH scores. Parental punishment and neglect of sadness were related to higher DSH scores, and these associations were mediated by difficulties evaluating emotions. In other words, parental punishment and neglect of sadness may place individuals at risk for DSH by fostering negative evaluations of emotional experiences and the belief that nothing can be done to effectively manage emotions.