Little research has investigated factors that may moderate the intergenerational transmission of emotionally unsupportive parenting behaviors. The present study examined the role of two moderators, emotion dysregulation and maternal age at childbirth, on the relation between maternal childhood history of emotional maltreatment and current observations of emotionally unsupportive parenting behaviors in 64 mother–child dyads. Results indicated that mothers who were younger at childbirth seemed more likely to engage in emotionally unsupportive parenting behaviors in the context of high levels of sustained childhood emotional maltreatment, regardless of their level of emotion dysregulation. Mothers who were older at childbirth were at high risk for emotionally unsupportive parenting behaviors in the context of high levels of sustained emotional maltreatment histories and high emotion dysregulation, yet were not at such risk if emotion dysregulation was low. Implications for the buffering effects of emotion regulation on the risk for emotionally unsupportive behaviors were discussed.