Intensive mothering (IM) is increasingly being recognized as a dominant parenting discourse. IM, conceptualized as hyper-parenting ideals that place pressure on mothers to cultivate children's cognitive development, has also been demonstrated to have consequences for mothers' mental wellbeing. On the other hand, IM attitudes also appear to contribute to parenting strategies that can be considered beneficial for young children's developmental growth. Considering these complexities, the present research was grounded in a theoretical framework guided by ecological and risk and resilience theories to test a holistic model which positioned IM as having indirect associations with children's executive functioning (EF) through two pathways: positive parenting strategies and parenting stress. Contrary to the theoretical purposes of IM-informed parenting, IM did not contribute to better cognitive outcomes in 3–5-year-old children through positive parenting. Instead, IM indirectly contributed to higher reports of dysfunctions in children's EF through the mechanism of parenting stress. Further, a conditional process model advanced previous understandings of IM by illuminating the processes through which cumulative risk strengthened the associations between these core constructs. Based on the results presented in this research, IM ideology is argued to be a context of risk for families with an accumulation of contextual risk factors.