The present research examined how early temperamental predispositions, caregiving environment, and the interactions among these factors shape the developmental pathways to effortful control in early childhood. The developmental model of effortful control in this research involved two child factors, negativity and sustained attention, an environmental factor indexed by maternal sensitive behaviors, and the interaction effects among these variables. Both variable-oriented and person-oriented analyses were conducted to test the propositions of this model. The findings suggested that the distress to limitation scale of the IBQ-R and high distress in the arms restraint procedure at 6 months of child age had opposite effects on effortful control at 36 months. Mother-reported ratings on the distress to limitation scale were negatively associated with effortful control, while the percentage of time during which the child was observed in high levels of distress in lab was found to be positively related to effortful control under many conditions, when significant three-way interaction effects were probed. Secondly, there was general support for the notion that the relations between negative emotionality and reactivity were moderated through two pathways, the child's capacity to regulate attentional processes and maternal sensitivity, respectively. The findings involving sustained attention obtained in a social context highlighted the importance of employing multiple measures obtained in varying contexts to assess the same construct. Thirdly, consistent with extant literature, the protective effect of maternal sensitivity on effortful control was stronger for children who were perceived by their mother as more prone to distress. Interestingly, both child sex and maternal education emerged as important moderators in interaction effects. However, no support was found for the hypothesis that the pathways to effortful control may be best understood as a joint function of child negativity, child sustained attention and maternal sensitivity. Lastly, two group profiles revealed by latent class analyses fit nicely with the interaction effects from regression models. The findings highlight the processes of amplification or attenuation that operate in development by which children with similar beginnings end up taking different trajectories.