The relation of observed emotional reactivity and regulation in infancy to executive function in early childhood was examined in a prospective longitudinal sample of 1,292 children from predominantly low-income and rural communities. Children participated in a fear eliciting task at ages 7, 15, and 24 months and completed an executive function battery at age 48 months. Results indicated that the relation of child negative emotional reactivity at 15 months of age to executive functioning at 48 months of age was dependent on observed emotion regulation. High levels of executive function ability were observed among children who exhibited high levels of emotional reactivity and high levels of the regulation of this reactivity. In contrast, low levels of executive function ability were observed among children who exhibited high levels of reactivity but low levels of regulation. Among children exhibiting low levels of emotional reactivity, emotion regulation was unrelated to executive functioning. Moreover, emotionally reactive infants exhibiting high levels of emotion regulation were more likely to have primary caregivers who exhibited high levels of positive parenting behavior in a parent–child interaction task. Results provide support for a neurobiologically informed developmental model in which the regulation of emotional arousal is one mechanism whereby supportive environments are associated with higher levels of self-regulation ability for highly reactive infants. Findings are discussed with implications for differential susceptibility and biological sensitivity theories of child by context interaction.