Affective coldness is one of the main features of Machiavellianism. Recent studies have revealed that Machiavellians are emotionally detached and that this "affective blunting" is associated with intense feelings, emotional instability, negative emotions, and difficulty in enduring distress. We used brain-imaging techniques to investigate emotion regulation in Machiavellianism at a neuropsychological level. We used situations in which participants were required to demonstrate emotional flexibility to explore the controversy surrounding the fact that Machiavellianism is associated with both cold-mindedness and emotional instability. Participants performed a reappraisal task in which emotionally evocative pictures (from the International Affective Picture System) were presented in different contexts (negative, positive, and neutral). They were asked to interpret a scenario according to its title and to reinterpret it according to another context created by a new title (e.g., negatively labeled pictures shifted to positively labeled ones). During task performance, Machiavellians showed increased activation of brain regions associated with emotion generation-for example, the amygdala and insula. This indicates that Machiavellian individuals are able to be involved emotionally in social situations. Increased activation in the temporal and parahippocampal regions during reappraisal suggests that Machiavellians use semantic-perceptual processes to construct alternative interpretations of the same situation and have enhanced memory for emotional stimuli. Furthermore, they seem to possess an intense awareness that leads them to shift attention from external to internal information to detect environmental changes. These cognitive processes may enable them to adjust their behavior quickly. This study supports the flexibility hypothesis of Machiavellianism and suggests that Machiavellians' approach to emotion regulation is linked to their rational mode of thinking.