Psychopathy is characterized by a lack of empathy, callousness, and a range of severe antisocial behaviors. A deficit to accurately process social cues, which has been widely documented in psychopathic populations, is assumed to underlie their pathological development. Impaired attention to socially salient cues, such as the eyes of an interaction partner, is a possible mechanism compromising the development of social cognition. Preliminary evidence from static facial stimuli suggests that psychopathy is indeed linked to reduced eye gaze. However, no study to date has investigated whether these mechanisms apply to naturalistic interactions. This study is the first to examine patterns of visual attention during live social interactions and their association with symptom clusters of psychopathy. Eye contact was assessed in a sample of incarcerated offenders (N = 30) during semistructured face-to-face interactions with a mobile eye-tracking headset and analyzed using a novel automated areas of interest (e.g., eye region) labeling technique. The interactions included an exchange on neutral predetermined topics and included a condition in which the participants were active (talking) and passive (listening). The data reveal that across both listening and talking conditions higher affective psychopathy is a significant predictor of reduced eye contact (listening: r = -.39; talking: r = -.43). The present findings are in line with previous research suggesting impaired attention to social cues in psychopathy. This study is the first to document these deficits in naturalistic, live social interaction and therefore provides important evidence for their relevance to real-life behavior. (PsycInfo Database Record (c) 2020 APA, all rights reserved).