Despite similarity in their disinhibited behaviors, the cognitive-affective mechanisms that characterize psychopathy and externalizing are relatively distinct. One theoretical perspective suggests that psychopathy is associated with an early attention bottleneck that precludes the processing of contextual information, leading to a rigid goal-directed focus. Alternatively, externalizing may be associated with an overallocation of processing resources to motivationally salient information, which disrupts the use of cognitive control. In this study, male prisoners assessed on psychopathic and externalizing traits performed a new gaze detection task involving affective faces. As predicted, psychopathy but not externalizing was associated with superior performance on the gaze-detection task when the necessity of using contextual affect to regulate goal-directed behavior was minimized. Conversely, externalizing but not psychopathy was associated with increased errors on trials that required participants to use affective expressions, specifically fear, as a cue to inhibit dominant responses. These results have theoretical and applied significance for both psychopathic and externalizing forms of disinhibition. Recognition and utilization of facial affect are important for socialization and interpersonal interactions; therefore, any cognitive-affective processes that interrupt the fluency with which this information is processed may be important for understanding the underpinnings of disinhibition.