Fearless dominance (FD) generally manifests null to small relations with externalizing problems, leading some researchers to propose alternative paths by which FD features may relate to these problems. The current study provides a test of two possibilities, namely that FD (a) interacts statistically with self-centered impulsivity (SCI) such that FD is associated with externalizing problems only at high levels of SCI and (b) demonstrates curvilinear relations with externalizing problems such that FD is more strongly associated with these problems at high levels. We used a large correctional sample and item-response theory-related statistics to precisely estimate individuals’ scores at the extremes of each major psychopathic trait. FD was not significantly associated with externalizing problems in interaction with SCI or at higher levels of FD, suggesting that psychopathic traits linked to boldness are not especially relevant to generalized externalizing behavior.