Prior research suggests that individuals with higher rates of personality psychopathology are more likely to endorse insecure attachment patterns which can lead to stronger reactions towards perceived rejection. This study investigated how attachment style and gender moderate the strength of the association between personality psychopathology and reactions to perceived rejection. To examine the role of attachment and gender in the relationship between personality psychopathology and reactions to perceived rejection, an undergraduate sample of 150 students, as well as an Amazon Mechanical Turk (MTurk) sample of 278 individuals, completed various personality and attachment self-report measures and watched video clips addressing rejection from parents, peers, and romantic partners. Multivariate analyses of variance and moderation effects suggested that attachment patterns inconsistently moderate maladaptive reactions to rejection, and that gender moderates the relationship between personality psychopathology and externalizing reactions to rejection. Specifically, men with more pronounced Antagonism and Psychoticism trait facets demonstrated a higher propensity towards externalizing and internalizing reactions to rejection than women in these domains.