Typicality asymmetry in generalization refers to enhanced fear generalization when trained with typical compared to atypical exemplars. Typical exemplars are highly representative of their category, whereas atypical exemplars are less representative. Individual risk factors, such as trait anxiety, attenuate this effect, due to the high level of threat ambiguity of atypical exemplars. Although recent research provided evidence for generalization of safety behavior, it is unclear whether this generalization also follows typicality asymmetry. This study examined (1) whether participants exhibited typicality asymmetry in the generalization of safety behavior and (2) whether this effect would be attenuated by individual risk factors, such as intolerance of uncertainty and trait anxiety. Participants were trained with either typical (Typical group, n = 53) or atypical (Atypical group, n = 55) exemplars in a fear and avoidance conditioning procedure. Participants acquired differential conditioned fear and costly safety behavior to the threat- and safety-related exemplars. In a following Generalization Test, the degree of safety behavior to novel exemplars of the same categories was tested. The Atypical group showed greater differential safety behavior responses compared to the Typical group. Higher trait anxiety was associated with lower differential safety behavior generalization, driven by an increase in generalized responding to novel safety-related exemplars. This study used hypothetical cost instead of real cost. Training with atypical exemplars led to greater safety behavior generalization. Moreover, individuals with high trait anxiety show impaired safety behavior generalization.