A growing body of work suggests that group-based dissimilarity limits the influence of empathy on helping across group boundaries. The present research examines under which conditions empathy becomes “dis-inhibited” as a motivator of out-group helping. We propose that, when intergroup dissimilarity is high, empathy’s influence on helping critically depends upon the out-group target’s perceived benevolence, i.e. sociability and trustworthiness. Study 1 (N = 123) and 2 (N = 176) manipulated an out-group target’s intercultural dissimilarity and his or her individual features. Results confirmed that when dissimilarity was high, the target’s sociability (Study 1) and benevolence (Study 2) had a facilitative effect on the empathy-helping intentions relationship. When dissimilarity was low, in contrast, empathy predicted helping intentions independent of the target’s individual features. Study 3 (N = 178) manipulated trustworthiness and sociability orthogonally and confirmed the primary role of the out-group target’s trustworthiness over the target’s sociability in dis-inhibiting the empathy-helping relationship among participants with a conservative political orientation.