Despite having been widely studied by researchers of entrepreneurship, prior research has rarely explored entrepreneurial alertness in social entrepreneurship contexts. To address this gap, this study examined the relationship between prosocial motivation and social entrepreneurial alertness, the possible mediating effect of perspective taking on this relationship, and how this mechanism may be contingent on intrinsic motivation. Survey data was collected from a sample of 220 EMBA students from National Chengchi University in Taiwan. Results show that prosocial motivation positively affects social entrepreneurial alertness, perspective taking partially mediates the influence of prosocial motivation on social entrepreneurial alertness, and this indirect effect is positively conditioned by intrinsic motivation. This paper concludes with a discussion of theoretical and practical implications.