When individuals experience positive events, they often tell others about their good news—a concept referred to as capitalization. Existing research paints capitalization as a relationship-enhancing behavior, likely because theory on capitalization has predominantly been developed within the context of close relationships characterized by warmth, friendliness, and trustworthiness. Nevertheless, people capitalize in other contexts, such as leaders disclosing their positive events to employees. Importantly, while some leaders are considered warm and caring by employees, others are instead considered cold and uncaring. When viewed through a person perception theory lens, we would not expect the promised benefits of capitalization when an employee views a leader as cold (versus warm). Thus, we develop a model that positions employee perceptions of leader warmth as a boundary condition of the effects of leader capitalization (i.e., a leader’s propensity to share her/his positive events with her/his employees) on employee leader-directed helping. We further explain how employee perceptions of leader authenticity act as a mediating mechanism in this process. We test our model in two field studies and find support for our hypotheses. We find that when leader warmth is lower (versus higher), the positive effects of leader capitalization are fully neutralized. We extend theory on capitalization by highlighting the key role of perceived discloser warmth and by broadening the contexts of capitalization to leader-employee relationships.