Events occur at every level, from the external environmental level to the individual level in organizations, yet our understanding of organizational phenomena, such as leadership in an event context is limited (Johns, 2023; Morgeson et al., 2015). Drawing upon event system theory (EST), we develop a dual first stage moderated mediation model that examines the effect of servant leadership during an external crisis event exemplified by the COVID-19 pandemic and an internal organizational change event as a response to such an external crisis. Specifically, in two studies, we examine the indirect effect of servant leadership on employee task performance and prosocial behavior via work engagement, as well as the moderating effect of the event-related context (i.e., external event triggered psychological distress and telecommuting as the form of internal organizational change event) on the mediation models. Results from a field study and an experimental vignette study provide support for the mediating models. Additionally, our field study provides evidence for the moderated mediation model for telecommuting, but there is no support for psychological distress as the moderator in both studies. Overall, our findings highlight the utility of EST for the servant leadership literature by showing why and when leaders’ serving behaviors positively influence employees in times of uncertainty during critical crisis events. Theoretical and practical implications and future research directions are discussed.