Leadership literature offers limited evidence regarding the relationship between personality traits, notably extraversion and conscientiousness, and the emergence of leadership in virtual team settings. This is problematic particularly given the increasing prevalence of virtual team environments in contemporary organizations. This longitudinal study, drawing from the leadership emergence research and communication literature on media richness, investigates how team virtuality—the time length of using various virtual communication approaches (i.e., messages, phone, video calls), moderates the relationship between personalities and leadership emergence over time. Using unique datasets from the X-Culture project, an international project in which team members work together virtually, we found that the relationship between conscientiousness and leadership assessments increased over time, while the extraversion-leadership relationship did not. Moreover, the degree of using messages moderates the conscientiousness-leadership emergence relationship, while the degree of using phone and video moderates the extraversion-leadership emergence relationship. In addition, we also distinguish between team members’ overall assessments after a longer period of information gathering and cognitive processing (i.e., “retrospective assessment s”) and their more real-time impressions (i.e., “immediate assessments”) of leadership. We found that the moderating effect of the degree of virtuality is less pronounced for retrospective leadership assessments. This distinction highlights the dynamic nature of leadership perceptions. The study offers theoretical and practical implications for nurturing and recognizing leadership potential in increasingly virtual workplaces.