In this study, we integrate propositions of conservation of resources theory and role theory to examine between-person and reciprocal within-person relations among leader health, leader identity, and three forms of leadership behavior (i.e., transformational, contingent reward, and laissez-faire leadership). We collected monthly data from N = 1,244 leaders in a four-wave fully crossed and lagged panel study. To separate stable (i.e., between-person) differences from dynamic (i.e., within-person) relations, we analyzed the data using a random intercept cross-lagged panel model (RI-CLPM). At the between-person level, we found that leaders with better physical and mental health and reduced symptom experience engage in more transformational and contingent reward leadership and less laissez-faire leadership. At the within-person level, both symptom experience and mental health positively predicted laissez-faire leadership, and laissez-faire leadership positively predicted symptom experience. We did not find support for within-person relations between leader health and transformational and contingent reward leadership, and we found no evidence for mediating effects of leader identity in the relations between leader health and leadership behavior. We discuss these differential findings and their implications for promoting leader health in organizations and theorizing on temporal processes in research on leader health and leadership.