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This chapter focused on challenges and tensions that characterize leadership in the military context. It aims to identify and analyze key paradoxes that are reflected in this unique setting, while exploring the challenges, opportunities, and advantages posed by these core paradoxes for leadership. It addresses different types of paradoxes, among them: (a) shared leadership versus hierarchical leadership, (b) flexibility and creativity versus conformity and discipline, (c) complexity and chaos versus simplicity and linearity, (d) hegemonic and prototypical leadership versus leadership of multiple identities, and last (e) distant leadership and exchange relationship versus intimate leadership and communal relationship. For each focal paradox, we uncover the dynamics, processes, management tensions, and possible subsequent outcomes. We suggest that leadership that is able to effectively attend to competing expectations and paradoxical tensions is essential in the current hybrid and complex organizational structure and unique context of the military. The chapter draws on interviews and prior research of leadership in the Israeli military, as well as other global military contexts, to gain a more nuanced understanding of the challenges of modern military leadership.