In today’s digital age, cybersecurity is no longer confined to IT departments; it has become a high-level strategic concern across state institutions and private organizations. Unlike conventional forms of leadership, cyber leadership in this rapidly evolving landscape demands a distinct set of competencies, including the ability to manage high-skilled teams, make swift decisions under uncertainty and pressure, coordinate diverse stakeholders, and navigate the dual-use nature of emerging technologies. As cybersecurity becomes increasingly entangled with national security and societal resilience, the decisions of cyber leaders can have far-reaching consequences. Yet despite its growing significance, cyber leadership remains an underexplored topic in academic literature. This chapter aims to address this gap by examining the structural challenges faced by cyber leaders and offering insights drawn from prominent cases, such as the Colonial Pipeline incident.