The transition from one leader to the next represents a critical moment in the life cycle of insurgencies: it is a period of heightened uncertainty and vulnerability when roles and relationships are in flux. However, remarkably little scholarly attention has been paid to understanding this process. Building our case around the insurgency in Russia’s North Caucasus, we address this gap by developing a typology of key tasks that new leaders must perform in order to navigate the transition period. We argue that, within insurgencies that are weakly institutionalised, leadership can most usefully be conceived of as a negotiated relationship in which both leaders and followers have agency. Successful performance of these tasks helps ensure the maintenance of this relationship and, through this, movement continuity. Therefore, this paper contributes to both the empirical literature on insurgency and our understanding of leadership and transition within rebel movements.