ABSTRACT In UN peace operations, the special representatives (SRSGs) as heads of mission take on a range of complex, sometimes unfathomable, tasks. This article addresses the question of how individuals influence UN peace operations by focusing on SRSGs who served as heads of two major peace operations and who carried their pre-SRSG experience into their first tenure as SRSG and their experience from that tenure into their second tenure. Thus, the aim is to understand how professional experience influences continuity and change in SRSGs’ leadership practices when leading peace operations. The analysis is grounded in an interview-based approach and informed by a practice-centered approach. The case studies examined here are Alan C. Doss, who served as SRSG of UNMIL and MONUC, and Ellen M. Løj, who served as SRSG of UNMIL and UNMISS. The identified practices of both SRSGs show that certain areas were particularly influenced by experiences from their career paths: (1) mission administration, (2) working with the mission leadership team, (3) interacting with host-state actors, and (4) interactions with UN headquarters. Tracing how practices have been pursued in different contexts provides insights into the influence of individual experiences on UN peace operations and the dynamics of practice internalization.