What challenges are inherent for humanitarian practitioners when operating in a context of transition from protracted conflict to peace? This paper examines this question, focusing on Colombia as a case study. As a result of the decades long conflict in Colombia, as well as natural disasters, a host of serious humanitarian concerns persist in the country. The ongoing peace process between the government and the largest anti-government armed group in the country—the Revolutionary Armed Forces of Colombia, or FARC—while certainly a welcome development, yields an environment not only of protracted conflict but also of protracted transition. This paper discusses four particular issue areas relevant to operating in this context: grappling with the politics of denialism; the gap between the political negotiation agenda and the humanitarian issues facing the country; interactions between humanitarian actors and national transitional justice measures; and building linkages between humanitarian organizations and actors operating in other fields, such as development and peacebuilding.