Purpose: The purpose of this paper is to provide insight in how military expeditionary task forces cope with the dual challenge of organizing and learning, by reflecting on the experiences of Dutch expeditionary task forces in post-conflict missions in Bosnia, Iraq and Afghanistan. Design/methodology/approach: This paper reflects on the outcomes of a research project into the experiences of operators of different specific expeditionary task forces of the Dutch Armed Forces in dealing with everyday problems in their working environment. The case studies were based on interviews with military personnel of all ranks and focused on relating the process of making sense of environmental dynamics to characteristics of the organizational context. Findings: The case studies indicate that designing and learning become intertwined in the realities of everyday problem-solving in the more complex missions. As task forces are essentially tailor-made for the purpose of specific missions, units initially need to be selected. Subsequently, the design of the task force needs to be adapted to suit local conditions. This challenge interrelates with the everyday challenge for operators of making sense of their environment and finding pragmatic solutions for the everyday problems they are confronted with. In pragmatically solving everyday problems, operators in the cases engaged in working out incomplete or ill-fitting aspects of the task force design. Practical implications: The findings are relevant for military task forces and in general for organizations that are confronted with dynamically complex environments that rely on temporary structures. Originality/value: Existing literature on learning and on organizing generally treat these as two related, but essentially separate, phenomena. In the expeditionary military task forces, operators that aimed to develop pragmatic solutions to everyday problems, the processes of learning and organizing became intertwined: units needed to organize to learn and to learn to organize. The paper ends by suggesting a combination of specific circumstances that influences the nature of the interrelation between these processes.