The fact that contemporary peace support operations are multifunctional has meant a significant recasting of their character: the mandates are broader (support to peace processes and security sector reform is e.g. combined with reconstruction activities and military operations), phases are parallel and a multitude of different actors are often working simultaneously in the operations area. This has created mutual dependencies between intervening actors, not least between civilian and military ones, and increased the need for harmonization and coordination between them. In turn, these altered circumstances demand that actors are able to adjust to them. Concerning monitoring and evaluation, this is currently not the case. Especially within the military sector the need for development is vast. Experiences from inter alia Afghanistan has indicated significant deficiencies in the monitoring and evaluation processes. In order to address this need, it is first of all important to investigate the problems and challenges that multifunctional operations, and the environment in which they are obtained, pose to military organizations. Secondly, it is important to investigate how they can be solved. Since the multifunctional character of operations increase the need for coordination between civilian and military actors it is particularly important to investigate how, and to what extent, civil-military solutions can address existing problems and challenges. This study thus aims to 1) compile problems and challenges that military organizations need to relate to concerning monitoring and evaluation, and 2) investigate how civil-military solutions can help manage them. Existing problems and challenges can be divided into an external and internal perspective respectively. The external perspective is structural and inter alia encompasses lack of clear strategies; intangible objectives; political prerequisites; and a rapidly changing environment. The internal perspective is actor-oriented and inter alia encompasses modus operandi and evaluation logic; focus on opponents rather than operational environment and conflict context; lacking connection between operational design, planning and evaluation; and overconfidence and quantitative data and methods. Overall, these problems and challenges are complex and difficult to manage. At the same time, this needs to be done and in that regard proposed solutions, i.e. District Stability Framework (DSF) and civil-military joint evaluations, constitute interesting examples of how it can be achieved. The solutions can inter alia provide military organizations with a system-wide perspective on operations; increase their contextual awareness of the conflict at hand; increase the connection between operational phases, and increase intervening actors ability to handle the political prerequisites of peace support operations. However, the potentially positive effects of DSF and civil-military joint evaluations must be further verified in empirical studies before their applicability can be fully established. It also important to be realistic about what methods and tools in general and proposed solutions in particular actually can achieve since strategic and political priorities are factors that crucially affect operations and, consequently, the evaluations of them. Still, DSF and civil-military joint evaluations constitute a first step that could enable necessary change of military organizations' approach to monitoring and evaluation in multifunctional operations.