There is a feminist scholarly debate on what role military institutions play in translating the goals of the Women, Peace and Security (WPS) agenda into practice. Where idealists on the one side question if militaries should ever be involved with such responsibilities and argue that feminist purposes risk being co-opted. Whereas pragmatists on the other, argue that military institutions can be ‘regendered’ and transformed to better engage with feminist visions of security and thus implement the agenda meaningfully. To go beyond this debate there is a need to include the perspectives of those who work with bringing these policies into practice during operations. The conclusions in this thesis rely on a qualitative interview study with Swedish civilian and military gender advisors (GENADs) to attempt to bridge the disagreement described above. These GENADs constitute a central mechanism within the implementation and can therefore provide an increased understanding of the military’s role in the implementation of the WPS agenda. It intends to explore how their experiences can shed further light on the debate between pragmatists and idealists. Through an abductive thematic analysis, it is possible to interpret the answers from the semi-structured interviews conducted as three dilemmas: instrumentalization, military hierarchies, and civil-military collaboration. The findings suggest that the debate is simplified as the arguments on both sides of the debate appear to correspond with reality within international operations. It is therefore suggested that the debate should leave its deterministic mentality between idealist and pragmatist notions and shift its focus from asking whether at all, to in which situations and how militaries should play a role within the implementation. It is also contended that more emphasis in research needs to be on how to create organizational change in norms and attitudes at a systemic level.