This chapter explores the challenges of addressing the women, peace, and security (WPS) agenda within humanitarian settings by examining experience and knowledge of field practitioners. Often WPS is seen as an issue to address only during post-conflict or development work, even though the same population is affected and there is no clear distinction between humanitarian and development environments. Local women’s organizations are humanitarian first-responders but their role in implementing WPS is neglected. This chapter argues that this artificial divide has limited efforts to promote women’s leadership, secure active participation, and promote the full protection of women’s rights in the humanitarian field. Recently, there has been progress on global commitments to address gender equality, women’s empowerment, and the protection of women and girls in disaster risk reduction and humanitarian response. Yet as this chapter demonstrates, accountability and the establishment of a cohesive link between these commitments remains a significant challenge. Throughout this chapter, the challenges of implementing the “orphan pillar” (relief and recovery) of Resolution 1325 is explored. Moreover, promising practices are highlighted in conflict and natural disaster response in Asia, Syria, and the European refugee crises, and Latin America.