This article highlights and critiques the underlying conceptualisations and assumptions of the women, peace and security (WPS) agenda that emerged with the adoption of United Nations Security Council Resolution 1325 in 2000. The main argument is that we need to rethink the WPS agenda to produce more holistic and groundbreaking responses for the types of challenges encountered, i.e., that gender inequality and insecurity are deep rooted and multi-layered, and thus negate mechanistic responses that do not deal with cultural and structural issues. It specifically focuses on gender and peace-making and gender and peacekeeping to point to the pitfalls in the current conceptions and practices in this arena.