The four pillars of UN Security Council Resolution 1325 are typically understood as prevention; protection; participation; and relief and recovery. While theoretically these pillars are conceived of as equally important to the advancement of the women, peace, and security (WPS) agenda, the operationalization of each has been highly uneven. Most Security Council resolutions that followed Resolution 1325 on WPS focused on protection, with participation and prevention receiving less attention. Similarly, WPS-related interventions in conflict-affected contexts frequently focus exclusively on protection without drawing possible synergies from the other pillars. This chapter explores the challenges and opportunities of “cross-pillar engagement” in conflict and post-conflict situations, arguing that greater emphasis on participation would lead to gains in all four areas and beyond. I suggest that understandings of participation need to evolve beyond merely taking part. To more effectively challenge the gendered power structures that continue to hinder progress, women seeking peace and equality need to adopt a transformative, feminist approach to participation.