Why do efforts to achieve a gendered security sector reform (SSR) in post-conflict states often fail? How come policies about integrating a gender perspective in SSR are rarely put into practice? This chapter attempts to answer these questions by identifying and analysing obstacles to a transformative, gendered SSR in both policy-oriented SSR literature and feminist research. Three challenges are identified: (1) the perceived tension between local ownership and gender; (2) intervening actors’ dubious credibility as role models as they, to a large majority, are men benefitting from patriarchal structures; and (3) the inability to take into account the private when reforming the public, which means that structural ‘ordinary violence’ such as domestic violence, remains invisible. In conclusion, the author argues that gendered SSR fails because a broader participation which takes into account the voices of the marginalised are not envisioned. Ultimately this means that SSR remains a conversation by, and for men.