In the contemporary global context, transitioning from conflict to peace and from authoritarian to democratic governance is a critical preoccupation of many states, particularly the United States. In these contexts, accountability for the abuses committed by prior regimes has been a priority for international institutions, states, and new governments. Equally, transitional justice goals have expanded to include fashioning new domestic political and legal institutions and a broad range of structural reform in multiple spheres. Gender concerns have been markedly absent across political contexts and jurisdictions experiencing change. This article examines the legal provision and conceptualization for gender security and accountability in times of transition. The article takes a close look at a range of contemporary issues that arise for women in these contexts including, an examination of post-conflict security from a gender perspective, gender and disarmament, gender and restorative justice processes in transitional societies, and the centrality and effect of security sector reform for women. The article pays particular attention to the under-theorized and under-researched role of international masculinities and the patriarchy that is imported with international oversight of transitional societies.