The Anglophone Caribbean islands are located between the major suppliers and consumers of illegal drugs. This geopolitical reality forces these Small Island Development States (SIDS) to grapple with the nuances and fallout as a critical transhipment point for guns and drugs globally. The high level of firearm-related deaths of young men is one such fallout, the product of a complex interface of global and local, sociocultural, socio-economic, historical and gendered forces at play as the region seeks to address its place in the global political economy of diversion of small arms and violence. This paper interrogates the Trinidad and Tobago-based activism of the Women’s Institute for Alternative Development (WINAD). Specifically, WINAD’s protracted work is to compel the United Nations (UN) to reorder its arms-related structures of global governance, the Arms Trade Treaty (ATT). WINAD’s work entreats the global community to re-imagine the power relations between arms producers and consumers; to pay particular attention to small, postcolonial, non-arms exporting countries impacted by the global movement of guns; and to pay homage to the multiple locations of women in the global arms conversation. WINAD’s work disrupted the gender script on national and regional gun violence, making women’s place as change agents and community leaders visible in the context of arms control. WINAD’s work was a necessary recasting of notions of human security, of how some women, in Trinidad and Tobago, negotiate personal and collective securities for themselves, families, communities and country, and interface with constructs of voice and agency.