The Tricontinental Conference in 1966 in Havana, Cuba, marked a moment of particular import for the development of an internationalism grounded in anti-imperialist and decolonial solidarity. Tricontinental took place at the height of crisis for many nations fighting for independence. The Organization of Solidarity of the People of Africa, Asia, and Latin America (OSPAAAL) sought to promote an internationalist political perspective that interrelated global revolutionary movements through their collective opposition to imperial and colonial governance and resource extraction. This essay focuses on two affective aesthetic tactics: the mobilization of images of women represented as actors in armed struggle, as well as more commonly gendered representations of motherhood. It examines imagery and writing that centers gender and focuses on the intersection of violence against women, aspects of capitalism, imperialism, interpersonal relationships, family and women’s reproductive rights, and culture. Ultimately, it demonstrates that OSPAAAL used artistic production as a tool of political dialogue.