The 1959 Cuban Revolution, the revolution’s subsequent strengthening, and the radical change that the process underwent beginning in 1961 marked a turning point in the history of Latin America. It implied the largest and most consistent regional challenge faced by the United States in an area where its influence had often been decisive. From then on, the Latin American Cold War intensified at every level. It was no longer about the “reactive” actions that took place among the conservative Latin American elite via the communism inspired by distant Moscow. In Cuba, the culture of the “revolution” was established, and the consequences were far from mere symbolism: Cubans also launched actions of “alternative diplomacy” to lend institutional support to the Latin American guerrilla movements. However, there is no documented study on Cuba’s role in Latin America. This is explicable in large part by the secrecy with which the Caribbean isle has made archival research in the country impossible. Although this secrecy is understandable in view of its nature as a heavily beleaguered revolution from abroad, this culture of secrecy contributed to expanding a production of journalistic and essay-based denunciation that habitually lacked rigor and interpretive frameworks. Since 2010, a certain spirit of openness has existed in the matter, an example of which is purported to be linked to the Cuban Ministry of Foreign Affairs, whose historical repository has slowly begun to receive researchers, principally from abroad. Drawing upon the anxiety and curiosity of the international historiographic community about the images originating from Havana, an initial approach and investigation was carried out in the aforementioned tradition, with the aim of shedding light on several of the actions deployed by the Cuban Embassy in Uruguay during the initial and intense years of the Caribbean revolution.