This article examines the diplomatic strategies of Revolutionary Guatemala between 1944 and 1951, situating them within the broader continental realignments that occurred at the onset of the Cold War. Contrary to prevailing interpretations that emphasize covert warfare or ideological rhetoric, it argues that Guatemala’s revolutionary governments pursued a deliberate, multilateral diplomatic agenda aimed at reshaping inter-American relations. Drawing on research in multiple archives in the Americas and Europe, the article demonstrates how Guatemala engaged in initiatives such as the nonrecognition of coup regimes, support for the Larreta Doctrine, and campaigns against Francoist Spain while forging alliances with Mexico, Venezuela, Cuba, and Southern Cone democracies. These efforts reveal both the agency and the limitations of states seeking to promote democracy amid shifting geopolitical pressures. By reframing Guatemala’s role, the article contributes to ongoing debates about Latin American agency, the contested nature of early Cold War alignments, and the evolution of inter-American diplomacy.