ABSTRACT Members of Sigma Delta Chi (SDX), the largest journalism professional organization based in the United States, engaged in advocacy for transnational freedom of information and press freedom in Cuba between 1959 and 1962, between the Cuban Revolution and the Cuban Missile Crisis. Analysis of archival sources—including SDX member records, correspondence, and declassified government reports—and content in the official SDX magazine, reveals three themes: justifying a Latin America section with a primary focus on Cuba, the throttling of the free flow of information in and from Cuba, and documenting transnational flows of propaganda from Cuba and news from United States-based Cuban exiles to Cuba. Communist threats to reporters and democratic news organizations increased, and news management from the Cuban government and US government influenced information flows during this period. These findings add to the histories on free press advocacy abroad, cross-border journalism, and international press-politics in the context of US and Cuba relations.