This article analyses the bilateral economic negotiations between Washington and Havana during the era of the Cuban PRCA (Auténtico) governments led by Ramón Grau San Martín and Carlos Prío Socarrás (1944–52). This work shows that, initially, the PRCA governments took advantage of the economic bargaining capacity that Cuba had developed with Washington during the Good Neighbor era, but after 1947 this declined as the Truman administration's Cold War foreign policy agenda assigned only a marginal position to Latin America and Cuba. Havana's inability to obtain further economic support from the United States had a powerful destabilising effect, complicating Cuba's economic governance and delegitimising the PRCA politically. The study of this episode enhances our comprehension of a period largely overlooked by the historiography on Cuba and our understanding of the demise of the Auténtico project, the last attempt to transform Cuba's social structures in a progressive and democratic manner.