This article examines the political and economic issues that arose in relations between the Soviet bloc and Cuba from 1959 through 1991, including the admission of Cuba into the Soviet-dominated Council for Economic Mutual Assistance (CMEA) in the early 1970s. The article breaks new ground by consulting previously unseen primary documents originating from the East European states and Cuba, which highlight the often contentious ties between the European CMEA states and Cuba. The East European governments were often dismayed by the egregious economic mismanagement of Fidel Castro's regime and tried, mostly unsuccessfully, to encourage better policies. The relationship that emerged was shaped in part by Cuba's ever-increasing demands, by the East European states’ own economic limitations, and by the Soviet Union's far-reaching political objectives.