With the breakdown of relations between Washington and Havana after the Cuban revolution in 1959, officials in Ottawa found themselves in an unenviable position. Increasingly, Canadian diplomats and politicians felt caught between, on one side, their most important ally and trading partner, and, on the other, a country that had not caused harm to Canada in any significant way. Alarmed by this state of affairs, Canadian officials on several occasions considered mediating the dispute between Cuba and the United States. Ultimately, however, policymakers in Ottawa stopped short of taking this step, largely because they recognized that their U.S. allies disapproved of mediation. Many historians, in playing up the differences between Canadian and U.S. foreign policies toward Cuba, have ignored Canada's caution in choosing an independent stance. This article shows that in dealings over Cuba, Canadian officials were mindful both of Canada's limited capabilities and of its position as a close ally of the United States.