Even after 40 years of sanctions, there remain huge differences of opinion on U.S.-Cuba relations. One point all sides agree on, however, is that sooner or later sanctions will be removed. Lifting sanctions raises several issues concerning sugar trade between the two countries. With U.S. sugar prices kept significantly higher than world levels, the U.S. market would be highly attractive for Cuban sugar exporters upon the removal of sanctions. Cuba almost certainly would request access to the U.S. sugar market based on U.S. trade obligations under the World Trade Organization (WTO). The purpose of this paper is to suggest the legal context of U.S. obligations under the WTO with respect to sugar imports from Cuba and to present several options for allocation of the U.S. sugar tariff-rate quota to Cuba under a normalized trade relationship.