United States efforts to bring about regime removal and democracy in Cuba through economic sanctions, travel restrictions and frozen diplomatic relations have not worked in over 55 years. Every President since Dwight D Eisenhower has corresponded through back channels to Cuba with the government, reviewed sanctions, property claimants, established negotiations, and largely left sanctions in place. This research paper reviews the history of U.S.-Cuban relations, analyzes U.S. sanctions against Cuba, and examines the security policy implications after the U.S. has to modify its policies towards Cuba. It examines whether the U.S. should “Spring Forward or Fall Back” in the motivation to drive change in Cuba with renewed U.S.-Cuban relations. Finally, it will determine if it is feasible, acceptable, and suitable to change the U.S. engagement with Cuba by renewing economic and diplomatic relations and remove the remaining travel restrictions and U.S. trade embargo.