The United States military base in Guantánamo Bay, Cuba exists in the minds of many people today as the site of the prison opened in 2002. However, what is now U.S. base territory in Guantánamo Bay has been a site of conflict, cooperation, and coexistence for hundreds of years. This thesis examines the ways in which the Cuban state, a non-monolithic combination of different forces, has constructed a temporal framework of the not-yet-arrived utopian socialist future with regard to the closest Cuban town to the base, Caimanera. According to this narrative, prosperity will arrive to Caimanera when the base territory is returned and, by extension, the socialist future triumphs. I weave together ethnographic observations, archival materials, and analyses of Cuban public cultural texts in order to examine how this utopian socialist dream, always deferred to the future, has been ruptured by its own non-arrival. I focus on the physical and ideological constructions of this temporal deferral of the socialist future, such as the militarization of the border and the experiences of base workers in the early 1960s, the refugee camp at the base in the 1990s and the experiences of Cubans waiting there, and the hotel built in Caimanera at the onset of the Special Period of the 1990s. I conclude by discussing the complex aftermaths of living within and beyond suffering and harm for the inhabitants of the town.