Havana’s relationship with Moscow that developed in the late 1950s and early 1960s very quickly became vital for the Cuban Revolution, but it originated very much as a result of timing, at the height of the Cold War. However, other reasons and pressures rapidly appeared that impacted on the relationship for the next 30 years. Some of these began to be questioned in the late 1980s as a result of the reform processes instigated in both countries, but many simply vanished in the aftermath of the implosion of the Soviet Union that simultaneously ended Cuban-Soviet relations. The relationship unquestionably suffered a dramatic political and economic downturn as a result of this, but not all the pressures evaporated and even in the years from 1992 to 1995 more than diplomatic relations continued to function, most noticeably oil for sugar swaps. As the 1990s progressed, new pressures began to appear and remarkably some from the Cold War era, including the geostrategic importance of the island for the Kremlin, began to resurface. The result has been an improvement in relations from 1995 onwards and in the twenty-first century it remains important for both countries, illustrating its enduring qualities.