This paper aims to analyze Yugo-Anglo-American relations during the first phase of the Yugo-Soviet rapprochement, which took place between 1953 and 1955. To this purpose, it is necessary to study some important events occurred in 1952, when a number of negative factors started to affect Yugo-Western relations, months before Stalin’s death and Khrushchev’s overtures to Tito. The failure of the military talks held in November 1952 had deep negative consequences on Yugo-Anglo-American relations. The US and Great Britain aimed to achieve some important goals by “keeping Tito afloat”: firstly, to encourage a joint military planning with Yugoslavia, in order to strengthen the Southern flank of NATO; secondly, to exploit the Yugoslav example as a sort of “wedge” to undermine the cohesion of the red Bloc; lastly, in the very long term, to favor a “regime change” in Yugoslavia, through the progressive democratization of the political life and free elections. From the very beginning, Tito and his closest associates judged Western economic and military cooperation as widely unsatisfactory for Yugoslavia, even if it was essential for its survival. In their opinion, the Western aid proved to be a form of political pressure, aimed at reducing Yugoslavia’s independence without providing a full guarantee in terms of security. As a consequence, when the USSR changed its approach towards Yugoslavia, Tito was eager to set up new relations with Moscow, and to develop his foreign policy towards equidistance and non-alignment. Given the Soviet not-so-hidden effort to reassert ideological and political control over Yugoslavia, the Yugo-Western relations retained a great importance for Yugoslavia; however, in Tito’s mind, these relations had to change deeply. In the new scenario, he needed political support and economic aid from the West, while military cooperation became useless, if not harmful, to his purposes. For the US and Great Britain, the problem was that all Western projects about Yugoslavia depended on a stable and fruitful military cooperation. Therefore, during the years analyzed in this paper, Yugo-Western relations continued to develop, but new problems arose: while the Western side tried to keep the military cooperation alive, Tito moved staunchly towards equidistance, refusing military commitments. The illusory successes kept in 1953-1954 (namely the Balkan Pact, the London memorandum on Trieste and many agreements in the economic and military field) could not prevent a progressive weakening of Yugo-Western relations, that ended up with the official recognition of East Germany and with the definitive interruption of military aid, both decided by Tito at the end of 1957. These traumatic events, however, had their roots in the slow but steady worsening of Yugo-Western relations that occurred between 1952 and 1955, in consequence of the Yugo-Soviet rapprochement.