After the Second World War the European continent stood divided between two clearly defined and competing systems of government, economic and social progress. Historians have repeatedly analyzed the formation of the Soviet bloc in the east, the subsequent superpower confrontation, and the resulting rise of Euro-Atlantic interconnection in the west. This dissertation provides a new view of how two borderlands steered clear of absorption into the Soviet bloc. It addresses the foreign relations of Yugoslavia and Finland with the Soviet Union and with each other between 1948 and 1958. Narrated here are their separate yet comparable and, to some extent, coordinated contests with the Soviet Union. Ending the presumed partnership with the Soviet Union, the Tito-Stalin split of 1948 launched Yugoslavia on a search for an alternative foreign policy, one that previously began before the split and helped to provoke it. After the split that search turned to avoiding violent conflict with the Soviet Union while creating alternative international partnerships to help the Communist state to survive in difficult postwar conditions. Finnish-Soviet relations between 1944 and 1948 showed the Yugoslav Foreign Ministry that in order to avoid invasion, it would have to demonstrate a commitment to minimizing security risks to the Soviet Union along its European political border and to not interfering in the Soviet domination of domestic politics elsewhere in Eastern Europe. Following Yugoslavia's expulsion from the Soviet bloc, its party leadership increasingly granted the Foreign Ministry resources needed to establish a wider and more important range of diplomatic relations than those of any East European state. The placement of Tito's closest associate Kardelj as Foreign Minister from August 1948 to January 1953 carried the process forward. It created a Yugoslav Foreign Ministry that produced political analysis independent from that of Tito's own committee on foreign relations. By 1953, the ministry regarded the Finnish model of neutralism as a solution to the Yugoslav security dilemma. It came to abandon that in favor of the Non-Aligned Movement only after 1958, when it became clear that relations between Yugoslav and Soviet parties would not be harmonious even after rapprochement.