Abstract: Following Joseph Stalin’s death in 1953, Nikita Khrushchev became leader of the Soviet Union and ushered in a liberalization campaign that reverberated outward to certain Eastern European nations. Canadian officials recognized that limited freedom of maneuver was conceded to certain Eastern European nations, in addition to Yugoslavia’s existing independent position. This proved important, as Communist Eastern Europe became a deliberate and considered factor in Canada’s foreign policy. Canadian Soviet policy thus evolved into a Canadian policy towards Communist Eastern Europe, equipped with various nuances. Specifically, this project examines Canadian policy with Yugoslavia, Poland, and the Soviet Union. By the mid 1950s, a general strategic stasis existed in the Cold War, which led to something of a political balance; as a result, discovering strategies to engage in the Cold War by “other means” became necessary. Prime Minister John Diefenbaker’s Progressive Conservative government was committed to preventing the spread of communism, and this was an integral component of its foreign policy with Communist Eastern Europe. This dissertation argues Canadian policy towards Communist Eastern Europe during the Diefenbaker-Khrushchev period was not solely driven by traditional geopolitical and geostrategic considerations, but was also concerned with non-military Communist tactics. As a result, Canadian officials pursued closer political, economic, and socio-cultural bilateral relations with select Communist Eastern European countries in order to challenge Soviet hegemony in that region and to combat Eastern European communism generally. Despite the differences among Poland, Yugoslavia, and the USSR, Canada’s broad policy objective was consistent: promote positive relations to expose Communist nations to Western modalities in hopes of lessening communist influence globally. The Canadian government during this period did not have a “grand strategy” that governed its policy with the region. Instead, pragmatism prevailed as a number of ad hoc developments in the fields of economic and cultural foreign relations contributed to the growing sense that Canada was engaged in Cold War diplomacy by “other means.”