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Malaya attained independence on August 31, 1957 from Britain. However this new nation faced a communist insurgency known today as the “Malayan Emergency” (1948-1960). Then in 1961, Tunku announced a wider federation of “Malaysia”, viz. Malaya, British Crown Colonies of Singapore, Sarawak and North Borneo, and the protectorate of Brunei. Countering communism was a principal motive for “Malaysia”. Sarawak’s leftist elements were rejected with an armed opposition. Malaysia was formed excluding Brunei. Amidst its birth pangs, Malaysia faced hostile neighbors Indonesia and the Philippines; the former objected by way of Konfrontasi (1963-1967) while the latter laid claim to Sabah (formerly North Borneo). Malaya/ Malaysia was borne in the midst of the Cold War (1947–1991), a bipolar world between the US and the USSR. Malaya/Malaysia is utilized as a case of analysis and evaluation in the context of the twin trends of continuities and transformations in tracing the historical developments from the 1950’s to the 1990’s. The risks, motives, and challenges that prompted the shift in foreign relations reveal as much of the personality of the political leadership, the prevailing situations, and conditions from within and circumstances from without.