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During the Cold War era, the most important security agenda that the United States and its allies was to contain the spread of the Soviet communism all around the world. After the overriding Soviet threat disappeared, however, the United States, a sole superpower in global politics, began to give a high priority to the danger of North Korea’s nuclear development. As a result, since then the North Korean nuclear problem has sparked various phases of security conditions on the Korean peninsula, which has ranged from a brink of military conflict to dynamic diplomatic negotiations to status quo or stalemate. In this context, why has it been so difficult to resolve North Korea’s nuclear weapons issue since the early 1990s when it first emerged as an international problem? How can the international community, particularly a key stakeholder the United States, effectively deal with this longstanding, complex issue? Addressing these questions, this paper argues that the issue of North Korea’s nuclear weapons has become a most complicated international affair due to the combination of multiple factors, such as deeply rooted mutual distrust, North Korean leaders’ growing will to develop nukes, differing interests of the U.S. and China, coordination problems within/between the U.S. and South Korea, and difficulty in implementing diplomatic agreements. The paper also illuminates that such multiple factors are closely intertwined with one another. It finally suggests a more flexible and realistic alternative that motivates North Korea to come to a negotiating table, as opposed to solely confrontational approaches based on military pressure and sanctions.