Despite the 20-year long counter-proliferation policy towards North Korea, why has the United States failed to dissuade North Korea's nuclear ambition? This issue has long triggered a highly divergent debate among policy analysts. One schoolof thought believes security assurance and economic assistance would diminish North Korea’s nuclear weapons‘ valuation and lead it to forgo its nuclear program.The other school of thought argues that regardless of the U.S policy, the abandonment of nuclear weapons program was never a policy option for North Korea. However both schools have given incomplete explanation to the entire spectrum of the North Korean nuclear weapons development dynamics. Faced with such incomplete explanations,this study revisited the first nuclear crisis, where the two divergent arguments originated. This study builds and tests a hypothesis that U.S. counter-proliferation policy was mismatched with what the North actually wanted,and such mismatch eventually caused the failure to completely terminate North Korea’s nuclear weapons program in the first nuclear crisis.This study confirms the hypothesis by using a research concept of critical juncture which method investigates by which factors an event occurs.With a comprehensive review of the history of the North Korean nuclear development and U.S.responses to the first nuclear crisis,this study examines whether U.S.policy was properly suited with North Korea’s internal and external requirements. Finally, This study supports the conclusion thatU.S.counter-proliferation policy has been misaligned with North Korea's actual motivations,and such policy resulted in thesecond North Korea's nuclear breakout in 2002. Keywords: North Korean Nuclear Weapons Development, Counter-proliferation Policy, Theories of Nuclear Proliferation, The First NorthKorean Nuclear Crisis.Weapons of Mass Destruction