Finding a diplomatic solution to the nuclear crisis on the Korean peninsula is among the most pressing challenges that the international community currently faces. Given that any diplomatic solution to the crises necessitates direct dialogue with the Democratic People’s Republic of Korea (DPRK, or North Korea), this study analyzes past dialogue initiatives of the international community with that country — thereby aiming to scrutinize the multiple challenges associated with such endeavors. Among the lessons that can be learned from the failure of past diplomatic initiatives to solve the nuclear crisis is the acknowledgment of the fact that such non-military solutions will constitute a long-term and gradual process, whose continued maintenance requires a tremendous amount of sustained political will. Moreover, North Korea’s transition to a de facto nuclear power has dramatically changed the baseline for dialogue with it.