Democratic transitions of highly autocratic regimes such as North Korea seem unlikely, but not impossible in theory. A systematic assessment of the possibilities and necessary conditions of democratization in such an outlier case has important implications for regime transition theories. This thesis attempts to anticipate the possibility of democratization in North Korea and forecast some signposts for its regime transition from authoritarianism to democracy. Whereas the existing research on democratization has mostly dealt with the successful cases of democratization, this study observes nine contemporary countries that have been persistently authoritarian: the Democratic Republic of the Congo, Equatorial Guinea, Iraq, Laos, North Korea, Somalia, Turkmenistan, Uzbekistan, and Vietnam. In order to analyze the commonalities and divergence between North Korea and the other eight test cases, nine critical factors associated with both democratic transition and authoritarian longevity are examined based on the previous research: "modernization", "popular mobilization", "division within the elites", "active civil society", "external influences", "concentration of coercive apparatus", "nominally democratic institutions", "symbiotic relationships among the regime/party/military", and "abundant natural resources". With these checklists, eight countries except North Korea are analyzed through matched comparison, which reveals five decisive attributes of enduring autocracy: absence of "modernization" and "active civil society", and presence of "concentration of coercive apparatus", "nominally democratic institutions", and "symbiotic relationships among the regime/party/military". In addition, a comparison target for the case study of North Korea is created as an "ideal type of enduring authoritarian regime" that possesses "all relevant" factors of authoritarian longevity: absence of "popular mobilization" and "external influences" as well as the abovementioned five decisive factors. The case study of North Korea by comparing to the ideal type shows that North Korea is so close to the ideal type of enduring authoritarian regimes that the possibility of its democratization is as remote as in any of the eight countries examined here. The presence of one democratic transition factor and the absence of one authoritarian longevity factor in North Korea, however, imply openings may exist for authoritarianism there to weaken.