1949-1950年是国民党政权败退台湾，在奄奄一息中挣扎顽抗的时期，对蒋介石来说也是极其重要的历史时期。从1948年下半年开始国民党政权所面临的局势已十分严峻，蒋介石亦面临前所未有的困境：军事上嫡系部队已被消灭迨尽；政治上被迫下野，领袖地位不保；经济崩溃，大失民心；外交上不仅蒋美关系发展至冰点，各国将有承认新政权的动议。蒋介石不得不为自身和国民党政权寻找政治出路。然而国内政治、经济、军事局面已无可为力之处。蒋介石极力谋求借助外力进行“自救”，以摆脱内外困局。
美苏冷战的国际态势是蒋介石谋求借助外力“自救”的环境基础。蒋介石和国民党内较为普遍的认知是，此时只有美国有能力挽救国民党政权的政治命运，但是美国已经放弃对蒋介石的支持，并考虑放弃对国民党政权的支持而重新调整其对华政策和远东政策。因此，防止美国从中国事务脱身，并将其推至亚洲和太平洋地区反苏反共的前线，是蒋介石进行外交“自救”的前提。
在“自救”策略上，蒋介石及其僚属通过联络日本、韩国、菲律宾等亲美反共国家，模仿北大西洋公约组织的形式，倡组环太平洋地区的反共联合阵线，以达到阻止中国新民主主义革命的胜利、避免国际的承认、防止美国脱身的目的。1949年夏，蒋介石高调出访菲律宾和韩国，希望先与菲律宾和韩国联合，构建远东反共联盟的基础，进而逐步扩大范围，将美国置身其中并予以支助。
进行区域联合计划主要目的是建立军事联盟，以外部军事力量参加国民党军队的反共战争。因此，蒋介石和国民党高层把日本视为反苏反共的突破口，企图在日本招募旧军官参加国民党军队的反共战争，进而组建国际反共志愿军，造成亚洲地区反苏反共的态势。然而，没有美国的支持，蒋介石和国民党政权为摆脱困境而制定的各项计划和开展的各项行动并未奏效，反而更加剧了美蒋关系危机和美国对国民党政权的厌弃。
鉴于中国共产党领导的新民主主义革命战争暴风骤雨式的胜利，蒋介石和国民党政权以反共联盟为切入点所作的外交“自救”活动都难以取得实效。蒋介石同时作了以台湾为落脚点的退却防御性“自救”措施，企图以天然的海洋屏障阻隔人民解放军的进攻，并利用美国对台湾战略地位的重视，谋取美国的保护，然而美国行政当局在反复权衡之后声明不会军事援助和保护国民党政权。
蒋介石和国民党政权为摆脱困境而进行的诸项外交“自救”计划和活动几乎都已失败，台湾基地的驻守也未有充分把握。美国反苏曾经是国民党反共的本钱，现在则是其挽救生存危机的关键。因此，竭力酝酿亚洲地区的紧张局势甚至军事冲突，进而营造美苏军事对抗的态势，以美苏战争的爆发为挽救自身政治命运的关键。蒋介石利用朝鲜半岛的紧张局势及朝鲜在美苏冷战中的特殊性，与李承晚进行了密切的外交互动，待机实施以朝鲜为爆炸点，酿成美苏热战从而获得美国保护的捆绑方案。
朝鲜战争的爆发是蒋介石和国民党政权摆脱困境的关键。朝鲜战争爆发后，美国决定干涉中国内政，以军事力量入侵中国台湾海峡，台湾国民党政权暂时获得美国的保护，蒋介石和国民党政权迎来政治命运的转机。蒋介石不断关注并或多或少的参与朝鲜的历史走向，朝鲜的历史走向尤其是朝鲜战争的爆发对蒋介石和国民党政权的命运也产生了重要而深远的影响。

During 1949 to 1950, the Kuomintang regime retreated to Taiwan and struggled tenaciously on the verge of death, which was also a critical stage for Chiang Kai-shek. Since the second half of 1948, Kuomintang regime faced a grim political environment, and Chiang Kai-shek encountered unprecedented difficulties. Militarily, his own military forces had been almost eliminated; Politically, he was forced to be ousted and lost his leadership position; Economically, the economy collapsed and he lost trust of the people; Diplomatically, Chiang Kai-shek's relations with the United States had reached a stalemate, what was worse, all countries grown an idea to recognize the new regime. Chiang Kai-shek had to find a political way out for himself and also for the Kuomintang regime. However, the domestical situations in politics, economy and military became hopeless. Chiang Kai-shek tried his best to rescue himself by seeking the help of external forces to break out of the internal and external crisis.
The international trend of the Cold War between the United States and the Soviet Union was the environmental basis on which Chiang Kai-shek sought for saving himself by external forces. The common understanding among Chiang Kai-shek and the Kuomintang was that the United States held the exclusive capacity of saving the political fate of the Kuomintang regime, but the United States had given up supporting Chiang Kai-shek, even considered giving up supporting the Kuomintang regime and readjusting its policy toward China and the Far East. Therefore, the prerequisite for Chiang Kai-shek’s diplomatic resort was to prevent the United States from extricating itself from Chinese affairs and to push it to the front of anti-Soviet and anti-communist activities in Asia and the Pacific.
Regarding to the strategy of self-help, Chiang Kai-shek and his subordinates liaised with Japan, South Korea, and Philippines and other pro-American and anti-communist nations, by imitating the North Atlantic Treaty Organization, to initiate an anti-communist United front in the Pacific Rim whose aim was to prevent the victory of China's new-democratic revolution,  and to avoid an universal recognition worldwide, and the pulling out of the United States. In the summer of 1949, Chiang Kai-shek paid a high-profile and visited to the Philippines and South Korea, hoping to unite with the Philippines and South Korea in advance to build the basis of the anti-communist alliance in the Far East, letting it gradually expand, then drawing the United States into the support for itself.
The main purpose of the regional joint plan was to establish a military alliance and absorbed external military forces to participate in the the Kuomintang army’s anti-communist war. Therefore, Chiang Kai-shek and the senior officials of Kuomintang regarded Japan as a breakthrough to deter the Soviet Union and the Communist Party, and attempted to solicit Japanese old officers to join in the anti-communist war of the Kuomintang army, then formed an international anti-communist volunteer army and created an anti-Soviet and anti-communist situation in Asia. However, without the support of the United States, Chiang Kai-shek and the Kuomintang regime’s plans and actions to get rid of the predicament didn’t work but aggravated the crisis of US-Chiang Kai-shek relations and caused America reject the Kuomintang regime more.
In view of the tremendous victory of the new democratic revolutionary war led by the Communist Party of China, the diplomatic self-rescue activities based on the anti-communist alliance hardly generated substantive efforts. At the same time, Chiang Kai-shek also made a defensive self-rescue measure based on Taiwan as a leeway, in an attempt to block the attack of the people's Liberation Army with a natural marine barrier. Meanwhile, by using the United States' concentration to Taiwan's strategic position, Chiang Kai-shek sought the protection from the United States. However, after weighing up the pros and cons, the US administration declared that it wouldn’t provide the Kuomintang regime with military assistance and protection.
Almost all the diplomatic self-rescue plans and activities of Chiang Kai-shek and the Kuomintang regime to get rid of the predicament have failed. They didn’t hold strong confidence that they could garrison Taiwan. The anti-Soviet Union of the United States was once the advantage of the Kuomintang's anti-communism, but now it turned to be the key factor to get out of survival crisis. Therefore, he made much effort to create tensions and military conflicts in the Asian region, and then created the military confrontation between the United States and the Soviet Union, considering the outbreak of the war between the United States and the Soviet Union as the key opportunity to save their own political destiny. By taking advantage of the tension on the Korean Peninsula and the particularity of North Korea in the Cold War between the United States and the Soviet Union, Chiang Kai-shek proceeded an intimate diplomatic interaction with Li Seung-Man, waiting for an opportunity to implement a bundling scheme that took North Korea as the explosion point and led to a fierce war between the United States and the Soviet Union to get protection from the United States.
The outbreak of the Korean War was critical for Chiang Kai-shek and the Kuomintang regime to get out of the predicament. After the outbreak of the Korean War, the United States decided to interfere in China's internal affairs and militarily invaded the Taiwan Strait. The Kuomintang regime in Taiwan got the temporary protection from the United States. Chiang Kai-shek and the Kuomintang regime took a turn for the better in their political fate. Chiang Kai-shek continued to pay attention to and had some effect on the historical trend of North Korea, which especially had an important and far-reaching impact on the fate of Chiang Kai-shek and the Kuomintang regime.