The rise of labor and environmental conservation movements after lifted the Martial Law of ROC in 1987, which lead to a soaring rise in labor and operating costs. As a result, Taiwan businesses gradually moved to Southeast Asian countries where labor costs are lower and most overseas Chinese gather. In 1994, the government aggressively promoted the "Policy of Investing in the Southeast Asia"; thereafter, for looking after both work and family, Taiwanese entrepreneurs and their employees took their families with them and set up new homes and factories or work in Southeast Asia region. However, due to these Taiwanese entrepreneurs, employees, and even the diplomatic personnel of the government, pursuant to the requirements of their jobs or the limitations of their employment periods, would have to return to Taiwan a few years later. Hence, the problem of their childrens schooling continuity upon their return has become their primary consideration. Since Chinese language education in Southeast Asian nations are limited by the local governments, there is a huge difference between the educational system, teaching materials, curriculum, and schooling hours of these schools and schools in Taiwan. The children of Taiwanese entrepreneurs attending local schools in this area often find it very difficult to connect with the educational system in Taiwan after they returned to Taiwan. The best solution that these overseas Taiwanese could think of is to set up "overseas Taipei schools" that comply with the educational system of the local countries, and at the same time help Taiwanese children reach the necessary educational standards and learn their own cultural heritage. Since 1989, the ROC government helped overseas Taiwanese entrepreneurs to establish the Malaysia Penang Taiwan Chinese School and Malaysia Kuala Lumpur Chinese Taipei School, the Jakarta Taipei School ad Jakarta Taipei School Campus B at Surabaya, the Thai-Chinese International School, and the Ho Chi Minh Taipei School in Vietnam to alleviate the educational problems of overseas Taiwanese. The program was in line with the "Policy of Investing in the Southeast Asia" of the government. It is aimed to help Taiwanese entrepreneurs in the declining industries of Taiwan find opportunities in Southeast Asian region, as well as reduce the dependence of ROC on China. Since education is a lifelong pursuit, matters are quite complicated. Situation is further aggravated by the absence of precedent "overseas Taipei schools" in the host countries. This paper delves into the development history, present conditions, difficulties and problem-solving methods, and prospect of the "overseas Taipei schools" and its role in the overseas Chinese education history.