By using prewar and early postwar archives and historical sources collected in Taiwan, Japan, the U.S.A. and Singapore, this paper reconstructs Japanese government's relation with Taiwanese investment in Southeast Asia (SEA) during the period of 1895-1945 and obtains the following findings: 1. Taiwan's investment in SEA is more important than the trade in between, by comparison with Taiwan's economic relation with southern China and Manchuria. 2. The common dialect shared by the Taiwanese and the overseas Chinese in SEA paved the way for Taiwanese investment in SEA. 3. Such cultural affinity had not continually motivated Japanese government's mobilization of Taiwanese to invest in SEA until 1935 when Japan's southern advance policy started to be more vigorously pushed. 4. Matching with Japan's total southern advance policy, which paced with the momentum of the second World War, institutions were established step by step to train Taiwanese, preparing them to serve as agents for Japanese companies in SEA selling Japanese goods to overseas Chinese. 5. Before political mobilization, both the holding of Japanese nationality by the Taiwanese and Japan's international political-economic relations helped Taiwanese investment in SEA. Enjoying an equal status to that of the European colonizers in the Dutch East Indies (Indonesia), Taiwanese merchants made the place to have shared more than half of Taiwanese migration in SEA. And, in comparison with small shops Taiwanese maintained in other places of the region, more Taiwanese investments in factories in the Dutch East Indies (Indonesia) would be attributed to the modern commercial law and more protection Japanese government gained for them there. 6. Those Taiwanese who benefited more from Japan's international political-economic order or were more mobilized by Japanese government tended to have more of the Japanese identity. Such Japanese identity these Taiwanese had also resulted in their being attacked by those who were anti-Japanese. 7. The scale of traditional Chinese merchants in international trade tended to be of medium or small size. Mainly extending this traditional character, the enterprises Taiwanese owned in SEA also tended to be so, yet, there were some big Taiwanese enterprises showing a sort of discontinuity from the tradition. Besides, some Taiwanese went even further with their management of international enterprises. 8. When Taiwanese sale of Japanese products in SEA was described by Japan as indispensable, and when the international entrepreneurial experience was being considerably obtained by the Taiwanese, the previous assertion of historians that Taiwan's overseas economic activities under Japanese colonial rule had been so monopolized by Japan's government and zaibatsu that the Taiwanese had no chance for such development has been found to be not well-grounded.