This panel seeks to understand the social and cultural strategies deployed by multi-national Overseas Chinese enterprises in creating Asia-wide business emporia in their confrontation with the British and Dutch colonial powers. It is by now well-known that after the establishment of colonial rule in Southeast Asia since the late 19th century, Overseas Chinese business communities continued to play an essential role in the development of trade and commerce in the Asiatic region and that diasporic networks were instrumental in this process. Far less attention has been paid to the role of Overseas Chinese capitalists in the confrontation between the Japanese and European colonial empires, their accommodation to these colonial regimes, their mutual rivalries, and their control over different diasporic networks. This panel aims to do just that by focusing on some of the largest Overseas Chinese conglomerates in colonial Southeast Asia: the Oei Tiong Ham Concern (OTHC), the Kwik Hoo Tong Trading Society (KHT) and the business empire of Aw Boon Haw. Although OTHC and KHT gained their first fortunes under Dutch colonial rule, the development of their subsequent business interests was quite different. OTHC expanded to Europe and, like Aw Boon Haw, to the British empire; KHT looked to Taiwan and the Japanese empire. Both companies became the largest exporters of Java sugar, while KHT also dominated Taiwan’s tea trade. KHT’s fortunes were thus closely connected to the Japanese colonial empire, whereas OTHC’s business empire had a far greater global reach. Japan’s retreat from the Java sugar market and its aggressive policy towards China negatively affected both conglomerates, but led to the bankruptcy of KHT, whereas OTHC managed to survive the sugar crisis and world economic depression. Just like Aw Boon Haw, OTHC carefully maneuvered between the Japanese and European colonial empires, at the same time developing close ties with the Chinese government. The dissimilar fates of these conglomerates seemed to have been related to the different world-views of their founders and the different social and cultural strategies they deployed in developing their enterprises. Their failures and successes should also lead us to think about the transformation of transnational Chinese entrepreneurship under Japanese military rule in Southeast Asia and in the postcolonial era. This could offer important perspectives to reflect upon the compatibility between diaspora capital and empire vis-à-vis the emergence of the “Chinese question” among indigenous nationalist campaigns in the Netherlands East Indies and British Malaya.