The article asks the basic question, how the Dutch East Indies Company (VOC) was unable to dislodge its long-time colonial enemy Portugal from the Timor area in the 17th century. It is shown how early Portuguese enterprises on this Southeast Asian island were able to achieve a degree of local recognition and even localization, especially with regard to the ethnically mixed 'Black Portuguese'. The serious Dutch efforts, on the other hand, came to late to overcome the Portuguese network. After the Dutch-Portuguese peace in 1663, the two powers resorted to warfare by proxy. A major reshuffle in 1749 seemed to forebode the fall of the Portuguese positions on Timor, but the Dutch were once again unable to efficiently bind indigenous polities to their cause. Eventually, this resulted in the rough 50-50 division of Timor found on the political map still today.