Launched by President Tsai Ing-wen in 2016, the New Southbound Policy (NSP-T) aims to enhance cooperation and exchange between Taiwan and 18 countries in Southeast Asia, South Asia and Australasia. The policy is a concerted effort designed to expand Taiwan’s presence across these broad regions by leveraging Taiwan’s cultural, educational, technological and economic resources. There is no doubt that the NSP-T has yielded results in terms of economic cooperation and people-to-people exchanges between Taipei and Southeast Asia. However, with Beijing pushing forward its own agenda and, at the same time, asserting more pressure on Taiwan, there are questions about how Taiwan should respond. This article argues that China, through its enormous economic influence and constant consolidation of ‘One China Policy’ in Southeast Asia has limited the success and effectiveness of the NSP-T in the region. The impact of this ‘China Factor’ has, however, differed among Southeast Asian countries due to their distinct relationships with China. This article also argues that while China’s economic diplomacy has earned Beijing considerable influence in the region, that influence has not been translated into Southeast Asian support for its foreign policies, principles nor values – leaving Taiwan with rooms to maneuver its strategic space in the region. Therefore, several policy directions, clusters and implementations have been identified for Taiwan’s consideration in order to enhance existing Taiwan-ASEAN relations. These are: the visible and viable institutionalisation of the NSP-T; addressing existing and emerging issues in the NSP-T; and the consolidation of Taiwan-ASEAN long term connectivity.