This article begins with a historical review of the rationale of Taiwan’s attempts to engage Southeast Asia since the 1990s. The rapid economic growth of South and/or Southeast Asia, Taiwan’s desire for greater regional participation, and Taiwan’s relations with mainland China are the three most important factors leading to such attempts. Then, based largely on official documents, this article introduces the objectives and framework of the New Southbound Policy (NSP) of May 2016 whose ultimate goal is to build up a sense of community between Taiwan and South and Southeast Asia in particular. Recognizing the necessity of the NSP, if implemented under a bigger context of Taiwan’s strategic development, this article holds a pessimistic view about this policy because of the funding issue, the lack of strong interagency coordination, and the recent waning cross-Taiwan Strait ties that have triggered mainland China’s preventive counter-measures and greater concern of the parties targeted by the NSP.