China's launch of the Asian Infrastructure Investment Bank (AIIB) to support its "One Belt, One Road" (OBOR) economic strategy has both been received with great enthusiasm and has sparked debate in East Asia and beyond. This paper begins with a circumstantial analysis of the relationship between the AIIB and OBOR. Then, it explores the implications of Taiwan's prospective membership and the external and internal challenges to its bid to join the AIIB. The paper finds a number of challenges and benefits of a prospective Taiwan membership in the institution. It concludes that Taiwan's participation in the China-led organization would not only encounter domestic divergence but also invite a power struggle between China and the U.S., thereby likely pulling Taipei into a great power confrontation. Nevertheless, membership would be beneficial for Taiwan's regional standing. So, the existing roadblocks, including the name issue, will have to be dealt with.