Singapore is an active and significant actor in the Asia Pacific region. Most of the analysis of Singapore's foreign policy falls on the theoretical spectrum between (neo)realism and (neo)liberalism—theories focusing on its economic and security interests and power politics. In this article I draw upon the theoretical framework of political adaptation to provide a fresh analytical perspective on Singapore's regional activity. I show how further refining the political adaptation framework beyond its existing dimensions to include active, passive, and reactive adaptation sheds light on how Singapore adapts its foreign policy to maximize its role in regional and inter-regional institutions. The article examines three empirical case studies at different levels of Singapore's external engagement: (1) ASEAN at the closest regional level, (2) APEC at the wider regional level, and (3) ASEM at the inter-regional level.