Over recent decades, a host of smaller jurisdictions have become extraordinarily dominant in specialized fields of cross-border corporate and financial services. Chief among them are Hong Kong and Singapore, both regarded as among the world’s most significant financial centers. This chapter analyzes their track records in achieving corporate sustainability and concludes that each is at once a leader and a laggard, depending on one’s perspective. The analysis highlights complex questions regarding how we ought to conceptualize and evaluate corporate sustainability in an era increasingly defined by the free movement of capital – because Hong Kong and Singapore represent microcosms of our increasingly globalized financial world. The challenges faced in assessing the sustainability of their corporate, financial, and economic models reflect underlying challenges in assessing the sustainability of unfettered global capital mobility.