Least developed countries often lack the requisite capacity to implement climate change adaptation projects. The Least Developed Countries Fund (LDCF) is a scheme where industrialized countries have (as of early 2016) disbursed $934.5 million in voluntary contributions, raised more than four times that amount in co-financing, and supported 213 adaptation projects across 51 least developed countries. But what sorts of challenges have arisen during implementation? Based on extensive field research in five least developed countries—Bangladesh, Bhutan, Cambodia, the Maldives, and Vanuatu—and original data collected from almost 150 research interviews, this article qualitatively explores both the benefits and challenges of LDCF projects in the Asia-Pacific. It finds that while LDCF projects do contribute to enhancing multiple types of infrastructural, institutional, and community-based adaptive capacity, they also suffer from uncertainty, a convoluted management structure, and an inability to fully respond to climate risks. Based on these findings, the study concludes that adaptation must be pursued as a multidimensional process; and that LDCF activities have tended to promote marginal rather than more radical or systematic transformations.