This essay assesses the “Integrating Climate Change Risks into Resilient Island Planning in the Maldives” Program, or ICCR, a four-year $9.3 million adaptation project supported by the Least Developed Countries Fund, Maldivian Government and the United Nations Development Program. The essay elaborates on the types of challenges that arise as a low-income country tries to utilize international development assistance to adapt to climate change. Based primarily on a series of semi-structured research interviews with Maldivian experts, discussed benefits to the ICCR include improving physical resilience by deploying “soft” infrastructure, institutional resilience by training policymakers, and community resilience by strengthening assets. Challenges include ensuring that adaptation efforts are sufficient to reduce vulnerability, lack of coordination, and the values and attitudes of business and community leaders.