The remarkable economic success of the Cayman Islands is primarily driven by its large expatriate population. Expatriates make up over one-third of the total population of the Islands and half of the labor force. This has led some Caymanians to demand more opportunities for local individuals. However in April 2014, one of the two local newspapers commented that the problem was that the quality of local graduates was below the standard required by the private sector. This suggests that there is a serious dislocation between the Caymanian education system and the labor market. This also suggests that there may be increasing tension in the future between expatriates and locals with regard to job opportunities, hiring policies, the role of the educational system and the quality of its outputs. This case study examined how local higher education is perceived by the key stakeholders within the Cayman Islands, with a specific focus on its efficacy in preparing students for the labor force. The study also examined what the higher education institutions are doing to help students develop the skills that are required by employers and desired by the labor force; and where there might be opportunities to improve the quality and efficiency of higher education systems and ensure a closer match to the needs of employers in the future. The study examined perceptions primarily through the viewpoint of employers, using human capital development theory, with additional perspectives from social theory and systems thinking. The primary sources of data were semi-structured interviews with employers in major industries in the islands, university faculty in higher education institutions, and recent graduates from these institutions. / Educational Leadership