The Caribbean ranks second only to Africa as the region with the highest levels of skilled emigration, which is defined as the outward migration of people holding a bachelor's degree or extensive/equivalent experience in a given field. Based on the cost of educating their citizens, there are strong arguments supporting the view that skilled emigration comes at significant economic and social cost, especially to small island developing states of the Caribbean. This paper, therefore, explores how the emigration of skilled labor from the CARICOM Caribbean impacts education policy nationally and regionally. Drawing on data collected through questionnaires and document analysis, the research unearths four dominant educational policy responses to skilled emigration: "bonding and compulsory service at the national level; regional cooperation on the movement of skilled labor through CARICOM's Single Market and Economy (CSME); market based approaches to educating skilled professionals; and education funding policy." The paper also analyses the efficacy of each of these four policy responses and their implications. Ultimately, these policy responses coalesce to highlight the national and regional complexities of educational policy-making under globalization, and the limitations of Caribbean national and regional educational policies aimed at controlling skilled emigration in the context of globalization's market forces.