Dialogue on diasporas and their role in the development of the home country has grown in the last twenty years and Caribbean states have begun to identify ways they can engage their nationals residing abroad in this process. Those in the region looking to harness the power of the diaspora have turned their attention to the example of Ireland, a country with a large diaspora that has contributed significantly to its national advancement. By highlighting the lessons of the Irish experience, this paper argues that while the Caribbean's diaspora has the desire to contribute and does help through remittances, there remain a number of challenges to this participation including perceptions of security and stability, establishing the conditions necessary for attracting investment and a lack of confidence in government institutions in the region.