This paper examines the potential benefits and challenges of regionally managed e-government development initiatives. It examines the current state of e-government in four Caribbean countries – Barbados, Jamaica, Saint Vincent and the Grenadines, and Trinidad and Tobago – in order to establish a broader understanding of the challenges that face e-government initiatives in the region. It also reviews a number of e-government initiatives that have been undertaken through projects managed at a regional level. Based on this analysis, it presents a set of best practices that are recommended to agencies engaged in the task of coordinating the implementation of regionally-based e-government initiatives.