While in theory, the benefits of e-government are numerous, global experience to date indicates that in reality they remain much more elusive. Given e-government’s high impact on good governance and on the promotion of progress in developing countries, in order to better enable communities to benefit from e-government, it is important that the most adequate approach to the transition of a country or of a number of countries to the information society be identified in order for key issues to be addressed expeditiously, correctly, and effectively for an e-government that is at once as comprehensive as possible but also sustainable and meaningful. This is particularly true for a region such as the Caribbean, which already came late to the assimilation of the industrial age paradigm and which still has to determine its role in the global information society as well as its digital age. While it is common belief that for the majority of countries e-government development is more efficiently and more effectively targeted through national programs tailored to specific needs and characteristics, this is not considered to be the case for countries in the Caribbean region. Over the last five years, an unprecedented international cooperation for administrative reform and e-government capacity building has taken place in the Caribbean region (i.e., Anguilla, Antigua, Barbuda, the Bahamas, Bermuda, Barbados, Belize, British Virgin Islands, Cayman Islands, Dominica, Grenada, Guyana, Haiti, Jamaica, Montserrat, Saint Lucia, St. Kitts, Nevis, St. Vincent, the Grenadines, Suriname, Trinidad, Tobago, Turks, and Caicos Islands). Such an effort has involved many regional and international organizations (e.g., the United Nations, the European Union, the World Bank, the Interamerican Development Bank, the OAS, etc.); a lot of work has been accomplished to assist countries in enhancing the application of ICT to government functions in order to advance public sector reform, improve government services, enhance knowledge management and decision making, and promote economic and social development. This international cooperation was carried out through a rich mix of ministerial consultations, working group meetings, meetings of experts, informal consultations, research and development, and country surveys. The rationale behind this kind of intervention was the conviction shared within the international community that a regional approach would permit dealing with the various issues related to e-government development more efficiently and more effectively.