Access to telecommunications and information services is widely recognized to be a precondition of economic growth and equally necessary to advance social policy goals, in developing and advanced countries alike. But what is the appropriate regulatory and policy strategy, which can serve both to advance economic interests possibly through ensuring firm profitability to attract investment, possibly implying monopoly or monopsony profits, and the social benefits of widespread, low-cost access to a plethora of information services? The growth of unlicensed or class-licensed services such as Wi-Fi, as well as the growth of Internet telephony, runs counter to the objective of raising government revenue in emerging market nations through either selling equity in incumbent firms, charging high fees for fiber optic landing rights, or selling spectrum. This paper discusses internet operations and business in Jamaica and the Caribbean against the background of administrative, technological and economic as well as policy considerations; the current and anticipated situation with respect to levels of access and use of the internet in Caribbean countries; and, programmatic and policy recommendations that will enable internet access and use by organizations, businesses, and individual citizens.