This paper is located in what is referred to as policy critique within the theoretical framework of International Political Economy (IPE) which, by origin, seeks to problematize issues of policy. In 1994, celebrated Brazilian economist, Reinaldo Gonsalves produced an important thesis and model on how to measure a country’s global insertion. At that time, Gonsalves could not have foreseen the influence of the Internet on global trade or on domestic trade policies. As such, the issue of global digital connectivity now presents itself as another pillar to measure global insertion. By examining regional Caribbean policy in this regard, this is an opportunity to advance Gonsalves’ model stimulate further on the opportunities associated with global digital connectivity.