Yet another attempt is being made in the Caribbean to modernize the agriculture sector through the adoption of technologies that have the potential of increasing the production and productivity of the vegetable sub-sector. The recent re-introduction of Greenhouse Technologies has once again generated heightened interest across the region. As in the past, several drawbacks have impeded full exploitation of the many advantages of this technology. This paper reviews the status of the sector in Trinidad and Tobago and Jamaica focusing on characterizing the various types of structures being used, crop management practices, the major constraints faced by producers, and the level of training. 16 farmers in Trinidad and Tobago and 22 Greenhouse Vegetable Producers in Jamaica were surveyed using detailed questionnaires. The data were presented as descriptive statistics. The results showed that the greenhouse vegetable producers rated the lack of information and adequate finance, insufficient technical support followed by heat and humidity as the major constraints to greenhouse vegetable production. These results are compared with information derived from key informants associated with previous attempts at establishing a greenhouse industry and suggestions are made to get the technology right in the shortest period this time around.