General studies speak to the benefits of e-Commerce globally for developing countries. However for developed countries of the Caribbean Community and Latin America, the barriers far outweigh the benefits for Micro, Small to Medium Enterprises (MSMEs). The barriers can be categorised in three main areas namely financial, technological and socio-political with possible educational issues associated with the research. Other external factors such as trust, security, logistics, management, and global competition were also identified. To determine if these barriers were issues affecting the Jamaican context, the author visited and interviewed six MSMEs, three major financial institutions, three tertiary institution to determine the challenges faced by them for the full adoption of e-Commerce. The method of analysis was qualitative and the data collection process comprised of semi-structured interviews.