As the global economy continues to expand and advance, the markets of small island developing states like those of the Caribbean Community (CARICOM) persistently experience stagnated levels of growth due to inadequate resources and policy development. While the CARICOM Single Market and Economy was established in 1989 with the goal of enhancing economic resilience, much of the taxation landscape of CARICOM has remained largely underdeveloped. This is exemplified by the fact that Jamaica is the only CARICOM member state that has enacted comprehensive legislation for transfer pricing. This article will discuss the contents of Jamaica’s regulations for transfer pricing legislation and compare them to the provisions implemented in other States. After that, there is further discourse as to why there is a need for other CARICOM Member States to implement provisions for transfer pricing.