Financial markets, particularly stock markets, have long been accepted as a key source of wealth generation and preservation. The potential for astronomical financial gain has tempted more sophisticated investors to make numerous irrational, speculative and risky investment decisions. The most notable of which is engaging in insider trading. While insider trading is more prevalent in economically advanced markets such as in the United States, Canada, England and Asia, the need for stringent regulation is not lost on lawmakers in the Commonwealth Caribbean. This article therefore seeks to examine the adequacy of the provisions in the Companies Acts of various Caribbean territories in curbing insider trading by analysing said provisions and their possible interpretations by reference to decided cases.