Governments of English-speaking Caribbean countries have begun to place greater emphasis on e-government to reduce bureaucratic inefficiencies and are encouraging, through legislation and other inducements, the expansion of e-commerce operations in order to enhance global competitiveness. This has expectedly led to a greater movement of data and with it information security risks. Information security managers continue to grapple with the difficulty of reengineering policies and standards to meet this new reality. Hence many Caribbean organizations have become more vulnerable to security risks that are initiated internally. This is of grave concern to the Financial Institutions of the Caribbean as they prepare to offer extended services in order to exploit the opportunities expected from the introduction of the Caribbean Single Market and Economy. In addition, these institutions attempt to increase their share of both remittances from the Caribbean Diaspora and foreign direct investments which also serve to exacerbate these issues. These organizations are less capable of stemming the tide of fraud through identity theft and by other means, which are on the rise globally. In most cases these acts are facilitated (inadvertently or deliberately) by the actions of insiders. This paper proposes an approach to the development of context-based information security policies for Caribbean Financial Institutions aimed at mitigating insider risks.