With an ever-increasing number of organizations and individuals relying on the Internet to exchange confidential and sensitive information, adequate message security continues to be a technological management concern. Serviceable standard electronic commerce (E-commerce) models include Business-to-Business (B2B), Business-to-Consumer (B2C), Business-to-Employee (B2E), and Business-to-Government (B2G) architectures. In order to programmatically manage E-commerce related IT security risks, management must designate an information assets protection perimeter. Axiomatically, the primary purpose of establishing a security perimeter is to provide a defined ambit for entity-centric policies and safeguards. However, with the advent of E-commerce, erecting layered protective barriers that preserve IT configurations can introduce a tactical security quagmire.