The boundary-less world has increased the number of "wicked" problems facing managers today. The Internet has created a potentially open electronic world at the same time that organizations are tying themselves to proprietary enterprise system infrastructures. The basic concepts of doing business electronically have not been worked out. The security infrastructure underlying the foundations of electronic commerce is in its infancy, and the issues of confidentiality, authentication, data integrity, and non-repudiation remain barriers to truly removing boundaries between enterprises (Bhimani 1996). The five types of evidence generating information systems laid out by Mason and Mitroff (1973); Lockean, Leibnizian. Kantian, Hegelian, and Singer - Churchmanian, are discussed here in the context of internet agents. The convergence of these perspectives is then demonstrated in the architecture of the FRAANK (Financial Reporting Auditing Agent with Net Knowledge) intelligent agent (Kogan et. al, 1998).