For almost five decades, since the advent of the first computers for commercial use, the dream of the Paperless Office, a.k.a. total Information flow automation, has eluded the industry. Now, with the emergence of Internet- and Web-based technologies, daily we see examples of organizations like eBay and Amazon that perform their business in a fully automated manner without the use of paper or pen. However, bigger and older organizations that have more complex functions, like government organizations, have not been very successful in harnessing the latest technological innovations to completely automate their Information flow. We propose a Structured Information Flow (SIF) framework that provides the conceptual infrastructure to automate small and big, new and old organizations alike. The ease of the transformation is due to three key features of SIF that set it apart from any other Information flow automation scheme. First, SIF utilizes the attributes of the organization, such as the existing reporting structure, to model the automated Information flow. The rules governing the flow of Information are based on the hierarchy already in place, for example: A senior can view any Information owned by any of his/her direct subordinates. Second, SIF characterizes external organization entities as a special case of internal organization entities, allowing for seamless integration of the Information flow to and from them. Third, the SIF framework is independent of platform, method, organization, or technology. This gives it a generic nature that makes it applicable as a platform to implement multiple types of automated e-systems such as e-commerce, e-education, e-training, e-governance, etc. In this body of work, we formally define the SIF framework using state transformation language and a visual representation scheme specifically developed for this purpose. We also define the Information Interfaces, which are the mechanism for implementing rules- and constraint-based Information flow in SIF. / Master of Science