The Cold War context outlined in this chapter is complicated by a brief account of civil rights and anti-war movements over the same period, with their bearing on computing circles in view. This chapter then turns to the development of hypertext systems from a why-do-it perspective, with conditional attention to various how-to-do-it solutions. First, the concept of hypertext is outlined in relation to information and knowledge management, and the principle of precedent individuation is explained. Then phases in the development of hypertext systems are considered. The earlier concepts and attempts are outlined; then the features of the dominant system from the 1990s, the World Wide Web (WWW), are described. The chapter thereafter takes up security controls as a feature in Internet Technology. These were not quite conceived and designed in the way protocols and hypertext systems were. They came to be instilled through gradual and pragmatic interventions. Changing philosophies of security are taken on board, and the early development of security controls that came to be integrated with Internet Technology recalled. The principle of targeted collective regulation is presented in the process.