The Internet is only the latest example of a complex technological system that fundamentally alters the way that we act in and think about our world. During the last two centuries such complex technological systems have emerged, ranging from transportation systems such as the railroad and mass-produces automobiles running on paved roads and superhighways to networked information systems including the telegraph, the telephone, and radio and television. What are the common features of these complex technological systems? When do they emerge? How far reaching are their consequences in society, business, and in other complex technological systems? Can they be predicted? Can they be controlled? Can such complex technological systems be fully comprehended and modeled? These are but some of the questions this lecture and discussion course will tackle using cases from the past, the present, and the future.