This chapter outlines the history of digital government in criminal justice, starting with the Johnson Administration’s findings concerning automation in its report, “The Challenge of Crime in a Free Society,” the development of the national criminal justice network, and the creation of SEARCH Group, a consortium of states that led the effort to create computerized criminal histories of individual offenders. A brief discussion of the issues these efforts attempted to solve will be developed. The narrative will describe how these initial activities created the basic parameters for all subsequent developments in the area of criminal justice automation. Several major problems and controversies of criminal justice automation will be described and placed in their historical context. Examples of criminal justice initiatives will be provided and their success in solving some of the problems discussed will be described. The chapter concludes that it is time to rethink the older criminal justice digital government paradigm from the 1960s and create a new model more in tune with today’s developments in a highly mobile, digital and integrated society. Questions about the impact of this new model on traditional constitutional safeguards, including individual liberty and privacy will be raised.