As the Cold War came to a close, a new informational economy and society emerged in the last decade of the 20th century. As such, new approaches to the flow of information were needed. This historical study follows the contentions between academics and counterculturalists and their adversaries in the intelligence community such as the NSA. In doing so, this narrative illustrates how these contentions were deeply ingrained in a Cold War dialogue between open and closed information theories. From the Cold War to the Crypto War follows individuals from the center of the early 1990s Crypto Wars. By exploring their arguments, their associations, and their assumptions from the Computer, Freedom, and Privacy conference as well as from the Whole Earth 'Lectronic Link (an early internet forum). As Americans came to terms with the World Trade Center bombing and the bloody siege at Waco, TX in 1993, counterculturalists and the NSA battled over the future of informational access. Would it be one where the government had full control over encryption methods (as had been over hundreds of years) or would new paradigms be necessary for the new millennium?