The Digital Society Brian M. O'Connell Central Connecticut State University, USA The close relationship between the social and technological has been recognized from the beginning of scholarly history. With the advent of computer-mediated technologies, however, the depth and reciprocity of this relationship has been revisited. Scholars of both the humanities and computing have suggested that the terms of this interaction are more bilateral and require a new form of human-machine dialogue than with former generations of tools. This paper will employ the author's perspective as a computer scientist and professor of philosophy to explore such humanistic conversations that our digital society presents, including those concerning the role of human agency in the creation of artificial systems, their advancement and justification. Throughout, the presentation will emphasize the role of human creativity and choice in the development of computational devices and lifestyles. It will identify the means by which our freedoms to clearly recognize dangers, opportunities and responsibilities are often hampered by the dynamics of computing and engineering, including how they are taught to future engineers and are related to the public, to our advisors, colleagues and our fellow decision makers in the humanities. The result is frequently the production of untrustworthy dangerous decisions that exaggerate technological capabilities, inflate expectations and excite hubris. In many ways, this presentation will seek to emulate the thought processes recorded by Saint Thomas More in "A Dialogue of Comfort Against Tribulation", in which issues touching the heart of humanity and of truth were treated through close conversation, relating at once to present questions and to those values that transcended the moment. Likewise, to properly address the challenges of the digital society, the multi-dimensional elements of engineering, computing, the humanities, values, public and professional responsibility must presently be brought into meaningful and vital conversation.