Chapter 8 broaches our understanding of communication systems and their intimacy with strategic practice. Beginning with the general (strategist) Napoleon’s forms of communication–technological warfare and the subsequent reliance on innovation in communication devices, especially those of coding and decoding communications in military conflicts, we consider the workings and implications of electronic, digital computing systems for strategy. Via Alan Turing’s Imitation Game, we introduce the debate on the nature of intelligence, consciousness and conscience (self-awareness), setting the scene for an elaboration on the development from cybernetics to contemporary machine-learning algorithms in the subsequent chapter.