Guided by a contemporary interpretation of Hegelian dialectics, this chapter offers a detailed social-scientific analysis of digital society. The analysis considers all ten agents generating digital society, their goals and ideals as well as the cultural models and meta-level conceptual and normative conditions defining and structuring the world in which they find themselves and allowing them to think, imagine and act as they do. The dialectics of digital society involves the relation between the two major collective coalitions—the technology and critical agents—as well as between their respective ideas of digital society—‘technological singularity’ and ‘digital humanism’. The outcome of this dialectical mediation of incommensurable dimensions in need of harmonisation, if not unification, is the central question: either the danger of technocratic domination by an oligarchical autocracy or a balanced integration of technology in the human, historical, sociocultural world. Against the technocrats and their insidious ideology, therefore, are not simply the humanists, who are in danger of being misled by the ideological mechanism of ‘post-humanism’, but rather those humanists who nevertheless recognise the anthropological necessity of technology. For them, we urgently need the creation of a human society in which technology is embedded and is both socioculturally and politically governed and regulated. Instead of profiling digitisation against the imaginary projection of humanity, therefore, the analysis employs a theoretically more profound and analytically much sharper notion of humanity—in the sense of the real and essential features of being human—as an integral element of society at all levels, from the subjective to the objective. Dialectically, the formation of both the major agents and their projected ideas of digital society is analysed in terms of Hegel’s logic of singularity-particularity-universality, which incidentally coincides with the logic of cognitive sociological reasoning. Similarly, the historical construction and realisation of digital society is understood in terms of this same dialectical pattern, which accords precisely with Hegel’s requirement for ‘the realisation of the Idea’ in a ‘concrete universal’.