The twenty-first century has witnessed unprecedented growth of digitalization and digital transformation of individual lives, families, states, and societies across the globe. The rise of technology is branded as technological and digital revolution without revolutionary characters. The transnational communication and culture of digital capitalism is spreading worldwide without the growth of transnational solidarity for revolutionary changes to uphold ideas of individual freedom, science, reason, and secularism. The digital transformation is giving rise to authoritarian forces in society led by reactionary states and governments. The rise of science and technology has not halted the barbarism of wars, conflicts, and other forms of violence in everyday life. The pervasive digitalization and automation in an increasingly rationalized world, driven by AI, have accelerated various forms of barbarism, as predicted by Max Horkheimer. This chapter revisits Horkheimer’s ideas and examines their relevance in the age of the digital transformation. This chapter locates digital transformation within the context of individual, family, society, and state. It outlines the failures of reason and limits of digital desires of enlightenment through the philosophies of Horkheimer.