Several key themes of this volume make Kant’s appearance inevitable. First, it was Kant, a provincial spectator of the debates and action in London, Paris, and Berlin, who summed it up and wrote what became the manifesto for the historical era of the Enlightenment. Since then, it has become common practice to regularly turn to the Kantian understanding of the ends and workings of enlightenment to compare it with the current condition—it is enough to recall the seminal essays of 1984 by Foucault, Marquardt, and others. Today, digital transformation requires yet another revision. Second, AI, the protagonist of today’s digital world, according to the more ambitious views lays claim to the comprehensive role that Kant once assigned to reason. What brings digital “intelligence” and Kantian reason together, and what distinguishes it? In the most general terms, it can be argued that Kantian reason differs from AI in its orientation toward abstract regulative ideas. This brings us to the third topic: the philosophy of history. Kant’s view of history as a difficult and risky movement of humanity toward civil society and ethical community, toward the “kingdom of ends” and “perpetual peace,” as a self-construction of human nature, does not lose its relevance in the digital age. These and other regulative ideas are essential for our orientation “in thinking” and navigation through the turbulence of history. Will AI be a support or perhaps even a guide in this navigation, or will it become an obstacle to it? How is “alignment” possible in this condition, that is, how can we bring machine operations in line with the ends of humanity? This chapter will investigate the resources Kant’s philosophy provides for answering these and related questions.