The purpose of this chapter is to present an interpretation of Langdon Winner’s perspective on the problem of autonomous technology, which relates to the debate on the notion of alienation. I also intend to show here that by decoding the phenomenon of autonomous and alienated technology, we can more clearly observe the current processes of knowledge and power centralization that actually existing Artificial Intelligence is promoting. The theoretical tools brought by Winner in his two books, Autonomous Technology (1978) and The Whale and the Reactor (1986), allow us to observe the automated systems and their current technopolitical implications in depth. Despite having a different perspective, the application of the concept of alienation that Winner makes can align with Gilbert Simondon’s critique of the separation between culture and technology. For Simondon, the distance between humans and technical objects leads to a lack of understanding of technicality, a phenomenon that, through the prism of AI, is exacerbated by corporate structures that hold a monopoly over technological development. This distance prevents individuals and society from understanding the cultural, social, and political implications of the technologies that shape their lives. When analyzing this issue, it becomes clear that actually existing AI not only reproduces existing inequalities but also reconfigures society to maintain and expand these power structures.