Critical theorists of recent decades have not only delineated the political nature of technology, but also its malleability, and the possibility for a more democratic technological society. More recently, developments in Artificial Intelligence (AI) technologies not only shape how we communicate, but also how we think, what we expect, and how we relate to others. Therefore, critical theory of technology must examine the possibilities for society to shape technology while dialectically addressing the ways in which technology is shaping society. My thesis here includes three main arguments that build one upon the other: First, a contemporary critical theory of AI technologies needs a comprehensive political-theoretical framework through which to critique technology and its role in a democratic society. Second, Jurgen Habermas’s theory of law and democracy offers a necessary framework through which to ground a critical theory of AI. Third, equipped with the Habermasian discourse-based democratic framework, I offer some considerations for public reason in the age of AI. These include the role of media power, designing for trust, and the importance of nurturing the political imagination.