Abstract: Most contemporary attempts to draw inspiration from Kant's cosmopolitan project focus exclusively on the prescriptive recommendations he makes in his article, ‘On Perpetual Peace’. In this essay, I argue that there is more to his cosmopolitan point of view than his normative agenda. Kant has a unique and interesting way of problematizing the way individuals and peoples relate to one another on the stage of world history, based on a notion that human beings who share the earth in common ‘originally’ constitute a ‘commercium’ of thoroughgoing interaction. By unpacking this concept of ‘commercium’, we can uncover in Kant a more critical perspective on world history that sets up the cosmopolitan as a specific kind of historical-political challenge. I will show that we can distinguish this level of problematization from the prescriptive level at which Kant formulates his familiar recommendations in ‘Perpetual Peace’. I will further show how his particular way of framing the cosmopolitan problematic can be expanded and expatiated upon to develop a more critical, reflexive, and open-ended conception of cosmopolitan thinking.