Recent decades have seen sustained theoretical interest in how a cosmopolitan legal order could be created in a manner consistent with the liberal human rights ideals and democratic principles it is supposed to realize. I argue that this “democratic cosmopolitan” account of the genesis of cosmopolitan law faces at least two dilemmas. Both concern the role that “learning processes” play in its explanation of how a genuine cosmopolitan legal order can emerge from a global transformation in the meaning of sovereignty and citizenship. The first dilemma is the theory’s reliance on underdeveloped sociological claims about the nature of democratic political processes, while the second concerns its one-sided analysis of how global trade and interdependence might produce a kind of “cosmopolitan learning.” In light of these issues, I propose that cosmopolitan theorists think beyond democracy as an ideal that should strictly guide the creation of a cosmopolitan legal order.