European eighteenth-century thinkers were fascinated by what they took to be the astonishing modern creation of the largest possible human community, a kind of global society. Many of them were also critical of the extensive violence, domination, exploitation, and injustice that cross-continental connections routinely enabled. They were, in short, deeply ambivalent about global connections, and their theorizations about global affairs were often informed by such ambivalence. I examine the manner in which an illuminating and influential subset of such thinkers—including Jean-Jacques Rousseau, Denis Diderot, Adam Smith, Ottobah Cugoano, and Immanuel Kant—engaged in a diagnosis of the pathologies of the nascent cosmopolitan community of their time and the potential for reform in the future. Each of these thinkers, in his distinctive way, favoured a form of transcontinental relations that would balance local self-determination and autonomy with global aspirations of robust contact, exchange, and communication, and each one believed that this possibility in their time was routinely and tragically flouted primarily by European governments and chartered companies.