Between 1812 and 1828 Friedrich von Gentz acted as political correspondent for three successive princes of Wallachia. This chapter reveals the complex relationship between the freelance diplomat and his generous clients, in which Gentz acted as an unofficial diplomatic agent, confidant and tutor, thereby engaging in a process of ‘distance social teaching’ in relation to his princely correspondents, who themselves were ‘intelligence brokers’ in Europe’s southeastern periphery. In turn, the hospodars kept Gentz regularly updated on the Danubian principalities' political situation, and appealed to Gentz’s expertise for guidance in the diplomatic conflict between Russia and the Ottoman Empire, in which ambassadorial conferences worked for the cooperative management and resolution of international crises. The relationship between Gentz and his Wallachian correspondents provides a telling example of a practice that disseminated to southeastern Europe a new political and security culture.