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By drawing on documents from European archives, this article addresses everyday aspects of diplomacy in sixteenth-century Constantinople. It focuses on how various go-betweens mediated political, cultural, religious, and linguistic boundaries in the encounters between Ottoman grandees and European diplomats. By doing so, it shifts the focus from the office of the ambassador to a large number of informal diplomatic actors (Jewish brokers, dragomans, renegades, go-betweens, etc.) with different areas of competence, functioning in diverse networks of contact and exchange. Moreover, it accentuates the importance of Constantinople as a space of encounter between diverse ethnic and religious communities as well as a Mediterranean-wide center of diplomacy and espionage. The essay calls for a reevaluation of Eurocentric views that associate the birth and development of modern diplomacy only with Christian Europe and revises the historiography on Ottoman diplomacy by concentrating on vernacular diplomacy rather than the rigid theoretical framework drawn by the Islamic Law.