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In a world where empires have risen and fallen, borders shifted, and sovereignty evolved, one polity has remained remarkably constant: the Holy See. What is it — a sovereign subject of international law or the supreme authority of the Catholic Church? How does it relate to the Vatican City State, negotiate treaties, receive ambassadors, and hold permanent observer status at the United Nations while preserving moral authority? This work presents a novel analysis of the debate on the Holy See’s international legal status, distinguishing it from the Church and Vatican City, examining UN Resolution 58/314, and drawing on over 160 sources and rare archival materials to reveal contemporary multilateral practice.