The article is written with the twofold purpose of bringing up to date and clarifying specific controversial issues regarding the legal personality of the Holy See, of the Catholic Church, and the Order of Malta. Which specific moments determined a shift in the international legal role and position of the Holy See or of the Order of Malta? Do they have a consolidated legal status, within international law, and are they still relevant as international law subjects? How much and in which manner do they participate in international relations? How does their interaction with the host states look like and how much autonomy do they actually enjoy within the territory of the host states? Is the specific anatomy of such legal subjects compatible with the genetic structure of the current international legal system? If not, how can we explain their survival? The article aims to clarify or, at least, search for possible answers to such questions. However, these questions are addressed at the level of international law, entering as little as possible into theological or administrative distinctions.