Although rooted in the canonical tradition of the Ecumenical Councils, in Christian Orthodoxy autocephaly as a juridical and ecclesiological conceptis largely a modern construct, shaped in the nineteenth century by the rise of national states. Between 1967 and 2022, however, a series of contested autocephalies emerged that cannot be adequately explained within this classical paradigm. Developing in post-imperial, Cold War, and post-Cold War contexts of intensified geopolitical competition, these cases challenged prevailing models of Orthodox unity, raised unresolved questions concerning the authority to grant autocephaly, and exposed the enduring entanglement of ecclesiastical structures with state power. Focusing on the cases of Orthodox Church in America (1970), Orthodox Church of Ukraine (2018-2019), and Macedonian Orthodox Church (1967-2022), this paper analyses the interplay of ecclesiology, church policy, and geopolitics.