This chapter examines the political challenges, potential, and environment of the Macedonian Orthodox Church since 1870, but with an especial focus on the years since 1945. It interprets the Church’s place in shaping Macedonian identity, expressed by the idea of Church as a national “pillar,” and support of its quest for acknowledged “autocephaly,” proclaimed unilaterally in 1967. The chapter develops several themes. First it examines the Macedonian Church’s relations with the Serbian Orthodox Church, the abortive “Niš Agreement,” and Serbian formation of a rival Orthodox entity under Bishop Jovan Vraniškovski. Second, the chapter comments on a “syndrome” of attitudes and values associated with the Macedonian Church: intolerance, homophobia, nationalism, and conservatism. A conclusion attempts to compare the recent history of Greek and Macedonian Orthodoxy regarding the matter of LGBTI rights and North Macedonia’s entry into the European Union.