This article discusses the shifting perception of Metropolitan Kiprian’s image in Muscovy. My analysis focuses on three aspects: Kiprian as a “pro-Lithuanian” actor and the complicated succession of Metropolitan Aleksii in Moscow, Kiprian as a legitimate metropolitan in the accounts and iconographical representations of the 1395 miracle of the icon of the Theotokos of Vladimir, defending Moscow from the Tatar attack, and Kiprian as a rightful member of a legitimate, Moscow-based ecclesiastical succession, after the 1472 discovery of the relics of all metropolitans buried in the Dormition Cathedral. I argue that the initially contested metropolitan became a saintly protector beginning with the second half of the 15th century, due to the emergent Muscovite ideology of power, aiming to illustrate a political and ecclesiastical unity of Rus’ polities under Muscovite rule. In Kiprian’s case, this culminated with his portrait as an ideal (and legitimate) spiritual father in the 16th -century Nikon chronicle, and with some minor attempts to include him among the local saintly protectors of the city.