Cyprian was a clergyman with Bulgarian antecedents. He is supposed to have been born in aristocratic family of :bg:Цамблак|Tsamblak from Great Tarnovo. After his upbringing, education, and worldview, he was a hesychast. As a young man Cyprian had studied at Kilifarevo, just south of Tarnovo, where he possible accepted his monastic vows and where a disciple of Gregory of Sinai named Theodosius of Tarnovo had founded a Hesychast monastery. In :bg:Килифаревски манастир|Kilifarevo monastery Cyprian met with future Bulgarian patriarch Euthymius who also was studying hesychasm. In 1363 along with Euthymius, Theodosius, and two of Theodosius's followers, Cyprian arrived to Constantinople where he was introduced to Patriarch Callistus I and few months studied at the Monastery of Stoudios. Following the death of Theodosius, Cyprian continued his studies at Mount Athos, becoming a Hesychast. On the other hand according to Dimitri Obolensky, Cyprian became a monk only in early 1370s in Constantinople. At Mount Athos Cyprian befriended with Philotheus Kokkinos. In the beginning of 1370s after return of Philotheus to patriarchal throne, Cyprian became "his closest monk". In 1373 following three unsuccessful raids of the Grand Duke of LithuaniaAlgirdas against Muscovy as part of the Lithuanian–Muscovite War and the schism of Metropolitan of Kiev on Muscovite and Litvin parts. Cyprian was sent by the Patriarch as "trustee" to the Lithuanian and Muscovite Russias with the goal to reconcile Litvin and Tverite princes with de-facto Muscovite Metropolitan Alexius and prevent total division of the Church politically between Wilno and Moscow. Perhaps, in winter of the same year Cyprian visited Kievfor the first time along with other cities of the Grand Duchy of Lithuania. On 9 March 1374 he visited Tver on consecration of the bishop of Tver Euthymius and later along with Metropolitan Alexius left for Pereslavl-Zalessky. To Constantinople Cyprian returned from the Grand Duchy of Lithuania carrying with him a letter from Orthodox Christian Lithuanian-Ruthenian with a request to the patriarch to consecrate him as the Metropolitan of Lithuania. Following renewed hostilities between Moscow and Lithuania in August of 1375 after capturing of Tver by the Muscovite troops, facing with a potential threat of Catholization of Eastern Orthodox population of the Grand Duchy of Lithuania and prevent total division of the Ruthenian metropolitan diocese, Philotheus I agreed to satisfy the previous petitions of Grand Duke of Lithuania Algirdas to create a separate metropolitan diocese in the Grand Duchy of Lithuania as well as the last petitions of his Eastern Orthodox princes to have Cyprian as their metropolitan. On 2 December 1375 at the Constantinople Council Philotheus I consecrated Cyprian as "Metropolitan of Kiev, Russia and Lithuania", but under a condition that “upon the death of Alexis, Cyprian should become the Metropolitan of Kiev and All Rus”. On 6 June 1376 Cyprian arrived to Kiev as his residence and immediately attempted to get recognition of his rights onto whole metropolitan diocese from the Grand Duke of MoscowDmitri Donskoi, Novgorod, and Pskov, but futile. In 1378, Metropolitan Alexius died. As a result of the ensuing skirmishes and intrigues, Cyprian became Metropolitan of Moscow in 1381. At Moscow, Cyprian endured many sorrows from the Great Prince, so at first he lived either in Lithuania or at Constantinople. In 1379, however, he fled from Moscow due to the approaching armies of Tokhtamysh. Subsequently, he was removed from Russia and replaced with Metropolitan Pimen. The latter was succeeded by Metropolitan Dionysius. In 1390, Cyprian was returned to Moscow by Vasili II, who he had always supported, and appointed Metropolitan of Moscow and All Russia. He held this title from 1390 till 1406. During his term his main objectives as Metropolitan of Moscow and All Russia were to preserve a unified metropolitanate with Moscow and secure pith with Lithuania.
Achievements
Cyprian is remembered as a wise and experienced church administrator who fought for the unity of the Russian church. In fact, he is mainly responsible for uniting the Church in Russia and the Grand Duchy of Lithuania. He faced serious opposition during his metropolitanate; Dmitry Donskoy and his advisors were excommunicated for opposing Cyprian's efforts to take up his place in Moscow, and Novgorod the Great – especially Archbishops Aleksei and Ioann II – also opposed his efforts to adjudicate ecclesiastical cases there, which would have allowed him to gain the court fees from Novgorod during the time he sat in judgement there. Cyprian was an erudite person and oversaw the copying and creation of a number of important works, including the Troitskaia Chronicle and, probably, the Metropolitan Justice. He also rewrote the Life of Metropolitan Peter, originally written around 1327. He also corrected biblical books and translated a number of ecclesiastic works from Greek into Old Church Slavic. The Book of Degrees, which grouped Russian monarchs in the order of their generations, was started by Cyprian in 1390.