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Cyril fulfilled his monastic obediences under the guidance of the Elder Michael, later Bishop of Smolensk. Cyril carried out his obedience in the bakery, carrying water, chopping firewood, and distributing bread. When St. Sergius of Radonezh visited Simonov [[monastery]] to see his nephew Theodore he would first seek out Cyril in the bakery to converse with him about spiritual matters before seeing anyone else. After Cyril was transferred to the kitchen, he found himself gazing into the blazing fire which caused him to react and tell himself, "Beware, Cyril, lest you fall into fire eternal". Cyril worked in the kitchen for nine years, and God granted him such tender emotion that he was unable to eat the bread he baked without tears, blessing the Lord.
In an attempt to flee the glory of man, Cyril began to act as a [[fool-for-Christ[[]]. As punishment for transgressing against propriety, the Superior of the monastery placed him on bread and water for forty days. Cyril underwent this punishment with happiness. However, he could not conceal his spirituality. The experienced elders of the [[monastery]] understood his true soul. Against his objection they forced him to accept [[ordination]] to the [[priest]]hood. When he was not serving in church, Cyril continued to occupy himself with heavy work.
When Theodore became Archbishop of Rostov in 1388, the brethren of Simonov Monastery chose Cyril as abbot of the monastery. As more and more people came to seek his guidance his desire to maintain a humble, ascetically, and spiritually centered life was disturbed leading him to yearn for solitude. In time he decided he would no longer remain an abbot and secluded himself in his [[cell]]. Even remaining in his cell did not end the arrival of frequent visitors. His soul continued to yearn for solitude.