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After the first wooden [[cathedral]] and monastic [[cell]]s were completed, the monastery grew rapidly as it proved to be in a significant location during the expansion of the Moscow state into the northern area. Considered by Prince Dmitri Donskoy, the prince of Moscow, an influencial point in the expansion to the north, the princes, and later tsars, were among the principal benefactors of the monastery.
Hegumen Dmitri reposed in 1392 and was buried near the southern wall of the wooden Cathedral of the Saviour. His [[relics]] soon became a [[shrine]] for many [[pilgrimage|pilgrims]]. In the late fifteenth century the Russian [[iconographer]] [[DionysisDionisius]] rendered an [[icon]] of St. Dmitri that was later "commandeered" by Grand Prince Ivan III before his Kazan campaign, having already become esteemed as an miracle-working icon. After his victory at Kazan Ivan returned the icon to the monastery on [[June 3]], 1503, adorned with silver and gold.
The monastery became the visiting place for the Russian grand princes and tsars during the sixteenth century. The Grand Prince Basil II came to Spaso-Prilutsky in 1528 with his wife Elena Glisnkaya to pray for a child. Tsar [[Ivan IV of Russia|Ivan IV]] visited the monastery in 1545 to worship, and then in 1552 to take the Kilikievsky cross as he prepared for his campaign against Kazan.