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The daughter of Petru Rares, Rucsandra, and her husband, Alexandru Lapusneanu, who later became a monk with the name Pachomios, funded the complete construction of the six-storey south wing, with its many balconies facing the sea. These 16th century buildings characterize the image of the Monastery today, especially as they emerged after the recent restoration.

Very soon after the 1520 renovations, however, on 25 October 1535, a devastating fire destroyed most of the Monastery. This gave the opportunity to another prince, Petru Rares of Moldova, to finance the reconstruction of the eastern wing – from the gallery and the entire gateway to the cellar – and of the cathedral, which he even built taller than the old one. He also paid the expenses of the frescoes.

The Wallachian ruler, Neagoe Basarab, was a spiritual child of Saint Nifon. In 1520, he funded the construction of the Monastery's impressive defensive tower and the arched aqueduct that replaced the previous wooden one. He also donated an important relic to the Monastery: the cranium of St John the Baptist (which was unfortunately later stolen), in a golden case, and a gold-plated box in the shape of a church, where the relics of Saint Nifon were placed.

After a disagreement with Radu, Nifon left Wallachia as an old man, and returned to the Dionysios Monastery, where he lived in anonymity, concealing his identity. Indeed, the duties given to him were insignificant, routine ones, such as the care of the animals and the observation of the sea to give advance warning of any potential incursion by pirates, at the same spot where a chapel was later built in his honour. At one point, however, his true identity was miraculously revealed to the monks. He resided in the Monastery until his death on August 11, 1508, at the age of 90. His tomb is in the cemetery of the Monastery, outside the chapel of All Saints.

According to the sources, Nifon first travelled as a monk and calligrapher to Illyric and Dalmatia, where he was copying manuscripts and preaching against the unionist council of Florence. Then he came to Athos, to the monasteries of Vatopedios, Pantokratoros, and finally to Dionysios, where he was ordained a priest and remained. He was later appointed as a bishop of Thessaloniki, and twice served as Patriarch of Konstantinople, in 1486-1489 and 1497-1498. Then he finally resigned from the Ecumenical Throne and went to Adrianople, where Radu IV, the ruler of Wallachia, invited to his kingdom as a spiritual advisor. Although Nifon again received a proposal to become Patriarch, he declined it, preferring to devote himself to the spiritual well-being of the Wallachian people.