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In February 1322, the monastery benefited from a chrysobull by the Emperor Andronikos II Palaiologos, following the intervention of the Protos Isaac. In the documents of that period, it is referred to as a 'venerable royal monastery'.

On behalf of the Emperor Nikiforos Botaneiates, Simeon successfully intervened with the rebel Vassilakis in Thessaloniki, resulting in the reward of a number of imperial benefits, including the donation of important manuscripts and artifacts. The two large portable mosaics of St Georgios and St Demetrios, the largest in the world today, are believed to have come from this donation. After his forced removal from Mount Athos in 1081, Simeon returned in 1089 and continued his founding work, leading the monastery to a period of significant flourishing, as evidenced by the large number of fifty-five monks residing there at that time.

Simeon is probably the person referred to as the Holy Elder Abbot Symeon, a eunuch who had established a monastery of eunuchs in Thessaloniki, and who was praised by Theofyloctos of Ochrid in his speech in support of the eunuchs: One of them is Simeon from Athens, whom we saw in that city; I am talking about that tender and compassionate elder, who has a household wisdom. While very meticulously leading a fraternity on the Holy Mountain, he managed to establish also here (in Thessaloniki) a community of eunuch monks.

The second important milestone in the history of the monastery was the arrival on Mount Athos in 1078 of an important Byzantine officer who wanted to adopt a monastic life: Stefanos, who had been awarded the most prestigious court position (Μέγας δρουγγάριος της βίγλης/βίγλας, 'Great Commander of the Watch') by Emperor Konstantine IV, was born of an eminent family of Athens and possessed considerable wealth. Stefanos was assigned to the monastery of Xenofontos by the Protos of Mount Athos, after he had donated a considerable sum of money for the restoration of the Protaton church in Karyes. He settled at the Monastery with three followers, became a monk, changed his name to Simeon, and assumed the leadership of the almost-deserted monastery. He sponsored major renovation works, which made him a new founder.

In 1018, after the resignation of St Xenofontos, his brother Theodore assumed the role of Abbot, and led the monastery at least until 1035. In that year, the Monastery is mentioned for the first time, apparently in honour of the deceased founder, as the 'Monastery of St Georgios of Xenofontos'.

As was customary in Byzantium, the founder of the monastery established a Typikon, (i.e. a set of rules regulating various spiritual and practical aspects of the functioning of the fraternity) which unfortunately has not been preserved. The existence of this document is confirmed by the phrase 'as Xenofontos the founder has ordered', which appears on the oldest preserved document in the Monastery's archive.

St Xenofontos is also mentioned as an abbot of one of the mountain's establishments in the Life of St Athanasios of Athos on the occasion of the healing of St Xenofontos' brother, Theodore, by St Athanasios in Mylopotamos. St Xenofontos had a significant education, as evidenced by the documents he authored. He also actively participated in the resolution of certain issues involving other monasteries on Mt Athos until 1017, when his siguature appears on relevant documents for the last time.

The 'life' of the Monastery begins somewhere in the late 10th century, when it was founded by St Xenofontos, who signed two documents at Vatopedio Monastery in 998 and 1001 as 'monk and Abbot of the monastery of St Georgios'. The personality of the founder always plays a decisive role in shaping the particular character of each monastery.