Just like in the past, the most important works involving painting where headed by masters invited from major artistic centres. Sometimes they would remain in the monastery for many years, creating icons of local saints and renovating the panels of the numerous old iconostases. The two-story icon hall, where these works were mostly done, can be seen in a 1720 engraving by Aleksei Rostovtsev.

From a local Synodicon (memorial book for the dead and sick) we know the name of Trifon, former archimandrite (prior) of the Nikolo-Uleiminski (St. Nicholas) Monastery near Uglich. The master lived in Kirillo-Belozerski Monastery from 1606 to 1621, “painted images and repaired old ones in all churches”. In 1607 he decorated a door leading to the credence alter of the Church of the Presentation of the Virgin in the Temple. Here we can see a number of subjects: “Laudation of the Virgin”, “The Fold of Abraham”, “Adam and Eve Driven from Paradise”, “The merciful Fornicator”, “Deathe of a Righteous Man”, “Death of a sinner”. In the lower part of the panel the artist depicted the “Caves of the Penitent in the Raifa Monastery”. All the images contain extensive commentaries taken from hagiographic and liturgical texts, as well as from the works of the Holy Fathers. Originally an inscription telling the name of the master ran along the lower border of the door, which was later sewed off. It was seen and published by Archimandrite Varlaam in 1856. Afterwards the icon served as a shutter of the sanctuary window of the church of St. John Climacus, where it was accidentally discovered in 1973. Today it is one of the few extant objects from the interior of the Presentation Church.

In 1630 the Boyar Vasili Streshnev, stolnik of Tsar Mikhail Romanov, financed the creation of the forefather range of the Assumption Iconostasis. It was executed by Vologda painter Zhdan Dementiev. Six icons of this tier are presently exhibited in the Russian Museum (St. Petersburg).

The forefather range, depicting biblical personages from Adam to Moses, symbolizes the old Testament Church, its central image being “Paternity”. God the Father, sitting on a magnificent throne, is making a blessing with His two hands. On His lap is God the Son, portrayed as an infant, with the dove, representing the Holy Spirit, over His head. The panel is flanked by the images of the forefathers. The icons have ogee tops, their gold ground covered by chases settings of gilded silver.