[4] Among his many rich and notable patrons, Joseph of Volokolamsk alone commissioned him to paint more than 80 icons, primarily for the Joseph-Volokolamsk and Pavlo-Obnorsky cloisters.
The most comprehensive and the best preserved work of Dionisius is the monumental fresco painting of the Virgin Nativity Cathedral of the Ferapontov Monastery in Vologda Oblast (c. 1502–1503).
[4] The frescoes, depicting scenes from the life of the Virgin in singularly pure and gentle colours, are permeated with a solemn and festal mood.
Dionisius's career coincided with the conflict between Nilus of Sora (1433–1508) and Joseph of Volokolamsk (1439–1515) and their followers in the Russian Orthodox Church, known as the "non-possessors" and "possessors", respectively.
During the same period, the Russian Orthodox Church worked to put an end to the iconoclastic tendencies in the heresies of the strigolniki and the Judaizers.