Although Kiprensky was born a serf, he was released from the serfdom upon his birth and later his father helped him to enter a boarding school at the Imperial Academy of Arts in Saint Petersburg in 1788 (when Orest was only six years old).

He lived at the academy for three more years as a pensioner to fulfill requirements necessary to win the Major Gold medal.

Winning the first prize for his work Prince Dmitri Donskoi after the Battle of Kulikovo (1805) enabled the young artist to go abroad to study art in Europe.

The portrait so impressed his contemporaries, that later members of the Naples Academy of Arts took it for the painting by some Old Master – Rubens or van Dyck.

In 1828, Kiprensky came back to Italy, as he got a letter from his friend Samuil Galberg, informing him that they had lost track of Mariucci.