Today, the Russian flag could fly over Hawaii, the Ionian Islands, Madagascar, Sumatra, New Guinea, Kuwait, the Azores and many other overseas territories. However, Russia did not become a colonial empire, such as Great Britain, France or Spain. Why all attempts by the Russian Empire to expand its borders through the acquisition of overseas territories were unsuccessful? What was the role of pirates in the fact that Madagascar never became Russian territory? For what reason, when and how was Alaska sold? Was it possible to satisfy the request of the King of Hawaii to accept his islands into the Russian Empire? Why, despite all the efforts of N.N. Miklouho-Maclay, the Russian flag raised by him has not been preserved over New Guinea?