This review presents some reflections on the new book by well-known Cossack historian Dmitrii V. Sen’ which collects his articles and papers on Northern Black Sea history under new conditions developed when the Ottoman Empire lost the war with the Holy League of European powers, concluded the treatises of Karlowitz and Constantinople, and political initiative in the region passed into the hands of Russia. The author’s attention is focused on various individual and collective strategies of adaptation to new life conditions among frontier populations (Crimean Tatars and the Nogais of the steppe, various groups of Cossacks, including those who escaped from the Russian authorities to the areas controlled by Crimean khans). The Russian authorities in the region also had to adapt themselves and learn how to control a complicated borderland country in close contact with the Ottomans, Crimeans, and residents of the North Caucasus. The book uncovers a complicated “mosaic-like” picture of the region where numerous groups and particular persons interacted, each having a specific way of life, interests, aims, and ambitions. The author outlines prospective ways of further research on the eighteenth-century history of the Northern Black Sea Area.