Based on documentary materials, the article examines the settlement of the Cossack villages of the Psekup Cossack regiment and the description of the resettlement movement in the North-Western Caucasus. The author focuses, first of all, on the civil-settlement aspect, since historical settlements arose from a complex interweaving of politics and geography, power and settlement way of life, reflecting not only the way of life familiar to the Cossacks, but also the Cossack identity. The Psekup Cossack Cavalry Regiment, which was both a military unit of the Kuban Cossack army and an administrative unit within the Kuban region is considered. It is emphasized that, in fact, a military-civilian administration was formed with the maximum sphere of competence in this territory. The problematic aspects of surveying and land use in the Cossack villages of the regiment are revealed. The purpose of the study is to analyze the processes of development of the Trans-Kuban spaces in the form of fortified stanitsa settlements, as well as the penetration of Russian influence in a new area of the historical region of Kuban. The author comes to the conclusion that the villages of the Psekup cavalry regiment were interconnected with the regimental military organization, acting as a stronghold for securing Russian positions in the TransKuban region.