Based on an analysis of primary sources and historical literature, this article brings to light the policy of the Bolshevik government in the southern region of Ukraine during the final stage of the First World War. Against the backdrop of the political, social, and national changes in Ukraine during the period of the Central Rada, we explore the goals and methods of establishing Bolshevik control over key southern infrastructure objects, along with the attitudes of local elites toward this control and the reasons for the end of the Bolshevik occupation in 1918. We provide evidence for the idea that territorial issues were a cornerstone in both the communication between the Central Rada and the Provisional Government, as well as in the relations between the Ukrainian People’s Republic (UNR) and Bolshevik Russia. Despite the completely opposing trends in Russia’s political development during the Provisional Government and after the October Revolution, neither government – Provisional nor Bolshevik – considered Ukraine a unified political and economic entity and regarded the southern region as an integral part of ethnic Russia. In this matter the Bolsheviks essentially continued the policy of the Provisional Government regarding Ukraine’s southern region as, in November 1917, the Russian Council of Peoples Commissars, or the Sovnarkom, did not recognize the jurisdiction of the Central Rada over the southeastern territories, which, according to the Provisional Government’s Instruction to the General Secretariat, were not included in autonomous Ukraine in July 1917. One manifestation of this policy was the attempt to create Bolshevik republics referred to as “Soviet republics”: Donetsk-Kryvyi Rih, Odesa, and Taurida. The establishment of these republics followed different scenarios but had a common characteristic: the Bolshevik governments of these quasi-republics did not formally consider themselves Ukrainian. The main goal of Bolshevik Russia was to maintain control over the Donetsk industrial basin and the Black Sea ports.