Abstract The 1917 February Revolution opened a window of opportunity to establish a centralized Ukrainian administration and form Ukrainian gubernias into one polity. In the period between the February Revolution and spring 1918, all main political parties active in Ukraine, including the Bolsheviks, understood the political benefits of a Kyiv-based administration. In 1918–1919, Ukraine-based Bolsheviks focused their efforts on persuading the resistant Russian Bolshevik leadership to accept Ukraine as a separate administrative unit that needed a territorial administration. Lenin’s acceptance of the Ukrainian Socialist Soviet Republic generated an expectation of genuine administrative self-government among Ukrainian Bolshevik leaders, legitimized their claims for policymaking authority, and thus created a new dynamic in the relationship between the latter and the Russian Bolshevik leadership. The chapter illustrates that in the case of Bolshevism, the struggle for the same ideas did not equate to the struggle for the interests of the same institutions.