The spread of digital technology around the world is accompanied by the uneven development of digitalization processes on the territory of different countries. Russia is no exception. The problem of digitalization management in the Russian Federation must be solved by building an effective system of its management. In order to implement digitalization management throughout the country, it is necessary, first of all, to establish this process on the territory of federal cities: Moscow, St. Petersburg and Sevastopol. Federal cities have all opportunities for building an effective system of digitalization management which in the future could be applied in other Russia’s regions without any serious failures and significant losses. The review and assessment of trends in the current development of digitalization in Russia’s cities of federal importance, the identification of priority digital technologies and priority areas of digitalization in them, the evaluation of their digital life level indicates the unresolved issues of digitalization management in the cities under consideration. A competent organization of digitalization management in federal cities based on the proposed directions will ensure the successful development of digital transformation processes within their territories, and other Russia’s regions will be able to adopt their experience in the future.