The growth of cities and the transformation of their urban structure reflect the impact of numerous factors: economic, political, social, ideological and others. The Ural region with its concentration of larger cities is among the most urbanised in Russia. The paper explores the urbanistic processes in the Ural region at the turn of the 20th–21st centuries in the context general economic, political and moral factors. The methodological basis of the research rests on the theories of urbanisation and urban development, and the evolutionary approach. The study uses analytical, statistical, and comparative methods. The data for 1989–2022 reflecting the dynamics of urbanistic processes is taken from the Federal State Statistics Service of the Russian Federation. The boundaries of the Ural agglomerations are sourced from the official territorial and strategic planning documents. The findings indicate several trends in the transformation of the Ural settlement system and its urbanistic structure, in particular, a qualitative change of the cities’ industrial structure, a decrease in the employment in industry and a fall in the urban population, intensification of agglomerations processes and population tending to concentrate in larger cities. The indicated processes of deurbanisation and deindustrialisation of the Ural region result in the augmented share of larger cities, greater imbalance between size groups of cities. The paper is the first to describe the Ural Urban Square that encompasses four larger urban agglomerations – Ekaterinburg, Chelyabinsk, Ufa, and Perm. The paper underscores that the Ural Urban Square becomes a place of concentration of investment, human, economic, and social resources, the core of the development of the Ural macroregion and its neighboring territories.