Digital transformation of socio-economic processes, the development of the urban environment, and smart cities are important trends in the transformation of the economic system at all levels of territorial structure—global, national, regional, and individual municipalities. Small and medium-sized cities of the Russian Federation are currently experiencing a transformational challenge—whether the city will be able to integrate into the modern system of digital society will determine both the further pace of economic development and the level of well-being of the population. In this study, the authors analyze existing approaches to assessing the development of smart cities and reindustrialization of old industrial areas, highlighting the most significant factors and criteria used in the analysis of the processes of digital transformation and reindustrialization. The authors consider the experience of such an assessment taking into account the peculiarities of the system of statistical indicators available in the Russian Federation. © 2023, The Author(s), under exclusive license to Springer Nature Switzerland AG.