Sustainable development of regions is a priority of the state socio-economic policy. It actualizes the need to create tools for assessing the sustainability of regional socio-economic systems. The aim of this research is to determine the degree of sustainability of a regional economic system (“slave” system) relative to the country’s economic system (“master” system). The study involves the use of different macro-economic indicators that describe the regions’ sustainability, the sustainability of businesses and sustainability of households. A methodological approach to sustainability assessment of the constituent regions of the Russian Federation was proposed using the time series analysis of macroeconomic indicators. A classification of the sustainability of region economic system according to changes, which take place in the economy of the country was the result of the study. Based on this method, a software product was developed in order to automate the process of evaluation and classification of the sustainability of the Russian Federation. The article describes the functionality and possibility of practical use of the software product. The program has flexible settings and allows the user to quickly identify the main trends in performance and, when used appropriately, it generates conditions for their forecast. The proposed approach has been tested on the industrial production index. The software product makes it possible to create maps of Russian Federation which illustrate the classes of the regions’ sustainability in terms of the industrial production index, which allows for assessing the reaction of the industry to the crises of 1998 and 2009. The main conclusion is based on the definition of the key trends in the development of regions that can be used by the authorities for administrative decisions in modeling strategies for the development of the Russian regions.