In this work, the authors consider digitalization as an innovative stage in the development of the entrepreneurial sector of the penitentiary system (PS) in the regions of Russia. The main attention is paid to the development of digitalization areas that comply with the current legislative framework and safety requirements, and contribute to the innovative development of entrepreneurship in penal institutions in the current economic conditions. In particular, the focus is on the creation of web resources that provide information support for the production activities of PS institutions, such as labor adaptation centers (LACs) and production workshops (PWs). A generalized structure of the content of the websites is proposed, covering key aspects of the functioning of these institutions, including vocational training, services and products of the entrepreneurial sector of the PS, legal documents. The use of Internet platforms to support entrepreneurship in the penal system is studied, and the possibilities of their promising application in production, educational and rehabilitation processes are considered. The importance of data integration and «alignment» of digitalization between regions is emphasized, which is a necessary step towards effective automation of the criminal justice sector under consideration. It was concluded that digitalization not only improves the functioning of the penal system, but also promotes innovative development of territories, creating new opportunities for interaction with business structures, society and increasing the level of reintegration of convicts.