Abstract: The subject of this article is the problem of the introduction of distance learning technologies in the process of education by convicts in the context of digital transformation. The article examines the main normative legal acts regulating the right of convicts to education; characterizes the problems existing in the penitentiary system when convicts receive education; examines the experience of using distance learning technologies by foreign countries, evaluates the possibility of applying their experience in the Russian penitentiary system. The relevance of the topic is due to the fact that the possibility of convicts receiving education in Russia applies only to certain categories of convicts, which is considered ineffective in the current conditions of humanization. In addition, remote technologies that have proven their worth and importance are practically not used in the modern penitentiary system, which is seen as a serious disadvantage and requires special attention. The main purpose of the study is to develop the possibilities and prospects for the implementation of the process of distance learning of convicts in Russia. Along with general scientific methods, the authors also used special legal methods (system-analytical, comparative legal, statistical) in the preparation of this article. Based on the conducted research, prospects have been identified that contribute to the successful introduction of distance learning technologies into the Russian penal system. The optimal way to solve the stated problems will be the legislative regulation of the possibility of obtaining education using distance learning technologies for all categories of convicts, as well as the development of effective programs and courses through which persons serving imprisonment could gain knowledge and master a particular profession.