The subject of this article is the problem of professional training of current and future employees of the Russian penitentiary enforcement system in the context of the digital transformation of the penitentiary system in the country and the world. The relevance of the stated topic is due to the fact that the current employees of the penal enforcement system have a low level of knowledge of information technologies. In addition, modern professional training of future personnel of the penitentiary system is carried out without the use of such information innovations as distance education technologies and digital security. The article examines the current level of information technology proficiency of current employees of the penitentiary system; describes the problems existing in the system of training future personnel when they receive education in institutions under the jurisdiction of the Federal Penitentiary Service of the Russian Federation, as well as in civilian universities training personnel in the field of "Jurisprudence", "Law Enforcement"; the problem of the lack of courses is considered improving the digital literacy of current employees of the penitentiary system; the experience of using distance learning technologies by foreign countries in the process of obtaining education by current employees who have the opportunity to improve their competence without interrupting their direct official duties; the possibility of applying foreign experience in the Russian penitentiary system was assessed. Along with general scientific methods, the authors also used special legal methods (system-analytical, comparative legal, statistical). The novelty of the research lies in the development of the main ways to solve the problems of professional training of employees of the penitentiary system within the framework of the digital transformation of the penitentiary system, providing for improving the training of existing employees, as well as introducing certain innovations in the training of future personnel of the penitentiary system. On the basis of the conducted research, difficulties were identified and opportunities for improving the modern professional training of future personnel, as well as current employees of the penitentiary enforcement system, contributing to the optimization of processes and improving the quality of the penitentiary system were identified. The best way to solve these problems will be the introduction of a mandatory requirement to improve the digital literacy of existing employees of the system. For institutions that train future personnel of the penitentiary system, it is necessary to introduce disciplines into the educational program aimed at obtaining practical skills in working with automated information systems used in the activities of the Federal Penitentiary Service of the Russian Federation.