Introduction. In today's world, every professional environment has begun to focus on “supraprofessional skills,” which help professionals express themselves within teamwork when solving problems or completing projects. Such flexible skills are valuable for development in professional activity and working life, they help students interact during their studies at the university. The purpose of the work is to show that extracurricular activities in the application of digital technologies in the educational organization of the Federal Penitentiary Service of Russia contribute to the formation of flexible skills of cadets. Due to the fact that various names denoting soft skills (“soft skills”, “supra-professional skills”) are used in the psychological and pedagogical literature, the authors of the article single out the term “flexible skills”, which is used as a synonym for the concept of “universal competencies”. The hypothesis is put forward that cadets studying in educational institutions of the Federal Penitentiary Service of Russia will develop the flexible skills necessary in their professional activities if the development of educational material takes place by involving students in extracurricular activities using digital technologies. Materials and methods: scientific works of Russian and foreign authors describing the importance of the formation of flexible skills; normative legal acts regulating the organization of the educational process in universities; modern statistical data of analytical centers on the level of assessment of the formation of flexible skills of young people; conceptual and terminological method, methods of analysis, synthesis and comparison of information, questionnaires, method of statistical processing information. Research results: based on the survey of cadets, the data were obtained reflecting the level of formation of the following flexible skills of students: critical thinking, communication, creativity, coordination. The authors of the article described their positive experience involving cadets in extracurricular activities of an educational and outreach nature aimed at building flexible skills. Conclusion: the authors conclude that the use of digital technologies in extracurricular activities as part of the educational process at the university is aimed at the development and further formation of flexible skills of future employees of the penal system of the Russian Federation.