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The article presents the influence of artificial intelligence on the quality of the criteria-diagnostic apparatus of the system of pedagogical monitoring. The necessity of creating automated tools for assessing the existing competencies of the listener and necessary for participating in the process of mastering the discipline is noted; automated diagnostic systems in digitalization to form an individual training route. The authors have developed methods for providing an automated process of pedagogical monitoring, describe the principles of work of the developed methods from the technical and pedagogical side, and also give examples of their implementation. It also offers the implementation of an expert assessment method using image theory and machine learning. The article confirms that AI allows you to expand the range of possibilities of pedagogical monitoring in digitalization, while maintaining the principles of traditional pedagogy. Based on the proposed technology and the creation of a training automated system, the proposed approach will solve this problem and improve the accuracy of the individual educational route and disabled people employment.