Представлены результаты исследования анализа данных педагогами и их руководителями в условиях цифровой образовательной среды (ЦОС). Планирование исследования базировалось на авторской трактовке пилотного эксперимента по внедрению цифровой образовательной среды в регионах России, архитектуры данных цифровых образовательных платформ, эволюции поколений киберсемиотических систем аналитики данных и проблемы аналитики данных на цифровых образовательных платформах. Сама трактовка была определена концепцией кибернетики второго порядка. В статье проведено разграничение концептуальных пределов применимости киберсемиотики и постнеклассической семиотики для методологии моделирования массового и элитного образования. Это разграничение позволило акцентировать прагматическую функцию семиотики для анализа визуализированных данных ЦОС. Проведенное исследование зафиксировало дефициты в семиотических компетенциях педагогов для анализа данных при проектировании персонализированного образования и разработки педагогического дизайна конвергентно организованного образовательного контента. The article deals with the problem of cybersemiotics of the analysis of educational data and human development data in digital educational environments. In the context of the formation of anthropological ideas about the learner as a subject of activity and the implementation of project-oriented education, the cybernetics of digital educational platforms remains in the logic of “didactics of object learning” and does not sufficiently contribute to the logic of “didactics of the development of the subject of cognition and activity”. The cybernetics of digital educational environments determines the cybersemiotics of educational data analysis: the pedagogical meaning and pedagogical tasks of development are often constructed in distorted optics in relation to a developing person. In the conditions of digital educational platforms and data analytics in digital environments as special cybersemiotic systems, a request is being formed for conceptual approaches that allow social research, technological programming, and pedagogical design of developing, learning environments. The aim of the research presented in the article is to study the semiosis of the analysis of educational data and data on human development in digital educational environments. The research was carried out in two aspects: the technological aspect – the study of digital artificial intelligence (AI) services on educational platforms of Russian education; the pedagogical aspect – the study of data competencies of teachers in working with the semiotics of data analysis in education. The article reveals how cybersemiotic AI systems of digital educational platforms (these systems are based on the concept of the pragmatic function in visual semiotics semiotics) become the object of management, the object of pedagogical analysis, the object of technological development in the design of digital artificial intelligence services of digital educational platforms, and the object of procurement for the development of digital educational environments. The study is significant for the development of the theory and practice of digital didactics and the methodology of cybersemiotics of digital educational environments. The prospects of the research are the development of a conceptual adjustment of cybersemiotic systems of AI services for data analysis in the context of the National Data Management System development.