The formation of professional skills is one of the urgent problems in training specialists at a military university, especially in the created diagnostic and stimulating educational environment. The authors of the article turn to the analysis of a complex of pedagogical conditions that reflect the phased development of actions, the sequence of using the point-rating system when teaching cadets. The purpose of the article is to consider the technology (forms, techniques, means) for checking the pedagogical conditions for the implementation of the model of the formation of professional skills (cognitive, practical, generalized) in cadets in the process of the actions they have mastered (search, reproductive, productive), based on the developed point-rating system, a didactic bank of control and measuring materials for assessing the educational achievements of cadets at a low, sufficient, increased level in the diagnostic and stimulating environment of a military university. To achieve this goal, the authors use the methods of theoretical and problem analysis, systematize the data obtained in previous studies on this issue. The result of the research carried out in the article is the characteristic of the complex of pedagogical conditions for organizing the training of cadets in the diagnostic and stimulating environment of a military university. The results obtained in the article can be used in the development of teaching materials for cadets of various specialties, as well as for undergraduate and graduate students.