Relevance. Understanding the factors of ensuring the stability of psychological well-being (PWB) will provide teachers and psychologists with a tool that allows them to provide timely Purpose of the study. The study investigates the differences in the relationship of psychological well-being with regulatory and motivational characteristics in students with different dynamics of psychological well-being in fifth and 6th grades.and adequate assistance to younger adolescents, supporting the development of their regulatory and motivational resources.Research methods and sample. Longitudinal data of 155 secondary school pupils (Moscow and Kaluga) aged 10–12 years (M = 11 ± 0.28) are analyzed. According to two 5th and 6th grades surveys, we identified groups with decreasing, increasing, and stable PWB. Research methods: "Well-Being Manifestation Measure Scale" (modification: V.I. Morosanova et al., 2018), "The Self-Regulation Profile of Learning Activity Questionnaire (SRPLAQ)" (V.I. Morosanova, I.N. Bondarenko, 2018), "Academic Motivation Scale – School (AMS-S)" (T.O. Gordeeva et al., 2017). The academic performance indicator: the average score of success in learning Russian and mathematics.Main results. The decrease in PWB is associated with a weakening of the links between PWB and students' motivational and regulatory characteristics. In comparison with the 5th grade, in the 6th grade, conscious self-regulation ceases to be a regulatory resource for both PWB and academic performance. PWB stability is ensured by the strong relationship between self-regulation and PWB and the "inclusion" of all regulatory and motivational factors in this process. The increase in PWB is primarily associated with the actualization of personal development: an accentuated and stable relationship between PWB and self-esteem motivation is revealed.Conclusion. The study results allow us to obtain new data on changes occurring in the system of PWB and academic performance predictors during the beginning of secondary school education.