This paper addresses the problem of providing wellbeing in the education system of the Republic of Moldova, which mirrors the contemporary society in constant change that results in multiple tensions and states with a negative effect on the human being. The analysis of currently existing scientific research with reference to the conceptualization and assurance of wellbeing allows the finding of contradictory positions regarding: the use of terminology specific to the respective phenomenon, the identification of its structural components, the negligence of the importance of wellbeing for favoring the balance and progress of the personality in stressful everyday conditions and the insufficiency of the methodology for stimulating the wellbeing of the subjects in the education system. The objectives of the study aim to analyze the situation regarding the approach to wellbeing in education policy documents, scientific research, higher education study plans; determining the wellbeing of the subjects involved in the educational process; the development of the Pedagogical Model for ensuring the wellbeing of the beneficiaries of the education system. The paper reflects the results of experimental research carried out during the last two years in general and higher education institutions within the Republic of Moldova, which reflect the current situation regarding the wellbeing of various categories of subjects: teenagers, young people and adults. The results of the investigation formed the basis for the elaboration of the Pedagogical Model for Ensuring the Wellbeing of the beneficiaries of the education system and the practical recommendations. The results of the study highlight the need to respect continuity in the conceptualization and evaluation of wellbeing, its promotion and assurance among contemporary generations.