This paper aims to identify the factors that are positively or negatively impacting students’ well-being and their academic engagement. We used partial least-squares structural equation modeling (PLS-SEM) using the data collected through a questionnaire from four countries: Romania, Turkey, Slovakia, and Bulgaria. The model includes seven factors that influence the well-being of students and indirectly their academic engagement: stressors in the students’ lives; professors’ support; social support from family and friends; the students’ perceived satisfaction in their lives; engaging in activities during their leisure time; self-exploration regarding their careers; and environmental exploration regarding their careers. The results show that all factors, except for stressors and environmental exploration regarding their careers, positively influence the students’ well-being and thus their academic engagement. These findings are useful for university professors and managers in better organizing activities to increase academic performance.