The current research aims to explore the relationships between self-regulated learning, digital wisdom, digital stress, and academic flourishing among undergraduate students. It also aims to measure the level of each variable and differences between males and females in the four variables. In addition, it explores the mediating role of self-regulated learning and digital wisdom in the relationship between digital stress and academic flourishing. A descriptive-analytic design was utilized. The sample includes 360 randomly selected students at the Faculty of Education, Kafrelsheikh University. Data was collected using self-regulated learning, digital wisdom, digital stress, and academic flourishing scales, and their psychometric properties were verified using different validity and reliability methods. The results revealed that self-regulated learning is positively linked to digital wisdom (r = .843, p < .01) and academic flourishing (r = .736, p < .01), but it is negatively linked to digital stress (r = -.791, p < .01). Similarly, digital wisdom is positively related to academic flourishing (r = .848, p < .01) and negatively related to stress (r = -.795, p < .01). Digital stress shows a strong negative effect on academic flourishing (r = -0.835, p < 0.01). The results also showed moderate levels of self-regulated learning, digital wisdom, and academic flourishing, and moderate to high levels of digital stress among the research sample, with no differences attributed to gender or academic specialization. Lastly, self-regulated learning and digital wisdom help students do better in school by reducing the negative effects of digital stress. This shows how important these factors are for success in environments that are becoming more digital. This integrated approach enhances teachers' roles as facilitators of sustainable digital learning environments, where students are encouraged to engage positively with technology, balance personal learning and digital use, and flourish in the digital age. It also suggests conducting additional studies to broaden the scope of the results to other categories.