The era of the digital world has redefined education, to be conducted online as a major mode of learning that eliminates spatial as well as temporal dimensions. In this chapter, we undertake a study of the convergence of online education with mental health, attempting to strike a balance between academic success and well-being. A qualitative research design is used with a twofold approach: the descriptive method integrates extant literature to identify trends, challenges, and opportunities in digital education; and the analytical method assesses these findings to create a nuanced discussion. The results underline the fact that although online education increases access and quality, it also brings about some problems related to mental health, such as workload stress and feelings of disconnection—problems that are not intrinsic but extrinsic to the system. The chapter highlights the need for policymakers, educators, and institutions to work together to optimize the positive benefits of online education and simultaneously address, through an enabling environment, its mental health implications to ensure students’ academic and emotional well-being.