This review critically examines empirical evidence from 50 studies over two decades on technology-mediated self-assessment (TMSA) in higher education, providing a comprehensive overview of the tools used, and the benefits and challenges encountered in its application. The findings suggest that TMSA not only retains the benefits of traditional self-assessment, such as enhancing students’ academic performance and fostering long-term learning, but also introduces unique advantages. It amplifies student engagement via interactive and multimedia elements, provides flexibility for self-assessment, and assists educators with data-driven insights while easing administrative tasks. However, it also brings challenges, including technical issues like software glitches, connectivity problems, and compatibility issues with various devices or operating systems. The review concludes with recommendations for optimizing TMSA implementation.