The rapid advancement of digital technologies has fundamentally altered the landscape of educational leadership, necessitating a re-examination of how principal supervision is conducted. This systematic review synthesizes the current literature on the integration of digital technologies in principal supervision, focusing specifically on e-supervision platforms, virtual coaching models, and AI-powered observation tools. Following PRISMA 2020 guidelines, 24 empirical studies and conceptual frameworks were analyzed to understand how technology mediates the supervisory relationship. The findings reveal that while digital tools—such as Video Capture and Annotation Technology (VCAT) and virtual professional learning communities—significantly enhance the frequency of feedback, reduce geographical barriers, and improve principal self-efficacy, they also introduce new challenges, including the digital divide, observation anxiety, and the potential erosion of relational trust. The review concludes that effective e-supervision requires more than mere technological adoption; it demands a paradigm shift toward “digital humbleness” and intentional technology leadership. Practical implications for school districts and future research directions are discussed.