The quick integration of digital technologies in education has changed teaching and learning processes, creating new challenges for school leaders. This study, titled “Navigating the Shift: Exploring Challenges Elementary School Leaders Face in Managing Digital Teaching Practices,” aims to look at the experiences of elementary school leaders as they manage digital teaching practices within their schools. Using a qualitative research design with a phenomenological approach, the study collected data from selected elementary school leaders through in-depth interviews. The findings showed several main challenges, such as technological limitations and connectivity issues, lack of teacher training and digital skills, increased workload and time pressures, and weaknesses in policy and support systems. School leaders also struggled with keeping students engaged and ensuring instructional quality in digital settings. Despite these challenges, the study highlights the strategies school leaders use, such as ongoing professional development, fostering collaborative learning communities, using available digital resources, and building partnerships with stakeholders. These strategies show resilience and proactive leadership in managing the shift to digital education. The study concludes that effectively managing digital teaching practices requires not only technological resources but also strong leadership, institutional support, and ongoing skill development. It recommends improving training programs, upgrading infrastructure, and creating clear policies to support sustainable digital integration in elementary education.