The rapid advancement of information and communication technology has encouraged schools to integrate digital tools into teaching and learning. Technology-based learning media have become increasingly important to improve instructional quality and enhance student learning outcomes. However, many elementary schools still face difficulties in implementing technology-based learning effectively, particularly related to teacher readiness and the role of school leadership. This study examines the implementation of adaptive leadership by the principal of SDN Inpres 01 Bumiraya in supporting technology-based learning, identifies the challenges encountered, and analyzes its effectiveness in improving student learning outcomes. A qualitative approach was employed, with data collected through classroom observations, in-depth interviews with the principal and teachers, and analysis of school documents. The findings show that limited digital literacy, the perception of technology as additional workload, reliance on traditional teaching methods, and differing views between senior and junior teachers have created resistance to change and slowed the adoption of technology in classrooms. Despite these obstacles, the principal’s adaptive leadership has played a significant role in promoting educational transformation. By setting an example, providing professional training and mentoring, utilizing available school resources, and fostering an open and collaborative school climate, teachers have gradually become more confident and motivated to integrate technology into their teaching. This study concludes that adaptive leadership is essential in managing change, strengthening digital literacy, and supporting sustainable technology-based learning to enhance overall educational quality and student achievement in line with contemporary educational demands.