This research study explores the challenges and barriers in school digital transformation based on the perspectives and experiences of school leaders within the Republic of Cyprus. This study employs a qualitative research approach, using interviews to collect insights from 11 purposively selected primary and secondary school leaders. The identified obstacles to digital transformation primarily center around equipment and infrastructure, professional development, digital literacy skills, cybersecurity, lack of alignment with the curricula, and lack of time and support. Given the highly bureaucratic and conservative nature of the Cypriot educational system, this research aims to offer a comprehensive understanding of these challenges, highlighting their multifaceted nature and impact on digital transformation efforts. This study contributes significantly to the educational landscape by informing policy decisions, guiding educational practices, and shaping professional development initiatives in this context.