Purpose: The rapid digitalization and emergence of AI tools are transforming school organizations. However, limited research exists on how school leaders integrate these technologies into their leadership practices. This study focuses on the experiences of school leaders in Cyprus, exploring the benefits and challenges of adopting digital and AI tools in their roles. The research seeks to enhance understanding of these topics as they relate to the pandemic aftermath and the current emergence of cutting-edge technologies. Design/methodology/approach: A qualitative research approach was used, with semi-structured interviews serving as the primary data collection method. The sample consisted of 43 school leaders from primary and secondary schools across five districts in Cyprus, who voluntarily participated in the study. Findings: The findings reveal that while digital tools enhance communication and administrative efficiency, challenges associated with poor infrastructure and inadequate targeted training were disclosed. In addition, school leaders acknowledge the potential of AI to support their leadership practice, while also addressing the challenges of integrating these tools due to limited knowledge and understanding, lack of appropriate training and the need of an ongoing support. Practical implications: The study emphasizes the need for tailored professional development, better infrastructure and continuous support to help school leaders effectively integrate digital and AI tools into their daily leadership practices. Originality/value: This research contributes uniquely to the field by focusing on the integration of digital tools, while also exploring, to some extent, perspectives on AI within school leadership in Cyprus, in an area that has been largely underexplored.