This book discusses school leaders’ ability to use digital technologies successfully through specific approaches and techniques. It also discusses the technological challenges arising from the COVID-19 pandemic, and the obstacles derived from the lack of digital capacity of school leaders in various contexts. The work addresses school leaders’ experiences, confidence, competence, skills, and practices to use digital technologies effectively. Also, it explores how the COVID-19 pandemic influenced school leaders’ role in establishing effective processes towards educational digital transformation, and provides further knowledge as part of school leaders’ digital professional development aspect.The book draws information and knowledge from the thematic areas of technology and school leadership in educational practice and includes both conceptual and empirical information on autonomous and less autonomous educational systems (centralized and decentralized education systems). Overall, this edited book fills the gap with information on the connection between school leadership and technology, as an aftermath of the COVID-19 pandemic in school organizations.