Successful school leadership is an issue currently being debated up and down Caribbean territories. Key issues in the ongoing debate include: students’ outcomes and participation in the regional Caribbean Secondary Examinations (CSEC); teacher recruitment and retention; teacher training and continuing professional development (upgrading); and parental involvement. These issues point to leadership at various levels, whether in its exercise or in its influence, and are examined within and across national and regional education systems. Particular attention is given to debates around improving outcomes for students, teacher development and the role of the principal in leading school improvement. A source of debate about practice of school leadership in the Caribbean surrounds the issue of gender. Where are men in teaching? Where are men in leadership positions and positions of responsibility? Unlike in some countries where, for example, men tend to hold more leadership positions than women, especially at the secondary phase of education, in the Caribbean this is not the case: there are more female teachers at every level and more female teachers occupy leadership positions at every level. Within this book, gendered leadership as practised and enacted in the Caribbean is examined from religious, social, historical and political positions, pointing to a clear political dichotomy. There is no unitary definition of what can count as school leadership in the Caribbean, despite clear similarities of practices and approaches. What this volume argues, however, is that within the Caribbean region there are many similarities of experience for the practice and exercise of school leadership which draw on a common framework of teacher training, a common language and a common socio-political history that existed well before the formation of CARICOM through British colonisation. This book does not dwell on the period of British colonisation but discusses the extent to which this period in Caribbean history has influenced the practice of school leadership today, most notably in areas such as curricular and teacher training models. Education in emergency situations, such teaching and learning in severe weather conditions such as hurricanes, is also spotlighted. As a whole, the themes in this edited volume proffer an evidence-based approach to contemporary issues in school leadership in the Caribbean and extend the current literature in the field.