Purpose: This article seeks to investigate the leadership challenges in international schools in one region in the Kingdom of Saudi Arabia (KSA). It particularly examines the dissonance between the more liberal approaches to education prevalent in international schools and the conservative nature of those observed in the Saudi context, unveiling the challenges that this posed for school leaders. Research Methodology: In view of the sensitive and complex nature of the study, it was designed as an exploratory study located within qualitative paradigm, using interviewing for data generation. Individual, semistructured interviews were undertaken with 10 senior leaders from five international schools located in Al-Ahsa Governorate in KSA. Findings: The study highlighted a number of complex challenges faced by international school leaders in KSA mainly linked to issues such as sex segregation, Saudization, and parental expectations. The study also unveiled two coping strategies developed by school leaders--namely, compliance and circumvention. Implications for Research and Practice: The findings of this interesting study will have implications for both research and practice. By venturing into this underexplored and sensitive area, the study not only seeks to develop an empirical picture of leadership practices and challenges in international schools in KSA but also stresses the need for further research to gain insight into cross-cultural complexities. Moreover, highlighting the impact of cultural dissonance on leadership practices will be useful for both the practicing and the future leaders of international schools not only in KSA but in other parts of the world too.