This article reports findings from a case study of school principals in Southern Thailand who work in areas targeted by Muslim separatist groups. Data were gathered and analyzed using a conceptual framework that conceived of trust as five interrelated constructs: benevolence, honesty, openness, reliability, and competence. This study builds on prior trust research by examining trust in a specific non-Western cultural context that is moderated by two cultural phenomena: violence and ethno-religious difference. This study is a unique contribution to both the broader research on trust and to our understanding of how leadership is enacted in different cultural contexts. More narrowly, this study also helps us understand the way school leaders in southernmost Thailand build and sustain trust with community leaders. Findings suggested that school principals experienced each of these forms of trust, yet each individual principal interpreted them in a unique manner. In addition, in regards to principal work, fear and problems with communication were found to hinder leadership efforts.