This article reports on the challenges facing public school leadership in southern Thailand, a region destabilized by renewal of a longstanding insurgency. Seeking to implement national educational reforms on shifting social, political and cultural terrain, educators in this region face extraordinary challenges as they reconsider and renegotiate an institutional position once perceived as secure. Focusing on two schools in one province, this article offers an account of the variety of challenges reported by principals working in this difficult environment. We find the principals employing number of bridging and buffering strategies as improvisational efforts to re-organize, re-establish and re-position the schools in their respective communities. In the concluding discussion, we surface concerns regarding the nature and naturalness, reason and reasonableness of these strategies within local administrative hegemony premised on market and colonial ideologies that may obscure impending legitimation issues.