This article challenges researchers and practitioners to reconsider the utility of insider/outsider constructs of the rural school superintendency. We draw on case studies of two diverse rural Rust Belt communities and the school superintendents to demonstrate the new demands placed on rural superintendents given changing social and economic community structures. We assert critical place-conscious leadership as potentially responsive to contemporary rural realities, but provide a number of suggestions for theoretical development to increase applicability to the realities of the rural superintendency in practice.