The purpose of this cross-case study is to explore educational leaders' understanding and practice of ethical preparedness in two riparian school districts located along the Ohio River in counties determined by the Appalachian Regional Commission to be at-risk and distressed. As a cross-case analysis study, this research was conducted in the Appalachian region of Southeast Ohio and includes two districts in that region. The approach uses qualitative approaches (observations, semi-structured in-depth interviews, follow up interviews) to collect data from the participants in the two cases. The six individuals that participated in our interviews were representative school leaders within two riverine Appalachian school districts, one distressed and the other transitional. Descriptions and thematic data are reported in the study. Implications for practice indicate school leaders have a responsibility to make ethical decisions that are grounded in their ethical preparedness to promote holistic equality within the education system.