Both superintendents and principals create a foundation for student achievement, school culture, and the vision of a school building or district. When combined, these two similar yet distinct administrative roles become one unique position with less time and resources to fulfill individual job responsibilities. A dual-role administrator is defined as an individual serving as a superintendent and principal simultaneously. Using a comparative case design, rural dual-role administrators' roles, responsibilities, and experiences are explored. By interviewing and observing two rural practitioners and reviewing public documents, an in-depth investigation of the cases developed. Results from this study indicate that dual-role administrators had time constraints in completing their job responsibilities; valued relationships with students, staff, and school board members; and used a team approach to manage rural school districts. Further, supportive leadership behaviors aligned with principal responsibilities, while directive leadership behaviors aligned with superintendent responsibilities. This research provides an increased understanding of the day-to-day operations of rural dual-role administrators and how their unique identities are situated within their situational leadership approaches. These findings may help with dual-role administrator retention in rural settings.