This qualitative case study explores the perceptions of school leadership that future school counselors have regarding leadership roles for women in rural Appalachia. Using a feminist-geographical lens, several cultural, economic, geographic, and identity-based themes were found. Participants' definitions of ideal school leadership included strong community collaboration, advocacy, and leading by example. Some aspects of participants' rural hometowns supported these ideals, such as a community culture offering high levels of cohesion and familial support, leading to them wanting to live there again. However, other characteristics of the community culture, such as being closed to change, sexism against women in leadership, and a lack of women role models, were perceived barriers. In addition, participants' leadership identity was nascent and context based. These factors, combined with poor perceptions of schools in the community, led to participants not to want to live and work in their hometowns. Overall, these participants appear to experience a complex push and pull between pursuing their careers in educational leadership and their desire to take on school leadership roles in rural communities.