Educational leadership has been the focus of many studies; however, leadership does not occur in a vacuum. Understanding the context in which it occurs will in turn help to explain the phenomenon itself. Rural communities in the United States have many differences when compared to urban and suburban areas. Twenty-eight percent of schools in the United States are rural, and within those rural districts seven million students attend schools (Sherwood, 2001). Even with the large number of rural schools, there are significant deficiencies in rural research, including available raw data (Sherwood & Arnold, 2001, 2004). Moreover, when research is done, the rural context is almost always seen as a limitation (Howley & Howley, 1999). Many times research that is conducted in urban and suburban settings is generalized to the rural setting. Ethical educational leadership is drawing increased attention in research. The bulk of ethical decision-making research has focused on administrators in urban and suburban settings. The rural context is silent when one looks to ethical leadership work. This study explores four rural high school principals' perceptions of how the rural context influences their ethical leadership, career aspirations and advancement opportunities. This study also explores the principals' perceptions about their personal history and their gender to determine whether either has been a hindrance or a help to their leadership in the rural context. A case study methodology was utilized while conducting this study. Over a twelve month period; 18 site visits were conducted at four rural high schools in central Pennsylvania. Twelve semi-structured interviews were conducted along with eight days of shadowing to explore the respondents' perceptions on leading in the rural context. The findings indicate that the respondents of this study did perceive differences in the rural context as compared to urban and suburban areas. Those differences were perceived by the respondents to have an impact on their work as educational leaders. This study suggests that the principals' personal histories impact their leadership within the rural context. All of the respondents lead in districts where they once attended school. This phenomenon strengthened the impact of social reproduction as the principals struggled to maintain a way of life that they valued, while competing with the ideals of the educational institution. The principals maintained programs with a focus on local interests such as logging, shop programs, fish farming and agriculture education. They did this with limited resources and at the expense of offering other programs. Students entering these programs often ended their formal education with high school. They entered the local economy and reproduced their parents' class position in the wider society. The principals' ties to their communities impacted their expectations for students in their schools. This study suggests that the rural context impacts opportunities for advancement. While opportunities for advancement were perceived to be present, they often required principals to move their families due to geographic distance. None of the respondents were willing to relocate to take advantage of opportunities. Gender barriers were rampant within the rural context. The two female principals had experienced gender discrimination. The two male candidates acknowledged gender barriers in their districts. All the respondents affirmed that the stereotype for a high school principal in their respective districts was a male. The principals used multiple paradigms when solving difficult ethical decisions, and their personal history influenced the paradigms they used most frequently. The respondents all used the ethic of care and critique more than the ethics of justice and the profession. Critical life incidents shared by the principals were from a caring or critical perspective and tied to the paradigms they used most frequently. Competing values about the educational mission of the school, the purpose of school and social mobility of students were found to impact leadership. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]