Background: Research on rural educational leadership is often overlooked in educational research, specifically within the context of homegrown leaders, or leaders who have been lifelong residents in the districts where they were students, teachers, and now lead as principal. Rural districts face many challenges that differ from urban districts. Looking at how these homegrown leaders use transformational leadership to overcome these challenges can assist principal preparation programs in preparing administrators to lead in rural districts as well as policymakers as they look at policies and funding that impact rural districts. Purpose: The purpose of this study is to address the following research questions: 1) How do these participants identify themselves as educational leaders? 2) How do these rural principals, identified as transformational leaders, use transformational leadership to contend with challenges unique to rural districts? 3) Do the principals’ prior experience and personal history within a school district influence transformational leadership practices, such as building trust, maintaining a positive school culture, and enacting change? If so, how? Setting: Research for this study took place in two rural school districts in neighboring Midwestern states. The communities the participants in this study reside in are over 100 miles apart, yet both the school districts and towns share similar characteristics. These districts are housed in farming communities with a population between 1,500 and 1,800 residents. The demographics of both districts are very similar consisting of over 97% white students, with the town’s population matching that of the school. The similarities are also present in the physical description of the school sites and collaboration with neighboring districts. Both of these districts consist of one large building housing all students, and superintendent on the same campus, and share resources such as staff, transportation, and athletic and academic programs with neighboring districts. Participants: The two school principals in this study were chosen due to similar characteristics of being homegrown leaders who both reside in similar rural districts and communities in neighboring states. In addition to having similar contexts, the participants in this study share many similarities as well. Both are male and have lived in the district where they were former students, teachers, and coaches prior to becoming the school principal. In addition, both of the principals in this study were chosen via convenience sampling due to prior experience of the researcher within both of these communities and their qualifications of being homegrown leaders. Research Design: This is a qualitative case study analyzing two cases with two participants. Data Collection and Analysis: Data collected for this qualitative case study include multiple interviews with both participants; observations in school and community events; observations at staff, parent, and student meetings; district handbooks and information collected from the district website and state reporting agencies, including demographics, free and reduced lunch status, number of staff, per pupil funding, assessment scores, and school improvement plans. Open and axial coding is used to analyze data. Member checks, triangulation of data, memos, and peer review are used to help ensure validity. Findings: The findings of this study reveal that being a rural, homegrown, transformational leader is a strength to overcome rural challenges. These principals’ prior history and relationships within the district and community, as well as the deep understanding and background knowledge they have of the values and culture of the district and community, allow them an easier time building and maintaining trust and relationships, creating a positive school culture, and enacting change. Additionally, their understanding of the challenges of rural districts based on their prior knowledge as a student and teacher have given them foresight to help them better understand and manage the challenges they encounter specific to rural districts. Conclusions: This study demonstrates how transformational leadership assists rural principals in managing challenges specific to rural districts. Additionally, it adds to the literature addressing the challenges rural districts encounter from first hand experiences of two principals who have lived in their respective districts their whole lives. This study provides insight to principal preparation programs, especially those training principals in states with a high percentage of rural districts, regarding how transformational leadership can assist rural principals in managing the challenges they will encounter in a rural district. This study is also beneficial to rural superintendents as they look to hire new principals.