Dropping out of high school is an issue that has faced the educational system for years. At a high school in Mississippi, the dropout prevention plan implemented was not beneficial to all at-risk students because it mainly focused on academic issues. The purpose of this qualitative case study was to understand why students dropped out of high school and to gather strategies for a dropout prevention plan. The conceptual framework was based on 5 factors: general deviancy, deviant affiliation, family socialization, structural strain, and academic quandary. The research questions inquired about experiences that caused students to drop out and suggested strategies for a new dropout prevention plan. Data collection methods included interviews with 18 teachers, 3 counselors, and 20 former students who dropped out between 2007 and 2012. Interpretive data analysis was used to analyze data. Open and axial coding was used to develop themes about why students dropped out of high school. Those themes included behavioral issues, peer and work-related influences, family structure, school environment, and academic problems. Data analyses indicated that tutoring, staff development, mentoring, counseling, parental involvement, teenage mother programs, and alternative options were useful in preventing students from dropping out. These findings were used to develop a high school dropout prevention plan to benefit at-risk students. The overall goal for this project was to decrease high school dropout rates. By implementing the high school dropout prevention plan, schools may enable more students to further their education and become productive citizens within their communities.