Urban high schools in America are not generating the desired results. Many factors contribute to school dropout, which has an impact on the individual and society. Several of the potential causes are examined and connections between multiple causes are noted. Quantitative and qualitative studies were used to create a complete view of this issue. Dropout prevention methods and programs are described, as is the role of school counselors in dropout prevention. A phenomenological study was also conducted to gain the personal perspective of individuals who dropped out of an urban school district. The specific goal of the research was to determine what factors contributed to students deciding to drop out of high school. Seven individuals participating in a General Education Diploma program shared their experience of dropping out of high school. Individual and small group interviews were conducted. The experiences reported were compared among each participant and were also related to the existing research. Results varied among participants, they reflected both the individual and the school community. Conclusions are reported as they relate to the role of school counselors.