The purpose of the study was to explore the lived experiences of African American urban high school students that dropped out of school in an urban Alabama city and their teachers that taught the students between 2004 and 2008. In addition, the purpose of this study focused on the dropout phenomenon by interviewing students and their former teachers to determine their perceptions and share expressions of school experiences that may characterize why students decided to drop out of high school in an urban Alabama city between 2004 and 2008. A total of 8 student dropouts and 5 former teachers in an urban Alabama city met inclusion criteria, agreed to the conditions of informed consent, and scheduled face-to-face or telephonic interviews with the researcher at a mutually convenient time and location with privacy. The student group was asked 13 interview questions and the teacher group 14 interview questions. The interview questions were constructed by the researcher in order to provide baseline measures of content and construct validity and reviewed by two experts in the field with qualifications. Based on the review and recommendations, interview questions were finalized and categorized based on the theoretical framework and Tinto's retention categories of academic, sociocultural, motivational/attitudinal/behavioral, and financial factors. This phenomenological study will serve as blueprint of starting focus groups/conversations with middle school and high school students to gain insight on how to keep students from dropping out of school in Alabama. [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.]