After being identified as a school in need of improvement, one struggling inner city high school implemented an evening school alternative program to reduce their suspension, failure, and dropout rates. In its first year, the program graduated 100% of the student participants, all of whom were in danger of dropping out, or being kicked out of high school. This case study, completed during the second year of the program, identifies characteristics of the evening school program that contributed to its initial success and shares information on the experiences and perceptions of students and staff members involved in the program. Student participants, many of who were experiencing problems related to physical altercations, involvement with gangs, and use of illegal substances, shared their educational and career aspirations. Study findings suggest these students appreciate the structure of the program and the opportunities they are being provided. Implications for schools and school leaders are presented.