Abstract Juvenile detention facilities, the equivalent of jail for juveniles, are obligated to provide educational services to detained youth, but these classrooms, teachers, and students are exempted from the normal accountability measures employed in regular schools. The educational outcomes of these classrooms do not have a very good record, and efforts to reform or improve the educational offerings have been weak or ineffective. This study addressed the fact that these efforts have failed to accomplish their stated objectives because they have failed to address the ways that treating children as deserving to be incarcerated may undermine efforts within the facility to treat them as deserving to be taught. Furthermore, reform efforts have turned a blind eye to much of the educational research and theory of the last 50 years. Failing to consider the ways that separate is not equal, promoters of education in detention suggest that detention facility classrooms can and will reform their way to excellence. This study exposes the error in that claim through qualitative investigation of the experiences of four certified teachers working in four different publicly operated juvenile detention facilities in Alabama.