This article presents the results of a study in which five women in a detention facility were interviewed and asked about their prior educational histories and their experiences of GED education in jail. Three central themes emerged from the interviews. The women in the study had positive academic experiences in their early school years which were often the result of the positive influence of compassionate teachers at these early levels of schooling. The women had a traumatic, life-changing event that affected their continued ability to succeed at the middle school or high school levels. Finally,the women had a keen awareness of the learning environment in jail and its compatibility with their own comfort levels in education. The implications of these themes for the correctional educator's practice are discussed.