Educational backgrounds of incarcerated women differ from study to study, proportionate to the rest of the country; incarcerated women possess lower levels of educational attainment when they enter prison. Approximately 56% of women incarcerated in state prison entered without a high school diploma. Prior research on urban prisons indicates cyclical victimization affects school performance and many inmates report poor academic performance as a by-product of their parents' lack of interest in their school achievement. Neglect and severe abuses (physical, emotional, and sexual) undermine motivation and ability to concentrate. This case study reveals the factors 15 women incarcerated in a state-run prison attribute to the abandonment of their high school education. The question leading this case study is: What factors do incarcerated women identify as reasons for dropping out of high school? Two central themes emerged from the interviews. First, the women in the study suffered negative educational experiences due to a lack of parental support. Second, the women in the study suffered school alienation. The findings of the study may contribute to scholarly inquiry of women's pathway to prison, a construct now underrepresented in the literature.