This autoethnographic work was written after the author had heard that teaching in the prison environment was challenging and difficult. Although she had previously worked in that environment for five years, she had not read the literature about being a prison educator and the comments made about prison being a difficult place to work were quite different to her own experience. Using analytic autoethnography, which links the individual experience to the academic literature as a methodological approach, she reviewed the academic literature finding that in the literature there were several viewpoints. Some of these matched her own experience and others indicated the difficulties and challenges faced by prison educators. Some of these challenges were faced by the author but accepted as part of the context. One of the outcomes of autoethnography is the raising of awareness and in this paper the author has brought together both viewpoints present in the literature and explained her own experience. Reflection on her own experiences and how they were represented in the literature and becoming aware of the other viewpoints resulted in this paper in which she brings together the importance of potential prison educators understanding the prison context and the interactions between the individual prison context and the personality of the prison educator with flexibility and resilience identified as important factors.