School teacher Joseph Akeroyd was appointed Inspector General of Victoria's prison system in 1924. He held this role until 1947 becoming the longest serving Inspector General in Victoria's history. This book examines the experiences, achievements and failures of Joseph Akeroyd, the longest serving Inspector General of Victoria's (Australia) penal system, in reforming that system. This is not a traditional biography. It traverses Akeroyd's experiences in his time and reflects on reforms through the author's experiences as a contemporary prison educator. Drawing on his education background, Akeroyd revolutionised the ways prisons and prisoners in Victoria were managed and many of these reforms are embedded in current practice. Access to his personal diaries, letters, official reports, newspaper reports and other private documentation gave insights so his single-minded reform agenda establishing Victoria's unique relationship between education and prison management can now be recognised and acknowledged. There are many personal stories where Akeroyd interacted with infamous criminals. The examination of thwarted escape plans, rectifying wrongful convictions, recording the final days of those awaiting the noose, interviewing those about to be whipped or birched and following up after the events are moderated with contemporary stories of modern day interactions between teachers and prisoner students- some humorous, some sad, some sobering. Finally, this book will challenge all readers to reflect on the role of education in prisons, gain insights following stories of conversations with inmates, challenges in changing practice, involved in education, especially prisoner education, whether you are forming policy, advising policy and practice, delivering programs, supporting those undertaking studies, managing those who teach and /or preparing to teach in these unique environments to reflect on your own learnings and how to adequately prepare for those undertaking this vocation in the future.