Operation Challenge is a highly structured, disciplined 17-week program for 14 young adult male offenders who are in contact with the prison system primarily for the first time. It gives them the opportunity to address their offending behavior through education, team oriented physical fitness, cognitive skills, core programs, employment, and reparation to the community. Staff selection, training, and direction plays an important part in the program, as they are role models and responsible to show support and be encouraging and motivational to participants. The paper describes identification of participants, medical clearance, interviews, criteria, and the contract outlining expectations of the Operation Challenge team. It also describes an average day in the life of a team member, educational/vocational training, core programs (Cognitive Skills, Anger Management, Literacy and Numeracy, Alcohol and Other Drugs, Victim Awareness, and Domestic Violence), physical fitness, and throughcare. The paper concludes that this program represents best practice in prison management of young offenders and can be used as the benchmark for future strategic planning of prisoner development and management programs.