The goal of this study was to gather information from Aboriginal offenders and describe the factors that help and hinder them from maintaining a crime-free life after incarceration. The information obtained provides an increased understanding of the needs of Aboriginal offenders and offers guidance concerning useful strategies to incorporate into their wellness plans when entering the community, most notably respecting Aboriginal culture and traditional practices. The critical-incident technique was utilized to examine forty-two Aboriginal offenders’ journeys from prison to the community, revealing nine major themes that were helpful in maintaining a crime-free life: transformation of self, cultural and traditional experiences, healthy relationships, having routine and structure in daily living, freedom from prison, purpose and fulfillment in life, attempting to live alcohol- and drug-free, professional support and programming, and learning to identify and express oneself. Also represented were four themes of obstacles that interfere with maintaining a crime-free life: self, unhealthy relationships, substance use, and lack of opportunity and professional support. The findings also add awareness of those circumstances, issues, and problems that arise during transition that may be harmful or create obstacles to a successful transition.