Abstract: This chapter describes and reflects on an intensive four-week pre-release educaring program run with Aboriginal women in Alice Springs Correctional Centre Northern Territory, Australia. The behaviours, or symptoms, that contributed to the incarceration of these women, who comprise 2.2 per cent of the Australian population and are 34 per cent of women in prison in Australia, reflect their stories in a colonised space—demonstrating Australia as a continuing penal colony. There is systemic failure across the whole service delivery, with incapacity to acknowledge, understand and respond to the women’s trauma experiences and provide alternatives to prison. Taking healing into a prison with the Kunga Stopping Violence Program required a journey through their layers of loss grief and trauma, walking the circle of wellbeing into anger violence boundaries and safety. This chapter discusses the outcome of this process which drew on indigenous methods of art in feelings and story in poetry that show the strength of culture in healing from generational trauma, with the opportunity to ‘circle into truth through stories’.