This paper examines the contemporary issue of the overrepresentation of Aboriginal women in Canadian prisons and suggests that the systemic discrimination and myriad disadvantages that these women face, both within the context of the justice system and in society in general, results in an ongoing cycle of victimization and offending. Specifically, this paper addresses the historical and contemporary forms of violence and victimization that these women face, and examines the impact that this victimization has on offending behaviors. Finally, through an exploration of policing practices, and the complex issue of sentencing Aboriginal offenders, this paper concludes that Aboriginal women are severely disadvantaged at all stages of the criminal justice system, largely as a result of pervasive cultural stereotypes, resulting in worse outcomes for these offenders, and ultimately contributing to the issue of overrepresentation.