Aboriginal peoples have been recognized as statistically overrepresented in the Canadian prison system, incarcerated at a rate nearly ten times the rate of the non-Aboriginal population. Despite their overrepresentation being recognized in academic literature, government reports, and Supreme Court rulings, the rate of Aboriginal incarceration has not decreased. In 1996, section 718.2(e) of the Canadian Criminal Code was enacted. Its purpose was to address the overrepresentation of Aboriginal peoples in Canadian prisons by requiring sentencing judges to consider sanctions other than imprisonment for all offenders, and specifically pay attention to the unique circumstances of Aboriginal offenders. In 1999, the Supreme Court of Canada’s decision in R v Gladue reaffirmed the application and importance of this section for sentencing judges. This paper addresses the question: what was the legislative purpose of enacting s.718.2(e) of the Criminal Code, and why has it failed up to this point? It is argued that the Supreme Court’s clarifications and section 718.2(e) alone cannot remedy the issue of Aboriginal overrepresentation as the section only applies to sentencing, one aspect of the larger institutional criminal justice structure. In enacting this provision, the Canadian government overlooked the systemic social, financial, and historic inequalities that contribute to Aboriginal criminality. Thus, section 718.2(e) alone is unable to reduce the disproportionate incarceration rates as the root causes of Aboriginal criminality continue to go unaddressed.