Indigenous offenders are heavily over-represented in the Australian and Canadian criminal justice systems. In the case of R v Gladue, the Supreme Court of Canada held that sentencing judges are to recognise the adverse systemic and background factors that many Aboriginal Canadians face and consider all reasonable alternatives to imprisonment in light of this. In R v Ipeelee, the Court reiterated the need to fully acknowledge the oppressive environment faced by Aboriginal Canadians throughout their lives and the importance of sentencing courts applying appropriate sentencing options. In 2013, the High Court of Australia handed down its decision in Bugmy v The Queen. The Court affirmed that deprivation is a relevant consideration and worthy of mitigation in sentencing. However, the Court refused to accept that judicial notice should be taken of the systemic background of deprivation of many Indigenous offenders. The High Court also fell short of applying the Canadian principle that sentencing should promote restorative sentences for Indigenous offenders, given this oft-present deprivation and their over-representation in prison. In this article, we argue that Bugmy v The Queen represents a missed opportunity by the High Court to grapple with the complex interrelationship between individualised justice and Indigenous circumstances in the sentencing of Indigenous offenders.