The statistical "over-representation" of Aboriginal people in the criminal justice systems (especially prisons) of Canada, Australia, and New Zealand is not disputed. Sentencing is often perceived as a point in the criminal justice system where, potentially, the problem of Aboriginal over-representation could be addressed. During the last 20 years there have been robust discussions in Canada, Australia, and New Zealand as to whether (and if so how) Aboriginality should be taken into account in sentencing. Reviewing and comparing the trajectories of these debates within the three countries during the last 20 years, in terms of legislative provisions, court decisions, and innovative sentencing practices, suggests that although the problem of over-incarceration is viewed similarly, sentencing responses have varied between nations, but have been equally unsuccessful in actually reducing rates of Aboriginal imprisonment.