This chapter considers reparations for mass human rights abuses against Indigenous peoples, and essential elements for reconciliation. The chapter examines this topic from the experience of the writer as a primary negotiator in the settling of the historic Indian Residential School Settlement Agreement. The chapter argues that the largest and most comprehensive settlement in Canadian history for 150,000 claimants and over a period of 150 years could not have been accomplished through normal legal processes, either in courts or in traditional settlement negotiations. The chapter further argues that the formal justice system and the lawyers that operate within it do not have the capacity, values or training to deal with the mass harms perpetrated by state violations of human rights against Indigenous peoples. The chapter concludes by arguing that in post-colonial societies, traditional social, cultural and philosophical orientations to injuries and reparations must be rethought to allow for Indigenous perspectives and engagement. Legal processes, institutions and professional education must change.