This dissertation explores the promise of bail-oriented interventions vis-à-vis the overrepresentation of Indigenous peoples in Canadian prisons. While this research project argues that the bail system's underlying risk logic is inherently discriminatory against Indigenous peoples, it is proposed that specialized courts for Indigenous peoples - Gladue Courts - may be well-positioned to overcome systemic barriers to Indigenous peoples' release on bail. This research explores the extent to which two Toronto Gladue Courts have been able to produce equitable bail outcomes, as well as potential downstream effects of these outcomes, utilizing two unique and complementary longitudinal datasets from the Ontario Ministry of the Attorney General which span from 2006 to 2017. Analyses examine i) bail case characteristics, ii) bail processing and court processing measures, and iii) final case outcomes and sentences for Indigenous peoples' bail cases which were processed in these Gladue Courts compared to (predominantly non-Indigenous people's) bail cases processed in the conventional bail courts of these same courthouses. Study findings suggest that while these two bail populations shared many similarities, charges against the administration of justice were particularly widespread among Gladue bail cases. While Gladue Courts appeared largely successful in producing substantively equitable bail outcomes, the impact of these courts is limited by Gladue bail cases' disproportionate early guilty pleas and waiving of the right to bail. Despite the apparent successes of Gladue Courts with regards to bail, Indigenous peoples in Gladue bail cases continued to be disproportionately convicted and sentenced to custody compared to their conventional bail counterparts. Study findings are considered within the wider context of settler colonialism and Indigenous peoples' overincarceration and possible targeted solutions to this phenomenon are discussed.