In this article, the author explores the criminal justice relationship between Canadian courts and Indigenous laws. More specifically, by examining two recent criminal law judgments from Nunavut that rely on Inuit customary law in their reasons, R v Itturiligaq and R v Ippak, the author queries and seeks to answer whether Canadian courts ought to engage with Indigenous laws, and if so, what appropriate engagement might look like. Through identifying both the promising and cautionary elements of these judgments, the author argues that Canadian courts should actively engage with Indigenous laws to achieve more responsive legal outcomes, but that great care and caution must accompany these efforts. The author proposes guidelines for engagement that involve establishing ethical space with Indigenous legal orders at the outset of judicial analysis to determine commensurability, followed by concurrent application where principles are mutually reinforcing or deference to Indigenous laws where principles conflict. The author concedes that judicial use of Indigenous laws is no panacea; rather, its use represents an important way in which the Canadian legal system can coexist alongside revitalized Indigenous legal systems and their institutions. The article is divided into four parts. In Part I, the author introduces the Nunavut court system and analyzes Itturiligaq and its application of Inuit Qaujimajatuqangit in light of the pluralist promise of R v Ipeelee, concluding that its reasoning instills both optimism and caution. Part II explores the philosophical and normative questions of whether Canadian and Indigenous laws are commensurate and whether non-Indigenous judges ought to engage with Indigenous laws in their judgments. In Part III, the author argues that Ippak best exemplifies judicial reasoning across legal orders that appropriately upholds both Indigenous and Canadian legal systems while respecting their incommensurabilities. Drawing on the lessons learned from Itturiligaq and Ippak, the author then develops his proposal for responsible engagement. Lastly, in Part IV, the author offers suggestions for institutional and legislative reform that must accompany judicial engagement with Indigenous laws. As the author indicates, the success of Indigenous-Canadian pluralism requires rebalancing sentencing objectives away from the rigid Canadian application of deterrence and denunciation and towards a system more focused on rehabilitation.