Following the arrival of the MV Ocean Lady in 2009, four men were charged with human smuggling under s. 117 of the Immigration and Refugee Protection Act for having helped Sri Lankan asylum seekers reach Canada. Section 117 made it a criminal offence to aid and abet the unauthorized entry of asylum seekers, including when this was done for humanitarian reasons, to help family members, or as a matter of mutual aid. The case made its way to the Supreme Court and, in 2015, the court ruled in R v Appulonappa that s. 117 was too broad, potentially criminalizing humanitarian workers and family members who help transport asylum seekers, and should be interpreted in a strict manner. This article draws from pragmatic sociology to study the regimes of justification mobilized by various actors involved in, and around, R v Appulonappa between 2009 and 2015. It focuses on two sites of contestation that crystalized around divergent conceptions of fairness and safety, discussing how competing regimes of justification were used to advance stakeholder’s positions.