This article offers a transnational perspective on Canada’s legislative response to globally expanded national security intelligence activities in the War on Terror since 2001. I situate Canada’s new legislation against the backdrop of US and Japanese legislative responses and analyze the transition, including Bill C-13 (2014), Bill C-44 (2015), Bill C-51 (2015), and Bill C-59 (2019). I argue that the thrust of this legislative trend has been the active legalization of previously illegal surveillance activities by security intelligence agencies, rather than passive ineffectiveness in restricting state mass surveillance enabled by information and communication technologies. The transition is in synch with a global legislative trend that lowers the legal standards of privacy and personal data protection and weakens checks and balances in democratic governance. As a result, mass surveillance has increasingly undermined and regulated the rule of law, not vice versa.