For the first time since the introduction of the Canadian Charter of Rights and Freedoms, Canada is in an armed conflict with an insurgency that has actively recruited Canadians and directed them to use or promote violence against Canada. In the result, the Canadian government may ask its soldiers to target and kill fellow Canadians abroad or to assist allies in doing so. This situation raises a host of novel legal issues, including the question of “targeted killing.” This matter arose for the United Kingdom in 2015 when it directed the use of military force against several Britons believed to be plotting a terrorist attack against the United Kingdom from abroad. This incident sparked a report from the British Parliament highlighting legal dilemmas. This article does the same for Canada by focusing on the main legal implications surrounding a targeted killing by the Canadian government of a Canadian citizen abroad. This exercise shows that a Canadian policy of targeted killing would oblige Canada to make choices on several weighty legal matters. First, the article discusses the Canadian public law rules that apply when the Canadian Armed Forces deploy in armed conflicts overseas. It then analyzes international law governing state uses of military force, including the regulation of the use of force (jus ad bellum) and the law of armed conflict (jus in bello). It also examines an alternative body of international law: that governing peacetime uses of lethal force by states. The article concludes by weaving together these areas of law into a single set of legal questions that would necessarily need to be addressed prior to the targeted killing of a Canadian abroad.