Since 2001, thirty Canadian nationals have been kidnapped and held for ransom by terrorist groups while traveling or working abroad. This paper explores two questions relevant to policymakers and analysts assigned to kidnapping for ransom (KFR) files: why are Canadians targeted in kidnapping operations by terrorist groups; and what options are available to the Government of Canada moving forward? This paper will focus on six KFR operations carried out by Al-Qaeda in the Islamic Maghreb (AQIM), the Taliban, and the Abu Sayyaf Group (ASG) between 2001 and 2017. The selection of these groups is based on our ability to attribute well-documented KFR cases to them. The paper will therefore consist of an analysis of the terrorist groups themselves, and six KFR cases attributed to these groups that involve Canadian nationals. In comparing the terrorist entities and the respective KFR cases, commonalities and differences will be highlighted, as well as relevant trends and oddities. This two-part analysis is intended to produce findings that will assist in answering the aforementioned research questions.