In an era of instability, upheaval, and change Canada’s place in the world remains uncertain. This is an era of significant geopolitical shifts, nationalism, and identity politics. As a result, the institutions in which Canada has invested significant capital such as trade, political, and security organizations are being tested and stretched to the limit. In essence, Canada’s fate and future is structurally contingent on its relationship with the United States; a relationship that paradoxically is key to enhancing Canadian sovereignty while at the same time having the potential to reduce it. Canada’s foreign policy has been captivated by three or perhaps four ends: the establishment of peace and security through the rule of law, maintaining a harmonious and productive relationship with the United States, and ensuring economic prosperity and competitiveness through trade and investment. To these three core elements we might add enhancing national unity and its corollary strengthening Canadian sovereignty. While these ends remain largely unchanged, where we would find a great deal of variation over time is how various governments envision achieving them. The publications cited in this article examine these emerging issues as well as those grounded in overarching debates about Canada’s place in the world, its relationship to the United States, and the importance of international institutions in advancing Canadian interests and values. While some of the readings may be regarded as definitive and others seminal much of what is identified is intended to provide insights on different ways of thinking about Canada’s foreign policy, who shapes it, and to what end.