In the last decade, many leading universities throughout the world have modified their mission and vision statements to emphasize community service and broader societal aspirations. Examining the case of Canada within the global system of higher education, this chapter explores the community engagement approaches of Canadian postsecondary institutions. Following an analysis of the communities within and surrounding campuses and a summary of key stakeholders, it outlines the unique history of extension faculties and the special relationships with Indigenous peoples and linguistic minorities that have become pivotal to community engagement strategies. The chapter emphasizes lessons from the Canadian context that may serve global university leaders. It concludes with a synopsis of challenges and threats to navigate in the pursuit of effective and enriching university–community relationships.