This article critically discusses the practice of foundation collaboration in Canada and describes the context, vehicles, and forms that it takes. It is based on data from interviews with 23 key informants and a literature review of over 100 publications from grey and scholarly literature. Over the last decade, Canadian grantmaking foundations appear to be working together more often, motivated by goals of information sharing, coordination, impact, and risk mitigation. In Canada, as elsewhere, this growing practice is closely related to the trend toward strategic philanthropy, in which foundations position themselves as agents of change. The article raises cautions and criticisms about foundation collaboration, related to considerations of strategic and cultural fit as well as to existing challenges concerning philanthropy’s power and legitimacy in society.