Although the WrapAround process has been used in social services in Canada for some time, the literature remains focused on initiatives in the United States. Canadian WrapAround initiatives are particularly unique in that they focus on connecting children, youth, and their families to a supportive community. Service integration is crucial but only as a means to the end of connecting people to a supportive community. This article reviews the literature on WrapAround and its conceptual models in Canada and evaluates the successes and challenges encountered in developing effective community- based, volunteer-driven WrapAround initiatives through an examination of the implementation of WrapAround in Hamilton, Ontario. The results of a pilot evaluation suggest that a high fidelity WrapAround process can be achieved when implemented through a volunteer-driven approach. An understanding of and support for policy and funding that not only addresses staff-driven WrapAround, but also volunteer-driven, community owned initiatives should be further promoted and developed by governments and organizations.