The Caroline Families First Wraparound Program operationalizes cross-sectoral collaboration and planning, family peer support, and family-directed care consistent with strategic directions within the Mental Health Strategy for Canada. In this spotlight article, we present findings from a case study that describes what makes the program work, the barriers and facilitators to its success, and draw conclusions about the lessons learned. For example, while family-directed care is a core and essential value of the program, unless well understood, it can create tensions within teams. Similarly, structural factors such as provider reimbursement can inhibit physician involvement. Suggestions about these and other contextual factors can inform other efforts to mobilize the Mental Health Strategy.