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In recent years, certain hospitals, schools, and campuses across Canada have shown that they can transform their practices to serve more local and sustainable food. These changes have often been led by visionary champions, and in some cases aided by supportive public policies or programs. Yet the presence of these isolated success stories has so far not proven sufficient to tip a critical mass of institutions towards sustainability. There is great potential in leveraging institutional foodservices, with an estimated $8.5 billion market sales in Canada in 2016 (fsStrategy, 2016), to shift systems towards greater sustainability. In 2014, Food Secure Canada and the McConnell Foundation launched an action-research project and embarked on a learning journey to explore two key questions: how can food service operations and procurement practices be changed to increase local, sustainable institutional procurement; and how can this work be scaled. In 2014–2016, eight institutional food projects across Canada came together as a national Learning Group. Drawing from their experiences working in different contexts and scales, our action research project identified program and policy innovations to leverage systems change. This article explores how institutions currently buy food, and reveals the systemic barriers to increasing local, sustainable food procurement. We share lessons learned about the interplay of menus, food service operations, contracts, institutional demand, and food culture that helped to overcome these barriers. We identify enabling, peer-based learning and support as particularly relevant in a national context for the scaling out, up, and deep of local, sustainable food procurement.