By building community-based food systems informed by transformative ideologies and principles, Community-Based Food Organisation (CBFOs) can be understood as agents of critical food guidance from the bottom-up. This paper focuses on the notion of reflexivity as pivotal to the implementation of critical food guidance in CBFOs. Reflexivity is defined as the capacity of actors and organisations to establish as well as to self-reflect upon key food system principles and scale out these principles across communities. To examine reflexivity and its connection to critical food guidance, this paper retraces the story of FoodShare Toronto, a CBFO whose core mission is to foster “good healthy food for all”. Going through different stages of its life-course, this paper highlights the ways in which this organisation reframes core values and principle through time and how it attempts to scale out these principles through partnerships and programs. Learning from FoodShare´s trajectory, this paper highlights key lessons on how reflexivity can strengthen the capacity of food organisations to be vehicles for emancipatory and transformative food guidance.