In 2013 the City of Cape Town, South Africa, commissioned a food system and food security study. The process of writing the report highlighted a series of scale-related governance and data challenges. Given the historical lack of consideration of food as a local government competence, we found that available data were either poorly disaggregated or were unavailable, requiring the state to depend on poorly matched proxy indicators. This chapter reflects on the process, focussing on the politics and practicalities of data collection and disaggregation for municipal and regional food system assessments. Building on this experience, the chapter then considers the current challenges faced by local government reporting against externally generated indicators (such as the UN Sustainable Development Goals and the 100 Resilient Cities indicators), which are time-consuming to report against at best, and are often at odds with the logic of local development plans. The chapter concludes with an argument for a need for more micro-scale, collaborative, community-generated data and assessment frameworks.