Digital tools are spreading quickly in indoor dairy systems, but they continue to struggle in pasture-based farming. Most research explains this gap by focusing on farmers and their adoption decisions. This article takes a different approach. It shows that many failures originate upstream, in how dairy-tech startups imagine, design and commercialise their products. Drawing on 51 interviews with founders, engineers, product designers, dairy experts/advisors, board members/investors and farmers, the study examines a range of digital tools, including animal health and behaviour monitoring sensors, pasture measurement systems, herd management applications and decision-support applications. It identifies three types of systemic misfit that shape performance in grazing environments: Ecological-Design Misfits, Temporal-Commercial Misfits and Institutional-Prioritisation Misfits. These misfits arise from indoor-dairy design assumptions, year-round business models and investor expectations that favour fast scaling over local adaptation. The article contributes to socio-technical studies of agricultural innovation by showing how design logics and commercial models can misalign technologies with ecological and organisational realities. It concludes with practical recommendations for policymakers, funders, advisors and cooperatives to support ‘pasture-first’ innovation and improve the fit between digital tools and grazing-based dairy systems.