We report the experiences of vineyard managers and viticultural consultants during collaborative On-Farm Experimentation (OFE) designed to support business decisions. Previous research involving winegrape producers across Australia revealed constraints to farmers’ experiments even though these were valued for their potential to answer business-specific questions. In the study reported here, producers involved in four collaborative trials perceived a feasible approach that provided them with insights upon which they could act. The active engagement of researchers and consultants fostered a shared understanding of the capacities, capabilities, and resources needed for this approach while catalyzing further investigation and/or in-business conversations that would not have occurred otherwise. We explored the value proposition for collaborative OFE involving farmers, consultants, and institutional researchers aimed at generating rigorous results from trials aligned with the farming context.