This paper details a qualitative investigation of human factors relating to adoption of digital agricultural technologies on Australian farms. We employed an ‘ecosystems’ approach to undertake a case study of a cotton farm’s transition to digital farming. Interviews and participant observation were conducted across the farm’s supply chain to understand how the experiences, perceptions, and activities of different stakeholders constituted a community-level orientation to digital agriculture, which enabled and constrained on-farm adoption. Technology providers installed a variety of data-generating technologies – remote sensors, automation, satellite crop imagery, WiFi/4G connectivity, and a customised data dashboard on the farm. However, the farmers lacked digital and data literacy skills to access, manage and use data effectively and independently. Specialist expertise for data translation was required, and support and resourcing for the farmers to acquire data capabilities was limited. This ‘data divide’ between the generation and application of farm data was complicated by broader issues raised by participants about data ownership, portability, privacy, trust, liability, and sovereignty, which have been observed internationally. The paper raises questions about the level of expertise farmers should be expected to attain in the transition to digital farming, who in the ecosystem is best placed to fill this ‘data divide’, and what interventions are necessary to address significant barriers to adoption in rural communities. It also highlights a tension between farmers’ $2 as decision-makers on their own properties and their $2 on digital technologies – and the ecosystems that support uptake of digital AgTech – to inform on-farm decisions.