From the factory to the farm, industrialization and technological change has been a frequent purview in human life. A changing policy and regulatory sphere combined with the consistent labor shortage and the associated decrease in harvesting facing the Washington Apple Industry as well as other tree fruit industries has led to the development of new agricultural technology (AgTech) aimed at combating these challenges. Using interviews with the engineers developing these tools, this study examines the economic, physical, and social and cultural barriers currently preventing the wide scale implementation of an automated apple harvester and AgTech more generally. While some engineers, growers, and workers express a desire to work with and integrate these tools, the consistent financial challenges facing farmers combined with the lack of “technology ready” on-farm infrastructure, the struggle for the development of commercially viable technology, and both public and worker resistance present barriers to their integration on farm. This study also considers the implications of such technology on the labor force and on-farm jobs and work processes as well as the varied reception and opinions to these tools among stakeholders, groups, and industries. Findings suggest that while these barriers are unlikely to be fully overcome, interdisciplinary work, multi-level industry participation, and cross-sector collaboration are necessary to not only address the barriers to adoption of these tools but to prepare the industry for the changes likely to arise from automation.