The digital transformation of agriculture promises technical solutions for present and future challenges. However, it cannot be assumed that such promises will automatically lead to implementation of the technologies, nor if the technologies meet the user expectations. To this end, the authors conducted a novel review and characterization of over 200 digital tools for fruit cultivation by on-farm functions and 23 interviews with stakeholders related to fruit cultivation in the case-study region of Lake of Constance, Germany. Results indicate strengths and weaknesses in the development of digital tools. A cross-analysis of the available tools, stakeholder expectations, and implemented tools indicates commonalities and discrepancies. Tool characteristics that meet stakeholder expectations and adoption by farmers are identified, as well as those that may be impacted greatest by the reported barriers. An uneven distribution of knowledge on digitalisation in this sector was evident among stakeholders. The authors identify opportunities for technological development and recommendations to support a user-oriented transformation. Unsuitable tool development and an uneven distribution of digital knowledge in the fruit production industry could lead to a consequential sectoral, regional, and/or national digital divide between those with access to cutting-edge technologies and those without. To further improve the sustainability and resilience of food production, technological development must take into account the needs of stakeholders and support a more user-orientated strategy to support the transformation. Further research on stakeholders' perspectives on digital innovations is needed to investigate if the findings match to other fruit growing regions in Germany and abroad. © 2024 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.