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The fourth agricultural revolution (or Agriculture 4.0) promises to lead the way to an agricultural sector that is smarter, more efficient, and more environmentally and socially responsible. Digital and data generating tools are seen as critical enablers for this transformation and are expected to make farming more planned, predictive, productive, and efficient. To make this vision a reality, agricultural producers will first adopt and use the technologies, but this is easier said than done. Barriers such as limited digital infrastructure, low (digital) literacy, low incomes, and socio-cultural norms are major factors causing sub-optimal access to and use of digital technologies among smallholder farmers. Beyond these use challenges of access and usage, limited evidence exists to support the notion that extant digital technologies add enough value to provide substantial benefits for targeted farmers. In this paper, we unravel insights from a six-year digital agriculture innovation project which was implemented to develop and deploy multi-modal digital tools for the control of a major banana disease. By reaching over 272,200 smallholder farmers in Rwanda through a smartphone app, unstructured supplementary service data, a chatbot, and other ancillary channels, we assessed various assumptions regarding intrinsic motivation, incentives, and skills retention among the target digital tool users. These insights suggest that embedding digital innovation requires intentional user-engagement, proper incentivization of next-users, and targeted communication to foster adoption. We present ten (10) salient, but non-exhaustive, lessons to showcase the realities of developing and delivering digital tools to farmers over an extended period, spanning from ideation, development, and testing to scaling stages. The lessons are relevant for a broad audience, including stakeholders across the digital innovation space who can utilize our experiential notes to guide the development and deployment of similar digital innovations for improved outcomes in smallholder farming systems.