ICT-driven digital tools to support smallholder farmers are arguably inevitable for agricultural development, and they are gradually evolving with promising outlook. Yet, the development and delivery of these tools to target users are often fraught with non-trivial, and sometimes unanticipated, contextual realities that can make or mar their adoption and sustainability. This article unfolds the experiential learnings from a digital innovation project focusing on surveillance and control of a major banana disease in East Africa which is being piloted in Rwanda.