Digital agriculture is widely promoted as a transformative pathway to achieving food security, productivity, and climate resilience across agri-food systems. Yet in practice, its implementation often reflects conflicting priorities, uneven adoption, and unresolved questions around inclusion, equity, and environmental sustainability. This paper examines how digital agriculture is unfolding in Kenya, one of the most active hubs of agri-digital innovation in sub-Saharan Africa, through a structured review of global academic literature, national policies, and emerging digital initiatives. Framed against broader debates on sustainable agri-food system transformations, the study investigates the types of agricultural development trajectories digital technologies currently support, the ways these technologies are shaped by and involve different actors, and the implications for equity, power, and environmental outcomes. Findings reveal a strong emphasis in Kenyan policies on productivity and commercialization, with digital technologies frequently embedded in efficiency-oriented and market-driven models. However, the review also identifies promising but under-recognized initiatives described as “seeds of change” that reflect inclusive, participatory, and agroecological digital practices. These include platforms that integrate local knowledge, prioritize the needs of smallholder farmers, and redistribute power within agri-food systems. Despite their potential, such efforts remain marginal to dominant science, technology, and innovation strategies due to regulatory gaps, fragmented governance, and limited institutional support. This study contributes to ongoing debates on the direction of agri-food system transformations by aligning Kenya's experiences with global narratives and identifying pathways toward more equitable and sustainable digital futures. It proposes a research and practice agenda to support the co-design and scaling of inclusive digital tools, while calling for institutional reforms to ensure digitalisation promotes equity, resilience, and farmer agency. The paper argues that realizing the transformative potential of digital agriculture requires enabling governance structures, iterative learning mechanisms, and inclusive innovation ecosystems.