Digitization in agriculture is gaining momentum in developing countries. Digital technology aims to improve linkages along the agriculture value chain, thereby enabling farming communities and systems to recover from stresses and to absorb shocks to which farmers are exposed. However, there is the concern that digital technologies have not benefited the agricultural sector in a sustainable way. Stakeholders along the agriculture value chain need significant amounts of information to which they do not have access. In Mali, smartphones and earth observation data are used to support the development of land tenure information services and to improve agriculture statistics. To multiply business opportunities, the scope of the use of these technologies is being expanded to include agronomic advisory next-gen, franchised farm extension services. This article aims to evaluate these initiatives to further understand the way digitization could contribute to sustainable agricultural development and food security. In addition, it aims to determine how effective these technologies are under different conditions and how they can contribute to better sustainable development outcomes. Most evaluation studies of agriculture technology place emphasis on the economic aspects of productivity, profitability, and technical efficiency of the technology and the implications for users’ livelihoods. This study considers technology as a socio-technical phenomenon to understand the underlying processes that may enable or constrain the takeoff and the sustainability of technology. Furthermore, understanding these processes provides valuable theoretical and methodological insights to stakeholders for necessary adjustments of technology to given biophysical, socioeconomic, cultural, and cognitive conditions.