Increasingly, digitization is impacting upon work and life in a range of ways, yet the influence of digitization within farming processes has not been well examined. This chapter aims to fill this gap by looking at the practices of Kenyan farmers who use digital technologies in managing their farm from a distance, a practice termed “telephone farming”. Telephone farming involves using digital artifacts such as mobile phones to manage and coordinate farming processes from a distance and as such migrating some of the traditional physical management activities of farming to virtual environments. Drawing on the theory of affordances, this chapter examines how an emerging category of “telephone farmer” has been able to virtualize key farming processes and farm at distance, and with what benefits and consequences. Preliminary findings from interviews with 25 Kenyan telephone farmers suggest that material features of mobile phones offer three technology affordances related to spatiality, relationality, and contextuality, which enables telephone farmers to virtualize some farming processes along the value chain. This work in progress suggests that a new pathway of farming is emerging in Kenya, which involves the use of mobile phones to carry out farming as an enterprise remotely. Understanding the context behind these trends and the challenges being faced by African farmers embracing agro-food technologies sheds light on the factors that will contribute to sustainable regenerative food system of Africa in the future.