Smallholder African systems operate in harsh environments of climate changes, resource scarcity, environmental degradation, market failures, and weak public and/or donor support. The smallholders must therefore be prepared to survive by self-provisioning. This chapter examines the nature of vulnerability of smallholders' food security caused by above conditions in the context of system dynamics modelling. The results show that smallholders co-exist whereby the non-resilient households offer labor to the resilient households for survival during turbulent seasons irrespective of the magnitude of external shocks and stressors. In addition, non-resilient households cannot be liberated by external handouts but rather through building their capacity for self-reliance. Using simulation evidence, this chapter supports the claim that in the next decade only resilient households will endure the extreme situations highlighted above. Future research that employs similar systems-based methods are encouraged to explore how long-term food security among smallholders can be sustained.