This chapter aims at providing an overview of the diversity of agroecological conditions, features of main farming systems, agricultural land use, its dynamics and drivers during the last two decades as well as major threats in ten countries of southern Africa (SA10). Based on this, we attempt to identify the resultant challenges for sustainable land management and outline potential interventions with a focus on smallholder farmers. By analyzing cropland dynamics during 2000–2019, we show how land use has been shaped by climate, demographic development, economic imperatives and policy realities. Concrete examples of these complex interactions illustrate both considerable shrinkage in South Africa and Zimbabwe or expansion of cropland in Mozambique and Zambia. During the past 20 years, cropland increased by 37% on average across SA10 mainly at the expense of forestland—showing huge spatiotemporal heterogeneity among countries. Most smallholders face shrinking farm size and other resource limitations that have resulted in soil nutrient mining and low agricultural productivity—a highly unsustainable situation. We conclude with an outlook on potential transformation pathways (“TechnoGarden” and “AdaptiveMosaic”) for the near future and thereby provide a frame for further studies on sustainable land management options under given local settings.