Soil erosion is a global environmental problem and a pervasive form of land degradation that threatens land productivity and food and water security. Some of the biggest sources of sediment in catchments are cultivated and abandoned lands. However, the abandonment of cultivated fields is not well-researched. Our study assesses the level of degradation in cultivated and abandoned lands using a case study in South Africa. We answer three main questions: (1) What is the extent of crop field degradation on used, partly used, and abandoned fields? (2) What are the drivers of field abandonment in relation to land degradation? (3) Can proposed sustainable land management interventions tackle the dynamics of land abandonment and associated degradation? To answer these questions, cultivated and abandoned lands were mapped in a pilot catchment with ArcGIS tools and assigned severity codes and classified according to status, degradation, and encroachment. Systems diagrams were developed to show the interactions between agricultural land use and the level of degradation and leverage points in the system, with interventions assessed via a multi-criteria analysis. The results revealed that 37% of the total mapped area of croplands in the pilot site was abandoned and 20% of those lands were highly degraded. We argue that the innovative application of systems thinking through causal loop diagrams (CLDs) and leverage point analysis, combined with spatial and multi-criteria analyses, can assist with planning SLM interventions in similar contexts in the developing world.