This chapter examines desertification risk within Spanish olive cultivation, a dominant Mediterranean agricultural system. It defines four main orchard typologies: traditional (steep slopes/flat-rolling landscapes), intensive, and super-intensive, highlighting a significant productivity gradient between them. The primary sustainability threats identified are soil degradation (primarily water erosion and low organic carbon) and pressure on water resources due to irrigation expansion. Historically, soil management practices maintaining bare soil accelerated erosion, with studies showing losses quadrupling (e.g., from ~20 to ~80 t ha−1 year−1) post-1960s mechanization. Research demonstrates that temporary cover crops (CV) significantly reduce erosion and improve topsoil quality compared to tillage (LC) or no-till herbicide (NLH) management. However, CV implementation carries a significant risk of yield loss due to water competition if not managed properly. Irrigation, largely deficit-based, has increased yields but intensifies pressure on water resources, especially in vulnerable areas, potentially worsening with climate change. Despite this, economic constraints on farms and technical advisory gaps hinder widespread adoption of conservation practices. Addressing desertification requires integrated farm-level solutions: optimizing cover crop use, enforcing water governance, supporting sustainable rainfed production, compensating land-use reversion, and developing drought-resistant varieties. The diversity of olive systems requires tailored strategies combining socioeconomic and technical measures.