This manuscript presents a questionnaire-based study aimed to provide a detailed analysis on the different soil management carried out by olive farmers in two representative olive-growing areas in southern Spain (Cordoba and Estepa), their perceptions on cover crop use and the possible influence of the different types of farms and farmers’ typologies on these perceptions. Our results show a relatively large variability of soil management, with fourteen options, as a result of a combination of different alternatives for bare soil and cover crops with the use or not of pruning residues, but with a great similarity between both areas. The results indicate a high adoption of soil conservation measures in the two study areas, with 63% of farmers using cover crops and 80% a mulch of pruning residues, higher than that reported in previous studies in Southern Spain, and a trend of lower use of these techniques by less experienced and younger farmers. This high penetration of soil conservation measures resulted in a significant reduction of soil erosion risk, as indicated by the relatively low values for the cover and management factor (C) of RUSLE, also calculated and presented in this study, but also the possibility of focusing further efforts on farmers with less experience. Our results indicate the persistence of a minor, but relevant, percentage of farmers using bare soil management (37%) and no mulching (20%), with a moderate concern on the impact of soil erosion on soil degradation and provision of ecosystem services. This suggests the need to concentrate efforts also on this cluster of farmers to enhance the success of what seems to be a remarkable expansion of the use of soil conservation measures in recent decades in Southern Spain, but also in similar areas in the Mediterranean basin.