Farm abandonment and over-extensification trends in less-favored livestock breeding areas in the Mediterranean have led to socio-environmental issues that are difficult to assess and address, due to the characteristics of these areas (e.g., poor data availability and reliability). In a study case that presents many of the characteristics common to these areas, we combine qualitative and quantitative approaches to assess (i) the relationship between livestock production and land-cover change and (ii) the drivers of farmer decisions, concerning the types of livestock they breed. We show that the Common Agricultural Policy’s objective of open-landscape preservation cannot be achieved through the observed livestock management practices, with the most heavily CAP subsidy-dependent activities (e.g., suckler-cow breeding) having one of the weakest contributions to this objective. We also econometrically show that suckler-cow breeding is more likely to be adopted as a complementary or main activity in farms facing a labor scarcity and land abundance context. These results complement the literature and contribute to the discussion regarding the design of CAP support for less-favored Mediterranean areas.