Europe’s traditional cultural landscapes have undergone significant land-use and land-cover changes in the past 50 years. Land-cover inventories facilitate the quantification of the conversion from one land-cover unit to another. However, they often fail to detect fine-grained modifications that occur within one land-cover category. This study aims to detect such land-cover modification at two farms in a traditional agroforestry system in Spain. The focus is on the dynamics of holm oak (Quercusilex) stands as the key landscape element of dehesas. Aerial photography and satellite imagery were used to measure tree expansion and regression between 1956 and 1984, and between 1984 and 2003. With < 0.01–0.03% of the tree cover recruited per year, current recruitment seems too low by a factor of 10 to 50 to maintain existing stand densities. Recruitment rates between 1956 and 2003 were slightly higher, but loss rates were dramatically higher on privately owned land compared to common property. Although higher grazing pressure on common property may have inhibited recruitment, the complexity of land tenure can act as a barrier to forest clearing. The synopsis of high loss rates from 1956 to 1984, low loss rates from 1984 to 2003, and low recruitment rates over both periods indicates that deliberate oak cutting has stopped, but that the problem of regeneration failure still remains unresolved. The analysis of oak expansion and regression as a precursor of land conversion can provide a powerful tool for subtle structural changes and can be used as an early warning system before conversion becomes visible.