In this paper, we present a comparison of two rural landscapes in the southeast of the Iberian Peninsula, where the dynamics of occupation have differed since the end of the ancient world in terms of both the degree of resilience of settlements and the land use. Our purpose was to explore the social, political, economic, and environmental factors that could explain why there has been a long-term cross-cultural occupation of some resilient sites and landscapes for almost a millennium, while there have been only very specific temporary occupations in other areas. The first part of this paper describes the archaeological investigations carried out by means of intensive survey methods, geophysics, and some excavations in peripheral and peri-urban spaces. In the second part, we reflect on whether the use of the same methodology in all cases allows us to compare and understand what makes societies sustainable (or not) over time through their archaeological record.