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Land degradation is a process negatively affecting environmental sustainability and requires permanent monitoring for understanding its nonlinear trajectories of change over time and space. Environmental sustainability is linked to a theoretical definition of dynamic balance among various components contributing to the ecosystem quality and functioning. The aim of this study is to develop a diachronic analysis (1960–2010) of the equilibrium/disequilibrium condition of key environmental factors (climate, soil, vegetation, land-use) influencing the vulnerability of land to degradation in a Mediterranean country experiencing processes of desertification at the local scale. Three indicators of components’ balance have been proposed and tested for spatial and temporal coherence. Land classified at high vulnerability and low component’s balance has been identified as a possible target for mitigation strategies against desertification; the surface area of this class increased rapidly during 1960–2010 and concentrated in high-intensity agricultural lowlands of northern Italy.