The role of the hydraulic conditions in the stability of an abandoned mine is investigated at the interface of two materials characterized by a high contrast of both intrinsic permeability and mechanical strength. Two dimensional Finite Element simulations in the framework of partially saturated porous media have been performed. The degradation is modelled by the plastic deviatoric strain defined by the Drucker-Prager constitutive law. The hydraulic conditions are determined by the history cycles of the mine: (a) during the mine exploitation, the rock mass is desaturated due to the ventilation of the chamber; (b) at the end of the mining operations, the rock is resaturated either from the chamber owing to the change in its atmospheric relative humidity or owing to the re-equilibrium of the rock mass interstitial pressure. The yielding of the roof begins during the first phase and the induced failure zone is extended due to the increase in the water pressure at the chamber during the resaturation process. Besides, the weathering process of the hydraulic properties is assessed with the introduction of a preliminary coupled permeability/damage model. The latter shows an acceleration of the degradation process compared to the non-coupled permeability/damage model.