Measurements taken on a historical dike in the Netherlands over one year showed that interaction with the atmosphere led to oscillation of the piezometric surface of about 0.7 m. The observation raised concerns about the long-term performance of similar dikes and promoted a deeper investigation of the response of the cover layer to increasing climatic stresses. An experimental and numerical study was undertaken, which included an investigation in the laboratory of the unsaturated behavior of a scaled replica of the field cover. A sample extracted from the top clayey layer in the dike was subjected to eight drying and wetting cycles in a HYPROP™ device. Data recorded during the test provide an indication of the delayed response with depth during evaporation and infiltration. The measurements taken during this continuous dynamic process were simulated by means of a finite element discretization of the time-dependent coupled thermohydraulic response. The results of the numerical simulations are affected by the way in which the environmental loads are translated into numerical boundary conditions. Here, it was chosen to model drying considering only the transport of water vapor after equilibrium with the room atmosphere, while water in the liquid phase was added upon wetting. The simulation was able to reproduce the water mass balance exchange observed during four complete drying–wetting cycles, although the simulated drying rate was faster than the observed one. The numerical curves describing suction, the amount of vapor and temperature are identical, confirming that vapor generation and its equilibrium is control the hydraulic response of the material. Vapor generation and diffusion depend on temperature; therefore, correct characterization of the thermal properties of the soil is of paramount importance when dealing with evaporation and related non-steady equilibrium states.