This paper focuses on the Deep Seated Gravitational Slope Deformation (DSGSD) affecting Val Roncaglia (Northern Italy). Based on the state of the art about DSGSD, the study area was characterized from geologic, tectonic, geomorphological, and hydrogeological points of view in order to reconstruct the conceptual model of the slope (geometry, geomaterials and their properties). Moreover, based on the available monitoring data, the landslide kinematics was pointed out together with its possible evolution and the related triggering factors. Then, the conceptual model of the landslide was implemented into a 2D numerical stress-strain model, which was calibrated based on monitoring data of displacement arising from inclinometric probes. Finally, the numerical model was employed to simulated the slope evolution for different geomechanical and hydrogeological conditions in order to find out the factors that affect stability the most. The results of the present study provide a comprehensive understanding of the causes and dynamics of the DSGSD affecting the Val Roncaglia slope and give insights useful for the general comprehension of this kind of large phenomena, therefore enanching a proper management of the related risks.