This study explores the hydrogeological conditions of a landslide-prone hillslope in the Upper Mosel valley, Luxembourg. The investigation program included the monitoring of piezometer wells, hydrogeological field tests, analysis of drillcore records, and geophysical surveys. Monitoring and field testing in some of the observation wells indicated very pronounced preferential flow. Electrical resistivity tomography (ERT) and self-potential geophysical methods were employed in the study area for exploration of the morphology of preferential flowpaths. Possible signals associated with flowing groundwater in the subsurface were detected; however, they were diffusively spread over a relatively large zone, which did not allow for the determination of an exact morphology of the conduit. Analysis of drillcore records indicated that flowpaths are caused by the dissolution of thin gypsum interlayers in marls. For better understanding of the site’s hydrogeological settings, a 3D hydrogeological model was compiled. By applying different subsurface flow mechanisms, a hydrogeological model with thin, laterally extending flowpaths embedded in a porous media matrix showed the best correspondence with field observations. Simulated groundwater heads in a preferential flow conduit exactly corresponded with the observed heads in the piezometer wells. This study illustrates how hydrogeological monitoring and geophysical surveys in conjunction with the newest hydrogeological models allow for better conceptualization and parametrization of preferential flow.