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The mechanisms controlling the onset of minor slope instability at the edges of rocky plateaux exhibiting lateral spreading phenomena are yet to be fully understood. Hypotheses have recently been introduced to explain the influence of groundwater within these plateaux on geomorphological processes leading to slope instability. We present a back analysis of a recent landslide which occurred on 27th February 2014 in the town of San Leo, Italy. The role of the softening of basal clay shales and erosion due to seepage is investigated using finite element geomechanical models. Both processes were observed in the field and are related to groundwater discharging along the contact between the rocky slab and the clay-rich substratum. Fracture propagation paths involving pre-existing discontinuities and intact rock bridges failure were simulated using a simplified discrete fracture network (DFN) model coupled with a Voronoi polygonal mesh approach. Model results allow the failure to be classified as a secondary toppling phenomenon. Moreover, a critical amount of undermining was indicated by the models agreeing with field observations made prior to the failure. Based on the modelling results, an interpretation of the overall mechanism inducing failures at the edges of fractured rock slabs is given. In particular, the inter-relationships between groundwater flow and geomorphic processes acting within the rock masses are presented.