This paper focuses on numerical modelling and back analysis of the Hell’s Mouth landslide to provide improved understanding of the evolution of a section of the north coast of Cornwall, UK. Discontinuity control is highlighted through the formation of a ‘zawn’ or inlet, the occurrence of two successive landslides and evidence of ongoing instability through opening of tension cracks behind the cliff top. Several integrated remote sensing (RS) techniques have been utilised for data acquisition to characterise the slope geometry, landslide features and tension crack extent and development. In view of the structural control on the rock slope failures, a 3D distinct element method (DEM) code incorporating a discrete fracture network and rigid blocks has been adopted for the stability analysis. The onset and opening of tension cracks behind the modelled slope failure zones has also been studied by analysing the displacements of two adjoining landslide blocks, between which, a joint-related tension crack developed. In addition, a sensitivity analysis has been undertaken to provide further insight into the influence of key discontinuity parameters (i.e. dip, dip direction, persistence and friction angle) on the stability of this section of the coastline. Numerical modelling and field observations indicate that block removal and preferential erosion along a fault resulted in the formation of the inlet. The development of the inlet provides daylighting conditions for discontinuities exposed on the inlet slope wall, triggering the initial landslide which occurred on 23rd September 2011. Numerical modelling, and evidence from a video of the initial landslide, suggests that the cliff instability is characterised by a combination of planar sliding, wedge sliding and toppling modes of failure controlled by the discrete fracture network geometry.