The stability of high rock slopes is largely controlled by the location and orientation of geological features, such as faults, folds, joints, and bedding planes, which can induce structurally controlled slope instability. Under certain conditions, slope kinematics may vary with time, as propagation of existing fractures due to brittle failure may allow development of fully persistent release surfaces. In this paper, the progressive accumulation of brittle damage that occurred prior to and during the 2014 San Leo landslide (northern Italy) is investigated using a synthetic rock mass (SRM) approach. Mapping of brittle fractures, rock bridge failures, and major structures is undertaken using terrestrial laser scanning, photogrammetry, and high-resolution photography. Numerical analyses are conducted to investigate the role of intact rock fracturing on the evolution of kinematic freedom using the two-dimensional Finite-discrete element method (FDEM) code Elfen, and the three-dimensional lattice-spring scheme code Slope Model. Numerical analyses show that the gradual erosion of clay-rich material below the base of the plateau drives the brittle propagation of fractures within the rock mass, until a fully persistent, subvertical rupture surface form, causing toppling of fault-bounded rock columns. This study clearly highlights the potential role of intact rock fracturing on the slope kinematics, and the interaction between intact rock strength, structural geology, and slope morphology.provide kinematic release to blocks that were previously nonremovable [9]. The accumulation of brittle damage is a critical component in the development of footwall failures and large-scale, biplanar, and compound rockslides, due to the formation of a highly damaged transition zone at the interface between active and passive blocks [10][11][12]. Additionally, intact rock fracturing may cause the failure of nondaylighting rock wedges, due to the formation of a basal rupture surface caused by failure of rock bridges and coalescence of brittle cracks [13].The strength of intact rock is orders of magnitude higher than discontinuities; therefore, strength and size of intact rock bridges between discontinuities have a great impact on the stability of rock slopes [9]. A small amount (0.1-10%) of rock bridges favorably distributed within a rock slope strongly increases the stability of the slope [14,15]. Despite the major significance of intact rock bridges in controlling the behavior of rock masses, their characterization remains an extremely challenging task [14], and the deterministic quantification of the rock bridges existing along a rupture surface may be undertaken only after failure occurs [15][16][17]. Discrete fracture networks (DFNs) are consequently being increasingly employed in rock engineering to investigate the distribution and dimensions of rock bridges using a stochastic approach [18].In this paper, the effects of intact rock fracturing on the evolution of the kinematic freedom of rock slopes are investigated using the 2014 San...