The strength decay that occurs in the post-peak stage, under low confinement stress, represents a key factor of the stress–strain behaviour of rocks. However, for soft rocks this issue is generally underestimated or even neglected in the solution of boundary value problems, as for example those concerning the stability of underground cavities or rocky cliffs. In these cases, the constitutive models frequently used in limit equilibrium analyses or more sophisticated numerical calculations are, respectively, rigid-plastic or elastic–perfectly plastic. In particular, most of commercial continuum-based numerical codes propose a variety of constitutive models, including elasticity, elasto-plasticity, strain-softening and elasto-viscoplasticity, which are not exhaustive in simulating the progressive failure mechanisms affecting brittle rock materials, these being characterized by material detachment and crack opening and propagation. As a consequence, a numerical coupling with mechanical joint propagation is needed to cope with fracture mechanics. Therefore, continuum-based applications that treat the simulation of the failure processes of intact rock masses at low stress levels may need the adoption of numerical techniques capable of implementing fracture mechanics and rock brittleness concepts, as it is shown in this paper. This work is aimed at highlighting, for some applications of rock mechanics, the essential role of post-peak brittleness of soft rocks by means of the application of a hybrid finite–discrete element method. This method allows for a proper simulation of the brittle rock behaviour and the related mechanism of fracture propagation. In particular, the paper presents two ideal problems, represented by a shallow underground cave and a vertical cliff, for which the evolution of the stability conditions is investigated by comparing the solutions obtained implementing different brittle material responses with those resulting from the assumption of perfectly plastic behaviour. To this purpose, a series of petrophysical and mechanical tests were conducted on samples of soft calcarenite belonging to the Calcarenite di Gravina Fm. (Apulia, Southern Italy), focusing specific attention on the post-peak behaviour of the material under three types of loading (compression, indirect tension and shear). Typical geometrical features representative of real rock engineering problems observed in Southern Italy were assumed in the problems examined. The numerical results indicate the impact of soft rock brittleness in the assessment of stability and highlight the need for the adoption of innovative numerical techniques to analyse these types of problems properly.