In this study, the authors compare analytical voussoir-analogue based solutions with numerical ones, implemented through 2D distinct-element-method based simulations, in the context of the application of these analyses to the design of underground rooms in bedded rock masses, based on the conditions found in a particular underground room and pillar carbonate mine. Some guidelines are given on how to derive key parameters required for both approaches based on laboratory rock testing, rock mass characterization, and in-situ observations. Particular attention is devoted to quantifying the influence of the roof span, bedding dip, and the occurrence of an overload (associated with highly-fractured beds over the already-detached roof). The performance of the analytical solution in calculating the maximum deflection and compressive stresses within a beam is verified through several 2D numerical models, which, in turn, are capable of capturing the instability mechanisms occurring in the mine.