In coal room and pillar, and pillar extraction panels, the sidewall conditions were investigated based on underground measurements and numerical simulations. Three-dimensional linear elastic models provided a useful and quick prediction of the amount of sidewall spalling. However, more complex constitutive models were required to simulate more accurately the extent of fracturing and its effect on the stress re-distribution. The input parameters of a Mohr-Coulomb model were determined by back-analysis of underground measurements, and the effect of the depth of the workings and the time dependent occcurrence of coal pillar fracturing were analyzed.