Wellbore drilling operations frequently entail the combination of a wide range of variables. This is underpinned by the numerous factors that must be considered in order to ensure safety and productivity. The heterogeneity and sometimes unpredictable behaviour of underground systems increases the sensitivity of drilling activities. Quite often the operating parameters are set to certify effective and efficient working processes. However, failings in the management of drilling and operating conditions sometimes result in catastrophes such as well collapse or fluid loss. This study investigates the hypothesis that optimising drilling parameters, for instance mud pressure, is crucial if the margin of safe operating conditions is to be properly defined. This was conducted via two main stages: first a deterministic analysis—where the operating conditions are predicted by conventional modelling procedures—and then a probabilistic analysis via stochastic simulations—where a window of optimised operation conditions can be obtained. The outcome of additional stochastic analyses can be used to improve results derived from deterministic models. The incorporation of stochastic techniques in the evaluation of wellbore instability indicates that margins of the safe mud weight window are adjustable and can be extended considerably beyond the limits of deterministic predictions. The safe mud window is influenced and hence can also be amended based on the degree of uncertainty and the permissible level of confidence. The refinement of results from deterministic analyses by additional stochastic simulations is vital if a more accurate and reliable representation of safe in situ and operating conditions is to be obtained during wellbore operations.