The massive integration of intermittent renewable generation and the increasing variability of demand raise concerns about the high level of uncertainty in the security assessment of power systems. In this context, the main contribution of this study is the proposal of a new definition of contingency criticality, which is based on the violation probability of the voltage security margin (VSM) while considering correlated uncertainties in both system loads and wind power generation. From this new definition, a contingency ranking can be derived and used to determine preventive control actions. To calculate this probability for each contingency, a new approach based on the cross-entropy (CE) method is developed and applied. The CE method is well-suited to handle high levels of uncertainty, as it typically provides faster and more accurate results compared with Monte Carlo simulation, particularly for cases with low violation probabilities of the VSM. Another innovative feature of this approach is the consideration of correlated uncertainties through the use of multivariate normal distributions and Gaussian copulas. Furthermore, the proposed definition is implemented using a formulation that is capable of detecting either saddle-node or limit-induced bifurcations to accurately identify the maximum loadability point. A proof of concept is presented for a comprehensive explanation of the proposed definition, followed by an application of this definition to the IEEE 118-bus test system. The findings of this paper highlight the need to carefully select critical contingencies for voltage security assessment in the context of increasing uncertainties.