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Integration of wind power generation into the grid raises a need to re-consider current power system planning and operation approaches due to variable nature of the wind power. This paper presents a probabilistic approach in power system security assessment with significant wind power penetration within operational context taken into account the uncertainty of wind. An example using a modified IEEE 14-bus system is used to illustrate the advantages of the proposed probabilistic approach compared with the traditional deterministic approach. The results show that the probabilistic approach provides a better view on the system security leading to better operational decision-making.