This paper presents an approach for assessing, in operation planning studies, the security of a large-scale power system by decomposing it into elementary subproblems, each one corresponding to a structural weak-point of the system. We suppose that the structural weak-points are known a priori by the system operators, and are each one described by a set of constraints that are localized in some relatively small area of the system. The security analysis with respect to a given weakpoint thus reduces to the identification of the combinations of power system configurations and disturbances that could lead to the violation of some of its constraints. We propose an iterative rare-event simulation approach for identifying such combinations among the very large set of possible ones. The procedure is illustrated on a simplified version of this problem applied to the Belgian transmission system.