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The introduction of sustainable and renewable energy sources into traditional networks will be limited if we continue to use inappropriate methods for security analysis. The probabilistic nature of variable and non-schedulable renewable generation is not well represented in current on-line security assessment schemes. This paper presents a novel method of analyzing and comparing system security schemes and provides initial results of one such scheme. It does so by dynamic simulation of Monte Carlo samples on the IEEE Reliability Test System (IEEE-RTS). It aims to provide information on both how often and how badly the system security scheme fails. After testing on the IEEE-RTS it can be shown that there are credible failures that N-1 does not consider. It highlights the need for a new security assessment scheme that goes beyond a small deterministic set of test cases.