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In this paper, we present a joint approach to automate software security testing using two approaches, namely team edit automata (TEA), and the security chaining approach. Team edit automata is used to formally specify the security properties to be tested. It also composes the monitoring engine of the vulnerability detection process. The security chaining approach is used to generate test-data for the purpose of proving that a vulnerability is not only present in the software being tested but it is also exploitable. The combined approach provides elements of a solution towards the automation of security testing of software.