Abstract: Current security tools in the marketplace fall into different categories: Security Enforcement Tools which identify and block malicious activity, and Security Vulnerability Testing Tools which scan and identify security threats within an organisation. The disclosure describes Silently (invisible to the user) but as if it is the user, within the User's Context, Executing applications to test whether third party security products and security settings exhibit the correct behaviour. The application can continuously perform a test(s) and expects a security product to behave in a certain way, records the result of the test(s) and reports those results.