A method and system of applying a security vulnerability assessment of a software program. The method comprises directing, from a security assessing server, to a software program under execution, a plurality of attack vectors, diagnosing a set of results associated with the software program under execution as comprising a security vulnerability, the set of results produced based at least in part on the plurality of attack vectors, and assessing a monetary premium of a risk insurance policy merited by an enterprise based at least in part on a level of control ceded to an attacker in accordance with the set of results.