Software Hardening against memory safety exploits can be achieved from the silicon, up to the software, with both compilers and operating systems features. Unfortunately, due to the growing evolution of attacks, security architects have no guarantees, at an early stage of the development, that defenses will match the security needs and overcome the targeted threats. In addition, after product release, it is difficult to evaluate the architecture performance against new threats. This paper presents a dynamic analysis technique that allows the evaluation of the security profile of a given architecture during design exploration. The method is designed to highlight and quantify the security threats covered by the countermeasures embedded at any level of a given architecture. The provided results will help for protection evaluation, classification, and architecture choices. The method comes with a tool that implements this approach and has been applied to several architectures. This tool helps to classify architecture along with its alternatives thanks to metrics.