A system and method that enables the configuration of computer security of a subject entity at a computer security platform includes collecting a corpus of security data relating to one or more security configurations of the network maintained by the subject entity, analyzing the corpus of security data to determine one or more vulnerability factors and one or more security behaviors relating to the subject entity, generating a security assessment for the subject entity based on the analysis of the corpus of security data, generating a computer security policy for the security environment based on the security assessment, and providing, to the subject entity, a security policy recommendation incorporating at least a subset of the generated computer security policy.