A system and method for generating comprehensive security profiles and ratings for organizations that takes into account the organization's infrastructure and operations in generating the profile, and the context and purpose of the rating to be generated related to the profile. The system and method may further comprise gathering data about the totality of the organization's infrastructure and operations, generating a cybersecurity profile using active and passive internal and external reconnaissance of the organization to determine cybersecurity vulnerabilities and potential impacts to the business in light of the information gathered about the organization's infrastructure and operations, and generating cybersecurity scores and ratings that take into account all of the above information, plus the context and purpose of the score or rating to be generated based on the cybersecurity profile.