Systems, methods, and computer program products for evaluating situational awareness of a cyberspace operational environment in a security control server in connection with a cyber-liability insurance transaction. The system may include a security control server that generates a model representing a cyber-liability insurance transaction. The security control server may further generate a ranked list of recommended security controls that are designed to reduce cyber-risks, and thereby the premium, associated with the cyber-liability insurance transaction model. Additionally, the security control server may continuously and automatically monitor one or more security controls implemented by a cyber-liability insurance consumer to insured information technology assets to evaluate compliance with the cyber-liability insurance transaction model.