A system, method, and computer-readable medium are disclosed for implementing a cybersecurity system having a digital certificate reputation system. At least one embodiment is directed to a computer-implemented method executing operations including receiving a communication having an internet protocol (IP) address and a digital certificate at a device within the secured network; determining whether the IP address is identified as having a high-security risk level; if the IP address has a high-security risk level, assigning a security risk level to the digital certificate based on the security risk level of the IP address; and using the security risk level for the digital certificate in executing the one or more security policies. Other embodiments include corresponding computer systems, apparatus, and computer programs recorded on one or more computer storage devices.