A network security assessment engine can assess security on a remote computer network. Agent programs on computing devices on the remote network can execute security tests. The network security assessment engine receives security test results produced by the security tests. The network security assessment engine can determine security test scores based, at least in part, on the security test results. The network security assessment engine can determine an overall network security score based, at least in part, on the security test scores and present the overall network security score. As an example, a network services provider can utilize the network security assessment engine to provide an adaptive, expressive scoring mechanism, allowing the network services provided to more efficiently digest, assess, and report network anomalies within a multitenant context.