Several standards and best practices have been proposed for critical infrastructure protection. However, the scale and complexity of critical infrastructure assets renders manual compliance checking difficult, if not impossible. This paper focuses on the automated assessment of security compliance of electrical power grid assets. A security model based on predicate calculus is used to express infrastructure elements (e.g., devices, services, protocols, access control implementations) as "acts" and security standards and best practices as "rules" that specify constraints on the facts. A tool chain is applied to automatically generate the security model from specifications and to check compliance with standards and best practices. The tool chain also supports the visualization of network topology and security assessment results to reveal possible points of attack.