System and method for monitoring the security of computing resources. A server agent and client agents can be deployed to provide a method and a means for monitoring security-related settings for a plurality of computing systems deployed throughout an enterprise. The status of each setting can be recorded, and these results can be used to produce a compliance report for the computing system, as well as reports for groups of computing system or the entire enterprise. The reports or portions of a report or reports can be provide to users of the system via a Web site, Email alerts, or any other suitable mechanism. A compliance score for a system or collection of systems can be calculated and used and/or displayed as part of the reports that are generated.