A prevention-based network auditing system includes a central compliance server storing both natural language policy documents and machine-processable policy rules in an audit repository. The compliance server provides a client-side user interface allowing a user to easily generate a machine-auditable policy by selecting/generating a natural language policy source document, and linking the applicable machine-processable policy rules to the applicable portions of the source document. The selected machine-processable policy rules are then applied to information gathered about the network during a scheduled network audit session for efficiently and systematically determining whether policy violations and/or vulnerabilities exist.