Email is a critical channel for communication and data movement in direct support of business processes. Yet, it also represents a major risk to information security. Both enterprise email (Outlook and Notes) and web-based email (Gmail, Hotmail, etc.) are high risk egress points that enterprises are finding increasingly difficult to monitor and control. Visibility, control and audit of information movement via email is also an important compliance requirement as part of regulatory laws including the Health Insurance Portability Act (HIPAA), Gramm-Leach-Bliley (GLB), the newly added HITECH Act, as well as many state enforced privacy laws.