A monitoring system for a corporate network includes a client that exchanges information with a target server to establish an SSL communication channel through which cryptographically protected data is exchanged between the client and the target server using an SSL protocol and a monitoring server through which the cryptographically protected data is routed as part of its exchange between the client and the target server. The client sends enabling data to the monitoring server that enables the monitoring server to read the cryptographically protected data received at the monitoring server as decoded cryptographically protected data. The monitoring server also analyzes the decoded cryptographically protected data to determine if it is suspect data, and at times when the monitoring data determines that the decoded cryptographically protected data is suspect data the monitoring server prevents the transmission of the cryptographically protected data between the client and the target server.