A computer assisted method for detecting encrypted tunneling or proxy avoidance is presented. The method may include electronically receiving information from a proxy server, extracting information regarding a CONNECT function of Hyper Text Transport Protocol (HTTP) from the electronically received information, determining at least one destination to which the extracted information regarding the CONNECT function of HTTP corresponds and attempting to negotiate a standard HTTPS session with each of the at least one destination. Further, the computer assisted method may further include, for each of the at least one destination, determining whether the destination is hosting an encrypted tunneling or proxy avoidance application, wherein such a determining may be based on characteristics of an Secure Socket Layer (SSL) certificate associated with the destination or a response received from the destination over a TCP/IP connection.