A cloud based system that facilitates inspection of secure content and inexpensively detects the presence of a Man-in-the-Middle attack in a client-server communication is disclosed. Through inspection of the server certificate, no Man-in-the-Middle attack between server and the system is ensured; through inspection and designation of the client certificate, absence of a Man-in-the-Middle attack between the cloud based system and the client is ensured. In this way, the cloud based system can perform its usual policy enforcement functions with respect to secure content while avoiding Man-in-the-Middle attacks.