Abstract: In one embodiment, a transparent relay receives diverted e-mail communications between an e-mail client and an e-mail server. The transparent relay may be configured to examine the e-mail communications for network security policy violations. E-mail communications that do not violate a network security policy may be relayed to their intended destination. Policy actions, such as discarding or redirection, may be performed on those that violate one or more network security policies. The transparent relay may include a pair of communications interfaces running in promiscuous mode, one for downstream communications and another for upstream communications. The transparent relay may decompose a network communication protocol to look network security policy violations.