Abstract: A cryptographic-enabled messaging system providing a “Policy Management Agent” is described. The Policy Management Agent works in conjunction with a standard mail server, such as an SMTP (Simple Mail Transport Protocol) mail server, to ensure that incoming and outgoing e-mail adheres to the policies that are specified for a given site. Specifically, the Agent intercepts e-mail normally bound for the mail server and checks to make sure that it conforms with policies configured for one's site (e.g., corporate site). If the e-mail adheres to the policies for the site, it is forwarded to the mail server where it is routed to the intended recipient. If the e-mail does not adhere to the policies specified for the site, a message of one's choosing is sent to the client indicating that the e-mail was rejected. In an exemplary embodiment (e.g.