An electronic mail ("e-mail") system is described that enforces authentication or encryption to/from Mail Transfer Agents and from Mail User Agents. In one embodiment, for example, an electronic mail (e-mail) system is described that comprises: a message transfer agent (MTA) available for a client to connect to; program logic for authenticating the client, through use of a certificate, in order to identify the client as approved for establishing a secured connection with the MTA; program logic for establishing a secured connection between the client and the MTA in instances where the client can be authenticated; program logic for testing encryption strength of the secured connection; and program logic for terminating the secured connection in instances where the secured connection has inadequate encryption strength.