This present invention provides users with secure transparent electronic communication, allowing them to send and receive encrypted and/or signed messages with little or no user involvement. In various embodiments, the present invention provides a user with e-mail security via automated hierarchical techniques for transparently sending and receiving secure messages, and lowers the burden on administrators. Such a system can also manage cryptographic keys and certificates for the users, and creates such keys and certificates for the users when necessary. A server according to the present invention can intercept unsecured messages from a user, automatically transform those messages into secured messages, and transmit those secure messages to the intended recipients. The server can also automatically transform messages after the recipient sends a digital identity to the server and downloads the software necessary for transforming the secured messages back into readable messages (i.e., from ciphertext into plaintext). The server can further intercept an unsecured message from a user, search for a digital identity of the intended recipient, secure the unsecured message upon finding such a digital identity, and transparently send the secured message to the intended recipient.