Systems and methods for automated exchange of encryption certificates for transmitting and receiving encrypted email messages are disclosed. In one embodiment, a method of communicating an encrypted email message includes providing a recipient identifier, creating an unencrypted email message, automatically querying a recipient email domain for a recipient encryption key corresponding to the recipient identifier, automatically receiving the recipient encryption key from the recipient email domain, automatically encrypting the unencrypted email message using the recipient encryption key, and transmitting the encrypted email message to the recipient identifier.