At least a portion of a transmission of an outgoing first email from a first email account to at least a second email account is encrypted. Second email address data is changed corresponding to the second email account to cause replies to the first email intended for the second email account to be sent to an intermediate device prior to being routed to the second email account. Replies to the first email are then sent to the intermediate device and sent over one or more encrypted channels. Replies to the first email including the changed email address data are decoded to identify the second email address data associated with the second email account. A reply to the first email is then sent to the second email account based on the identified second email address data.