A system is provided for remotely configuring automatic reply message settings. The system comprises an email server configured to receive email messages addressed to an email address allocated for a user. The email server is configurable to generate an automatic reply message in response to receiving email messages addressed to the email address, to examine each received email message addressed to the email address for one or more specified conditions, and to execute one or more specified actions configuring settings for the automatic reply message when the one or more specified conditions are met by a received email message addressed to the email address.