Systems and methods of confirming an addressee of an email message include receiving an email message addressed to one or more forwarding addresses. At least one email address associated with each of the one or more forwarding addresses is obtained. A potential discrepancy in the email message is detected in response to the at least one obtained email address. Before sending the email message, an alert is issued to a sender of the email message. The alert provides a recommendation regarding whether to continue with sending the email message and identifies content associated with the email message that led to detecting the potential discrepancy.