A system and method to provide a message handling system (eg email) user an alert when one or more messages remain in the outbox of the message handling system after the message transmission process has completed more than a user definable number of times or has been in the outbox longer than a user definable amount of time. Once alerted the user will have the option to take one or more actions (independent of the system and method) to remove the message or messages from the outbox.