One of the many items in the list of "We need someone to deal with these requests and you're it" items is to make a change on one aspect of Automail.
When a bug is reported, either internally or externally, and is rejected as not a valid bug, the Status is set to "Rejected" (logical, no?) These decisions may be reviewed and the ruling may be overridden, which results in the bug being "Reopened" (but usually with a very low Sev/Priority level) or, confirmed - and the status will be made "Closed."
The the request is when a bug is Closed, to have an automail sent to the person who made the "Rejected" decision intially, not usually the person who is in the Reportedby field.
I could not see a way around this intially - and then said "AH! Create a new User field to capture the userid of the person who rejects the bug! When the bug is closed, have an email sent to them!" Simple, right? HAH! Here I was figuring I could add the field to the Automail configuration screen - and HAH! WRONG!
Do I need to add conditions for each person to conditionally get an automail when the status is closed and their userid is in the saved user field?
If you have set up the capturing of the individual who set it to rejected in a user entity field already, why not look to the work flow code?
If you are only capturing information in your new field when the status us moved to rejected, then you can monitor the Defects_Bug_FieldChange event and if the status field changes, and you have information in your custom field, then you can send the email out. If you have linked your custom field to the user's list information, it won't be difficult to send the mail out to the individual.
Insanity: doing the same thing over and over again and expecting different results