Out-of-Office replies are dropped due to empty MAIL FROM
Today I had an interesting support call. A customer noticed that Out-of-Office replies were not received by recipients, even though the OoO option were enabled for internal and external recipients. Internal recipients got the OoO reply, but none of the external recipients.
The Message Tracking Log is a good point to start. I quickly discovered that the Exchange server was unable to send the OoO mails. You can use the eventid FAIL to get a list of all failed messages.
