As a “don’t try this at home” anecdote, last week we had an all staff retreat, and we were asked to put up away messages. I put a perfectly professional one up for outside email, but in a fit of whimsy, the internal mail triggered an away message that said “Why are you emailing? We are supposed to be paying attention to the retreat!” I figured, we were all at the retreat, so nobody would ever know. Of course, someone did email me 30 minutes before everything started, and triggered the message. Fortunately, he figured out it was an away message and thought it was funny.
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Depends on the system. Our Outlook is set up so that if you’ve got someone with an OOO in the “To” field, a note shows up saying that they are sending automated messages, and you can see the message. Convenient, since then I can add the person covering their stuff to the email without sending a second email.