I believe this is not possible using just the Out of Office Assistant. This was done to stop infinite OOO message loops, bringing Exchange servers to their knees in the event of two people having OOO messages set, with a message being sent from one to the other.
It can be done however, using Message Rules, but this is not advisable (for the aforementioned reason).
UPDATE:
Ok, found a dirty hack that will allow you to do what you requested - however, it is a really dirty hack.
You'd need to customise the script for an individual user (if you have many users, they need one each). Place the script on the Exchange server, and Schedule the script to run once a day. The reason this works is because each time you re-enable the OOA, it wipes the list of people it has sent OOO messages to. You would of course need to remember to remove the script when the user returns to work, otherwise everyday it would re-enable their OOA.
Also, change line 3 and 4 for your environment, and the user in question.
Set objMAPISession = CreateObject(”MAPI.Session”)
strExchangeSvr = "svr-exch-01.yourdomain.loc"
strMailbox = "jane.doe"
strMAPI = strExchangeSvr & vbLf & strMailbox
On error Resume Next
objMAPISession.Logon “”, “”, False, True, 0, False, strMAPI
If err <> 0 Then
Wscript.Echo “An Error occured: ” & err.description
Err.clear
Wscript.Sleep 7000
Wscript.Quit
End If
strOOOMessage = "Jane is having babies and will be absent for a while. Please try again after October. Ciao"
objMAPISession.OutOfOffice = False
objMAPISession.OutOfOfficeText = strOOOMessage
objMAPISession.OutOfOffice = True
strOOOMessage = objMAPISession.OutOfOfficeText
objMAPISession.Logoff
Set objMAPISession = Nothing
Please note: I have not tested this. You will need to deploy it with a test Mailbox, and do some testing with it.
Wow, I need a shower after that.
I admit I'm no expert at this, but why it would do that is beyond me. I haven't had an Exchange installation do that as far as I recall, it will send the auto-reply once per sender. However, the end-user could with Outlook set up a manual rule that does that (or perhaps this Outlook 2000 KB about orphaned rules causing this is helpful).
Exchange can also be configured to not allow auto-reply outside the organisation at all regardless of user-configured rules, which may be seen as a good practice.
Best Answer
Out of Office auto-replies are setup within Exchange, and reply to any incoming messages- not sure if that's what you are looking to do?