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David Barman
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Exchange 2013 - forward incoming emails AND send an auto reply to the sender

Exchange user has left the company.  We need to forward all incoming messages to forward to another user in the company.  This is not the issue, I can do that through ECP.  However, while the new messages are forwarding, how do we ALSO send a reply message to the sender to let them know that user is no longer with the company, etc
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timgreen7077

8/22/2022 - Mon
timgreen7077

you will need to create an out of office reply. you can see the below link and it will give you different options for creating this and also how to use the exchange shell if you choose.

https://www.msoutlook.info/question/enable-automatic-replies-for-another-mailbox
David Barman

ASKER
I was under the impression that out of office won't activate if messages are being forwarded to another mailbox
timgreen7077

I think it will but give it a try and if not let me know and I think of something else if possible.
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David Barman

ASKER
Unfortunately it doesn't work.  I assume since the message never hits the user's mailbox, the automatic reply never gets triggered.
timgreen7077

You can set the forward to deliver to both the original mailbox and also the forwarded mailbox. The original mailbox should then be able to send the reply, so change the forward to be delivered to both the mailbox and the forward mailbox.
David Barman

ASKER
I did try that as well, and I still don't receive the auto reply.  I logged into the users account using OWA and confirmed that the message was delivered to the account.  Additionally, OWA stated that auto replies were set as active.
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timgreen7077

Make sure your auto-reply is set to go to both internal and external recipients, also the out of office will only be sent once to a recipient and every time, so if it has been sent once it will not be sent again to the recipient unless you turn off the out of office and the re-active it again.
David Barman

ASKER
It is set to both internal and external users.
timgreen7077

can you confirm that it has never once set the out of office? if you cant I would suggest disabling it for about an hour and then reenable and test to confirm. again it will not continue sending to a recipient if it sent it once already.
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David Barman

ASKER
I definitely can try that.  However, I just enabled the out of office when I started this process.
timgreen7077

oh ok and can you confirm no out of office was sent?
David Barman

ASKER
I can confirm that I didn't receive it to my external email address.
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timgreen7077

how about internal?
David Barman

ASKER
Perhaps something is wrong with out of office.  I turned it back on, and I still am not received the messages.
David Barman

ASKER
Internally it works, just not externally, which is what I need.
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timgreen7077

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David Barman

ASKER
They weren't not, but I have enabled them and sent another test email from 2 different accounts and didn't receive a reply.  I logged into the users account and both messages were received.
timgreen7077

Now that you have enabled them, make sure also there is not transport mail rule in place that may also be preventing the successful delivery of the out of office.
Once you confirm that, disable the Out of office on the mailbox and wait a bit and then re-enable it.
David Barman

ASKER
In ECP under mail flow we don't have any rules in place.
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timgreen7077

ok. turn off the out of office and after about an hour turn it back on and test.
David Barman

ASKER
Ok.  It looks like it was an issue with our SMTP relay service.  They re-enabled blank senders and now the out of office messages are working.
timgreen7077

nice. glad you got it working now.
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