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Exchange 2013 - Forwarding To External SMTP Address Not Working

Posted on 2015-01-07
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Last Modified: 2015-01-19
Exchange 2013 install and trying to get email retained in the users Exchange mailbox *and* get a copy forwarded to an external email address. The external account is not receiving the email. It is hitting the internal Exchange mailbox for the user.

Stepped through the following article, entering this command via EMS:

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Set-Mailbox -Identity "test" -DeliverToMailboxAndForward $true -ForwardingSMTPAddress "test@external.com"

http://technet.microsoft.com/en-us/library/dd351134%28v=exchg.150%29.aspx
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My output to the above command shows:

ForwardingSmtpAddress: smtp:test@external.com
DeliverToMailboxAndForward: True

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Also reviewed this article which basically states the same PS command to enable this feature:
http://www.techieshelp.com/exchange-2013-forward-email-to-external-contact/

All looks simple enough, but is not working. Appreciate any assistance -
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Question by:hwtech
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SatyaPathak earned 250 total points
ID: 40535723
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Assisted Solution

by:Simon Butler (Sembee)
Simon Butler (Sembee) earned 250 total points
ID: 40535828
You need to check message tracking to see whether the message is actually being passed out or not.
The way that Exchange does automatically forwarding means that it is actually possible the messages get blocked by the remote server. The messages appear to be spoofed by Exchange, so if the original source of the message and the destination are using anti-spoofing measures, then the email can be rejected.
Message Tracking will tell you if Exchange is sending the email out or not.

Simon.
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Author Comment

by:hwtech
ID: 40536425
On the message tracking, I'm not seeing it. If I check the internal acct *test@domain.com* for an email object that, when received on the account, is forwarded to external acct *test@external.com* using:

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Get-MessageTrackingLog -Sender test@domain.com -Recipients test@external.com
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.....I don't see the subject email listed in the resultant output.

If I generate a new email from internal *test@domain.com* and send to external *test@domain.com* - I DO see it in the resultant output using the above command.

Still learning my way around EX-2013, but can I assume that the forwarding function is not working?
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Expert Comment

by:Simon Butler (Sembee)
ID: 40537633
Stepping back a bit...

If you run

get-mailbox -identity user.name | select identity, ForwardingSmtpAddress

Does the forward show?

If you send an email internally to the internal recipient, does it forward to the external recipient?

Simon.
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Author Comment

by:hwtech
ID: 40537796
Was incorrect on the MessageTrackingLog command format noted earlier:

Get-MessageTrackingLog -Sender test@domain.com -Recipients test@external.com

The section highlighted in bold, was the internal Exchange user acct mailbox that was to do the forwarding (thinking this was the acct doing the actual forwarding to the external acct) - WRONG.

Changed that section of the command to the *originating* email acct that initiated the email  (my business account that I was doing all this testing with) - the remainder of the command syntax staying the same - I then get intelligible output to this issue.

There's a sequence of EventID's, with the last EventID of "DROP" - I've not gotten to the point of deciphering each of these ID's and their meaning, but I'm guessing DROP was doing exactly that, as the email was never received on the forwarded acct destination.

Per the linked articles in SatyaPathak, I wasn't clear if a mail-enabled contact required to be setup or not for each of these forwarding accts.  So I began with just this command which got me working:

set-remotedomain Default -AutoForwardEnabled $true

What I'm not clear on is if enabling this *remotedomain* has in any way compromised the security on this Exchange server.  Will need to do some reading.
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Expert Comment

by:Simon Butler (Sembee)
ID: 40537950
"set-remotedomain Default -AutoForwardEnabled $true"

There is no need to run that command.

It would allow anyone in your environment to configure a rule to automatically forward an email to an external recipient. Not only is that a security risk, but also puts your server at risk of an email loop.

Simon.
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Author Comment

by:hwtech
ID: 40538541
Appreciate that bit of info. I'll need to on/off that setting and test forwarding function operations. That's what got me working initially, at least that's what it appears.
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Author Closing Comment

by:hwtech
ID: 40557660
Sorry for delay in followup. Closing as haven't had a chance yet for followup on this issue. Appreciate the assistance.
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