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Unable to forward user email in Exchange 2003 Server. (Deliver email to external email Account)

Posted on 2009-07-06
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Last Modified: 2012-05-07
I'm Unable to forward a users' email in Exchange 2003 Server. (Deliver email to external email Account).

I've gone in and create the email as a contact and selected deliver email to local address as well as external email address. However the email is not showing up in the users external mail.
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Question by:sf1elds
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Expert Comment

by:debuggerau
ID: 24791772
are there delivery restrictions from the originating sender?

spam filters?

I'd enable the SMTP log and see what is exactly what is getting sent and is getting returned..
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LVL 65

Expert Comment

by:Mestha
ID: 24793074
Message tracking is the tool to use here. Look to see if the messages are actually being sent out.
What I am finding is becoming more common is the remote recipient ISP rejects the messages because it looks like spoofing. The message header isn't changed, so it looks like the message is coming from the senders domain, but from your server, which isn't responsible for that domain. Therefore the message is blocked.

Simon.
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Author Comment

by:sf1elds
ID: 24797043
I do have message tracking turned on.

I'll include a screen shoot.
Picture-1.png
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LVL 65

Expert Comment

by:Mestha
ID: 24799570
That shows the message was sent out. Therefore the recipients server is most likely dropping the message as I outlined above.

Simon.
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Author Comment

by:sf1elds
ID: 24799598
Humm ok thanks. Is there anyway around this tht you know off?
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LVL 23

Expert Comment

by:debuggerau
ID: 24799652
You could try and set up a rule instead to redirect the email, then the header will be modified to appear from your user..
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Author Comment

by:sf1elds
ID: 24799679
If I set up a rule this means the user needs to run outlook in order for the rule to function correct? The user sometimes does not start the outlook for weeks.
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LVL 65

Expert Comment

by:Mestha
ID: 24799684
I am now advising clients against this kind of forwarding altogether because it looks like spoofing. You cannot guarantee that the message will be delivered.
A rule in Outlook means you have to enable the feature in Exchange, which means anyone can setup an automatic forward to the an internet account, and it can cause loops if you aren't careful.

Simon.
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Author Comment

by:sf1elds
ID: 24799700
So I'm a bit lost here at exactly which option you're suggesting. Should I not set up a rule then in Outlook for this user then?
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LVL 23

Expert Comment

by:debuggerau
ID: 24799715
Exchange 2007 allows for server side rules, would this allow you to forward by rule while not being in outlook..
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Author Comment

by:sf1elds
ID: 24799719
Humm ok. Darn we're still using Exchange 2003.
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Accepted Solution

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debuggerau earned 1500 total points
ID: 24799774
worth considering upgrading with all the spam features and added features, sounds like you've got a reason now..
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Author Comment

by:sf1elds
ID: 24799786
:) Thanks I'll take your advice.
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