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

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.
sf1eldsAsked:
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debuggerauCommented:
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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MesthaCommented:
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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sf1eldsAuthor Commented:
I do have message tracking turned on.

I'll include a screen shoot.
Picture-1.png
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MesthaCommented:
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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sf1eldsAuthor Commented:
Humm ok thanks. Is there anyway around this tht you know off?
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debuggerauCommented:
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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sf1eldsAuthor Commented:
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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MesthaCommented:
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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sf1eldsAuthor Commented:
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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debuggerauCommented:
Exchange 2007 allows for server side rules, would this allow you to forward by rule while not being in outlook..
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sf1eldsAuthor Commented:
Humm ok. Darn we're still using Exchange 2003.
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debuggerauCommented:
worth considering upgrading with all the spam features and added features, sounds like you've got a reason now..
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sf1eldsAuthor Commented:
:) Thanks I'll take your advice.
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