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Auto response and message forwarding for secondary smtp

Posted on 2014-11-06
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Last Modified: 2014-11-13
Hi Experts,

I have to configure a auto reply and forward rule for about 500 mailboxes.
Our systems running on an exchange 2010 cluster.

An example what i need to do ....

User "John Doe" with following smtp:
Primary: john.doe@new.com
Secondary: john.doe@old.com

When now anyone send an e-mail to john.doe@old.com (secondary smtp) he must got a auto reponse text message like "John Doe is now reachable with john.doe@new.com ...." and the original message must be forwarded to the primary smtp john.doe@new.com

Is there any possible solution with transport rules on exchange management or server side rules for the mailbox?

If something is not clear I will try to explain it.

Thanks for your help!
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Question by:it_slu
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Expert Comment

by:Jamie McKillop
ID: 40428324
Hello,

How I would go about this is to create distribution groups for each user and move the old.com addresses to the distribution groups. Each group would have the corresponding mailbox as a member. You can then setup a server-side autoreply rule in each mailbox to fire when an email is sent to the distribution group.

-JJ
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Author Comment

by:it_slu
ID: 40428468
Hallo,

Thanks for your reply. Your solution sounds like a lot of work for about 500 mailboxes. Of course it would be possible with powershell but this would exceed my skills in scripting.

But it looks like there is no other way. Because every Mailbox with the old Domain (@old.com) need a personally mail forwarding rule. This is not possible to configure on the management console, right?

Thanks!
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LVL 37

Expert Comment

by:Jamie McKillop
ID: 40428696
The issue is with the way Exchange routes mail and with the way rules work. You need to create rules based on object, not SMTP address. You won't be able to create separate rules for different SMTP addresses on the same object.

Yes, you could script this with powershell as it would be a lot of work manually.

-JJ
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Author Comment

by:it_slu
ID: 40439429
I have created a server side rule that looks for the secondary smtp address in the message header and auto reply with text message that this e-mail address is no longer active. That's all fine. But there is some issue when I send a message from the internal network.

If a user from our company send a message to john.doe@old.com (secondary smtp / old address) outlook e-mail address resolution would dissolve the e-mail address to the username. And then the e-mail will be sent to john.doe@new.com (Primary smtp / new address) and not to the secondary smtp address. As a result of this the server side rule for auto reply won't work because the old e-mail address is not detected in the mail header.

Is there a solution for this? Apart from this  your soltuion works fine. I've just tested it. Thanks!
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Accepted Solution

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Jamie McKillop earned 500 total points
ID: 40439678
No, unfortunately, this is a function of how Exchange routes messages. Exchange doesn't actually use SMTP addresses internally, it uses X500 addresses. All SMTP addresses are resolved to the object. This is why you can't create a rule based on individual SMTP addresses on an object and why you need to use the distribution group method I outlined above.

-JJ
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