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I have gotten awesome advice from users on here for getting Exchange on Windows SBS 2008 set up. I think this is the final piece and I'm ready for roll-out!

I need to set up Exchange so that it RECEIVES mail from our existing mail server as a Forward [aliases on the existing mail server to forward mail from to] (not using the POP3 Connector), and SENDS mail through that server as well (sends from to and then out to the world, showing in the headers as from or at absolute least have the reply-to set as this).

Alternatively, as long as the .net email address doesn't show in the From and replies are directed to the .com account, email can go from Exchange to the outside world without directing through the existing mail server.

External Domain:
Internal Domain: domain.local
Internet Domain Name Set in SBS Console:

When I go to I get the Remote Web Workspace, and can login to both Sharepoint and OWA.

I can send an email from OWA to a GMail account. I receive it from, which is an alias of

I cannot, however, send an email from OWA to ANY email addresses. I am also not receiving any email to this Exchange account (except for NDRs).

When I try sending an email to a account, here is the error (I had to replace all < and > with { and }):

Delivery has failed to these recipients or distribution lists:
The recipient's e-mail address was not found in the recipient's e-mail system. Microsoft Exchange will not try to redeliver this message for you. Please check the e-mail address and try resending this message, or provide the following diagnostic text to your system administrator.

Generating server: IFEXCHANGE.domain.local
#550 5.1.1 RESOLVER.ADR.RecipNotFound; not found ##

Original message headers:

Received: from IFEXCHANGE.domain.local ([fe80::4d34:abc5:f7fd:e51a]) by
 IFEXCHANGE.domain.local ([fe80::4d34:abc5:f7fd:e51a%10]) with mapi; Tue,
 17 Aug 2010 14:14:14 -0400
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: John Doe {}
To: "" {}
Date: Tue, 17 Aug 2010 14:14:12 -0400
Subject: asdf
Thread-Topic: asdf
Thread-Index: AQHLPjf+h6hA5MJ1JUu1WS4I4CiWeA==
Message-ID: {E4E10393768D784D8760A51938BA456A029934BA30@IFEXCHANGE.domain.local}
Accept-Language: en-US
Content-Language: en-US
X-MS-TNEF-Correlator: {E4E10393768D784D8760A51938BA456A029934BA30@IFEXCHANGE.domain.local}
MIME-Version: 1.0

I hope I explained the situation well enough for someone to be able to explain to me what I'm missing.

If I could, I'd be putting a 10K bounty, but unfortunately I've got only 74 reputation (hey, I'm a newbie here!).

I'm pretty sure the obvious "RecipNotFound" error is why its not working, my question is how to resolve this. The email account exists, it receives mail just fine, yet when I send it from the Exchange server it fails.


In OC->Hub Transport, the Email Address Policies has 2 entries.

"Windows SBS Email Address Policy" is set up to:

  • Include All Recipient Types, no conditions, and SMTP

"Default Policy" set to:

  • Include All Recipient Types, no conditions, and SMTP

Three Authoritative Accepted domains

  • domain.local (Default)

Remote Domains tab has two entries.

  • Default with domain *
  • Windows SBS Company Web Domain with domain companyweb.
share|improve this question

What you are asking help to set up is a disaster waiting to happen.

First off lets see if we can get a clearer picture of your needs.

  1. I am guessing that you have put in a new SBS 2008 server with Exchange 2007 on it
  2. You have another email server you are using now for production
  3. You want to move off of the old mail server but you want them to work together first
  4. You are wanting to stay with as the default email addresses but want .net also

Questions: 1. What is your other email server? Exchange? 2. Are both servers members of the same domain?

We might can get started with that info...


share|improve this answer
Answers: 1. Linux box using sendmail and aliases. 2. No, the other server is not on a member of any domain. | Points 1, 2, 4 are correct. 3, not entirely. We're going to keep the old mail server in production, as we have accounts on that mail server that we are not migrating to Exchange. – Mistiry Aug 17 '10 at 21:18

I suspect your answer will lie in the config within Organization Configuration - Hub Transport.

I'm a little fuzzy on the specifics - is your default address policy? Did you set up as an additional address policy? Is setup as a remote domain or accepted domain?

share|improve this answer
see my edit for the additional info - thanks for any help! – Mistiry Aug 17 '10 at 20:27
I'm not sure you can send from an accepted domain, but you can with remote domains. I'd sound more certain if I had my VMs finished - don't have access to a production system right now. – Kara Marfia Aug 18 '10 at 13:16

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