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 [email protected] to [email protected]] (not using the POP3 Connector), and SENDS mail through that server as well (sends from [email protected] to [email protected] and then out to the world, showing in the headers as from [email protected] 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: domain.com
Internal Domain: domain.local
Internet Domain Name Set in SBS Console: domain.net

When I go to http://remote.domain.net 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 [email protected], which is an alias of [email protected].

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

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

Delivery has failed to these recipients or distribution lists:

[email protected]
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

[email protected]
#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 {[email protected]}
To: "[email protected]" {[email protected]}
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-Has-Attach:
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.

EDIT

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 %[email protected].

"Default Policy" set to:

• Include All Recipient Types, no conditions, and SMTP @domain.net.

Three Authoritative Accepted domains

• domain.com
• domain.local (Default)
• domain.net

Remote Domains tab has two entries.

• Default with domain *
• Windows SBS Company Web Domain with domain companyweb.