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Forward email of 2 users in same domain to other site

Posted on 2009-07-10
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Last Modified: 2012-05-07
I have an Microsoft 2003 SBS R2 server with 14 users.  I have 2 other users that are not part of the SBS and will never be part of it but are on the same LAN as the other 14.  The problem is these 2 users have the same domain for email, ourdoman.com, as the other 14 sbs users.  I have these 2 users setup on a POP3 server externally, outside of the SBS.  The can send and recieve external email with not problem.  The only problem is when the 14 SBS users send an email to the 2 non SBS users, they get the following  error message:  "The email account does not exist at the organization this message was sent to.  Check the email address, or contact the recipient for correct address."  Of course this makes sense because the 2 users are not in AD of the SBS.  I am wonder how, if possible,  to route the 2 user outbound mail to the external POP3 server.  Does anyone have any ideas and a procedure to do so?
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Question by:Hackitx
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by:Alan Hardisty
ID: 24824943
If you set your external users up with HTTP over RPC and use Outlook with this and not SMTP / POP3, then you live will become much easier.  All users can use emails held on your server and your external users will access their emails as if they were internal users and your other users won't get error messages.
Follow this link for advice on setting this up (it also shows you how to set up the Outlook clients too - which can be done remotely):
http://www.amset.info/exchange/rpc-http.asp
Once you have set it up, test connectivity on https://testexchangeconnectivity.com  
Problem solved.
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by:Hackitx
ID: 24825068
I see a problem with this.  When the other 14 SBS users email the 2 non SBS users, they will still get the error message.  The 2 users are not the problem, they work find except with email from the other 14 SBS users.  I believe this is an exchange problem and I am not sure how http would solve it.
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by:Alan Hardisty
ID: 24825087
Is the email address domain the same for the 14 internal users and the 2 external ones?
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tigermatt earned 250 total points
ID: 24825119

The problem is not an Exchange problem; it is simply the fact that the SBS server believes it is authoritative for the whole email domain.

In my mind, you have two options:

The first is to configure SMTP namespace sharing. This is defined at http://www.msexchange.org/tutorials/Exchange-2003-SMTP-Namespace-Sharing.html and allows the two email systems to integrate with each other. However, it is complicated.

The second route (my preferred route) is the RPC over HTTPS route. This means the users will be located ON THE SBS SERVER (not on any POP3 server outside the network). They will have a user account and a mailbox on the SBS server, so will have an SBS email address. You then configure them with Outlook in RPC/HTTPS mode, or have them use OWA. This approach *will* work because they are local users on the SBS server, just like any other.

Simon's site referenced above has guides for how to configure the server for RPC/HTTPS, and then how to set up an Outlook account on a machine off the domain to access the server.

-Matt
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by:mikennedy
ID: 24827583
If you could add an additional email address on the POP3 server for each of the 2 users with a different domain name (a subdomain perhaps). You could create mail enabled public folders with the addresses of the 2 users and have that public folder forward the emails to the newly created subdomain addresses.

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Author Comment

by:Hackitx
ID: 24827750
Alan, yes they have the same email domain.

Tiger, I will check out the first choice and see what it take.  However, the second choice will never happen due to internal politics.  The 2 users cannot be on the SBS, different company even though its the same domain name.

Mike, I am thinking seriously of configuring the routers so that they are on a different network all together with there own external IP.  But this still will not solve the issue of when the other 14 SBS user send them email.  As tiger explained, the "SBS server believes it is authoritative for the whole email domain" and I will agree wholey.
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by:Hackitx
ID: 24827775
Mike, sorry I misread your comment.  That is a good idea.  I will see if it can be pulled off. Any idea of where I can go to find out how to create mail enabled public folders?
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by:Alan Hardisty
ID: 24827781
The only way round this that I can think of is to setup your SBS with the 2 users accounts on for mail purposes and then have the external POP3 server pull the mail from your SBS box.  That way there would not be any errors internally and the external users get their email.
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by:tigermatt
ID: 24829909

As the users are not going to be members of the SBS domain, the correct way to achieve this is to use SMTP namespace sharing as I linked to in my first post (http://www.msexchange.org/tutorials/Exchange-2003-SMTP-Namespace-Sharing.html).

It is perfectly plausible to use namespace sharing successfully between two different email systems without ever having to create user accounts for these users on the internal SBS server.

The mail-enabled public folder route has the potential to cause problems, only because you end up having to manage several sets of email domains. If I went down this route, I would create Contact objects to map to the external address rather than mail-enabled public folders.

-Matt
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Author Comment

by:Hackitx
ID: 24831021
Tiger, thanks for the advice.  Always good to have experience lead the way.  I will try, if time permits next week, your SMTP suggestion.  Have you ever done it?
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by:tigermatt
ID: 24831089

I haven't actually had a need to implement it myself because most of my customers are either very small clients with just a few users all located on their Exchange Server, or they are large corporate clients who wouldn't dream of running two mail systems side-by-side for very long :-)

I have, however, implemented it in test labs and overseen it used elsewhere in other deployments.

-Matt
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