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Issue with Outlook 2010, SBS 2008, Exchange 2007

Posted on 2011-02-21
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Last Modified: 2012-05-11
So I have an exchange 2007 server setup on SBS2008 which has been functioning for some time.
I have 2 laptops with the following issue in outlook 2010.

When I configure the server in outlook 2010, my SMTP server is mail.xxx.xxx externally.  
This works while they are outside the building.
When they come into the building, or it is configured inside the building, the SMTP server is changed to the SBS2008 FQDN, even if I erase it, and try again, or completely reconfigure outlook 2010.

This is an issue for laptop users, and I have more laptop users coming in soon.

I thought it might be a DNS issue, so I tried to create a record manually in DNS to resolve the issue pointing mail.xxx.xxx to the internal IP address, and it did not help.
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Question by:tfreyder
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by:Rob Williams
ID: 34942862
With SBS 2008 there should be a forward lookup zone for mail.YourExternalDoaminName.xyz. Does this exist? This forward lookup zone should have a host record pointing mail.YourExternalDoaminName.xyz to the LAN IP of the server to resolve the external address to the internal address of the SBS.
This should have been automatically created by the "set my internet address wizard", assuming you ran it when you set up the server.
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by:tfreyder
ID: 34942948
In my DNS, I have 2 forward zones.
One for the internal domain, and one for the external domain.  (it is not preceded with mail.)
In the external domain, there is a single host record for "mail" and it points to the internal IP.
The SOA and the NS's are both pointing to the FQDN of the server, if that matters.
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Rob Williams earned 500 total points
ID: 34943120
Forward lookup zones would normally be:
_msdcs.YourInternalDomainName.local
YourInternalDomainName.local
mail.YourExternalDoaminName.xyz

If not you can re-run the "set up your internet address" wizard and in step #7 choose advanced options and change remote to mail.
HOWEVER: doing so will create a new self-signed certificate. If you you are not using a 3rd part certificate but using the self signed cert and you have already distributed this to mobile clients, you will have to redistribute the new one. Following outlines the wizard:
http://blogs.technet.com/b/sbs/archive/2008/10/15/introducing-the-internet-address-management-wizard-part-1-of-3.aspx
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Author Comment

by:tfreyder
ID: 34943847
I assume this came over like this because it was a migration from SBS2003.
When I run the "set up your internet address", it wants base information about what domain to join... I am not sure this is what I want to do, as the server is in use, and on the domain already.

Can I add the forward lookup manually?  If I create a new one for mail.domain.xyz, what records do I need to populate in in?
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Expert Comment

by:Rob Williams
ID: 34944069
The wizard sets up the external domain connection information, not your internal domain, you cannot change the latter. This sets up Exchange to receive e-mail for that domain, configures RWW access, IIS, the certificate, and such. The only issue that "should" arise by re-running is the certificate as mentioned.

If concerned try running the Bets Pact ices Analyzer and see if it points out that or any other issues:
http://www.microsoft.com/downloads/en/details.aspx?familyid=86a1aa32-9814-484e-bd43-3e42aec7f731&displaylang=en

And, yes you can manually create it. It is just best you always use the wizards with SBS.
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Author Closing Comment

by:tfreyder
ID: 34944339
Thanks!
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