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Outlook Anywhere setup where local domain is same as company domain

Posted on 2009-06-30
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Last Modified: 2012-05-07
I have just migrated a SBS 2003 domain to SBS 2008. The previous IT guy set up the network so the local domain is the same as the company domain (so company.com.au not company.local). Everything works except Outlook Anywhere. When I run Exchange BPA it reports that there is a certificate mismatch. Now I am using a 3rd party certificate linked to the external FQDN of the SBS Server. RWW and OWA work fine. But the detail of the Exchange BPA says that the principal name is set to domain.com.au not office.domain.com.au. I have used the Exchange Management Shell to update the principal name as suggested by the BPA but this has made no difference.

So any suggestions on how to fix this situation?

Regards,
Ben
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Question by:muaddib32
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by:PlusIT
ID: 24754785
yes the behaviour of outlook anywhere changed in 2008.  The mismatch error on the SSL certificate is because teh client first tries to connect to autodiscover.domain before connecting to the outlook anywhere FQDN.

There are different solutions to this:
- use a self signed certificate that you trust on your domain (all pc's using outlook any should be in the domain!)
- use a 600$ ssl certificate which supports multiple cn's
- use one host to connect and change DNS settings according to KB940881 (this is what i do) this makes sure it works with a single cn ssl cert.

If you need further assistance just let me know but i'm sure with the information i just gave you you'll find it out.  Make sure you write this so you understand how the new behaviour is: http://technet.microsoft.com/en-us/library/bb232838.aspx
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by:muaddib32
ID: 24759059
This is the third SBS2008 server I have configured. I have not configured autodiscover on the other two and yet Outlook Anywhere works fine on them.  If your theory is correct, shouldn't it fail on the other two also?

And the Outlook 2003 RPC/HTTP test at https://www.testexchangeconnectivity.com/ fails and that is not using Autodiscover.

Are you sure that Autodiscover is the problem?
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by:PlusIT
ID: 24776794
yes and no, it shoudn't fail if you are using self signed ceritifcates and those computers are domain joined, if the cert is domain wide trusted you dont get ssl errors.

You said it yourself you are using a third party ssl cert, can you check how many CN fields it has?  If it only has one CN field then you will have to go around this problem with the info provided on KB940881
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Author Comment

by:muaddib32
ID: 24776842
After further tests is has become apparent that the error message I am getting about the mismatched principal name is a red herring.  The step that is failing is the authentication at the TS Gateway.  RWW and TS services are failing as well as Outlook Anywhere.  Apparently this is commonly caused by the authentication settings for the RCP website being modified. But not this time! I have Microsoft PSS on the case but they are puzzled too.
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by:PlusIT
ID: 24784539
my english is not that good, what do you mean with a red herring?

btw is their an ISA server between it or any other web proxy?
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Author Comment

by:muaddib32
ID: 24784640
Red herring just means a clue that leads in the wrong direction. So I don't think my problem has anything to do with the mismatched principal name. I can access other SSL sites without any problem - OWA, Sharepoint (through port 987)

No, no ISA server. That is not included with SBS 2008 Premium.
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by:PlusIT
ID: 24785048
yes but arent you accessing those with a domain joined computer, have you tried with a computer that is out of the domain to see if you get a cert warning then?
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by:muaddib32
ID: 24785198
I have only been testing it with non-domain computers. Without any problems with the certificate. As expected, since it is a third-party certificate.
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muaddib32 earned 0 total points
ID: 24922492
Please close this question as I still have the problem and no-one seems to have any suggestions. No points awarded.
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