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Outlook anywhere will not work with exchange 2007 on a Winsows 2008 server

Posted on 2008-10-27
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Last Modified: 2012-05-05
We have two servers with Windows 2008. One exchange Cas server and one backend server. Webmail, active sync works great. The cas server certificate is a webserver ssl certificate from thawte.  The only name in the certificate is mail.domain.net. The problem is that we cant get Outlook anywhere to work from outside the office.
Can it be OAB that creates the problem? We get a lot of errors in the event viewer.
Have anyone experienced something familiar?
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Question by:onordli
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7 Comments
 
LVL 1

Expert Comment

by:JeremyPhillips
ID: 22817592
Disable IPv6, edit the hosts file to reference the IPv4 addresses of the box and restart the server.

Example of what needs to be added to c:\windows\system32\drivers\etc\hosts (obviously replacing the IP address and the hostname)

10.0.0.1   server
10.0.0.1   server.domain.com

You can test the connectivity afterwards at http://www.testexchangeconnectivity.com
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Author Comment

by:onordli
ID: 22835862
Have tested that. Did not help.
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LVL 1

Expert Comment

by:JeremyPhillips
ID: 22835882
Where do the tests at http://www.testexchangeconnectivity.com fail?
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Author Comment

by:onordli
ID: 22839006
It seems that the problem is that we don't have a certificate with required Subject Alternative Names. Another way is to set up a SRV record in the DNS a use the ssl web certificate.
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Accepted Solution

by:
JeremyPhillips earned 500 total points
ID: 22843004
Correct. Here is an excellent article on the configuration: http://www.amset.info/exchange/singlenamessl.asp
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Author Comment

by:onordli
ID: 22916335
It did not work at first. I did not have Exchange rollup 4 installed on the server. After installing this rollup. Ewerything worked like a dream. Thanks.
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Author Closing Comment

by:onordli
ID: 31510461
Thanks a lot
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