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Exchange 2010/Outlook 2007 certificate error mismatch

Posted on 2014-09-16
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Last Modified: 2014-09-17
I have just converted from Exchange 2003 to Exchange 2010. I installed a UCC SSL certificate from go daddy on my exchange 2010 server. The Outlook 2007 clients started getting a certificate mismatch warning because the built in certificate that the Outlook clients were pointing to was the internal name of the server (blgexchserv1.blg.local).
I did some research and came accross this post:
http://exchangeserverpro.com/outlook-2007-clients-display-certificate-mismatch-error-after-mailbox-migration/
I attempted to  change the URL of the Autodiscover services within Exchange 2010. I completed the first entry, but the outlook clients are still getting the certificate error. I did not think I needed to modify the web services url at all. I tested OWA internally and it is resolving fine. What am i doing wrong? what else do I need to do to get rid of the error.
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Accepted Solution

by:
-MAS earned 350 total points
ID: 40327314
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Author Comment

by:williamstechnologygroup
ID: 40327332
the auto discover internal is set correctly.... I know that IIS is using the Godaddy cert because active sync and OWA are both working correctly with no certificate errors. I am not sure why the clients are persisting in looking for the internal cert with the .local name....
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Author Comment

by:williamstechnologygroup
ID: 40327352
the OAB default website for internal is pointing to the .local name of the server, but would that generate the certificate error in outlook?
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Expert Comment

by:Zacharia Kurian
ID: 40327362
The certificate mismatch occurs because the Autodiscover Service and/or Availability Service use the FQDN of the Exchange 2010 host in their URL (eg https://your server.domain.local/AutoDiscover/AutoDiscover.xml) but the IIS instance has an SSL certificate that does not match that name.

So just follow the links Posted by the expert MAS.
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Assisted Solution

by:SreRaj
SreRaj earned 100 total points
ID: 40327381
Hi,

You could add internal FQDN name of the CAS server as a Subject Alternate Name in UCC. This helps to get rid of certificate warnings internally.

https://www.digicert.com/ssl-support/exchange-2010-san-names.htm

Also, it is good to add EWS URL, because of OOF uses web services. You could run 'Test E-mail Configuration' from a connected machine. This will list all the URLs used by Outlook both thru RPC and using HTTP. You could verify that all these URL names are added as SANs in the UCC.

http://premnair.wordpress.com/2010/07/03/configure-ews-autodiscover-owa-oab-ecp-on-exchange-server-2010/
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LVL 24

Expert Comment

by:-MAS
ID: 40327387
@SreRaj
You wont be able to add internal FQDN in your certificate in the near future.
Almost all CAs stopped adding internal FQDN to the certificate.

And it is not a good practice to add internal FQDN in your exchange certificate.
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LVL 9

Assisted Solution

by:Zacharia Kurian
Zacharia Kurian earned 50 total points
ID: 40327415
You wont be able to add internal FQDN in your certificate in the near future.
Almost all CAs stopped adding internal FQDN to the certificate.

And it is not a good practice to add internal FQDN in your exchange certificate.

very true MAS. Adding the internal name to SSL was just tweak but then all started to realize the security issues related to it and I think many SSL providers do not do so now, rather they do issue wild card SSL.
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Author Comment

by:williamstechnologygroup
ID: 40329084
Yes, the internal names on a san cert are going away. Godaddy made that clear. I ended up calling Microsoft after I had exhausted all other possibilities. I had performed the correct scripts, but the outlook clients were not responding. THanks to MAS for the tip on the Outlook Test email auto configuration. will reward points based on relativity.... thanks...
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Author Closing Comment

by:williamstechnologygroup
ID: 40329087
Contact Microsoft for final resolution
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