I had this same issue, my internal domain name was different from my external 
and outlook 2007 clients were initially connecting to the CAS checking the 
certificate which had the external domain name causing a certificate error.

http://support.microsoft.com/kb/940726 fixed it for me to.








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-----Original Message-----

From: Kennedy, Jim [mailto:kennedy...@elyriaschools.org]
Sent: 13 February 2009 00:50
To: MS-Exchange Admin Issues
Subject: RE: Multiple cert (Ex 2007) Internal vs. Eternal


I think you are on the correct motorcycle. The article below is how I fixed 
this issue with us.

http://support.microsoft.com/kb/940726


________________________________________
From: Troy Meyer [troy.me...@monacocoach.com]
Sent: Thursday, February 12, 2009 5:09 PM
To: MS-Exchange Admin Issues
Subject: RE: Multiple cert (Ex 2007) Internal vs. Eternal

My money is on the autodiscover service using an internal cert and causing the 
prompt when Outlook 2007 looks for availability info

http://technet.microsoft.com/en-us/library/bb397225.aspx


-troy

-----Original Message-----
From: Michael B. Smith [mailto:mich...@theessentialexchange.com]
Sent: Thursday, February 12, 2009 2:05 PM
To: MS-Exchange Admin Issues
Subject: RE: Multiple cert (Ex 2007) Internal vs. Eternal

What?



Are you deploying Outlook 2007 using Outlook Anywhere for your internal users?



Regards,



Michael B. Smith, MCITP:SA,EMA/MCSE/Exchange MVP

My blog: http://TheEssentialExchange.com/blogs/michael

I'll be at TEC'2009! http://www.tec2009.com/vegas/index.php



From: Marty Nelson [mailto:mnel...@transdyn.com]
Sent: Thursday, February 12, 2009 5:01 PM
To: MS-Exchange Admin Issues
Subject: Multiple cert (Ex 2007) Internal vs. Eternal



Greeting all.



I]m running into a problem where, as we roll out Office 2007 the users are 
prompted with security dialog boxes warning that the certificate doesn't match 
the server name.  We currently have a certificate of the external web address 
(webmail ,etc.) but the internal Exchange server has a completely different 
name.  Is there any way around this?  This problem has reached the upper 
echelon of or organization.  It was fine was it was just me, but now it has 
become a problem.



Any help would be appreciated.



-Martt











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