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SSL certificate error in Outlook 2010

Posted on 2013-12-17
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Last Modified: 2013-12-24
Hi everyone, I have a client that gets a SSL pop-up box when she's outside her domain, she can click yes and it will work fine afterwards. Screenshot of the pop-up error. They have on-premise Exchange 2010, and when I use a tool like SSL Checker I get different certificates for mail.wrightwater.com and autodiscover.wrightwater.com. Please tell me what other information you'll need to help resolve this. I have access to their DNS settings in Network Solutions also.
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Question by:blakefletcher
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by:becraig
ID: 39725234
Your issue here seems simple:
autodiscover.wrightwater.com seems to have a cert that does not have autodiscover.wrightwater.com as the subject/CN

They simply need to check the autodiscover servers to see which one has another cert bound to that endpoint and proceed to bind the SSL certificate that maps to autodiscover.wrightwater.com


Here is a little more information on troubleshooting this:
http://www.msexchange.org/articles-tutorials/exchange-server-2010/management-administration/exchange-autodiscover.html
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by:blakefletcher
ID: 39725296
I started to follow the guide, but when I came across check what the SAN names are in the cert I found that it does include autodiscover.wrightwater.com. Their OWA is on remote.wrightwater.com/owa, below is a screen shot of the cert.

Picture of the ssl cert
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becraig earned 2000 total points
ID: 39725389
Here is some additional info:
http://support.microsoft.com/kb/940726


I am not sure of your internal configuration but the above link will help you to identify the values for your exchange urls.


Also you should think of redacting the domain info when you post.
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