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password prompt for a few users after new Exchange 2010 certificate is installed...

I have Exchange 2010 SP1 running and I just put on a new certificate (3rd party) and then assigned the services to it. However, there are a few users that said Outlook is now continually prompting for username and password. I have restarted IIS after the install of the certificate, but is there something else I have to do on the clients to get it to accept the new cert?

I have the feeling that this is not unrelated since it started right after the new certificate went on...
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willlandymore
Asked:
willlandymore
1 Solution
 
askurat1Commented:
I would try clearing the browser data on the pc  and restart outlook. Also try restarting the server if possible.

You may have to reconfigure outlook settings.
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lamaslanyCommented:
Is there any chance you've affected the supported authentication mechanism?  For example changed from Basic to NTLM/Windows Integrated?  
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willlandymoreAuthor Commented:
no, no change to that. The difference would be that the CN is another one, but the old server alias is on the certificate as well
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willlandymoreAuthor Commented:
autodiscover seems to be overwriting the outlook settings as well because if you change it to the CN on the cert and they restart it is okay, but then there are some users that it changes the settings back to the way they were
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Brian GeeCommented:
Here is an article composed by one of our EE Experts here:

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_2300-Outlook-continually-prompting-for-username-and-password.html

Despite noting Exchange 2007, I'm sure that the information therein will be helpful with Exchange 2010 as well.
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willlandymoreAuthor Commented:
yeah, I've seen that article via another website but the DNS, autodiscover and everything else seems to be okay. The only thing that changes was the Common Name on the certificate. However, the old one was still listed on the certificate, it just wasn't the common name
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willlandymoreAuthor Commented:
When I reassigned IIS to be on the old certificate everything started working again. I'm not sure why Exchange is giving me this behavior, but that's why it's happening
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willlandymoreAuthor Commented:
worked
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