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Exchange 2010 Self Sign Cert popping up and other issue

Posted on 2011-02-15
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I recently migrated from Exchange 2003 to 2010 and am having a couple of strange issues.

1) I did (correctly) install a GoDaddy UCC SSL Cert but when any (internal) Outlook 2007 or 2010 clients connect, I get a Security Alert dialog box that says the name on the security certificate is invalid- and is a self-signed cert for my Exchange server. I did assign the correct services to my UCC public cert, and removed the self-signed cert from my Exchange server. How do I go about resolving this issue?

Additionally, my Outlook clients receive an error while attempting to download the OAB. I did move this over from the old Ex2003 server and when I noticed it still wasnt downloading, I recreated it and made sure to path to the new OAB on the Mailbox Store properties. How do I go about fixing this as well??
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Question by:Trihimbulus
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by:LLMorrisson
ID: 34896533
Have you checked your internal service URLs are set correctly as per your cert etc? Check this article which discusses this issue.

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_3704-Troubleshooting-Outlook-Certificate-Errors.html

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by:LLMorrisson
ID: 34896588
With regards to the OAB error received by your clients, what is the actual error?

Have you checked the event log for any specific messages relating to the OAB?

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by:Glen Knight
ID: 34897374
doesn't sound like you completed the wizard for the Exchange Certificate with the correct names in it?
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by:Trihimbulus
ID: 34897633
Yes Dematz - you are correct. For some reasone one of the domain names listed is www.mail.mycompany.com but I went through the certificate import directions to a T and didn't see this listed. By chance, did enableing this for all services (specifically IIS) add this to the cert? How do I fix this?
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by:Glen Knight
ID: 34897647
It will add this automatically if there is a spare SAN/UCC in the 5 domain list.

Does the name you are seeing on the error message appear on the certificate?

You should have at a minimum the following names:

owa.domainname.com (the URL used for Outlook Web Access)
autodiscover.domainname.com (where domainname.com is the part after the @ in your email address)
servername.domainname.local (the internal fully qualified domain name of your server)
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Author Comment

by:Trihimbulus
ID: 34898236
Ok - so I should have added the internal name of my Exchange Server when setting up the UCC Cert with godaddy? Isn't that bad to let the world know what that name is? Also, we hit OWA via mail.mycompany.com.
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LLMorrisson earned 500 total points
ID: 34898625
Adding your local computer name to the UCC is a common way, but it is not necessary if you prefer not to. You just need an internally resolvable namepointing to your client acces server and need to change your internal service URLs to match this name, and to the names in your cert. So long as that all matches up, it will still work and you can leave the real internal server names out of the certificate.
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by:Glen Knight
ID: 35010980
You mind if I ask what was in that last solution that i hadn't already offered?
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