Exchange 2010 SSL Cert

Have Exchange 2010 Server
Have Outlook 2010 Clients

Everything has been working correctly for over 2 years.

Had to renew SSL Cert (via Godaddy)
5 UCC Cert, All Alternative Names were related to external references (i.e.,,

Renewed, Installed, Assigned Services, All External connections and references are working correctly.

When my Outlook users login at the office, they get an SSL Cert warning.
If you view it and try to install it, it won't install, even though it says its installed.  When you open Outlook the next time, the SSL warning presents itself again.

My question is should I have put the internal name of the mail server on the SSL cert as one of the Alternative names, is that why I have this issue?

Need some guidance
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Nick RhodeIT DirectorCommented:
depends on how the outlook client is connecting to is and how its resolving through DNS.  If the internal name was excluded from it and thats how it was working that is the issue.
did you contact godaddy customer care ?
tech911Author Commented:
Didn't contact anyone yet, wanted to get my arms around the problem before looking for help.

Internally it is  referencing the internal server via auto-discover.  So I am guessing that I need the internal name on the cert.

What names are required on the SSL cert for exchange to work correctly?

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Simon Butler (Sembee)ConsultantCommented:
You cannot put the internal name on the SSL certificate.
Therefore you need to setup a split DNS system and configure Exchange to use the external names internally.

tech911Author Commented:
I understand what you are saying.

Read your split DNS and Webservices posts.

Pretty sure I would be replacing single host, but honestly it seems a little confusing as to the particulars.

Your Split DNS Instructions below:

    On your primary DNS server, start the DNS administration tool.
    Right click on the server and choose New Zone.
    Step through the wizard. You need a FORWARD primary zone that is NOT AD integrated    
    (you may have to deselect an option).
When asked for the domain name, enter the host that you want to replace... ??????

This is where I am confused:

 For example if you want to replace then you would enter

Do I want a public address to be replaced like or do I want my private theclientmailserver.local to be replaced?  

If I have multiple to be replaced like, autodiscover.theclientmailserver.local and theclientmailserver.local

Do I need to repeat the process for each one that I need to resolve internally?


    Accept the option about creating a file.
    As this is not an AD integrated zone, disable dynamic updates.

I will comment on my confusion or concerns with the Adding a Host instructions after we get this figured out.
Simon Butler (Sembee)ConsultantCommented:
You are only replacing external hosts.
That allows to resolve to an internal IP address.
In the main, most people have two hosts that they replace: (the common name, used for OWA, Outlook Anywhere etc)

You have to do it for each host name that you want to resolve internally.

You don't have autodiscover.example.local, as Outlook doesn't use it.

tech911Author Commented:
You are only replacing external hosts.
That allows to resolve to an internal IP address.

This would only allow to resolve to an internal address only from behind our firewall using our internal DNS server.

Is that correct?
Nick RhodeIT DirectorCommented:
Basically you have to point your DNS correctly so for instance.


ExchangeServer - IP:

DNS records to resolve (again this is only to how you have your environment)

All these records point to your exchange server IP so these are what you want on your certificate.  I used to simplify my records for an easier understanding but yours might be different for your mail.  So if I wanted to get to OWA i would type in  

What we are trying to say is your naming schema has to match whats on exchange so if you check the URLs on the exchange server you would get a better idea of what to have on the certificate.  The above is a general guidline for I do not know what URLs you specified on the exchange server.

**If you do not have Split DNS setup and your internal DNS is domain.local you would have to create a 2nd zone in your DNS for**
Simon Butler (Sembee)ConsultantCommented:
That is pretty much correct.
I would advise against creating a zone for the root of the domain though - as that means you have to replace everything in that external zone - such as www and FTP. If you do a single host name as you have already discovered it doesn't affect everything else.


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tech911Author Commented:
It took me awhile to figure out what you guys were talking about.  It is important to note that there are two steps to this process...

Step 1 :  Setup your split DNS, basically providing users behind your firewall with the ability to use an external URL (the ones on your certificate that you feel are necessary to use) so that they will in-actuality route/resolve to the internal IP of your Exchange server if you try to access them behind your firewall.

Step 2 :  Modify the internal URi's of autodiscover and web services using the Exchange Power Shell ( I can remember what its called right now) then make them match the external URL's you have on your certificate, these will be the same ones you setup in your split DNS in step 1.

Thanks again for the help, I am grateful for the assistance.
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