Help with Exchange 2007 Certificates:

Hi all. We have 2 issues at the moment and I'm hoping someone can help.
We have an SSL UCC certificate which we use for webmail from outside the company.
The first issue is that users are now getting a security alert when launching Outlook internally.
The message is from mailserver.domain.local and it says the name on the security cert is invalid or does not match the name of the site.
The SSL cert is setup with the name webmail.domain.com
and it has the following SANs:
autodiscover.domain.com
mail.domain.com
mailserver.domain.com

I tried adding mailserver.domain.local to the SSL certificate as a SAN but it looks like I have to wait for CertificatesForExchange.com to get back to me.  Will this fix the issue?  

The second issue I'm seeing is event ID 12014 in the Event Viewer.
It states that it can't find a certificate that contains the domain name mail.domain.com in the personal store.

I don't think this is causing any issues that I can see but it seems like it should be an easy fix.

Any and all help would be appreciated.
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homerslmpsonAsked:
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Seth SimmonsSr. Systems AdministratorCommented:
you need to configure your URLs to match your external domain; don't use .local there or in your cert

Configuring Exchange Server 2007 Web Services URLs
http://www.msexchange.org/articles-tutorials/exchange-server-2007/management-administration/configuring-exchange-server-2007-web-services-urls.html

may also need to configure split dns

Windows - Setting Up Split DNS
http://www.petenetlive.com/KB/Article/0000830.htm
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homerslmpsonAuthor Commented:
I don't understand what this means:
"you need to configure your URLs to match your external domain; don't use .local there or in your cert"

Are you trying to help me with the first issue or the second issue?
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Seth SimmonsSr. Systems AdministratorCommented:
you need to configure autodiscover, owa...those URLs need to have the external domain (.com) not .local
you also don't use .local for the cert

the second issue, need to enable that cert for services (IIS, smpt, etc.)

Enable-ExchangeCertificate
http://technet.microsoft.com/en-us/library/aa997231%28v=exchg.80%29.aspx
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homerslmpsonAuthor Commented:
It looks like I already have the split DNS setup.
I have a Forward Lookup Zone named webmail.domain.com and have an A record pointing to the Exchange server's internal IP address.
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Seth SimmonsSr. Systems AdministratorCommented:
ok good
need to verify the exchange URLs are setup properly so that everything matches the cert
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homerslmpsonAuthor Commented:
Should I use webmail.domain.local for the internal URL or mail.domain.local?
The instructions mention using mail.domain.local but as I mentioned earlier the forward lookup zone and SSL cert use the name webmail.domain.com.
mail.domain.com
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Seth SimmonsSr. Systems AdministratorCommented:
where are these instructions from?
you don't want to use .local because your cert does not match that and will cause cert errors internally as you stated
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homerslmpsonAuthor Commented:
I was actually following the very first link you provided.

But yeah, you mentioned everything should match the SSL cert.
If that's the case should I make the following adjustments?

autodiscover = webmail.domain.com
OAB = webmail.domain.com
OOF = webmail.domain.com
Unified Messaging (we don't use) = webmail.domain.com
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homerslmpsonAuthor Commented:
But that link you provided is old (Nov 2007) so I'm thinking things changed over the last few years.
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Seth SimmonsSr. Systems AdministratorCommented:
it discusses using internally-created cert which is not what you want here; however the EMS commands are the same
you just put in the url of your server (the .com not .local)
scroll down to the autodiscover section for those commands

the link might be old but so is your exchange version :)
procedurally nothing has changed with that version over the years
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homerslmpsonAuthor Commented:
lol Exchange is expensive.
OK so does this make sense?
autodiscover = webmail.domain.com
OAB = webmail.domain.com
OOF = webmail.domain.com
Unified Messaging (we don't use) = webmail.domain.com
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Seth SimmonsSr. Systems AdministratorCommented:
yes it can be as long as DNS records are there and the name is on the cert (which you have)

here is the technet article i was looking for
a bit simpler to read

How to Configure Exchange Services for the Autodiscover Service
http://technet.microsoft.com/en-us/library/bb201695%28EXCHG.80%29.aspx
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homerslmpsonAuthor Commented:
I went ahead and made the changes.
I added webmail.domain.com for the internal Autodiscover, the internal OAB, the internal and external web services and I enabled Outlook Anywhere.
The error is still in the event viewer about not finding the domain name mail.domain.com in the personal store.
The image below shows the certs inside the personal store.
Some of them have the SAN of mail.domain.com while others don't.
Is there a way to see which one is being used?
personal store
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homerslmpsonAuthor Commented:
OK I've removed all of the certificates in the personal store except for the one self-signed certificate for SMTP and the SSL certificate for the other things.
After I narrowed down what self-signed certificate was being used for SMTP I ran the following command in EMC:
New-exchangecertificate -ServerName, ServerName.domain.local, mail.domain.com
The first 2 were already on the self signed certs but not the last one.
That idea was thanks to THIS link.
The error is no longer showing in the event log so I'd like to think this has been resolved.
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homerslmpsonAuthor Commented:
Thanks for your help.
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