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Hosting two mail domains on sbs 2008, getting ssl cert errors on 2nd domain

We have two email domains on our SBS 2008 server running Exchange 2007. The primary domain is generally accessed over LAN with Outlook 2010 in cached exchange mode. No issues there. The 2nd domain is a sister company that is primarily accessed with Outlook 2010 via RPC over HTTP, and a couple of accounts use POP3.

The problem is, the external clients are getting cert mismatch errors that actually freeze Outlook and the connection to the server drops. I have to reset IIS in the server to get mail to flow again, and it happens several times a day.

We have a Godaddy SSL cert with our primary domain name, internal domain name, autodiscover, etc. It wasn't an issue until the owner of the sister company moved the second domain to a new host that used cpanel which supports the autodiscover srv record. Because the cert is issued to the primary, autodiscover throws the error every 2 or three minutes.

I tried configuring Outlook 2010 to suppress name checking with a registry key, but no joy.

Do I need to buy a UCC cert with multiple domain names, and if so, can I successfully import such a cert into SBS 2008 since it isn't supported in the trusted cert authorities by default?
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1 Solution
Jaroslav MrazCTOCommented:
You can stop using autodiscover and setup it manauly. Just by using a name of domain that have certificate valid.

User mails are asignet on username so they can have server like mail.othercompany.com but use their username and get emails without certification isue.
How do you stop using autodiscover for exchange? / What affects would that have negatively on a setup that used to rely on autodiscover (either intentionally, or by default)?
Jaroslav MrazCTOCommented:
Simple after check you will select setup manually. You don't need to disable feature but it is just for help by automatic setup of Outlook it provide xml with configuration. But same configuration you can foo manually for example outlook 2003 don't support automatic cfg function.
riley71Author Commented:
Ok.. So I bought a UCC multi-domain certificate from GoDaddy. In it I had to list the main domain, mail.domain1.com, and these alternates...  mail.domain2.com, autodiscover.domain1.com, autodiscover.domain2.com, and myserver.domain.local. (Funny thing, the GoDaddy support guy told me later this year a FQDN of your server won't be accepted.. He couldn't explain what that was all about, but maybe someone here can.)

Then instead of using the SBS wizard to import the cert, I used powershell. The command was,

 Import-ExchangeCertificate -Path “C:\Cert\mail_ExternalDomaiName_com.crt” -FriendlyName “CompanyName UCC Cert"

Making sure that your path points to where your cert is downloaded, and your FriendlyName being your domain.

Then I went to the IIS manager and under Servername, then sites, I right clicked SBS Web Applications and then "edit bindings". On https on port 433 I hit edit to verify that the right cert was being used.

Then I went to both domain hosts and edited my dns zones to have a cname record of autodiscover that points to mail.domain1.com (or domain2 for the second site), and then an srv record that points to autodiscover.domain1.com.

The correct cert pulls on both mail domains, and now I no longer have the annoying cert error pop ups or password prompts.

Consequently, if you have internal clients that connect via exchange account, it helps to use the same certificate for both internal and external clients. Here's how you do that.

Open Exchange Power Shell with elevated permissions, and enter

Set-ClientAccessServer -Identity MAILSERVER-AutodiscoverServiceInternalUri https://mail.domain.com/autodiscover/autodiscover.xml

Set-WebServicesVirtualDirectory -Identity "MAILSERVER\EWS (SBS Web Applications)" -InternalUrl https://mail.domain.com/ews/exchange.asmx

Set-OABVirtualDirectory -Identity "MAILSERVER\oab (SBS Web Applications)" -InternalUrl https://mail.domain.com/oab

Set-UMVirtualDirectory -Identity "MAILSERVER\unifiedmessaging (SBS Web Applications)" -InternalUrl https://mail.domain.com/unifiedmessaging/service.asmx

Being sure to change out "MAILSERVER" for your CAS name, and domain for your domain name on the certificate. Then you won't have your internal clients prompting for certs either.

riley71Author Commented:
This was the solution that solved my problem.
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