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Ryan Mignosa
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Exchange 2010: Outlook anywhere/Outlook 20XX/ and OWA certificate error

Running Exchange 2010 SP3 on windows server 2008 R2 SP1
This is a single server exchange environment.
Exchange server name:  exchange.gpr.com
Default website:  webmail.grandpacificresorts.com

I recently renewed our exchange SSL certificate, because although Outlook Anywhere is configured there was no SAN for autodiscover.  The new certificate request was created using the EMC and installed the same way.  Lastly IMAP, POP, IIS, and SMTP services were assigned to the certificate.  FYI no virtual directories have been set/changed via powershell since installing the new certificate and IIS has not been reset.  Finally the website defined in the certificate is webmail.grandpacificresorts.com with a SAN of autodiscover.grandpacificresorts.com.

Since installing the new certificate running Outlook Connectivity and Outlook Autodiscover tests on https://testconnectivity.microsoft.com/ now pass, but internal outlook clients and OWA generate the following error:

gpresorts.com  The name on the security certificate is invalid or does not match the name of the site

I can't figure out why Outlook would be referencing gpresorts.com and not grandpacificresorts.com.  I also can't figure out if this an autodiscover virtual directory configuration problem, a DNS issue, or other.

Autodiscover:  see attached results for get-autodiscovervirtual directory | fl

DNS:  below are the exchange related entries in each scope
               -Scope gpresorts.com
  • (same as parent folder)               Mail Exchanger (MX)                    gprmail1.gpr.com
  •        webmail                                         Host(A)                                           webmail
             -Scope grandpacificresorts.com
  • (same as parent folder)              Mail Exchanger (MX)                    gprmail1.gpr.com
  •        autodiscover                                Host(A)                                 
  •        webmail                                        Host(A)                                 

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8/22/2022 - Mon