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Outlook Anywhere - Internal & External Hostname Issues

Hi,

We currently have two exchange 2013 servers with DAG configured and an old exchange 2010 server all part of a single exchange organisation.  These servers are:

Exch01 – exchange 2013
Exch02 – exchange 2013
Exchange1 – Exchange 2010

We are in the process of decommissioning the exchange 2010 server and are trying to sort out our Outlook Anywhere settings. We have a SAN certificate (with 9 domains) on both servers (duplicate SANs issues by our CA). Our current Outlook Anywhere settings are:

Exch01:
External: mail.mydomain.org
Internal: exch01.mydomain.local

Exch02:
External: mail.mydomain.org
Internal: exch01.mydomain.local

Exchange1:
External: mail.mypreviousdomain.org
Internal: exchange1.mydomain.local

Our SAN includes the following domains:

exch01.mydomain.local      <-- common name on SAN
exch02.mydomain.local
mail.mydomain.org
mail.mydomain2.org
mail.mydomain3.org
autodiscover.mydomain.org
autodiscover.mydomain2.org
autodiscover.mydomain3.org
hardwarelb.mydomain.local

We are trying to set the Outlook Anywhere settings to the following, in accordance to a few articles that we've read:

Exch01:External: mail.mydomain.org
Internal: mail.mydomain.org

Exch02:External: mail.mydomain.org
Internal: mail.mydomain.org

Exchange1:
External: mail.mypreviousdomain.org
Internal: exchange1.mydomain.local

When we run a test email autoconfiguration we get the following results<o:p></o:p>

SMTP=firstname.surname@mydomain.org
Attempting URL https://exchange1.mydomain.local/autodiscover/Autodiscover.xml found through SCP
Autodiscover to https://exchange1.mydomain.local/autodiscover/Autodiscover.xml starting
GetLastError=0; httpStatus=401.
GetLastError=0; httpStatus=302
Autodiscover to https://exchange1.mydomain.local/Autodiscover/Autodiscover.xml Failed (0x800C8204)
Autodiscover URL redirection to https://
exch02.mydomain.local:443/Autodiscover/firstname.surname..mydomain.org/Autodiscover....
Autodiscover to https://exch02.mydomain.local:443/Autodiscover/firstname.surname..mydomain.org/Autodiscover.xml
starting
GetLastError=0; httpStatus=401
GetLastError=0; httpStatus=200
Autodiscover to https://exch02.mydomain.local:443/Autodiscover/firstname.surname..mydomain.org/Autodiscover.xml
Succeeded.

We updated the SAN certificate to change the common name to mail.mydomain.org and updated the certificates on both servers. However, when we change these settings, clients are prompted for passwords (on XP machines) and Outlook loses connection (displays trying to connect) on all other OS machines (i.e. Win 7).

Can anyone shed any light on this?

Thanks,

Stephen





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