Server Name VS Outlook Anywhere Proxy Server and the behaviour I should expect when using SAN certificates...

(I'll upload screen captures if needed once my account gets verified)
I have a basic (as in freshly installed single exchange server 2010 SP3) Exchange Server installation. I've setup Outlook Anywhere. I've also setup a SAN (SubjectAltName) certificate.
My setup:
ex01.eci.XXXX.XX = is the server name and also the CN of my SAN certificate
mail.eci.XXXX.XX = an A record I've setup to access my exchange server. It is also a subjectAltName in my SAN certificate
When setting up Outlook, I enter the server name and specify the Outlook Anywhere proxy server in the Outlook Anywhere section. This works fine and I connect to my exchange server using RPC over HTTPS.
Now, I was under the impression that specifying SANs in the certificate would allow me to enter the SAN alt name (mail.eci.XXXX.XX) in the field reserved for the Server Name, in Outlook..
But it does not work. The proxy will give me an error each time, like that:
HTTP    544    RPC_IN_DATA /rpc/rpcproxy.dll?mail.eci.XXXX.XX:6002 HTTP/1.1 , NTLMSSP_NEGOTIATE
HTTP    635    HTTP/1.1 401 Unauthorized , NTLMSSP_CHALLENGE (text/html)
HTTP    123    HTTP/1.0 503 RPC Error: 6ba
My question is: is this the behaviour I should expect? Or should I be able to specify the SAN alt name in the Server Name in Outlook?
Thanks!

Hi,
Firstly, I’d like to explain, the server name tab should be filled with your mailbox server name in the process of configuring Exchange 2010 account.
And the Outlook Anywhere proxy server is configured at the server side and cannot be randomly defined at the client side. To check it, we can run: get-outlookanywhere |fl externalhostname
Thus, it’s an expected behavior that we would get error if we randomly enter name in the server name tab when we configure an account. If I misunderstand your meaning, please feel free to let me know.
Additionally, Autodiscover service can help us automatically complete the configuration of the Outlook account. And how about the result if you use the Autodiscover to automatically configure the account?
If you have any question, please feel free to let me know.
Thanks,
Angela Shi
TechNet Community Support

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    Here are the EXCRA results
    Here IP (x.x.x.x) returned is my Load Balancer IP (Webmail.xyz.com).    
    Connectivity Test Successful with Warnings
    Test Details
         Testing Outlook connectivity.
         The Outlook connectivity test completed successfully.
              Additional Details
         Elapsed Time: 9881 ms.
              Test Steps
              The Microsoft Connectivity Analyzer is attempting to test Autodiscover for [email protected].
         Autodiscover was tested successfully.
              Additional Details
         Elapsed Time: 2063 ms.
              Test Steps
              Attempting each method of contacting the Autodiscover service.
         The Autodiscover service was tested successfully.
              Additional Details
         Elapsed Time: 2063 ms.
              Test Steps
              Attempting to test potential Autodiscover URL https://xyz.com:443/Autodiscover/Autodiscover.xml
         Testing of this potential Autodiscover URL failed.
              Additional Details
         Elapsed Time: 186 ms.
              Test Steps
              Attempting to resolve the host name xyz.com in DNS.
         The host name couldn't be resolved.
           Tell me more about this issue and how to resolve it
              Additional Details
         Host xyz.com couldn't be resolved in DNS InfoNoRecords.
    Elapsed Time: 186 ms.
         Attempting to test potential Autodiscover URL https://autodiscover.xyz.com:443/Autodiscover/Autodiscover.xml
         Testing of the Autodiscover URL was successful.
              Additional Details
         Elapsed Time: 1876 ms.
              Test Steps
              Attempting to resolve the host name autodiscover.xyz.com in DNS.
         The host name resolved successfully.
              Additional Details
         IP addresses returned: x.x.x.x
    Elapsed Time: 338 ms.
         Testing TCP port 443 on host autodiscover.xyz.com to ensure it's listening and open.
         The port was opened successfully.
              Additional Details
         Elapsed Time: 173 ms.
         Testing the SSL certificate to make sure it's valid.
         The certificate passed all validation requirements.
              Additional Details
         Elapsed Time: 318 ms.
              Test Steps
              The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server autodiscover.xyz.com on port 443.
         The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
              Additional Details
         Remote Certificate Subject: CN=webmail.xyz.com, Issuer: CN=VeriSign Class 3 Secure Server CA - G3, OU=Terms of use at https://www.verisign.com/rpa (c)10, OU=VeriSign Trust Network, O="VeriSign, Inc.", C=US.
    Elapsed Time: 219 ms.
         Validating the certificate name.
         The certificate name was validated successfully.
              Additional Details
         Host name autodiscover.xyz.com was found in the Certificate Subject Alternative Name entry.
    Elapsed Time: 1 ms.
         Certificate trust is being validated.
         The certificate is trusted and all certificates are present in the chain.
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              The Microsoft Connectivity Analyzer is attempting to build certificate chains for certificate CN=webmail.xyz.com, OU=Terms of use at www.verisign.com/rpa (c)05,.
         One or more certificate chains were constructed successfully.
              Additional Details
         A total of 1 chains were built. The highest quality chain ends in root certificate CN=VeriSign Class 3 Public Primary Certification Authority - G5, OU="(c) 2006 VeriSign, Inc. - For authorized use only", OU=VeriSign Trust Network, O="VeriSign,
    Inc.", C=US.
    Elapsed Time: 36 ms.
         Analyzing the certificate chains for compatibility problems with versions of Windows.
         Potential compatibility problems were identified with some versions of Windows.
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    Elapsed Time: 0 ms.
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    <Autodiscover xmlns:xsd="http://www.w3.org/2001/XMLSchema" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">
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    <DeploymentId>4ec753c9-60d9-4c05-9451-5b24e2d527a7</DeploymentId>
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    <Account>
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    <Action>settings</Action>
    <Protocol>
    <Type>EXCH</Type>
    <Server>[email protected]</Server>
    <ServerDN>/o=DOMAIN/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/[email protected]</ServerDN>
    <ServerVersion>73C0834F</ServerVersion>
    <MdbDN>/o=DOMAIN/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/[email protected]/cn=Microsoft Private MDB</MdbDN>
    <ASUrl>https://webmail.xyz.com/ews/exchange.asmx</ASUrl>
    <OOFUrl>https://webmail.xyz.com/ews/exchange.asmx</OOFUrl>
    <OABUrl>https://webmail.xyz.com/OAB/6a6a06ad-4717-4636-bd98-0b4fa3aaf4a5/</OABUrl>
    <UMUrl>https://webmail.xyz.com/ews/UM2007Legacy.asmx</UMUrl>
    <Port>0</Port>
    <DirectoryPort>0</DirectoryPort>
    <ReferralPort>0</ReferralPort>
    <PublicFolderServer>webmail.xyz.com</PublicFolderServer>
    <AD>DC-03.domain.xyz.com</AD>
    <EwsUrl>https://webmail.xyz.com/ews/exchange.asmx</EwsUrl>
    <EmwsUrl>https://webmail.xyz.com/ews/exchange.asmx</EmwsUrl>
    <EcpUrl>https://webmail.xyz.com/ecp/</EcpUrl>
    <EcpUrl-um>?rfr=olk&amp;p=customize/voicemail.aspx&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-um>
    <EcpUrl-aggr>?rfr=olk&amp;p=personalsettings/EmailSubscriptions.slab&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-aggr>
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    <EcpUrl-photo>PersonalSettings/EditAccount.aspx?rfr=olk&amp;chgPhoto=1&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-photo>
    <EcpUrl-tm>?rfr=olk&amp;ftr=TeamMailbox&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tm>
    <EcpUrl-tmCreating>?rfr=olk&amp;ftr=TeamMailboxCreating&amp;SPUrl=&lt;SPUrl&gt;&amp;Title=&lt;Title&gt;&amp;SPTMAppUrl=&lt;SPTMAppUrl&gt;&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tmCreating>
    <EcpUrl-tmEditing>?rfr=olk&amp;ftr=TeamMailboxEditing&amp;Id=&lt;Id&gt;&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tmEditing>
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    <ASUrl>https://webmail.xyz.com/ews/exchange.asmx</ASUrl>
    <OOFUrl>https://webmail.xyz.com/ews/exchange.asmx</OOFUrl>
    <OABUrl>https://webmail.xyz.com/OAB/6a6a06ad-4717-4636-bd98-0b4fa3aaf4a5/</OABUrl>
    <UMUrl>https://webmail.xyz.com/ews/UM2007Legacy.asmx</UMUrl>
    <Port>0</Port>
    <DirectoryPort>0</DirectoryPort>
    <ReferralPort>0</ReferralPort>
    <SSL>On</SSL>
    <AuthPackage>Ntlm</AuthPackage>
    <EwsUrl>https://webmail.xyz.com/ews/exchange.asmx</EwsUrl>
    <EmwsUrl>https://webmail.xyz.com/ews/exchange.asmx</EmwsUrl>
    <EcpUrl>https://webmail.xyz.com/ecp/</EcpUrl>
    <EcpUrl-um>?rfr=olk&amp;p=customize/voicemail.aspx&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-um>
    <EcpUrl-aggr>?rfr=olk&amp;p=personalsettings/EmailSubscriptions.slab&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-aggr>
    <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?rfr=olk&amp;exsvurl=1&amp;IsOWA=&lt;IsOWA&gt;&amp;MsgID=&lt;MsgID&gt;&amp;Mbx=&lt;Mbx&gt;&amp;realm=domain.xyz.com</EcpUrl-mt>
    <EcpUrl-ret>?rfr=olk&amp;p=organize/retentionpolicytags.slab&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-ret>
    <EcpUrl-sms>?rfr=olk&amp;p=sms/textmessaging.slab&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-sms>
    <EcpUrl-photo>PersonalSettings/EditAccount.aspx?rfr=olk&amp;chgPhoto=1&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-photo>
    <EcpUrl-tm>?rfr=olk&amp;ftr=TeamMailbox&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tm>
    <EcpUrl-tmCreating>?rfr=olk&amp;ftr=TeamMailboxCreating&amp;SPUrl=&lt;SPUrl&gt;&amp;Title=&lt;Title&gt;&amp;SPTMAppUrl=&lt;SPTMAppUrl&gt;&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tmCreating>
    <EcpUrl-tmEditing>?rfr=olk&amp;ftr=TeamMailboxEditing&amp;Id=&lt;Id&gt;&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tmEditing>
    <EcpUrl-extinstall>Extension/InstalledExtensions.slab?rfr=olk&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-extinstall>
    <ServerExclusiveConnect>on</ServerExclusiveConnect>
    <EwsPartnerUrl>https://webmail.xyz.com/ews/exchange.asmx</EwsPartnerUrl>
    <GroupingInformation>Default-First-Site-Name</GroupingInformation>
    </Protocol>
    <Protocol>
    <Type>WEB</Type>
    <Port>0</Port>
    <DirectoryPort>0</DirectoryPort>
    <ReferralPort>0</ReferralPort>
    <Internal>
    <OWAUrl AuthenticationMethod="Basic, Fba">https://webmail.xyz.com/owa/</OWAUrl>
    <Protocol>
    <Type>EXCH</Type>
    <ASUrl>https://webmail.xyz.com/ews/exchange.asmx</ASUrl>
    </Protocol>
    </Internal>
    <External>
    <OWAUrl AuthenticationMethod="Fba">https://webmail.xyz.com/owa/</OWAUrl>
    <Protocol>
    <Type>EXPR</Type>
    <ASUrl>https://webmail.xyz.com/ews/exchange.asmx</ASUrl>
    </Protocol>
    </External>
    </Protocol>
    <Protocol>
    <Type>EXHTTP</Type>
    <Server>webmail.xyz.com</Server>
    <ASUrl>https://webmail.xyz.com/ews/exchange.asmx</ASUrl>
    <OOFUrl>https://webmail.xyz.com/ews/exchange.asmx</OOFUrl>
    <OABUrl>https://webmail.xyz.com/OAB/6a6a06ad-4717-4636-bd98-0b4fa3aaf4a5/</OABUrl>
    <UMUrl>https://webmail.xyz.com/ews/UM2007Legacy.asmx</UMUrl>
    <Port>0</Port>
    <DirectoryPort>0</DirectoryPort>
    <ReferralPort>0</ReferralPort>
    <SSL>On</SSL>
    <AuthPackage>Ntlm</AuthPackage>
    <EwsUrl>https://webmail.xyz.com/ews/exchange.asmx</EwsUrl>
    <EmwsUrl>https://webmail.xyz.com/ews/exchange.asmx</EmwsUrl>
    <EcpUrl>https://webmail.xyz.com/ecp/</EcpUrl>
    <EcpUrl-um>?rfr=olk&amp;p=customize/voicemail.aspx&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-um>
    <EcpUrl-aggr>?rfr=olk&amp;p=personalsettings/EmailSubscriptions.slab&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-aggr>
    <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?rfr=olk&amp;exsvurl=1&amp;IsOWA=&lt;IsOWA&gt;&amp;MsgID=&lt;MsgID&gt;&amp;Mbx=&lt;Mbx&gt;&amp;realm=domain.xyz.com</EcpUrl-mt>
    <EcpUrl-ret>?rfr=olk&amp;p=organize/retentionpolicytags.slab&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-ret>
    <EcpUrl-sms>?rfr=olk&amp;p=sms/textmessaging.slab&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-sms>
    <EcpUrl-photo>PersonalSettings/EditAccount.aspx?rfr=olk&amp;chgPhoto=1&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-photo>
    <EcpUrl-tm>?rfr=olk&amp;ftr=TeamMailbox&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tm>
    <EcpUrl-tmCreating>?rfr=olk&amp;ftr=TeamMailboxCreating&amp;SPUrl=&lt;SPUrl&gt;&amp;Title=&lt;Title&gt;&amp;SPTMAppUrl=&lt;SPTMAppUrl&gt;&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tmCreating>
    <EcpUrl-tmEditing>?rfr=olk&amp;ftr=TeamMailboxEditing&amp;Id=&lt;Id&gt;&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tmEditing>
    <EcpUrl-extinstall>Extension/InstalledExtensions.slab?rfr=olk&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-extinstall>
    <ServerExclusiveConnect>On</ServerExclusiveConnect>
    </Protocol>
    <Protocol>
    <Type>EXHTTP</Type>
    <Server>webmail.xyz.com</Server>
    <ASUrl>https://webmail.xyz.com/ews/exchange.asmx</ASUrl>
    <OOFUrl>https://webmail.xyz.com/ews/exchange.asmx</OOFUrl>
    <OABUrl>https://webmail.xyz.com/OAB/6a6a06ad-4717-4636-bd98-0b4fa3aaf4a5/</OABUrl>
    <UMUrl>https://webmail.xyz.com/ews/UM2007Legacy.asmx</UMUrl>
    <Port>0</Port>
    <DirectoryPort>0</DirectoryPort>
    <ReferralPort>0</ReferralPort>
    <SSL>On</SSL>
    <AuthPackage>Ntlm</AuthPackage>
    <EwsUrl>https://webmail.xyz.com/ews/exchange.asmx</EwsUrl>
    <EmwsUrl>https://webmail.xyz.com/ews/exchange.asmx</EmwsUrl>
    <EcpUrl>https://webmail.xyz.com/ecp/</EcpUrl>
    <EcpUrl-um>?rfr=olk&amp;p=customize/voicemail.aspx&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-um>
    <EcpUrl-aggr>?rfr=olk&amp;p=personalsettings/EmailSubscriptions.slab&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-aggr>
    <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?rfr=olk&amp;exsvurl=1&amp;IsOWA=&lt;IsOWA&gt;&amp;MsgID=&lt;MsgID&gt;&amp;Mbx=&lt;Mbx&gt;&amp;realm=domain.xyz.com</EcpUrl-mt>
    <EcpUrl-ret>?rfr=olk&amp;p=organize/retentionpolicytags.slab&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-ret>
    <EcpUrl-sms>?rfr=olk&amp;p=sms/textmessaging.slab&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-sms>
    <EcpUrl-photo>PersonalSettings/EditAccount.aspx?rfr=olk&amp;chgPhoto=1&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-photo>
    <EcpUrl-tm>?rfr=olk&amp;ftr=TeamMailbox&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tm>
    <EcpUrl-tmCreating>?rfr=olk&amp;ftr=TeamMailboxCreating&amp;SPUrl=&lt;SPUrl&gt;&amp;Title=&lt;Title&gt;&amp;SPTMAppUrl=&lt;SPTMAppUrl&gt;&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tmCreating>
    <EcpUrl-tmEditing>?rfr=olk&amp;ftr=TeamMailboxEditing&amp;Id=&lt;Id&gt;&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-tmEditing>
    <EcpUrl-extinstall>Extension/InstalledExtensions.slab?rfr=olk&amp;exsvurl=1&amp;realm=domain.xyz.com</EcpUrl-extinstall>
    <ServerExclusiveConnect>On</ServerExclusiveConnect>
    </Protocol>
    </Account>
    </Response>
    </Autodiscover>HTTP Response Headers:
    request-id: 9d325a80-f1fd-4496-ac48-2be6bb782c28
    X-CalculatedBETarget: Server01.domain.xyz.com
    X-DiagInfo: Server01
    X-BEServer: Server01
    Persistent-Auth: true
    X-FEServer: Server01
    Content-Length: 11756
    Cache-Control: private
    Content-Type: text/xml; charset=utf-8
    Date: Mon, 25 Aug 2014 19:12:25 GMT
    Set-Cookie: X-BackEndCookie=S-1-5-21-1293235207-2459173341-1304346827-14544=u56Lnp2ejJqBypqcnsfJx5nSy8ucnNLLnJzP0sfKz8/Sy5nHmsiamZrMyZrLgYHPxtDNy9DNz87L387Gxc7Nxc3J; expires=Thu, 25-Sep-2014 00:12:26 GMT; path=/Autodiscover; secure; HttpOnly
    Server: Microsoft-IIS/8.5
    X-AspNet-Version: 4.0.30319
    X-Powered-By: ASP.NET
    Elapsed Time: 756 ms.
         Autodiscover settings for Outlook connectivity are being validated.
         The Microsoft Connectivity Analyzer validated the Outlook Autodiscover settings.
              Additional Details
         Elapsed Time: 0 ms.
         Testing RPC over HTTP connectivity to server webmail.xyz.com
         RPC over HTTP connectivity was verified successfully.
              Additional Details
         HTTP Response Headers:
    request-id: 835acf95-78b7-40ae-b232-117318d1577e
    Server: Microsoft-IIS/8.5
    WWW-Authenticate: Basic realm="webmail.xyz.com",Negotiate,NTLM
    X-Powered-By: ASP.NET
    X-FEServer: Server01
    Date: Mon, 25 Aug 2014 19:12:26 GMT
    Content-Length: 0
    Elapsed Time: 7817 ms.
              Test Steps
              Attempting to resolve the host name webmail.xyz.com in DNS.
         The host name resolved successfully.
              Additional Details
         IP addresses returned: x.x.x.x
    Elapsed Time: 107 ms.
         Testing TCP port 443 on host webmail.xyz.com to ensure it's listening and open.
         The port was opened successfully.
              Additional Details
         Elapsed Time: 180 ms.
         Testing the SSL certificate to make sure it's valid.
         The certificate passed all validation requirements.
              Additional Details
         Elapsed Time: 303 ms.
              Test Steps
              The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server webmail.xyz.com on port 443.
         The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
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         Remote Certificate Subject: CN=webmail.xyz.com, OU=Terms of use at www.verisign.com/rpa (c)05, Issuer: CN=VeriSign Class 3 Secure Server CA - G3, OU=Terms of use at https://www.verisign.com/rpa (c)10, OU=VeriSign Trust Network, O="VeriSign,
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         Elapsed Time: 326 ms.

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