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irvcon

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Cannot Get Autodiscover to Set Up Outlook or Pass Free/Busy Information with 3rd Party UCC cert

I have a 3rd party UCC/SAN certificate from a trusted CA.  It is installed on an Exchange 2007 CAS server (single-server setup), the certificate automatically installs in the browser, and the autodiscover service passes all Exchange shell and remote tests that I have come across.  Yet, it will not configure Outlook, and inside the firewall free/busy information is not working.

I think I have a permissions issue, but let me lay out the problem first.

The firewall has 443, 80 and 25 open to this machine, and I am trying to do Autodiscover with Outlook 2007.  The Exchange server is patched through the 10/31 version of rollup 4, and running on Server 2008 patched all the way.  The AD is 2008.  OWA works perfectly.

Testing with Outlook's "Test E-mail Autoconfiguration" function seems to work for the Administrator account, but fails abjectly with any user account which is why I think there is an IIS permissions issue.

Using either the Administrator account, or a user account Outlook fails to set up a mail profile using the autodiscover service saying "the server cannot be contacted."

 I also don't seem to be able to set up an Outlook profile remotely in an RPC/HTTP setup using the same settings that would work on an Exchange 2003 server, but I am not certain the same settings are appropriate.

If I run the "Test E-mail Autoconfiguration" function from a remote Outlook client using the Administrator account, the "Results" tab resolves all internal and external URL's seemingly correct ( cannot copy the output.)  

The "Log" tab shows the following 4 lines with only the "Use Autodiscover" test being run (no Guessmart or Guessmart Authentication):

> Autodiscover to https://externaldomain.com/autodiscover/autodiscover.xml starting
> Autodiscover to https://externaldomain.com/autodiscover/autodiscover.xml FAILED (0x800C8203)
> Autodiscover to https://autodiscover.externaldomain.com/autodiscover/autodiscover.xml starting
> Autodiscover to https://autodiscover.externaldomain.com/autodiscover/autodiscover.xml succeeded (0x00000000)

The XML tab shows the following:

<?xml version="1.0" encoding="utf-8"?>
<Autodiscover xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">
  <Response xmlns="http://schemas.microsoft.com/exchange/autodiscover/outlook/responseschema/2006a">
    <User>
      <DisplayName>Administrator</DisplayName>
      <LegacyDN>/o=First Organization/ou=first administrative group/cn=Recipients/cn=Administrator</LegacyDN>
      <DeploymentId>dbb40376-adab-4d86-bcea-50c6659da487</DeploymentId>
    </User>
    <Account>
      <AccountType>email</AccountType>
      <Action>settings</Action>
      <Protocol>
        <Type>EXCH</Type>
        <Server>servername.internal.local</Server>
        <ServerDN>/o=First Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=servername</ServerDN>
        <ServerVersion>720180F0</ServerVersion>
        <MdbDN>/o=First Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=servername/cn=Microsoft Private MDB</MdbDN>
        <PublicFolderServer>servername.internal.local</PublicFolderServer>
        <AD>ADserver.internal.local</AD>
        <ASUrl>https://mail.externaldomain.com/ews/exchange.asmx</ASUrl>
        <EwsUrl>https://mail.externaldomain.com/ews/exchange.asmx</EwsUrl>
        <OOFUrl>https://mail.externaldomain.com/ews/exchange.asmx</OOFUrl>
        <UMUrl>https://mail.externaldomain.com/unifiedmessaging/service.asmx</UMUrl>
        <OABUrl>Public Folder</OABUrl>
      </Protocol>
      <Protocol>
        <Type>EXPR</Type>
        <Server>mail.externaldomain.com</Server>
        <SSL>On</SSL>
        <AuthPackage>Basic</AuthPackage>
        <ASUrl>https://mail.externaldomain.com/EWS/Exchange.asmx</ASUrl>
        <EwsUrl>https://mail.externaldomain.com/EWS/Exchange.asmx</EwsUrl>
        <OOFUrl>https://mail.externaldomain.com/EWS/Exchange.asmx</OOFUrl>
        <UMUrl>https://mail.externaldomain.com/UnifiedMessaging/Service.asmx</UMUrl>
        <OABUrl>Public Folder</OABUrl>
      </Protocol>
      <Protocol>
        <Type>WEB</Type>
        <Internal>
          <OWAUrl AuthenticationMethod="Basic, Fba">https://servername.internal.local/owa</OWAUrl>
          <Protocol>
            <Type>EXCH</Type>
            <ASUrl>https://mail.externaldomain.com/ews/exchange.asmx</ASUrl>
          </Protocol>
        </Internal>
      </Protocol>
    </Account>
  </Response>
</Autodiscover>

I would like to go over the IIS permissions, but IIS7 is kind of a pain and I cannot find any document so far that says for Exchange 2007 on IIS7 permissions should be set like so.

Thank you in advance for your attention and help!
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Pret0rian
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irvcon

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I went over it all with a fine-toothed comb and found a couple of small things which cumulatively seemed to do it.  I think the host file entries on the servers are what finally did the trick