Outlook anywhere Clients not connecting

Hi All,
I have recently set up Outlook anywhere on an Windows 2008 SP 2 box with Exchange 2010 and installed a 3rd SSL certificate bought explicitly for this purpose.
I'm having real issues trying to connect any outlook clients from the outside world. OWA works fine and doesn't ask for a certificate so I know that has installed successfully.
I have tried all combinations both basic and NTLM authentication I can think of to no avail.
The remote connectivity analyser tool (https://testconnectivity.microsoft.com/) passed everything bar and only shows a couple of warnings which I believe I can safely ignore:
1 - Your certificate may not be trusted on Windows if the "Update Root Certificates" feature isn't enabled
2 - The first refferal (without encryption) fails, but the subsequent one is successfull (require encryption is set up on my client)
All I'm getting on my client is a username and password box, once entering the authenticaition details it keeps on asking for authentication, then when cancelled throws an error that the server is not contactable and the name could not be resolved.
I can telnet to my fqdn (webmail.mycompany.com) on ports 80 and 443 with no issues.
Does anybody have any idea what I can do to troubleshoot this? It's been driving me insane for weeks!
Many thanks in advance

Hi Darren,
Yes outlook anywhere is enabled and the settings match, I have tried with the 'Only connect to proxy servers that have this principal name in their certificate' ticked and also without.
I'm convinced all of the normal config is correct, I've set up RPC over HTTP connections on a ton of other servers in the past and have never ran into this issue.
The remote connectivity analyser passes with flying colours, does anybody know of any other debugging tools or logs I can take a look at?
I'm close to un-installing the rpc over http feature from IIS and setting it all up from scratch but don't really want to do this as the server is in production and is the only exchange server in the organisation.

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  • Access to Outlook Anywhere does not work

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    I recently installed an Exchange Server 2013 CAS / MB.
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    related to the access from outside.
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    I've done a lot of research and testing without success.
    With regard to the first issue (which is not a priority but can relate to second one)
    add that in Firefox I get a first authentication request. If
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    Internet Explorer shows me only the first authentication request and if I cancel shows blank page.
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    a firewall (Pat on port 443, et al. not 80)
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    port 443 and try port 80, SPF isn't configured).
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    - Cmdlet and Autodiscover output -
    Get-OutlookAnywhere | fl name,*auth*,*ssl*,*host*
    Name                               : Rpc (Default Web site)
    ExternalClientAuthenticationMethod : Basic
    InternalClientAuthenticationMethod : Ntlm
    IISAuthenticationMethods           : {Basic, Ntlm, Negotiate}
    SSLOffloading                      : True
    ExternalClientsRequireSsl          : True
    InternalClientsRequireSsl          : True
    ExternalHostname                   : webmail.name_domain.test
    InternalHostname                   : webmail.name_domain.test
    Get-OutlookProvider | ft -autosize
    Name     Server CertPrincipalName                      TTL
    EXCH            msstd:webmail.name_domain.test         1  
    EXPR             msstd:webmail.name_domain.test         1  
    WEB                                              
         1  
    Get-AutodiscoverVirtualDirectory | fl name,*auth*,*url*
    Name                          : Autodiscover (Default Web site)
    InternalAuthenticationMethods : {Basic, WSSecu.testy, OAuth}
    ExternalAuthenticationMethods : {Basic, WSSecu.testy, OAuth}
    LiveIdNegotiateAuthentication : False
    WSSecu.testyAuthentication      : True
    LiveIdBasicAuthentication     : False
    BasicAuthentication           : True
    DigestAuthentication          : False
    WindowsAuthentication         : False
    OAuthAuthentication           : True
    AdfsAuthentication            : False
    InternalUrl                   :
    ExternalUrl                   :
    Get-MapiVirtualDirectory | fl name,*auth*,*url*
    Name                          : mapi (Default Web site)
    IISAuthenticationMethods      : {Basic, Ntlm, Negotiate}
    InternalAuthenticationMethods : {Basic, Ntlm, Negotiate}
    ExternalAuthenticationMethods : {Basic, Ntlm, Negotiate}
    InternalUrl                   : https://webmail.name_domain.test/mapi
    ExternalUrl                   : https://webmail.name_domain.test/mapi
    Autodiscover.xml
    <?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>user</DisplayName>
          <LegacyDN>/o=organization_name/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=e4c0c18c8f214afbb5152bb08823179d-user</LegacyDN>
          <AutoDiscoverSMTPAddress>user@name_domain.test</AutoDiscoverSMTPAddress>
          <DeploymentId>d60c71c9-3740-404c-a38c-aa24e6105432</DeploymentId>
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        <Account>
          <AccountType>email</AccountType>
          <Action>settings</Action>
          <MicrosoftOnline>False</MicrosoftOnline>
          <Protocol>
            <Type>EXCH</Type>
            <Server>72036b30-a4d4-4b42-9c39-445bd04c23a6@name_domain.test</Server>
            <ServerDN>/o=organization_name/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=72036b30-a4d4-4b42-9c39-445bd04c23a6@name_domain.test</ServerDN>
            <ServerVersion>73C082C8</ServerVersion>
            <MdbDN>/o=organization_name/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=72036b30-a4d4-4b42-9c39-445bd04c23a6@name_domain.test/cn=Microsoft Private MDB</MdbDN>
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            <AD>DC2.name_domain.test</AD>
            <ASUrl>https://webmail.name_domain.test/EWS/Exchange.asmx</ASUrl>
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            <EmwsUrl>https://webmail.name_domain.test/EWS/Exchange.asmx</EmwsUrl>
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            <EcpUrl-um>?rfr=olk&amp;p=customize/voicemail.aspx&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-um>
            <EcpUrl-aggr>?rfr=olk&amp;p=personalsettings/EmailSubscriptions.slab&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-aggr>
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            <EcpUrl-sms>?rfr=olk&amp;p=sms/textmessaging.slab&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-sms>
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            <EcpUrl-tm>?rfr=olk&amp;ftr=TeamMailbox&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-tm>
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            <EcpUrl-tmE.testing>?rfr=olk&amp;ftr=TeamMailboxE.testing&amp;Id=&lt;Id&gt;&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-tmE.testing>
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            <EcpUrl>https://webmail.name_domain.test/ecp/</EcpUrl>
            <EcpUrl-um>?rfr=olk&amp;p=customize/voicemail.aspx&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-um>
            <EcpUrl-aggr>?rfr=olk&amp;p=personalsettings/EmailSubscriptions.slab&amp;exsvurl=1&amp;realm=name_domain.test</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=name_domain.test</EcpUrl-mt>
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            <EcpUrl-photo>PersonalSettings/E.testAccount.aspx?rfr=olk&amp;chgPhoto=1&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-photo>
            <EcpUrl-tm>?rfr=olk&amp;ftr=TeamMailbox&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-tm>
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            <EcpUrl-tmE.testing>?rfr=olk&amp;ftr=TeamMailboxE.testing&amp;Id=&lt;Id&gt;&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-tmE.testing>
            <EcpUrl-extinstall>Extension/InstalledExtensions.slab?rfr=olk&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-extinstall>
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            <UMUrl>https://webmail.name_domain.test/ews/UM2007Legacy.asmx</UMUrl>
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            <GroupingInformation>LAN</GroupingInformation>
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            <Type>WEB</Type>
            <Internal>
              <OWAUrl AuthenticationMethod="Basic, Fba">https://webmail.name_domain.test/</OWAUrl>
              <Protocol>
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                <ASUrl>https://webmail.name_domain.test/EWS/Exchange.asmx</ASUrl>
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              <OWAUrl AuthenticationMethod="Basic">https://webmail.name_domain.test/</OWAUrl>
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                <Type>EXPR</Type>
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            <AuthPackage>Ntlm</AuthPackage>
            <ASUrl>https://webmail.name_domain.test/EWS/Exchange.asmx</ASUrl>
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            <EmwsUrl>https://webmail.name_domain.test/EWS/Exchange.asmx</EmwsUrl>
            <EcpUrl>https://webmail.name_domain.test/ecp/</EcpUrl>
            <EcpUrl-um>?rfr=olk&amp;p=customize/voicemail.aspx&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-um>
            <EcpUrl-aggr>?rfr=olk&amp;p=personalsettings/EmailSubscriptions.slab&amp;exsvurl=1&amp;realm=name_domain.test</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=name_domain.test</EcpUrl-mt>
            <EcpUrl-ret>?rfr=olk&amp;p=organize/retentionpolicytags.slab&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-ret>
            <EcpUrl-sms>?rfr=olk&amp;p=sms/textmessaging.slab&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-sms>
            <EcpUrl-publish>customize/calendarpublishing.slab?rfr=olk&amp;exsvurl=1&amp;FldID=&lt;FldID&gt;&amp;realm=name_domain.test</EcpUrl-publish>
            <EcpUrl-photo>PersonalSettings/E.testAccount.aspx?rfr=olk&amp;chgPhoto=1&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-photo>
            <EcpUrl-tm>?rfr=olk&amp;ftr=TeamMailbox&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-tm>
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            <EwsUrl>https://webmail.name_domain.test/ews/exchange.asmx</EwsUrl>
            <EmwsUrl>https://webmail.name_domain.test/ews/exchange.asmx</EmwsUrl>
            <EcpUrl>https://webmail.name_domain.test/ecp/</EcpUrl>
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            <EcpUrl-tm>?rfr=olk&amp;ftr=TeamMailbox&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-tm>
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            <EcpUrl-tmE.testing>?rfr=olk&amp;ftr=TeamMailboxE.testing&amp;Id=&lt;Id&gt;&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-tmE.testing>
            <EcpUrl-extinstall>Extension/InstalledExtensions.slab?rfr=olk&amp;exsvurl=1&amp;realm=name_domain.test</EcpUrl-extinstall>
            <OOFUrl>https://webmail.name_domain.test/ews/exchange.asmx</OOFUrl>
            <UMUrl>https://webmail.name_domain.test/ews/UM2007Legacy.asmx</UMUrl>
            <OABUrl>https://webmail.name_domain.test/OAB/e66d9a4a-6ed2-4512-b72f-522381524dd9/</OABUrl>
            <ServerExclusiveConnect>On</ServerExclusiveConnect>
            <CertPrincipalName>msstd:webmail.name_domain.test</CertPrincipalName>
          </Protocol>
        </Account>
      </Response>
    </Autodiscover>
    Get-OwaVirtualDirectory | fl name,*auth*,*url*
    Name                          : owa (Default Web Site)
    ClientAuthCleanupLevel        : High
    InternalAuthenticationMethods : {Basic, Fba}
    BasicAuthentication           : True
    WindowsAuthentication         : False
    DigestAuthentication          : False
    FormsAuthentication           : True
    LiveIdAuthentication          : False
    AdfsAuthentication            : False
    OAuthAuthentication           : False
    ExternalAuthenticationMethods : {Basic}
    Url                           : {}
    SetPhotoURL                   :
    Exchange2003Url               :
    FailbackUrl                   :
    InternalUrl                   : https://webmail.name_domain.test/
    ExternalUrl                   : https://webmail.name_domain.test/

    Follow the results of the test
    Outlook Anywhere (RPC over HTTP).
    Has been used an account for which
    outlook anywhere works. The account
    for which the outlook anywhere does not work is
    an administrative account and therefore
    can not be used in the test.
    Autodiscovery returns the
    same result for both mailbox.
    I'm testing RPC/HTTP connectivity.
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    Test steps
    Microsoft connectivity Analyzer is attempting to test the Autodiscover service for user_test@domain_name.test.
    Test the Autodiscover service has not been exceeded.
    Test steps
    I'm trying to contact the Autodiscover service with each method available.
    I was not able to contact the Autodiscover service with no method.
    Test steps
    I'm trying to test the possible URL for the Autodiscover service https://domain_name.test/AutoDiscover/AutoDiscover.xml
    The test of this potential URL for the Autodiscover service has not been exceeded.
    Test steps
    I'm trying to resolve the host name domain_name. DNS test.
    I was able to resolve the host name.
    IP addresses are returned: xxx.yyy.zzz.www
    I'm testing the TCP port 443 on the host domain_name. tests to check that is open and listening.
    The door has been opened properly.
    I'm testing the validity of your SSL certificate.
    The SSL certificate has not exceeded one or more validation controls.
    Test steps
    Microsoft connectivity Analyzer is attempting to obtain the SSL certificate from the remote server domain_name. test on port 443.
    Microsoft connectivity Analyzer got the remote SSL certificate.
    Remote certificate subject: E = it_staff@domain_name.test, CN = * domain_name. test, OU = it staff, O = domain_name, L = city, S = state, C = test issuer: E = it_staff@domain_name.test, CN = * domain_name. test, OU = it staff, O = domain_name,
    L = city, S = state, C = test.
    I am validating the certificate name.
    I could not validate the certificate name.
    More info about this issue and how to resove it
    The host name domain_name. testing does not match any name found on the certificate and server = it_staff@domain_name.test, CN = * domain_name. test, OU = it staff, O = domain_name, L = city, S = state, C = test.
    I'm trying to test the possible URL for the Autodiscover service https://autodiscover.domain_name.test/AutoDiscover/AutoDiscover.xml
    The test of this potential URL for the Autodiscover service has not been exceeded.
    Test steps
    I'm trying to resolve the host name autodiscover. domain_name. DNS test.
    I was able to resolve the host name.
    IP addresses are returned: xxx.yyy.zzz.kkk
    I'm testing the TCP port 443 on the host autodiscover. domain_name. tests to check that is open and listening.
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    I'm testing the validity of your SSL certificate.
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    Microsoft connectivity Analyzer is attempting to obtain the SSL certificate from the remote server autodiscover. domain_name. test on port 443.
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  • Outlook 2013 client, not in domain, can't connect to the Exchange 2013 server.

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  • Outlook client not connecting when a user is moved from 2010 to 2013

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    Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact [email protected]
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    TechNet Community Support

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