Outlook Anywhere clients being asked for password

I have an exchange 2010 server on the back end and when I am setting up outlook clients over the internet using https/rpc their accounts sync up fine the first time, but if I close outlook and re-open I am prompted for their passoword again.  when we enter the password it just keeps re-prompting us for it again.

This was a migration from a SBS2008 unit and everything has been migrated and uninstalled from the exchange 2007.

all pointers have been pointing to the new exchange 2010 unit for months now and people have been working until began the demotion work


All LAN clients are working fine
 
OWA works fine

I have done the microsoft test connectivity analyzer and only minimal errors....and the mailboxes download fine until I shut down the outlook client and reopen


Thanks for any help with this
bcameron70Asked:
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brendanmeyerCommented:
please go in to powershell and get the output from the following command

Get-OutlookAnywhere |select ExternalClientAuthenticationMethod,InternalClientAuthenticationMethod,IISAuthenticationMethods |fl

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bcameron70Author Commented:
ExternalClientAuthenticationMethod :
InternalClientAuthenticationMethod :
IISAuthenticationMethods           : {Basic}
brendanmeyerCommented:
please get the results from the Outlook 'Test E-Mail AutoConfiguration' tool

Start Outlook
Press and Hold Ctrl
Right Click on the Outlook icon in the System Tray.
Click Test.

Get results from internal and external user
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bcameron70Author Commented:
I cannot seem to copy and paste the results...here is something I noticed...

Usually the username should be ftc2\mikewadsworth however the name it is resolving to use is mikew which is his e-mail alias.  Does that help?  

otherwise how should I copy the results?
brendanmeyerCommented:
you can copy the XML tab
bcameron70Author Commented:
external

<?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>Mike Wadsworth</DisplayName>
      <LegacyDN>/o=First Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=MikeW</LegacyDN>
      <AutoDiscoverSMTPAddress>MikeW@Friendshiptrap.com</AutoDiscoverSMTPAddress>
      <DeploymentId>45663811-63de-463d-a924-50358688e04d</DeploymentId>
    </User>
    <Account>
      <AccountType>email</AccountType>
      <Action>settings</Action>
      <Protocol>
        <Type>EXCH</Type>
        <Server>EXCHANGE.ftc2.local</Server>
        <ServerDN>/o=First Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=EXCHANGE</ServerDN>
        <ServerVersion>738180DA</ServerVersion>
        <MdbDN>/o=First Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=EXCHANGE/cn=Microsoft Private MDB</MdbDN>
        <PublicFolderServer>EXCHANGE.ftc2.local</PublicFolderServer>
        <AD>SBS2008.ftc2.local</AD>
        <ASUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</ASUrl>
        <EwsUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</EwsUrl>
        <EcpUrl>https://remote.friendshiptrap.com/ecp/</EcpUrl>
        <EcpUrl-um>?p=customize/voicemail.aspx&amp;exsvurl=1</EcpUrl-um>
        <EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&amp;exsvurl=1</EcpUrl-aggr>
        <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&amp;IsOWA=&lt;IsOWA&gt;&amp;MsgID=&lt;MsgID&gt;&amp;Mbx=&lt;Mbx&gt;</EcpUrl-mt>
        <EcpUrl-ret>?p=organize/retentionpolicytags.slab&amp;exsvurl=1</EcpUrl-ret>
        <EcpUrl-sms>?p=sms/textmessaging.slab&amp;exsvurl=1</EcpUrl-sms>
        <OOFUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</OOFUrl>
        <UMUrl>https://remote.friendshiptrap.com/ews/UM2007Legacy.asmx</UMUrl>
        <OABUrl>https://remote.friendshiptrap.com/oab/a248969c-8a6b-4dc7-8d6c-0e9fbc8ccebe/</OABUrl>
      </Protocol>
      <Protocol>
        <Type>EXPR</Type>
        <Server>remote.friendshiptrap.com</Server>
        <SSL>On</SSL>
        <AuthPackage>Basic</AuthPackage>
        <ASUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</ASUrl>
        <EwsUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</EwsUrl>
        <EcpUrl>https://remote.friendshiptrap.com/ecp/</EcpUrl>
        <EcpUrl-um>?p=customize/voicemail.aspx&amp;exsvurl=1</EcpUrl-um>
        <EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&amp;exsvurl=1</EcpUrl-aggr>
        <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&amp;IsOWA=&lt;IsOWA&gt;&amp;MsgID=&lt;MsgID&gt;&amp;Mbx=&lt;Mbx&gt;</EcpUrl-mt>
        <EcpUrl-ret>?p=organize/retentionpolicytags.slab&amp;exsvurl=1</EcpUrl-ret>
        <EcpUrl-sms>?p=sms/textmessaging.slab&amp;exsvurl=1</EcpUrl-sms>
        <OOFUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</OOFUrl>
        <UMUrl>https://remote.friendshiptrap.com/ews/UM2007Legacy.asmx</UMUrl>
        <OABUrl>https://remote.friendshiptrap.com/OAB/a248969c-8a6b-4dc7-8d6c-0e9fbc8ccebe/</OABUrl>
        <CertPrincipalName>msstd:remote.friendshiptrap.com</CertPrincipalName>
      </Protocol>
      <Protocol>
        <Type>WEB</Type>
        <Internal>
          <OWAUrl AuthenticationMethod="Basic, Fba">https://remote.friendshiptrap.com/owa/</OWAUrl>
          <Protocol>
            <Type>EXCH</Type>
            <ASUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</ASUrl>
          </Protocol>
        </Internal>
        <External>
          <OWAUrl AuthenticationMethod="Fba">https://remote.friendshiptrap.com/owa/</OWAUrl>
          <Protocol>
            <Type>EXPR</Type>
            <ASUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</ASUrl>
          </Protocol>
        </External>
      </Protocol>
    </Account>
  </Response>
</Autodiscover>
bcameron70Author Commented:
Internal (different user)
<?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>Mark Wadsworth</DisplayName>
      <LegacyDN>/o=First Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=MarkWadsworth</LegacyDN>
      <AutoDiscoverSMTPAddress>MarkWadsworth@Friendshiptrap.com</AutoDiscoverSMTPAddress>
      <DeploymentId>45663811-63de-463d-a924-50358688e04d</DeploymentId>
    </User>
    <Account>
      <AccountType>email</AccountType>
      <Action>settings</Action>
      <Protocol>
        <Type>EXCH</Type>
        <Server>EXCHANGE.ftc2.local</Server>
        <ServerDN>/o=First Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=EXCHANGE</ServerDN>
        <ServerVersion>738180DA</ServerVersion>
        <MdbDN>/o=First Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=EXCHANGE/cn=Microsoft Private MDB</MdbDN>
        <PublicFolderServer>EXCHANGE.ftc2.local</PublicFolderServer>
        <AD>MAIN.ftc2.local</AD>
        <ASUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</ASUrl>
        <EwsUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</EwsUrl>
        <EcpUrl>https://remote.friendshiptrap.com/ecp/</EcpUrl>
        <EcpUrl-um>?p=customize/voicemail.aspx&amp;exsvurl=1</EcpUrl-um>
        <EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&amp;exsvurl=1</EcpUrl-aggr>
        <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&amp;IsOWA=&lt;IsOWA&gt;&amp;MsgID=&lt;MsgID&gt;&amp;Mbx=&lt;Mbx&gt;</EcpUrl-mt>
        <EcpUrl-ret>?p=organize/retentionpolicytags.slab&amp;exsvurl=1</EcpUrl-ret>
        <EcpUrl-sms>?p=sms/textmessaging.slab&amp;exsvurl=1</EcpUrl-sms>
        <OOFUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</OOFUrl>
        <UMUrl>https://remote.friendshiptrap.com/ews/UM2007Legacy.asmx</UMUrl>
        <OABUrl>https://remote.friendshiptrap.com/oab/a248969c-8a6b-4dc7-8d6c-0e9fbc8ccebe/</OABUrl>
      </Protocol>
      <Protocol>
        <Type>EXPR</Type>
        <Server>remote.friendshiptrap.com</Server>
        <SSL>On</SSL>
        <AuthPackage>Basic</AuthPackage>
        <ASUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</ASUrl>
        <EwsUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</EwsUrl>
        <EcpUrl>https://remote.friendshiptrap.com/ecp/</EcpUrl>
        <EcpUrl-um>?p=customize/voicemail.aspx&amp;exsvurl=1</EcpUrl-um>
        <EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&amp;exsvurl=1</EcpUrl-aggr>
        <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&amp;IsOWA=&lt;IsOWA&gt;&amp;MsgID=&lt;MsgID&gt;&amp;Mbx=&lt;Mbx&gt;</EcpUrl-mt>
        <EcpUrl-ret>?p=organize/retentionpolicytags.slab&amp;exsvurl=1</EcpUrl-ret>
        <EcpUrl-sms>?p=sms/textmessaging.slab&amp;exsvurl=1</EcpUrl-sms>
        <OOFUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</OOFUrl>
        <UMUrl>https://remote.friendshiptrap.com/ews/UM2007Legacy.asmx</UMUrl>
        <OABUrl>https://remote.friendshiptrap.com/OAB/a248969c-8a6b-4dc7-8d6c-0e9fbc8ccebe/</OABUrl>
        <CertPrincipalName>msstd:remote.friendshiptrap.com</CertPrincipalName>
      </Protocol>
      <Protocol>
        <Type>WEB</Type>
        <Internal>
          <OWAUrl AuthenticationMethod="Basic, Fba">https://remote.friendshiptrap.com/owa/</OWAUrl>
          <Protocol>
            <Type>EXCH</Type>
            <ASUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</ASUrl>
          </Protocol>
        </Internal>
        <External>
          <OWAUrl AuthenticationMethod="Fba">https://remote.friendshiptrap.com/owa/</OWAUrl>
          <Protocol>
            <Type>EXPR</Type>
            <ASUrl>https://remote.friendshiptrap.com/ews/exchange.asmx</ASUrl>
          </Protocol>
        </External>
      </Protocol>
    </Account>
  </Response>
</Autodiscover>
brendanmeyerCommented:
i would have a look at recreating the Virtual Directory for the AutoDiscover

https://technet.microsoft.com/en-us/library/ff629372%28v=exchg.141%29.aspx

Please make sure you have a backup first
bcameron70Author Commented:
ok, I'll give it a shot.  Does any of the info need to be masked or deleted, or is it pretty inert?
bcameron70Author Commented:
I did the reset of many and went back in to check the settings....still having the same issue with the external outlook clinet, I am re-creating their outlook profile each time with the same effect of working until I close outlook and re-open.  When re-opening I am prompted for the UN/PW and never authenticated after that
brendanmeyerCommented:
can you check the outlook anywhere settings in outlook for the users?
post a screen shot
bcameron70Author Commented:
I dropped back to basics and found XP does not resolve SAN names, only top level and I changed the certificate to match the top level for the machines in the wild....Thank you for your assistance though

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bcameron70Author Commented:
I found out it was an XP related issue with SSL certificates
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