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How to Check that Exchange 2016 Proxying/redirecting the outlook connection to Exchange 2010

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Monday, January 21, 2019 3:01 PM

We have deployed the Exchange 2016 in coexistance with Exchange 2010 server. Now before the cutover, we have to make sure that Exchange 2016 properly proxying the outlook connections to Exchange 2010 CAS server for the mailboxes which are reside on Exchange 2010. 

I have pointed the Autodisover and webmail to Exchange 2016 in local DNS and outlook is properly connecting. I have also tested the email configuration in outlook using the feature TEST EMAIL AUTOConfiguration. However, how I can clrealy check that this conection goes to Exchange 2016 and the redirected to Exchange 2010.

All replies (10)

Monday, January 21, 2019 3:20 PM

Hi,

Please Check logging folder under exchange installation directory on Exchange 2016 (Logging-->Http proxy-->RPC http)

Default location:-

C:\Program files\Microsoft\Exchange server\V15\Logging\http Proxy\RPC http

Thanks, Ashish (I can be wrong but can't be rude) “Tell me and I forget, teach me and I may remember, involve me and I learn.” MCITP, MCT, MCSE. Please remember to vote and mark the replies as answers if they help.

Tuesday, January 22, 2019 8:44 AM

Hi Asif,

Have you checked the Log tab of the Test Email Autoconfiguration result? It should show clear Outlook Autodiscover Lookup Process.

Regards,
Steve Fan

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Tuesday, January 22, 2019 9:03 AM

Hi Steve Fan, 

Thank you so much for replying. Actually, in my host file i have pointed the webmail.mydomain.com and autodiscover.mydomain.com to Exchange 2016 server. I have provided the logs below. Guys can you please look and let me know it is properly proxying the connection or not. 

**Note:  Till now IISAuthenticationMethods is still to BASIC against Exchange 2010 CAS Servers. But still connection is connecting fine. Is NTLM on Exchange 2010 is mandatory to proxy the connection from Exchange 2016 to Exchange 2010?  If yes then In my case why outlook is working fine even basic is enabled only. **

<?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>Test Migration4</DisplayName>
      <LegacyDN>/o=mydomain Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=Test Migration4877</LegacyDN>
      <AutoDiscoverSMTPAddress>test.migration4@mydomain</AutoDiscoverSMTPAddress>
      <DeploymentId>c8aa3ac0-75c7-47f1-8b87-29291c0f63cb</DeploymentId>
    </User>
    <Account>
      <AccountType>email</AccountType>
      <Action>settings</Action>
      <Protocol>
        <Type>EXCH</Type>
        <Server>webmail.mydomain</Server>
        <ServerDN>/o=mydomain Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=webmail.mydomain</ServerDN>
        <ServerVersion>7383807B</ServerVersion>
        <MdbDN>/o=mydomain Organization/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=webmail.mydomain/cn=Microsoft Private MDB</MdbDN>
        <PublicFolderServer>mainEXMB2.mydomain.local</PublicFolderServer>
        <AD>mainADVPKMS.mydomain.local</AD>
        <ASUrl>https://webmail.mydomain/EWS/Exchange.asmx</ASUrl>
        <EwsUrl>https://webmail.mydomain/EWS/Exchange.asmx</EwsUrl>
        <EcpUrl>https://webmail.mydomain/ecp/</EcpUrl>
        <EcpUrl-um>?p=customize/voicemail.aspx&exsvurl=1</EcpUrl-um>
        <EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&exsvurl=1</EcpUrl-aggr>
        <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&IsOWA=<IsOWA>&MsgID=<MsgID>&Mbx=<Mbx></EcpUrl-mt>
        <EcpUrl-ret>?p=organize/retentionpolicytags.slab&exsvurl=1</EcpUrl-ret>
        <EcpUrl-sms>?p=sms/textmessaging.slab&exsvurl=1</EcpUrl-sms>
        <OOFUrl>https://webmail.mydomain/EWS/Exchange.asmx</OOFUrl>
        <UMUrl>https://webmail.mydomain/EWS/UM2007Legacy.asmx</UMUrl>
        <OABUrl>https://webmail.mydomain/OAB/bf720f27-65fa-4592-998c-b5e9be0e844e/</OABUrl>
      </Protocol>
      <Protocol>
        <Type>EXPR</Type>
        <Server>webmail.mydomain</Server>
        <SSL>On</SSL>
        <AuthPackage>Basic</AuthPackage>
        <ASUrl>https://webmail.mydomain/EWS/Exchange.asmx</ASUrl>
        <EwsUrl>https://webmail.mydomain/EWS/Exchange.asmx</EwsUrl>
        <EcpUrl>https://webmail.mydomain/ecp/</EcpUrl>
        <EcpUrl-um>?p=customize/voicemail.aspx&exsvurl=1</EcpUrl-um>
        <EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&exsvurl=1</EcpUrl-aggr>
        <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&IsOWA=<IsOWA>&MsgID=<MsgID>&Mbx=<Mbx></EcpUrl-mt>
        <EcpUrl-ret>?p=organize/retentionpolicytags.slab&exsvurl=1</EcpUrl-ret>
        <EcpUrl-sms>?p=sms/textmessaging.slab&exsvurl=1</EcpUrl-sms>
        <OOFUrl>https://webmail.mydomain/EWS/Exchange.asmx</OOFUrl>
        <UMUrl>https://webmail.mydomain/EWS/UM2007Legacy.asmx</UMUrl>
        <OABUrl>https://webmail.mydomain/OAB/bf720f27-65fa-4592-998c-b5e9be0e844e/</OABUrl>
      </Protocol>
      <Protocol>
        <Type>WEB</Type>
        <Internal>
          <OWAUrl AuthenticationMethod="Basic, Ntlm, Fba, WindowsIntegrated">https://webmail.mydomain/owa/</OWAUrl>
          <Protocol>
            <Type>EXCH</Type>
            <ASUrl>https://webmail.mydomain/EWS/Exchange.asmx</ASUrl>
          </Protocol>
        </Internal>
        <External>
          <OWAUrl AuthenticationMethod="Fba">https://webmail.mydomain/owa/</OWAUrl>
          <Protocol>
            <Type>EXPR</Type>
            <ASUrl>https://webmail.mydomain/EWS/Exchange.asmx</ASUrl>
          </Protocol>
        </External>
      </Protocol>
    </Account>
  </Response>
</Autodiscover>

Tuesday, January 22, 2019 9:37 AM

Hi Ashish, 

I am getting below in RPCHTTP logs. Can you please look into below and let me know is it properly proxying the connection. 

Note: For security reason, I have replaced the domain name with mydomain.

2019-01-22T07:26:07.281Z,da5e7680-86ec-4c54-9f23-3d818d1c7e8b,15,1,1591,10,,RpcHttp,webmail.mydomain.com,/rpc/rpcproxy.dll,,Basic,true,mydomain

\test.migration4,,Url~https://servervpexhc1.mydomain.local/rpc/rpcproxy.dll?

webmail.mydomain.com:6002,MSRPC,10.80.90.11,ARDSPVEXMB01,200,,,RPC_IN_DATA,Proxy,servervpexhc1.mydomain.local,15.00.0000.000,IntraForest,RpcHttpProxyRules,,,,1073741824,,,,0,457,,0,,0,,0,0,,0,3376,0,2831,6,0,,,,,0,1,3376,0,,539,,545,3376,,?

webmail.mydomain.com:6002,,BeginRequest=2019-01-22T07:26:03.904Z;CorrelationID=<empty>;ProxyState-Run=None;FEAuth=BEVersion-

1941962752;NewConnection=10.0.0.115&0;H-BeginGetResponse=2019-01-22T07:26:04.362Z;H-OnResponseReady=2019-01-22T07:26:04.373Z;H-

EndGetResponse=2019-01-22T07:26:04.373Z;NewConnection=10.0.0.115&0;BeginGetRequestStream=2019-01-

22T07:26:04.374Z;OnRequestStreamReady=2019-01-22T07:26:04.380Z;ProxyState-Complete=ProxyRequestData;SharedCacheGuard=0;EndRequest=2019-

01-22T07:26:07.281Z;,WebExceptionStatus=ProtocolError;ResponseStatusCode=503;WebException=System.Net.WebException: The remote server
 
returned an error: (503) Server Unavailable.    at System.Net.HttpWebRequest.EndGetResponse(IAsyncResult asyncResult)    at 

Microsoft.Exchange.HttpProxy.RpcHttpProxyRequestHandler.<>c__DisplayClass29_0.<OnValidateBackendServerCacheCompleted>b__0

();SharedCache=AMCacheRemovalFailure;StreamProxy=StreamProxy-Request-ExpectReadCallback;,,,,,CafeV1

Tuesday, January 22, 2019 1:02 PM

Hi,

It will require more information. How you have designed and configured namespaces, url's, outlook anywhere setting etc.

In above logs I can see error 503 is showing.

And yes, if you are using outlook any where on Exchange 2010 then you must set IIS authentication to NTLM and Basic.

I will recommend to go through below article and use Exchange server deployment assistant which may help you in guiding in setting up co-existence.

https://blogs.technet.microsoft.com/exchange/2015/10/26/client-connectivity-in-an-exchange-2016-coexistence-environment-with-exchange-2010/

https://blogs.technet.microsoft.com/exchange/2013/05/23/ambiguous-urls-and-their-effect-on-exchange-2010-to-exchange-2013-migrations/

Thanks, Ashish (I can be wrong but can't be rude) “Tell me and I forget, teach me and I may remember, involve me and I learn.” MCITP, MCT, MCSE. Please remember to vote and mark the replies as answers if they help.

Wednesday, January 23, 2019 7:32 AM

Hi Ashish, 

Thanks for your reply. Actually right now I am using the same name space for both Exchange 2010 and Exchange 2016. 

Rigth now Basic Authenitcation for IISAuthentication Method is only enabled against Exchange 2010 CAS servers.

Outlook Connections For Mailboxes Exist on 2010:

I am able to use outlook  by pointing the webmail and autodiscover to Exchange 2016 using public IP of load balancer and it seems that connections are properly proxied by Exchange 2016 to Exchange 2010. I am wondering if NTLM is required then why outlook for 2010 mailbox is properly working from Exchange 2016 server when request is comming through public IP of Load Balancer. 

When I Point the webmail and autodiscover to Internal/Private IP of Exchange Server 2016 For Mailbox 2010:

****Can be there any reason due to which its working when webmail and autodiscover points to external public IP of Load Balancer pointing to Exchange 2016 and not when when points to private IP of Exchange 2016. ****

Wednesday, January 23, 2019 8:09 AM

Hi,

So your load balancer sending connections to Exchange 2016 or Exchange 2010.

Thanks, Ashish (I can be wrong but can't be rude) “Tell me and I forget, teach me and I may remember, involve me and I learn.” MCITP, MCT, MCSE. Please remember to vote and mark the replies as answers if they help.

Wednesday, January 23, 2019 8:15 AM

Hi,

Load Balancer is sending the connections to Exchange 2016.  That is why I am wondering, is it possible that even BASIC authentication is enabled on CAS 2010 and still Exchange able to proxy the connections. 

Friday, January 25, 2019 10:40 AM

Hi Asif,

NTLM is required to be enabled, if not, it could cause authentication issue and it will fail to proxy the connection to legacy version of Exchange. Here is a quotation from the official blog:

In order to support access for Outlook Anywhere clients whose mailboxes are on legacy versions of Exchange, you will need to make some changes to your environment which are documented in the steps within the Exchange Deployment Assistant. Specifically, you will need to enable Outlook Anywhere on your legacy Client Access servers and enable NTLM in addition to basic authentication for the IIS Authentication Method.

Regards,
Steve Fan

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Thursday, January 31, 2019 1:40 AM

Dear Asif,

Just wanted to say hi and check if there is anything that I can do for you on this problem. If so, please do not hesitate to let me know and I will be happy to help.

Best regards,
Steve Fan 

Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact [email protected].


Click here to learn more. Visit the dedicated forum to share, explore and talk to experts about Microsoft Teams.