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Exchange Server 2016 & Exchange Server 2010: Autodiscover Service during coexistence RRS feed

  • Question

  • We have Exchange 2010: 1 NLB (2x CAS/HUB) + 1 DAG (2x MX).

    mail.contoso.com points to that NLB. Autodiscover points to mail.contoso.com

    Now, we want to deploy Exchange 2016. How Does Outlook discover news Exchange Server 2016 Mailboxes ??

    Wednesday, October 14, 2015 9:00 AM

Answers

  • Hi,

    Ambiguous URLs: If you are using Exchange 2010 and the RPCClientAccessServer is set to the same as the Outlook Anywhere hostname then you can get a problem when upgrading to Exchange 2013. The reason is that when you change the mail.domain.com A record to Exchange 2013, the RPC/TCP clients will attempt to connect to the Exchange 2013 servers using RPC/TCP which won't work as this is no longer supported by Exchange 2013. To get around this, enable Outlook Anywhere and force the clients to use HTTPS on fast connections by configuring Autodiscover (Set-OutlookProvider). Once done, you can move the mail.domain.com A record to Exchange 2013 and Exchange 2013 will proxy the requests to Exchange 2016. Any non-Outlook Anywhere clients need to be configured to use Exchange 2010 by using host files. The same is applicable to Exchange 2016.

    For an Exchange 2013/2016 and 2010 coexistence scenario, Exchange 2016 will proxy the request to Exchange 2010 as per this article: http://blogs.technet.com/b/exchange/archive/2014/03/12/client-connectivity-in-an-exchange-2013-coexistence-environment.aspx.

    Thanks.


    Please mark as an answer if this answers your question

    Mark Gossa

    MCSE 2003, MCITP Enterprise Administrator 2008 R2, MCSA 2012 R2, MCTS Exchange 2010

    Blog: http://markgossa.blogspot.com

    Posts are provided “AS IS” without warranty of any kind, either expressed or implied.

    Saturday, October 17, 2015 1:40 PM
  • Actually, all Exchange 2010 CAS URLs (external & internal) point to mail.contoso.com. Internal DNS host record exists mail.contoso.com point to NLB CAS.

    Internal autodiscover points to mail.contoso.com. We don't have external autodiscover. External users access manually with mailweb.contoso.com. TMG publishing rule point to mail.contoso.com.

    If I configure Exchange Server 2016 URLs to mail.contoso.com...i need to modify host DNS record. When Exchange user opens Outlook, Outlook is going to Exchange Server 2016...How Does Exchange Server redirect user to Exchange 2010 ?? Must I change Exchange 2010 CAS URLs ?

    It will proxy the connection to the 2010 servers. But be aware of the ambigious URL issues when migrating that may be an issue for you. Important to read up on that:

    http://blogs.technet.com/b/exchange/archive/2013/05/23/ambiguous-urls-and-their-effect-on-exchange-2010-to-exchange-2013-migrations.aspx

    One thing to note. Its not absolutely required to move the all the client and autodiscover endpoints to 2016. You can also bring up new endpoints and "migrate" the 2010 endpoints later with DNS cnames and the correct subject names on a certificate.


    Twitter!: Please Note: My Posts are provided “AS IS” without warranty of any kind, either expressed or implied.

    Friday, October 16, 2015 6:58 PM
    Moderator

All replies

  • here you go

    http://exchangequery.com/2015/07/30/configure-exchange-2016-with-exchange-2010-coexistence/


    Remember to mark as helpful if you find my contribution useful or as an answer if it does answer your question.That will encourage me - and others - to take time out to help you Check out my latest blog posts on http://exchangequery.com Thanks Sathish (MVP)

    Wednesday, October 14, 2015 12:25 PM
  • I suppose that is like that Exchange Server 2013, not ??

    1) Configure External e Internal URL on Exchange Server 2016

    2) Configure Exchange Server 2013 to proxies request to Exchange 2010

    3) Modify mail.contoso.com to point new Exchange Server 2016 MX "MX1"

    4) Add a new host record mail.contoso.com to point new Exchange Server 2016 MX "MX2"

    5) Configure DNS Round Robin

    6) For external access, we use TMG, so I need to publish also Exchange Server 2016.

    7) External DNS record points to this new TMG Listener

    Wednesday, October 14, 2015 4:58 PM
  • Hi,

    The Autodiscover URLs need to be moved to Exchange 2016. This means you need to ensure that the AutodiscoverServiceInternalUri (Get-ClientAccessServer) uses a URL which resolves to Exchange 2016 and your autodiscover.domain.com external DNS resolves to Exchange 2016 also. 

    Your hostnames that are used for Outlook Anywhere need to resolve to Exchange 2016 as do other URLs. 

    To get detailed instructions on this, certificate requirements and the full migration from Exchange 2010 to 2016, please generate a task list for an Exchange 2010 - 2016 migration using the Exchange Deployment Assistant which can be found here: https://technet.microsoft.com/en-us/office/dn756393.aspx.

    Thanks.


    Please mark as an answer if this answers your question

    Mark Gossa

    MCSE 2003, MCITP Enterprise Administrator 2008 R2, MCSA 2012 R2, MCTS Exchange 2010

    Blog: http://markgossa.blogspot.com

    Posts are provided “AS IS” without warranty of any kind, either expressed or implied.

    Thursday, October 15, 2015 12:06 AM
  • Hi,

    Based on my knowledge, the Autodiscover service on Exchange 2016 can process Autodiscover requests for both Exchange 2010 and Exchange 2016 mailboxes in an coexistence environment.

    You can use the below command to configure autodiscover service:

    Set-ClientAccessServer -Identity CAS2016 –AutodiscoverServiceInternalURI https://mail.contoso.com /autodiscover/autodiscover.xml

    Please also make sure you have set related DNS records to solve autodiscover.domain.com and mail.contoso.com.

    More detailed information about client connectivity in an Exchange coexistence environment, you can have a look at the below link:

    http://blogs.technet.com/b/exchange/archive/2014/03/12/client-connectivity-in-an-exchange-2013-coexistence-environment.aspx

    Regards,

    David 


    Thursday, October 15, 2015 6:42 AM
    Moderator
  • Just an update

    From Exchange 2016 there is no Get-ClientAccessserver since the command is depreciated

    Instead you need to use Get-ClientAccessService and Set-ClientAccessService


    Remember to mark as helpful if you find my contribution useful or as an answer if it does answer your question.That will encourage me - and others - to take time out to help you Check out my latest blog posts on http://exchangequery.com Thanks Sathish (MVP)

    Friday, October 16, 2015 8:09 AM
  • Actually, all Exchange 2010 CAS URLs (external & internal) point to mail.contoso.com. Internal DNS host record exists mail.contoso.com point to NLB CAS.

    Internal autodiscover points to mail.contoso.com. We don't have external autodiscover. External users access manually with mailweb.contoso.com. TMG publishing rule point to mail.contoso.com.

    If I configure Exchange Server 2016 URLs to mail.contoso.com...i need to modify host DNS record. When Exchange user opens Outlook, Outlook is going to Exchange Server 2016...How Does Exchange Server redirect user to Exchange 2010 ?? Must I change Exchange 2010 CAS URLs ?

    Friday, October 16, 2015 6:46 PM
  • Actually, all Exchange 2010 CAS URLs (external & internal) point to mail.contoso.com. Internal DNS host record exists mail.contoso.com point to NLB CAS.

    Internal autodiscover points to mail.contoso.com. We don't have external autodiscover. External users access manually with mailweb.contoso.com. TMG publishing rule point to mail.contoso.com.

    If I configure Exchange Server 2016 URLs to mail.contoso.com...i need to modify host DNS record. When Exchange user opens Outlook, Outlook is going to Exchange Server 2016...How Does Exchange Server redirect user to Exchange 2010 ?? Must I change Exchange 2010 CAS URLs ?

    It will proxy the connection to the 2010 servers. But be aware of the ambigious URL issues when migrating that may be an issue for you. Important to read up on that:

    http://blogs.technet.com/b/exchange/archive/2013/05/23/ambiguous-urls-and-their-effect-on-exchange-2010-to-exchange-2013-migrations.aspx

    One thing to note. Its not absolutely required to move the all the client and autodiscover endpoints to 2016. You can also bring up new endpoints and "migrate" the 2010 endpoints later with DNS cnames and the correct subject names on a certificate.


    Twitter!: Please Note: My Posts are provided “AS IS” without warranty of any kind, either expressed or implied.

    Friday, October 16, 2015 6:58 PM
    Moderator
  • About ambigious URL.. Dou you refer to mail.contoso.com is assigned to Internal and External URL ?? Exactly we use mail.inter.contoso.com for External/internal Exchange 2010 URLs. External clients can't resolve mail.contoso.com and we use Host file to resolve names on perimetral/DMZ zone.

    Aboout Exchange proxies connection, ok...but in that situation...the performance on Exchange 2016 is worse, because when Exchange 2010 user opens outlook...he use Exchange 2016 + Exchange 2010 servers...I thought Exchange 2016 was to redirect user to Exchange 2010, not proxies it... it is different

    Saturday, October 17, 2015 5:57 AM
  • Hi,

    Ambiguous URLs: If you are using Exchange 2010 and the RPCClientAccessServer is set to the same as the Outlook Anywhere hostname then you can get a problem when upgrading to Exchange 2013. The reason is that when you change the mail.domain.com A record to Exchange 2013, the RPC/TCP clients will attempt to connect to the Exchange 2013 servers using RPC/TCP which won't work as this is no longer supported by Exchange 2013. To get around this, enable Outlook Anywhere and force the clients to use HTTPS on fast connections by configuring Autodiscover (Set-OutlookProvider). Once done, you can move the mail.domain.com A record to Exchange 2013 and Exchange 2013 will proxy the requests to Exchange 2016. Any non-Outlook Anywhere clients need to be configured to use Exchange 2010 by using host files. The same is applicable to Exchange 2016.

    For an Exchange 2013/2016 and 2010 coexistence scenario, Exchange 2016 will proxy the request to Exchange 2010 as per this article: http://blogs.technet.com/b/exchange/archive/2014/03/12/client-connectivity-in-an-exchange-2013-coexistence-environment.aspx.

    Thanks.


    Please mark as an answer if this answers your question

    Mark Gossa

    MCSE 2003, MCITP Enterprise Administrator 2008 R2, MCSA 2012 R2, MCTS Exchange 2010

    Blog: http://markgossa.blogspot.com

    Posts are provided “AS IS” without warranty of any kind, either expressed or implied.

    Saturday, October 17, 2015 1:40 PM
  • About ambigious URL.. Dou you refer to mail.contoso.com is assigned to Internal and External URL ?? Exactly we use mail.inter.contoso.com for External/internal Exchange 2010 URLs. External clients can't resolve mail.contoso.com and we use Host file to resolve names on perimetral/DMZ zone.

    Aboout Exchange proxies connection, ok...but in that situation...the performance on Exchange 2016 is worse, because when Exchange 2010 user opens outlook...he use Exchange 2016 + Exchange 2010 servers...I thought Exchange 2016 was to redirect user to Exchange 2010, not proxies it... it is different

    Check that link I posted about ambigious URLs for more info. Proxying connections does not make performance worse. Only if you have sized the servers incorrectly, and in that case its a moot point. :)

    As I mentioned above, its not required ( though preferred) that you move all the client endpoints to 2016 to migrate to 2016. You can create new endpoints in DNS and as long as the new endpoints/URLs resolve to the 2016 CAS and the cert subject names are there, it will work. (You can have seperate URLs and FQDNs for 2010 and 2016 )


    Twitter!: Please Note: My Posts are provided “AS IS” without warranty of any kind, either expressed or implied.


    Saturday, October 17, 2015 2:36 PM
    Moderator