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SOLVED - Exchange 2019 and Outlook 2016 fails to start on Windows 2008 R2 rds server RRS feed

  • Question

  • Hi everybody

    I'm trying to migrate an Exchange organization from 2013 to 2019.

    Everything is weel installed for my Exchange 2019 server (on a Windosw 2019 server).

    When i move the internal DNS records for autodiscover and webmail entries to the new server, everything is working fine except for users on 2008 R2 RDS Server.

    Everyone is using Outlook 2016. 

    Everything works on Windows 10 computers.

    Everything works on RDS 2012 R2 servers.

    Outlook fails to start and contact the Exchange 2019 Server only on 2008 R2 RDS (and non RDS) servers.

    Any idea of the cause? 

    Thanks



    • Edited by Iom84 Thursday, August 8, 2019 8:05 AM
    Thursday, May 23, 2019 10:54 AM

Answers

  • Hi Iom84,

    I had the same issue last week after migrating Exchange 2016 to 2019.

    The solution was to activate TLS 1.2 on the Server 2008 R2 und Windows 7 machines as default secure protocol:

    - Install KB3140245 if not already installed

    - Create the following registry settings:

    [HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Internet Settings\WinHttp]

    "DefaultSecureProtocols"=dword:00000800

    [HKEY_LOCAL_MACHINE\SOFTWARE\Wow6432Node\Microsoft\Windows\CurrentVersion\Internet Settings\WinHttp]

    "DefaultSecureProtocols"=dword:00000800

    [HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client]
    "DisabledByDefault"=dword:00000000

    [HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client]
    "Enabled"=dword:00000001

    - Reboot (but might work without reboot)

    Best Regards,

    Sascha

    • Marked as answer by Iom84 Thursday, August 8, 2019 8:05 AM
    Friday, July 19, 2019 10:57 AM

All replies

  • Hi lom84,

    How do users connect to outlook ? RemoteAPP or remote desktop?

    According to your description, as outlook works as expected on windows 10 computers, this seems not like an Exchange related issue, but an RDS server related issue. I recommend you compare all settings with RDS 2012 server to check if there is any difference. 

    Moreover, i also recommend you post this in RDS forum,  as they should have more professional knowledge on RDS and you may get effective solution timely.


    Best Regards,
    Niko Cheng


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.


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

    Friday, May 24, 2019 8:46 AM
    Moderator
  • HI. 

    The problem is not due to RDS functionnality, the error is the same on a 2008 R2 server which is not a rds server.

    I have put a KB (KB3140245)for W7 computers, but it's still not working. 

    There is another problem. And don't know what is is (no errors in computer logs, ...)

    Monday, May 27, 2019 7:50 AM
  • HI. 

    The problem is not due to RDS functionnality, the error is the same on a 2008 R2 server which is not a rds server.

    I have put a KB (KB3140245)for W7 computers, but it's still not working. 

    There is another problem. And don't know what is is (no errors in computer logs, ...)

    Did you mean that install outlook 2016 on Windows 2008 R2 server?

    What error did you get on Window 2008 R2 server?


    Best Regards,
    Niko Cheng


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.


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

    Wednesday, May 29, 2019 8:59 AM
    Moderator
  • Hi Niko. 

    The error I get is that Outlook cannot start, with a panel showing that the server cannot be contacted. 

    There is no errors while doing the same thing in another OS (2012 R2, 2016, W10, ...)

    Do you need screenshots? 

    Monday, June 3, 2019 3:15 PM
  • Hi lom84,

    You can upload the screenshot here, that would give us more clues to help troubleshoot the issue.

    Moreover, I also recommend you use a capture tool, such as fiddler, to track the startup process of outlook, that would show more details about the reason why start failed.


    Best Regards,
    Niko Cheng


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.


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

    Wednesday, June 5, 2019 1:54 AM
    Moderator
  • Hi guys. 

    Some news. 

    We opened a case at MS Support. One month working on it, and still no solution. 

    I'll tell you if they find something. 

    Cheers
    Friday, July 5, 2019 1:20 PM
  • Hi Iom84,

    I had the same issue last week after migrating Exchange 2016 to 2019.

    The solution was to activate TLS 1.2 on the Server 2008 R2 und Windows 7 machines as default secure protocol:

    - Install KB3140245 if not already installed

    - Create the following registry settings:

    [HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Internet Settings\WinHttp]

    "DefaultSecureProtocols"=dword:00000800

    [HKEY_LOCAL_MACHINE\SOFTWARE\Wow6432Node\Microsoft\Windows\CurrentVersion\Internet Settings\WinHttp]

    "DefaultSecureProtocols"=dword:00000800

    [HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client]
    "DisabledByDefault"=dword:00000000

    [HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client]
    "Enabled"=dword:00000001

    - Reboot (but might work without reboot)

    Best Regards,

    Sascha

    • Marked as answer by Iom84 Thursday, August 8, 2019 8:05 AM
    Friday, July 19, 2019 10:57 AM
  • Hi Sascha. 

    Thanks for your reply, I will try this quickly. 

    I'll tell you if it works. 
    Wednesday, August 7, 2019 3:14 PM
  • Hi Iom84,

    I had the same issue last week after migrating Exchange 2016 to 2019.

    The solution was to activate TLS 1.2 on the Server 2008 R2 und Windows 7 machines as default secure protocol:

    - Install KB3140245 if not already installed

    - Create the following registry settings:

    [HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Internet Settings\WinHttp]

    "DefaultSecureProtocols"=dword:00000800

    [HKEY_LOCAL_MACHINE\SOFTWARE\Wow6432Node\Microsoft\Windows\CurrentVersion\Internet Settings\WinHttp]

    "DefaultSecureProtocols"=dword:00000800

    [HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client]
    "DisabledByDefault"=dword:00000000

    [HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client]
    "Enabled"=dword:00000001

    - Reboot (but might work without reboot)

    Best Regards,

    Sascha

    Sascha, you rock !!! 
    That's the solution. I gave it to the MS Support team for the future. 
    Thanks a lot... 3 months with this case, this is the end. 
    Thursday, August 8, 2019 8:05 AM
  • Worked a charm, I had trouble with Exchange 2019 upgrade and our 2008R2 terminal server running office 2013. I could not open outlook, or even configure a profile. The testconnectivity tool showed everything working perfectly, my DNS was right and yet I could not connect outlook.

    Added the Registry Keys without rebooting and it worked straight away.

    Thank you Sascha so much for your guidance.



    • Edited by Andrew Rich Wednesday, July 1, 2020 3:12 AM
    Wednesday, July 1, 2020 3:11 AM