none
Upgrade Microsoft RDWeb from Windows 2012 R2 to Windows 2019 RRS feed

  • Question

  • Hi all,

    I have tried to upgrade Windows 2012 R2 standard running RDWeb to Windows 2019 Standard.

    I went successful but RDWeb having an issue with SSL certificate. It point to my internal SSL cert not to my wildcard SSL cert.

    I have change everything in configuration to the wildcard SSL Cert but still not working.

    is there any prerequisite that i need to prepared ?

    Thanks for your help

    Ashraf

    Wednesday, November 13, 2019 4:29 AM

All replies

  •  

    Hi Ashraf,

     

    1.Would you mind sharing us with the steps that you tried to change the Cert setting? The link of guidance will also be appreciated.

     

    2. Please let us know how many roles and servers are involved in your RDS deployment.

     

    Best Regards,

    Jenn


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

    Wednesday, November 13, 2019 8:27 AM
  • Hi Jenn,

    Thanks for your feedback. My step are below,

    Server hostname : RDWeb.test.com

    SSL Cert : RDweb.test.com

    Wildcard SSL Cert : *.company.com

    Current Setting;

    Server manager > RDS > Edit deployment overview
       
        RD Connection Broker - SSO - OK = SSL RDWeb.test.com
        RD CONNECTION Broker - PUblishing - OK SSL RDWeb.test.com
        RD Web Access - OK - SSL RDWeb.test.com
        RD Gateway - OK  - SSL RDWeb.test.com
    ----------------------------------------------------------------------------
        At RD Gateway Manager > Properties > SSL Certificate
        SSL RDWeb.test.com

    ---------------------------------------------------------------------------

    IIS > Bindings

    https = *.company.com

    http = *.company.com

    with current config we access via web with rdweb.company.com successfuly

    ---------------------------------------------------------------------------

    Step to upgrade

    1. MY server running VM and i take snapshot before upgrade to Windows2019.

    2. after complete upgrade to Windows 2019.

    3. RDweb running successful but browser detected that SSL are untrusted certificate and pointed to RDWeb.test.com not *.company.com

    4. Is there any config that i need to reassigned SSL due to upgrade ?

    Thursday, November 14, 2019 2:54 AM
  • Hi,

    In Server Manager -- RDS -- Overview -- Deployment Overview -- Tasks -- Edit Deployment Properties -- Certificates tab you need to assign your wildcard certificate (*.company.com) to all four purposes, one at a time.  This will make sure the correct certificate is set in IIS bindings for RDWeb.

    You may need to change the published FQDN for your deployment using Set-RDPublishedName script so that it matches your certificate.  On your internal network you need a DNS A record for this FQDN that points to your broker's private ip address.

    Additionally please make sure the FQDN for your RD Gateway in RDS deployment properties -- RD Gateway tab is set to a FQDN that points to your RDG's ip address (both on internal and external) and that this FQDN matches your wildcard certificate.

    Thanks.

    -TP

    Thursday, November 14, 2019 4:37 AM
    Moderator
  • Hi,

     

    Please try to change the SSL cert to wildcard SSL cert on the server manager:

    Server manager > RDS > Edit deployment overview

      

        RD Connection Broker - SSO - OK = *.company.com

        RD CONNECTION Broker - PUblishing - OK *.company.com

        RD Web Access - OK - *.company.com

        RD Gateway - OK  - *.company.com

     

    Reference link:

    https://ryanmangansitblog.com/2013/03/27/deploying-remote-desktop-gateway-rds-2012/

     

    Note: Since the websites are not hosted by Microsoft, the links may change without notice. Microsoft does not guarantee the accuracy of this information.

     

    Best Regards,

    Jenny


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

    Thursday, November 14, 2019 8:01 AM
  • Hi,

    Is there any update? Have you got a chance to verify above suggestions?

     

    Please feel free to let us know if more assistance needed.

     

    Thanks,

    Jenny



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

    Wednesday, November 20, 2019 5:34 AM