Is an OS Upgrade from Server 2016 to 2019 Supported when it is running a custom Azure AD Connect installation?

Diederik Janson 21 Reputation points
2020-03-11T10:44:54.027+00:00

Hi,

I tried an in-place upgrade of a Server 2016 installation to 2019 with a custom installation of Azure AD connect and Azure AD connect didn't work anymore after the upgrade. I tried to find on the internet whether this is supported but could not find this information.

Is there a path?

Best Regards,

Diederik.

Microsoft Entra ID
Microsoft Entra ID
A Microsoft Entra identity service that provides identity management and access control capabilities. Replaces Azure Active Directory.
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  1. saurabh sharma 76 Reputation points
    2020-03-12T23:36:11.537+00:00

    Azure AD connect is supported on all windows versions after 2008. However, Azure AD Connect cannot be installed on Small Business Server or Windows Server Essentials before 2019 (Windows Server Essentials 2019 is supported). The server must be using Windows Server standard or better. Please refer to the Azure AD Connect prerequisites documentation.

    Are you getting any errors after the upgrade ?

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  2. Diederik Janson 21 Reputation points
    2020-03-13T11:18:10.73+00:00

    Hi,

    You can find the error messages after the update in this post/question from two days ago.:

    Azure AD Connect not working after OS upgrade from 2016 to 2019
    https://learn.microsoft.com/answers/questions/11838/azure-ad-connect-not-working-after-os-upgrade-from.html

    Thank you for helping me.

    Diederik