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Upgrade Windows Server 2016 to Windows Server 2019


This document provides information about upgrading Windows Server 2016 to Windows Server 2019. Before you begin, ensure that you have a valid Windows Server 2019 key and the installation media. You can perform the upgrade from DVD, from a mounted ISO, or from files extracted from an ISO image.

Direct upgrades from Windows Server 2008 R2 to Windows Server 2019 are not supported. 

Before You Begin

The Windows Server 2019 Setup wizard is straightforward and requires the following input:

Download UpdatesSelect if you want to download Windows updates during the installation.
Product KeyEnter your Windows Server 2019 product key.
Select ImageSelect Windows Server 2019 Standard (Desktop Experience).
Notices and license termsRead and accept the Windows Server 2019 notice and license agreement.
Choose what to keep

Keep personal files and apps (in-place upgrade) or keep nothing (fresh install).

If you are upgrading an existing LogRhythm system, select Keep personal files and apps. If you are performing an upgrade, the setup wizard asks you to confirm your selection later.

Confirm installation optionsBefore starting the installation of Windows Server 2019, you will be prompted to confirm your image and upgrade/fresh install selection.

System Requirements

LogRhythm 7.9.0 or later is required before upgrading Windows Server. LogRhythm 7.9.0 introduced support for Windows Server 2019 on standard deployments; however, Windows Server 2019 is not required. Before upgrading to Windows Server 2019, upgrade to LogRhythm 7.9.0 or later.

Microsoft Licensing

LogRhythm customers may or may not be entitled to an update to Windows Server 2019.

LogRhythm appliances are shipped using the latest operating system license available at the time of purchase. However, appliances may be shipped with older operating systems depending on software support at the time of shipment.

  • If you purchased hardware from LogRhythm on or after Nov. 1, 2020, you purchased a Server 2019 license from LogRhythm. This license can be used to upgrade the operating system. You can use and validate your license by looking at the license sticker on top of the server. If you are unable to locate the license, you can open a support case. 
  • If you purchased hardware prior to Nov. 1, 2020, you must provide your own Server 2019 license to upgrade.*

    *Customer-provided Windows Server licenses fall outside the scope of LogRhythm Support. LogRhythm will no longer be able to work with Microsoft or Dell on behalf of the customer should there be any operating system issues. Customers will need to work directly with Microsoft.

Upgrade Instructions

To upgrade Windows Server 2016 to Windows Server 2019, do the following:

  1. Log in as an administrator on the server you want to upgrade.
  2. Insert the Windows Server 2019 DVD or mount the installation ISO.
  3. Browse to the root of the installation media and double-click setup.exe.
    The Windows Server 2019 Setup window appears.
  4. Follow the steps in the wizard according to the guidance in the Before You Begin section above. Note the following:

    • If you are upgrading from a DVD, you may be prompted to boot from DVD. You can let the request time out and the upgrade will continue.

    • When the upgrade is almost finished, a screen will indicate that settings are being finalized. When the upgrade is finished, you will be presented with the Windows Server 2019 login screen.

  5. After logging in, verify that all LogRhythm services have started and are functioning normally.

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