Windows Server

Perform an in-place upgrade from Windows Server 2016 to Windows Server 2019

The Windows Server 2016 is a cloud-ready operating system that delivers new layers of security and Azure-inspired innovation for the applications and infrastructure. If you would like to try this out in a lab environment, download it here. In some of my other posts, We have gone through the installation of Windows Server 2016 and the installation of Windows Server 2019. Also, I have configured and deployed Windows 10 via Windows Deployment Services (WDS). In this article, I will show you how to perform an in-place upgrade from Windows Server 2016 to Windows Server 2019.

See how to perform an Upgrade from Windows Server 2019 to 2022 via iDRAC, how to configure Windows LAPS, Learnt About installing Server 2016, how to install Windows Server 2016 Operating System on VirtualBox, and how to block upgrade to Windows 11 through Local Group Policy or Registry Editor from Windows 10.

Why Perform an Upgrade?

Running the latest version of Windows Server allows you to use the latest features. This includes running the latest security features that deliver the best performance. You can upgrade to a newer version of Windows Server by up to two versions at a time. The table below shows the supported upgrade paths, based on the version you’re currently on. See these guides for more information on how to set up a VM via PXE boot on a Generation 1 VM and how to set up a VM via PXE boot on a Generation 2 VM. Note: You can do an in-place upgrade from Windows Server 2012 R2 to Server 2019.

Perform upgrade from Windows Server 2016 to 2019

On my Windows Server 2016 lab VM. I mounted the Windows Server 2019 iso file, so let’s upgrade. In my next article, I will be demonstrating how a server can be upgraded from WS 2012 to 2019. As you can see below, we are currently running Windows Server 2016, Datacenter Evaluation Edition.

Windows Server 2019 Install Options

1: Server Core: It’s a smaller installation that includes the core components of Windows Server and supports all server roles, but does not include a graphical user interface (GUI).

2: Server with Desktop Experience: This is the complete installation and includes a full GUI for customers. Please see how to fix “The virtual machine has terminated unexpectedly during startup with exit code 1 (1×0): Failed to open a session for the virtual machine Windows Server 2019“-

Windows Server 2016 requires a direct upgrade process unlike Windows Server 2012. We will be proceeding with the installation as shown below.

Mount the ISO File

Mount the WS 2019 ISO Image on WS 2016 VM as shown below. Download Virtual Clone in order to do this.

Double-click on the mounted ISO in order to continue the setup

This will open up the Windows Server 2019 setup as shown below. Click on Download Updates, drivers and Optional Features (recommended). Click on Next

This will check for updates and also check your PC

Select The Image to Install

This will launch the setup “Select Image” window as shown below. Click on Next. See how to install Windows Server 2022 on VMware Workstation

Accept the License as shown below

Decide on what to keep

This will open up a new window instructing you on what to keep. I will go with “Nothing”. Click on Next

When you choose nothing, this will prompt you to select yes in order to be very sure you want to continue

Windows will collect updates and when prepare the system for installation.

This will make sure your system has enough space to install the Operating System and ensure everything is ok.

Install the Operating System

This will prompt the Read to Install Window as shown below. Click on Install as shown below.

Now the server upgrade process begins as shown below. This can take a while!

The following windows below show Windows Server 2019 is still installing.

Note: Your server will restart multiple times.

Customise the server

Let’s customise the server by entering the following information as it relates to you. When you are done, click on Next

Enter the password to your Administrators account as shown below. This step will finalise the Windows Server 2016 to Windows Server 2019 Upgrade

When Windows is done applying settings, you can now log on to your server a shown below.

Now we are logged on to the server, let’s access the server system properties as shown below.

Now we are done upgrading to Windows Server 2019. You can install additional roles and features needed to make this server operational. For some examples, see the following links below. how to set up a Domain Controller, how to add a second Domain Controller to your environment, how to install and configure Active Directory Federation Service (ADFS) in Windows Server, and how to install Dynamic Host Configuration Protocol on Windows Server 2019.

Here you can have a look at the basic settings such as the time zone, ITÉ security setting, firewall, and Remote Desktop, etc. For the configuration of a new server, see this guide “Post-installation of this server“.

To ensure everything was successfully upgraded, we need to access the registry.

On the server, run RegEdit. Check the value of the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\WindowsNT\CurrentVersion hive. The version should show Windows Server 2019. See the following articles below for more information about the Windows registry.

I hope you found this blog post helpful on how to perform an in-place upgrade from Windows Server 2016 to Windows Server 2019. If you have any questions, please let me know in the comment session.

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