Step-by-Step Guide for In-Place Upgrade to Windows Server 2019

Windows Server 2012 is the fifth version of the Windows Server server operating system built by Microsoft, as part of the Windows NT family of operating systems, and is the successor of Windows Server 2008 R2. In this guide, I will show you how to perform an in-place upgrade for Windows Server 2012 to Windows Server 2019. kindly refer to the following articles on how to Log Off WS2012: How to sign out of Windows Server 2012, and how to install Windows Server 2016 Operating System.

Windows Server 2012 is the server edition of Windows 8 and is available since September 2012. Its minor update (Windows Server 2012 R2) is available since October 2013. To simulate this in a lab environment download Windows Server 2012. Please see how to download and install Windows Server 2016.

An in-place upgrade is the installation of an operating system or application on the computer without removing the older version first and without saving any data beyond normal precautions. In-place installations of operating systems have a tendency to cause problems, especially if the new version is very different from the previous one. See how to perform an Upgrade Windows Server 2019 to 2022 via iDRAC, and how to configure Windows LAPS.

Reasons to perform an in-place upgrade

1: If you want to keep the same hardware and all the server roles you’ve already set up without flattening the server, you will want to do an in-place upgrade. An in-place upgrade allows you to go from an older operating system to a newer one while keeping your settings, server roles, and data intact. Here is additional information on how to upgrade to Windows Server 2019.

OS version	Version to Upgrade to	Upgrade process
Windows Server 2012	WS 2019	Upgrade to Windows Server 2016 Direct upgrade from 2016 to 2019

2: Also considering the Windows Server 2012 Life Cycle as shown below, There is a need to prepare for what is next with a valid operating system supported by Microsoft. Therefore, you can perform an in-place upgrade from Windows Server 2012 to Windows Server 2019.

Windows Server 2012 Life Cycle

Published released	Start date for life cycle	End date for basic support	Extended Support End date	Remarks
WS 2012 Datacenter	10/30/2012	09.10.2018	10/10/2023	The basic and extended support for this product has been extended to provide customers with a transition life that is a standard lifecycle.
WS 2012 Essentials	02/01/2013	09.10.2018	10/10/2023	Both mainstream support and extended support have been extended for this product so that all customers have the standard period to switch.
WS 2012 Foundation	10/30/2012	09.10.2018	10/10/2023	Both mainstream support and extended support have been extended for this product so that all customers have the standard period to switch.
WS 2012 R2 Datacenter	11/25/2013	09.10.2018	10/10/2023	The basic and extended support for this product has been extended to provide customers with a transition life that is standard lifecycle.
WS 2012 R2 Essentials	11/25/2013	09.10.2018	10/10/2023	Both mainstream support and extended support have been extended for this product so that all customers have the standard period to switch.
Windows Server 2012 R2 Foundation	11/25/2013	09.10.2018	10/10/2023	Both mainstream support and extended support have been extended for this product so that all customers have the standard period to switch.
WS 2012 R2 standard	11/25/2013	09.10.2018	10/10/2023	The basic and extended support for this product has been extended to provide customers with a transition life that is standard lifecycle.
WS 2012 standard	10/30/2012	09.10.2018	10/10/2023	The basic and extended support for this product has been extended to provide customers with a transition life that is standard lifecycle.

Current Windows Version

As you can see below, we are currently running Windows Server 2012, Datacenter Evaluation Edition.

Screenshot of Windows Server 2012 System information, displaying details such as Windows edition, processor information, installed memory, system type, and computer name.

Mount the ISO File

Begin the upgrade by mounting the Windows Server 2016 ISO image. Download DVDFab Virtual Drive in order to do this. Run the Setup and wait for the setup screen to appear. You see two options.

Screenshot of a file explorer window showing a folder named 'Operating_systems' with various Windows operating system ISO files listed.

The ISO file has been mounted, lets double click on the drive to run the setup

Screenshot of a Windows file explorer window showing the computer drives and details of removable storage devices.

This will open up the Windows Server 2016 setup as shown below. Click on Download Updates, drivers, and Optional Features (recommended). Click on Next

Windows file explorer showing 'Preparing 100%' message with a highlighted CD/DVD drive.

Windows Server 2016 Setup screen showing options to download and install updates or skip the update step, with 'Next' and 'Back' buttons.

This will check for updates and also check your PC

Windows Server 2016 setup screen displaying 'We’re getting a few things ready' with a loading animation and navigation buttons for 'Back' and 'Next'.

Select Image to Install

Select the Image as shown below. Click on Next

Windows Server 2016 setup screen displaying options to select the installation image, with 'Windows Server 2016 Datacenter Evaluation (Desktop Experience)' highlighted.

Accept the License as shown below

Screenshot of the Windows Server 2016 setup, displaying applicable notices and license terms with options to 'Decline' or 'Accept' the information collection settings.

This will open up a new window instructing you on what to keep. I will select “Nothing” as shown below. Click on Next

Windows Server 2016 setup screen showing options for keeping files, with 'Nothing' selected to delete all files, apps, and settings.

If you chose nothing, this will prompt you to choose yes in order to be very sure you want to continue. Next, Windows will collect updates

Windows Server 2016 setup screen showing 'Getting updates' with progress at 0%.

Windows Server 2016 setup screen showing 'Getting updates' with a progress indicator at 81%.

Windows is done collecting updates, the next process will be to check your system has enough space to install the Operating System and ensure everything is ok.

Windows Server 2016 installation screen displaying a progress message stating 'Making sure you’re ready to install' and prompting the user to 'Please wait.' Buttons for 'Back' and 'Next' are available.

Install Windows Server 2016

When the setup checks everything is okay, the next window will prompt you to install Windows Server 2016. Click on Install as shown below

Windows Server 2016 setup screen indicating readiness to install, with options to install Datacenter Evaluation and keep nothing. Buttons for 'Back' and 'Install' are visible.

The server upgrade process begins as shown below. This can take a while! When this is done, your device will restart multiple times.

Screen displaying the installation progress of Windows Server 2016, indicating 0% complete and stating that the PC will restart several times.

Windows Server 2012 restart screen displaying 'Restarting' on a blue background.

The following windows below show Windows Server 2016 is still installed. This process can take a while.

Blue screen displaying Windows installation progress at 12%, with messages advising not to turn off the PC and indicating that the PC will restart several times.

Customize Server

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

User interface screen with a blue background asking for home country/region, preferred app language, and keyboard layout, featuring dropdown menus for selection and a 'Next' button.

Accept the License terms as shown below

Screenshot of Microsoft Windows Server 2016 license terms, detailing diagnostic and usage information, choice and control options, and a prompt to accept the license agreement.

Enter the password to your Administrators account as shown below. This step will finalize the Windows Server 2012 to Windows Server 2016 Upgrade

Password setup screen for administrator account with fields for username, password, and reentered password.

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

Computer login screen displaying an Administrator account with a password input field over a beach landscape background.

As you can see below, the User Profile is currently being created on the Server. Please see For how to search through the Windows registry, and for what Registry Editor is and how to access the registry hives.

Here are some exciting articles: How to extend a VM Hard Disk on VMware Workstation, How to extend System Drive Partition on Windows, how to Fix unable to Extend Volume on Windows protected by BitLocker, 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.

Verify Windows In-place Upgrade

Now we are logged on to the server, let’s access the server system properties as shown below. The distribution point is now running fine on Windows Server 2019 Datacenter Evaluation.

Screenshot of the Windows System Information window displaying Windows Server 2016 edition, processor details, memory, system type, and computer name.

The next step would be to upgrade from Windows Server 2016 to Windows Server 2019. to do this follow the steps discussed in this article. When you are done, you should have a similar version of Windows Server 2019 running.

Screenshot of Windows System Information displaying Windows Server 2019 Datacenter Evaluation edition, processor details, RAM, system type, and copyright notice.

If you do not want to upgrade further to Windows Server 2019, then you can install the roles and features needed to make this server operate. For some examples see the following links.

For how to Setup a DC (Setting up the Two Domain Controllers).
How to setup (add) a second Domain Controller (DC) to your environment
How to install and configure Active Directory Federation Service (ADFS) in Windows Server.
How to install Dynamic Host Configuration Protocol on Windows Server 2019.

To ensure everything was successfully upgraded, we need to access the registry. On the server, run RegEdit. Check the value of the hive below. The version should show Windows Server 2016.

HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\WindowsNT\CurrentVersion

I hope you found this blog post helpful on how to perform In-place upgrade for Windows Server 2012 to Windows Server 2019. If you have any questions, please let me know in the comment session.