Windows Server 2008/2008 R2 have reached the end of support from Microsoft as of January 14, 2020. Running an in-place upgrade on Windows Server 2008/2008 R2 will allow upgrading to newer versions of Windows Server. Let's see what the process looks like to run a Windows Server 2008/2008 R2 in-place upgrade to Windows Server 2019.

As most are aware, support for Windows Server 2008/2008 R2 has ended as of January 14, 2020. This means that if you have any Windows Server 2008/2008 R2 hosts running in your environment, you are currently in an unsupported state. There are many great options out there for migrating away from Windows Server 2008/2008 R2. In this post, we will focus on Windows Server 2008/2008 R2 in-place upgrade and see what this involves.

Windows Server 2008/2008 R2 migration options ^

To take a step back for a moment, there are a few options to get from Windows Server 2008/2008 R2 to a supported version of Windows Server. What are these options? When does an in-place upgrade make the most sense? The following are viable options for moving your production services and data to a supported version of Microsoft Windows Server:

  • Migrate your on-premises Windows Server 2008/2008 R2 server to Azure
  • Use Windows Server Storage Migration
  • In-place upgrade

Migrating on-premises Windows Server 2008/2008 R2 server to Azure ^

Microsoft is dangling a carrot in front of businesses that may have production workloads still running inside Windows Server 2008/2008 R2 deployments. If you migrate these on-premises workloads to Azure, you will get another three years of extended security updates. Not only do you get three more years of updates and support, but it is free aside from the Azure cost.

This can be a good option for some who may already have a presence in Azure and who want the simplicity of rehosting the same exact server inside Azure. With free security updates, this allows much more time for deciding on a migration plan or refactoring of applications.

Three years of extended upgrade free when migrating to Azure (image courtesy of Microsoft)

Using Windows Server Storage migration ^

Windows Server Storage Migration is another option that allows using Windows Admin Center and the Windows Server Storage Migration module to migrate from a Windows Server 2008/2008 R2 platform to a supported platform such as Windows Server 2019.

Using Windows Server Storage Migration, you can completely move your data, permissions, and users and assume the identity of the server in an automated fashion; the heavy lifting is done for you. This enables easy migration of file servers running on legacy platforms up to a supported version of Windows Server.

Using the Storage Migration Service to migrate from Windows Server 2008

In-place upgrade ^

An in-place upgrade allows mounting the installation media for a newer version of Windows Server and running through the upgrade process on the legacy server. The Windows Server installation setup recognizes that an existing version of Windows Server is installed and will prompt you to choose between a clean installation or an upgrade. If an upgrade is chosen, the existing operating system, settings, and data are migrated (best effort) to the newer platform.

Windows Server 2008/2008 R2 in-place upgrade ^

There may be cases in which you simply want to keep your Windows Server 2008/2008 R2 server on-premises and upgrade it to a supported version of Windows Server and keep existing application installations in place. In this case, the in-place upgrade will most likely be the easiest option.

Upgrade path ^

It is important to note the upgrade path from Windows Server 2008/2008 R2 to newer Windows Server operating systems, such as Windows Server 2019. The below infographic from Microsoft helps to visualize the upgrade paths from Windows Server 2008/2008 R2 to Windows Server operating systems such as Windows Server 2012/2012 R2, Windows Server 2016, and Windows Server 2019.

Windows Server in-place upgrade to current versions of Windows Server (image courtesy of Microsoft)

If you want to perform an in-place upgrade from Windows Server 2008/2008 R2 all the way up to Windows Server 2019, what does the process look like?

You will need to perform two in-place upgrade processes. Since you can't perform an in-place upgrade directly from Windows Server 2008/2008 R2 to Windows Server 2019, you have to first upgrade to Windows Server 2012 R2 and then perform an in-place upgrade to Windows Server 2019.

Windows Server 2008/2008 R2 in-place upgrade process ^

Before actually running the in-place upgrade from Windows Server 2008/2008 R2 to a newer version of Windows Server, it is best practice to audit your legacy Windows Server. It is important to consider the following:

  • What roles and features are installed? Do these exist in the target version of Windows Server?
  • What software and software components are installed? Are there supported versions for these in the target version of Windows Server?
  • Do you have a good backup of the server? Other than creating a snapshot/checkpoint (if virtual), be sure to have a proper backup of the server.
  • Do you have enough free space on your system drive to perform the upgrade? In-place upgrades require additional available free space to be successful.
  • Start with the latest patch version available for your current legacy server. This helps to ensure you have the most current updates and patches available to ensure the in-place upgrade is successful.
  • Test the upgrade in a lab environment if possible

Once you have considered these items and others that may be important for your particular environment, you should be able to begin the in-place upgrade.

Below is a screenshot of the Windows Setup dialog box, which opens when you run the Windows Server 2012 R2 installation media from a Windows Server 2008/2008 R2 server. Click Install Now.

Running the in place upgrade to Windows Server 2012 R2

Running the in place upgrade to Windows Server 2012 R2

The upgrade includes screens asking about pulling the latest updates, entering the license key for Windows Server 2012 R2, and choosing the operating system you want to install.

Select the operating system you want to install with Windows Server 2012 R2

Select the operating system you want to install with Windows Server 2012 R2

You will eventually see the screen to choose which type of installation you want to install. Here, choose Upgrade: Install Windows and keep files, settings, and applications.

Choosing an upgrade for type of installation

Choosing an upgrade for type of installation

After you click the Upgrade option, you will see the normal Windows installer screens that retain your settings and update your Windows Server installation. Your server will reboot several times.

Once the upgrade process has completed, you will see the freshly upgraded Windows Server 2012 R2 installation. It should contain your previous apps, data, and settings.

Windows Server in place upgrade to Windows Server 2012 R2 is successful

Windows Server in place upgrade to Windows Server 2012 R2 is successful

Now, if Windows Server 2012 R2 is not your final destination, you will need to perform another in-place upgrade to reach your target Windows Server version.

As you recall, we have to perform this same process over again to get from Windows Server 2012 R2 up to Windows Server 2019. After mounting the Windows Server 2019 install media on the newly upgraded Windows Server 2012 R2 server, we run the upgrade again. The installer will prompt you to download updates to the installer itself.

Starting the Windows Server 2019 upgrade in Windows Server 2012 R2

Starting the Windows Server 2019 upgrade in Windows Server 2012 R2

You will need to enter a valid Windows Server 2019 license key and also select the Windows Server 2019 image you would like to install.

Choose the Windows Server 2019 image you want to upgrade to

Choose the Windows Server 2019 image you want to upgrade to

The wording of the upgrade vs. clean install with the Windows Server 2019 installer is a bit less obvious. On the Choose what to keep page, select Keep personal files and apps for an upgrade. Select Nothing if you want to perform a clean installation.

You will want to choose the first option for an upgrade.

Choose between an upgrade and clean install with Windows Server 2019 installer

Choose between an upgrade and clean install with Windows Server 2019 installer

The upgrade is ready to proceed with keeping your files and applications.

Ready to upgrade to Windows Server 2019

Ready to upgrade to Windows Server 2019

Just as with the upgrade to Windows Server 2012 R2, the server will reboot several times. After a short time, your server should successfully upgrade to Windows Server 2019.

Windows Server 2008 R2 successfully upgraded to Windows Server 2019

Windows Server 2008 R2 successfully upgraded to Windows Server 2019

Conclusion ^

With the end of support from Microsoft for Windows Server 2008/2008 R2 reached as of January 14, 2020, moving production workloads off Windows Server 2008/2008 R2 should be a priority. While there are several ways to move your workloads to newer versions of Windows Server, the in-place upgrade may be the best option for those who want to keep their server on-premises and who have many custom applications, settings, and data that would be difficult to migrate to a different server.

The Windows Server 2008/2008 R2 in-place upgrade to Windows Server 2019 involves two in-place upgrades: one to Windows Server 2012 R2 and then an upgrade from 2012 R2 to Windows Server 2019. All in all, the process is straightforward and should be easy to accomplish with planned down time.

Want to write for 4sysops? We are looking for new authors.

Read 4sysops without ads by becoming a member!

3+
avataravatar
Share
6 Comments
  1. Kell 2 months ago

    Hi 

    Is there any article for upgrading server 2012r2 to 2016? Thanks

    0

    • Id say you can easily use the main points covered here. Your upgrade is just one step upgrade, nothing special to write about. 🙂

      0

  2. Dbdmora 2 months ago

    What's the best path to upgrading 2008 32bit to 2012 64bit?

    1+
    avatar
    • Upgrade is not possible. You cant go cross platform. Clean installation is required.

      1+
      avatar
    • rufus 2 months ago

      You can't upgrade from x86 to x64 or vice versa. You have to migrate.

      0

  3. As already replied by Leos, upgrading from a 32bit to a 64bit version of Windows Server is not possible due to the different architecture of the operating system. The only solution in this case is upgrade from scratch .

    0

Leave a reply

Your email address will not be published. Required fields are marked *

*

© 4sysops 2006 - 2020

CONTACT US

Please ask IT administration questions in the forums. Any other messages are welcome.

Sending

Log in with your credentials

or    

Forgot your details?

Create Account