Upgrade Windows Server 2008 R2 to Windows Server 2012 R2

Windows Server 2008 R2 will reach to end of life on January 14, 2020. It is essential that all users who are using Windows Server 2008 R2 upgrade their server to Windows Server 2012 R2 or migrate to other higher operating system (i.e. Windows Server 2016).

In this knowledgebase article, we will illustrate how can you perform in-place upgrade Windows Server 2008 R2 to Windows Server 2012 R2. Since this is major version upgrade, you have to read and understand the upgrade instructions properly.

Before you start upgrading your server, please ensure that you have necessary license for Windows Server 2012 R2. For more information about license upgrade, you can refer the following URL:


It is essential that you have secured full backup of your data and you should be able to perform bare metal restore in case if the upgrade is failed. If upgrade is failed, you will have to restore the server from backup to boot from the old Windows Server 2008 R2. Also, if you have installed third party software or applications, please ensure that they are compatible with Windows Server 2012 R2.

Important Note: We are considering that you do not have any additional server role (i.e. IIS, FTP, DNS, Active Directory etc.) on the server. If you have additional server role, kindly refer their compatibility to perform in-place upgrade.

Upgrade Windows Server 2008 R2 to Windows Server 2012 R2

Before starting upgrade, please ensure that you have installed all pending updates for Windows Server 2008 R2. If there is any pending update, kindly install it first. Once all updates are installed, we are ready to perform this upgrade.

[1] Insert Windows Server 2012 R2 ISO in your server and start the installation. It will ask you to accept license terms. Select “I accept the license terms” and click on Next button as shown in the following image:

Microsoft License Terms

[2] On next step, it will ask you which type of installation do you want. You need to select “Upgrade: Install Windows and keep files, settings and applications” option to upgrade the existing operating system as shown in the following image:

Upgrade Windows

[3] Next step will check the compatibility and it will provide you report. Kindly the compatibility report. If it does not report any issue, you can click on Next button as shown in the following image:

Windows Compatibility Report

If this is Hyper-V virtual machine, you may see the following warning:

Installing Windows will affect these devices:

These devices might not work properly in Windows. We recommend updating the drivers for these devices before you continue. ? System devices: Microsoft Hyper-V S3 Cap

You can ignore this message and continue with upgrade. This will not cause any issue.

[4] Now it will start copying Windows files to upgrade the server’s operating system. During this process your system may restart several times. Please do not interrupt this process.

Windows Setup

Installing Windows

Rebooting Server

[5] On last step, you will see a screen with “Finalizing your settings” after reboot. Once again, do no interrupt or reboot your server while it is performing this. It may take some time. Once this step is complete, you should see that login screen.

Finalizing your settings

After login, you should verify your installed software and data to ensure that they are available after upgrade.

Upgrade Windows Server 2008 R2 to Windows Server 2012 R2

2 thoughts on “Upgrade Windows Server 2008 R2 to Windows Server 2012 R2

  • November 23, 2018 at 11:09 am

    Thanks for the detailed articles. I was able to upgrade my Windows Server 2008 R2 to Windows Server 2012 R2 without any trouble. I was hesitating to perform in-place upgrade but I found this article to walk through step by step to perform in-place upgrade. Thanks again!!!

  • November 23, 2018 at 3:50 pm

    Thanks for this excellent article. This helped to perform in-place upgrade from Windows 2008 R2 to Windows 2012 R2 without any trouble. Once again a huge thanks!


Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.