Full Guide: Windows Server 2008 R2 In-place Upgrade

How to in-place upgrade Windows Server efficiently? For example, Windows Server 2008 R2? Here comes the detailed steps for you.


By Maggie / Updated on June 28, 2023

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Overview of in-place upgrade

An in-place upgrade Windows Server provides the ability to transition from an older operating system to a more recent one while retaining existing settings, server roles, and data without any loss. To determine which version of Windows Server you can upgrade to based on your current version, refer to the figure provided below:

Windows Server Inplace Upgrade

Before you start upgrading, your computer must meet the following requirements:

⋆Determine which version of Windows Server to upgrade to.
⋆The hardware meets or exceeds the hardware requirements for Windows Server.
⋆Must not be running in Azure.
⋆The install media is ready to use
⋆A valid product key and activation method are available. Keys and methods may depend based on the distribution channel that you received Windows Server media from, for example, a Commercial Licensing program, Retail, Original Equipment Manufacturer (OEM), and so on.
⋆A location to store files away from your computer. For example, a USB flash drive or network location.

Can you in-place upgrade Windows Server 2008 R2?

On January 14th, 2020, Windows Server 2008 and Windows Server 2008 R2 reached the end of their support. Consequently, customers who are using these outdated versions will need to consider upgrading to a newer version of Windows Server.

Windows Server 2008 R2

It is important to note that performing an in-place upgrade directly to Windows Server 2019 from Windows Server 2008 R2 is not always possible. However, you can achieve this upgrade by executing two consecutive upgrade processes.

①First, you will need to upgrade from Windows Server 2008 R2 to Windows Server 2012;
②Second,  perform a second in-place upgrade, namely, an in-place upgrade Server 2012 R2 to 2019.

In this article, we will focus on explaining the process of performing a Windows Server 2008 in-place upgrade to 2012. By following the steps outlined, you will be able to successfully realize Windows Server 2008 R2 in-place upgrade.

Suggestion: make a backup plan to prevent irreversible data loss

While performing Windows Server in-place upgrade is designed to preserve existing content, including data, there is still a possibility of data loss in certain cases. Therefore, it is highly recommended to take proactive measures to safeguard your operating system and critical data by using backup software. AOMEI Backupper Server is the top-list backup and restore software that provides an additional layer of protection and ensures you can easily recover in the event of any unforeseen issues during the upgrade process. It offers:

⚘Flexible backup options: you are allowed to backup files and folders, also you can select to backup systems, partitions and disks. Also, when we talked about the best Samsung T7 SSD backup software, AOMEI Backupper is on the list.
⚘Windows Server compatibility: a full-featured backup and recovery software for all Windows Servers (Server 2003/2008 (R2)/2012 (R2)/2016/2019/2022) and PCs.
⚘Optional backup locations: it supports you to back up Server to different storages. For instance, you can choose to backup Server to external hard drive, NAS, network share, cloud service, etc. No matter what accidents happen, you can restore your backups from these places.

Download AOMEI Bakcupper Server and launch it. Here we take system backup as an example, also you are free to change the backup type.

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Step 1. click Backup in the left panel and then select System Backup to create a Windows Server backup.

System Backup

Step 2. The system partitions are selected by default as the source. Then choose the destination to save your Windows Server 2008 R2 image backup.

Select Backup Destination

Step 3. You can set a customized backup.

Under the bottom of the interface, click Schedule Backup, then you can set backup Server in daily/ weekly/ monthly/ event triggers and USB plug-in mode.

Schedule Settings General

Step 4. Then confirm your settings by clicking Start Backup.

Guide: upgrade Windows Server 2008 R2 to Windows Server 2012 R2

Step 1. Locate the Windows Server 2012 R2 setup media and click Install now.

Install Now

Step 2. If your server is connected to the internet, make sure you click on Go online to install updates now (recommended). This will download the latest updates to the installer.

Go Online to Install Updates Now Recommended

Step 3. Enter the Windows Server License Key for Windows Server 2012 R2 if needed. If you are not asked for the license key, you can skip that step.

Windows Server License Key

Step 4. Select the right Windows Server edition you want to install between selecting Server with a GUI and Server Core Installation, depending on your needs.

Select the Operation System to Install

Step 5. Please read and accept the license terms. And tick I accept the license terms.

I Accept the License Terms

Step 6. For an in-place upgrade select Upgrade: Install Windows and keep files, settings, and applications.

Select Installation Type

Step 7. The setup will check the application compatibility and create a compatibility report.

Compatibility Report

Step 8. Next, press Confirm to start upgrading Windows.

Upgrading Windows

Step 9. The setup will complete and automatically reboot. When the upgrade is done, you will see the Windows Server 2012 R2 login screen.


Patiently perform Windows Server 2008 R2 in-place upgrade to Windows Server 2012 R2, then you can execute further in-place upgrade consequently. As I mentioned above, keeping a good backup plan via AOMEI Backupper is needed. This way, even if unexpected data loss occurs during the in-place upgrade, you will have a reliable backup to restore from and safeguard your valuable information.

This software is not only excellent backup and restore software, but also provides featured clone utilities serving as the best external hard drive cloning software that offers you a full and careful data protection scheme.

Maggie · Editor
Maggie is a technical editor from AOMEI and troubleshoots technical problems against data protection. She has received professional and systematic technical training. With a focus on user experience, security, and problem-solving, she always puts herself in the readers' shoes and provides them with valuable technical insights.