How to Upgrade Windows Server 2012 R2 to 2019 without Losing Data

Can You Upgrade Windows Server 2012 r2 to 2019?

The answer is YES. You can directly upgrade Windows Server 2012 r2 to 2019 using the in-place upgrade way. It enables you to upgrade an older system to a newer one directly while keeping the same hardware and all the settings, server roles, and data intact without flattening the server, which is arguably the easiest approach for Windows Server upgrading.

However, if you want to upgrade Windows Server 2012 to 2019, you'll need to upgrade it to 2016, then 2016 to 2019. This is because you can usually only upgrade to a version from the previous two versions.​​

For cases where in-place upgrades are not applicable (failed or unsupported), you can clean install 2019 to overwrite the existing operating system and to avoid data loss, it’s necessary to back up the server in advance. This is also true for older OS like Windows Server 2008 (r2).

Why Upgrade Windows Server 2012 R2 to 2019?

Microsoft's Windows Server 2019 offers a range of improvements over 2012 R2, including enhanced security features, hybrid cloud capabilities, and better support for containerized applications. For businesses relying on outdated versions, upgrading ensures continued support and the benefits of cutting-edge server technology.

Requirements for Windows Server 2019 Upgrading

Before you upgrade to Windows Server 2012 r2, there is some relevant information you need to know.

✍Windows Server 2019 has its own system requirements

If your computer does not meet the minimum standards, you will not be able to upgrade to Server 2019.

✍Some third-party apps may not be compatible with the latest systems

This is another issue worth considering. To avoid subsequent troubles, you'd better check whether they support Windows Server 2019 or not before upgrading.

✍Also check with your cloud provider

In-place upgrade Server 2012 r2 to 2019 might also be supported by public or private cloud companies, but you need to check with your cloud provider for the details. Additionally, you cannot perform an in-place upgrade on any Windows Server configured to Boot from VHD. In-place upgrade from Windows Storage Server Editions to Windows Server 2019 is not supported, either. In this case, you could do a migration or clean installation instead.

In-place Upgrade Windows Server 2012 R2 to 2019 vs Clean Install

There are usually 2 methods of upgrading Windows Server 2012 r2 to 2019: In-place upgrade and clean install.

💻In-place upgrade >>Details

An in-place upgrade is a convenient way to avoid re-configuring and re-loading everything. However many users failed to upgrade Windows 2012 r2 to 2019 in place, which may result in a longer time for troubleshooting.

The main concern of in-place upgrades would be what apps cannot be upgraded (such as Domain Controllers, Exchange or email servers, SQL or Oracle servers, etc.), and what services should be disabled before upgrading.

💿Clean install >>Details

If you are not very sure about all this, then a better approach might be to first backup data on your current Windows Server 2012 r2 → fresh install Windows Server 2019 → then selectively restore data to Server 2019.

For more details, please check Windows Server in-place upgrade vs clean install.

Upgrade Server without Losing Data

To upgrade Windows Server 2012 r2 to 2019 without losing data, it’s highly recommended to make a backup of your operating system and important files. More »

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How to Upgrade Windows Server 2012 r2 to 2019 in Place

To upgrade Windows Server 2012 r2 to 2019 via in-place upgrading, read this step-by-step guide, and preferably make a backup of your server just in case.

Step 1. Prepare for the upgrade to Windows Server 2019.

1. Patch your Windows Server 2012 r2 with the latest updates.

2. Before upgrading, Microsoft suggests you collect some information of the device. You can use it for troubleshooting purpose when the upgrade fails.

• Go to C:\Windows\system32 and run “systeminfo.exe”. Copy and store the system information.
• Open Command Prompt, type “ipconfig /all” and press Enter. Copy and store the configuration information.
• Open Registry Editor, go to the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\WindowsNT\CurrentVersion, then copy and store the Windows Server BuildLabEx (version) and EditionID (edition).

*Note you can't have any virtual machines running during the in-place upgrade.

Step 2. Run setup.exe to start the in-place upgrade.

1. To upgrade your Windows Server, insert and mount the Windows Server 2019 setup media (DVD or ISO), run setup.exe directly.

2. Select "Download updates, drives, and optional features (recommended)" and click Next.

3. It will take some time to check device configuration, click Next when it’s done.

Whether you need to enter a license key to proceed depends on the distribution channel you received the Windows Server 2019 setup media.

Step 3. Select the Windows Server 2019 image to install.

Choose an edition of Windows Server 2019 that you want to install and click Next.

In this step, it's better to check the info you collect from Register Editor (CurrentVersion), because you cannot upgrade to a different product line without data loss.

Step 4. Choose what to keep after upgrading.

Accept the terms, then you can choose whether to keep personal files and apps. Click Next to continue.

✎Some users reported that the option to keep personal files and apps is GREYED OUT with the message: "you are trying to upgrade to a version of Windows that is different than the one installed". This indicates that you are trying to upgrade to a different product line - such as Datacenter to Standard.

If there’s anything incompatible with Windows Server 2019, it will prompt you a message requiring you to Confirm.

Step 5. Start upgrading Windows Server 2012 r2 to 2019.

Wait for a while and click Install to start upgrading. After finishing, your PC will automatically restart.

Now you’ve in-place upgraded Server 2012 r2 to 2019, you could take a little more time to make sure your operation is successful.

👉Check your current edition

You can open Registry Editor and go to HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\WindowsNT\CurrentVersion, then check the edition of your Windows Server in ProductName.

How to Clean Install Windows Server 2019 Step by Step

Before getting started, it’s important to understand that formatting or deleting data is different from wiping it completely. When you format a USB drive, the data isn’t removed; it’s just made inaccessible to the operating system. The data can still be recovered unless the sectors are overwritten. However, if you don’t have sensitive information on your USB drive, formatting may be enough.

Step 1. Preparation before installing Windows Server 2019.

First, download the Windows Server 2019 ISO file from Microsoft’s official site. Then, create a bootable USB drive (make sure it has at least 8 GB of storage) by burning the ISO file onto it.

Before proceeding with the installation, it’s essential to back up any important data or even the entire Windows Server 2012 (R2) operating system. This helps ensure that, in case of any issues, you can selectively restore critical files to the new server after the upgrade.

Step 2. Boot from the installation media.

Insert the bootable USB drive and restart your PC. Enter the BIOS settings and configure the USB as the first boot device.

After restarting, the Windows Setup screen will appear. Select your preferred language and other settings, click Next, and then choose Install Now to start the installation of Windows Server 2019.

Step 3. Select the operating system to install.

Select the version of Windows Server 2019 you want to install and click Next.

Then, accept the license terms and select Custom: Install Windows only (advanced) to perform a fresh install.

Step 4. Specify where to install Windows Server 2019.

Select the destination to install the Windows Server and click on Next.

Wait for the installation to complete, and the system should restart automatically afterward.

If everything runs well, you can then choose what to restore to the Windows Server 2019 system from the previous backup image.

Backup Windows Server in Case of Any Data Loss After Upgrading

Although Windows Server comes with a backup utility Windows Server Backup, if you ever used it, you’ll find it complicated, slow, and not fully functional. It also has some conspicuous limitations such as the 2 TB limit for backup, the number of backups it could keep, the lack of individual file backup features, etc.

With all these concerns, I prefer to use the AOMEI Backupper Server, which offers comprehensive backup & recovery features in an easy-to-use interface. It's an adequate Windows Server Backup alternative, only with more useful options and fewer restrictions.

Backup Windows 2012 r2 before upgrading or clean installation:

1. Click Backup on the left pane and choose a backup type. To show you how to perform individual file backup, I'll take File Backup as an example. Optionally, you can also use System Backup in case of an upgrade failure.

✍Tips: To backup large amounts of files, the best practice is to use the Cloud Backup feature. It enables you to backup folders to AOMEI Cloud, a cloud drive released by AOMEI Tech, which offers 1TB of free cloud storage from the time you sign up for an AOMEI account until 15 days.

2. Tap Add Folder or Add File to select the data you want to backup, then specify a destination to store it.

For the source folder, you can tap the funnel icon to include/exclude files with specific suffixes in Filter settings.
For the destination path, you can choose to Select a network location or Select a cloud in the drop-down menu.

3. After that, you can manage more settings to customize the backup, and then Start Backup.

Options: Manage compression level, image splitting, backup encryption, comment, email notification, etc.
Backup Schedule: Set up an automatic task on the basis of daily/weekly/monthly/event triggers/USB plug in.
Backup Scheme: You can choose backup method as full/incremental/differential, and enable automatic cleanup to delete obsolete backups automatically.

With this simple operation, you could backup whatever you want to keep before upgrading Windows Server 2012 r2 to 2019. Thus even if something goes wrong in the process of upgrading, you can easily retrieve important files or restore the operating system to an earlier state.

✍If you chose the clean installation way, you can also use the Explorer image feature to mount the backup image, and then choose certain data from it and restore it to the upgraded Windows Server 2019.

Supplement: Best Enterprise Data Backup Solution

If you are an enterprise user who has multiple Windows Server devices that need to be backed up, you can try the best enterprise backup software - AOMEI Cyber Backup. It offers you all-around enterprise data backup solutions:

• It enables you to create system/disk/partition backup for a bunch of Windows PCs and Servers, supporting Windows 11/10/8.1/8/7 and Windows Server 2022/2019/2016/2012 (R2)/2008 (R2).
• You are allowed to save backup images on a local disk, external hard drive, network share or NAS device, etc.
• You can schedule a backup task to run every day/week/month using the full/incremental/differential backup method.

Download this powerful enterprise backup software now to have a try!

To make backups for client computers, just log in to AOMEI Cyber Backup, and add the Windows device that you want to backup. Then click Backup Task on the left menu bar and select Backup Task > Create New Task.

Note: AOMEI Cyber Backup can not only help you backup physical machines but also virtual machines. It enables you to backup VMware and Hyper-V easily.

🔥Hot: Windows Server 2025 now available

Windows Server 2025 was officially released on November 1, 2024, bringing several exciting updates. Here are some of the key highlights:

• Desktop Shell: The first time you sign in, the desktop shell adopts the sleek look and feel of Windows 11, offering a modern and familiar user interface.
• Bluetooth Support: Windows Server 2025 now includes Bluetooth functionality, making it easy to connect and pair devices like mice, keyboards, headsets, and audio devices.
• DTrace Integration: DTrace is now a native tool in Windows Server 2025, providing a powerful command-line utility for real-time system performance monitoring and troubleshooting.
• Email & Accounts: You can now manage Microsoft Entra ID, Microsoft accounts, and Work or School accounts directly in Windows Settings under Accounts > Email & Accounts. However, note that domain joining remains necessary for most configurations.

If you'd like to experience all these wonderful features, you may make a Windows Server 2025 Media Creation Tool to install Server 2025 on a compatible device.

Conclusion

You can upgrade Windows Server 2012 r2 to 2019 directly, and this process shouldn’t delete any of your files. But to avoid any unwanted data loss, it’s still recommended to backup important files in advance. Besides, if you want to upgrade Server 2012 or 2008 to 2019 through clean installation, backup is especially essential.

AOMEI Backupper is an ideal backup & restore solution for Windows Server with its high compatibility and complete features. In addition to basic data protection, it also enables you to automatically backup Windows Server to the cloud, bare metal restore Windows Server to different hardware, restore Windows Server to the virtual machine, and so on.

Windows Server 2019 Upgrading FAQs