How to Upgrade Windows Server 2012 R2 to 2019 [2 Ways]

Can You Upgrade Windows Server 2012 r2 to 2019?

The answer is YES. You can upgrade Windows Server 2012 r2 to 2019 using the in-place upgrade way. It enables you to upgrade older system to a newer one directly while keeping the same hardware and all the settings, server roles, 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 in-place upgrade it to 2016, then 2016 to 2019. This is because you can usually only in-place 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 backup the server in advance. This is also true for older OS like Windows Server 2008 (r2).

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

In-place upgrade is a convenient way to avoid re-configuring and re-loading everything. But 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.

Whichever way you choose, backup first

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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Requirements for Windows Server 2019 Upgrading

Before you upgrade 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.

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 upgrading 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 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 from.

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

As mentioned earlier, in-place upgrade is a convenient but not always reliable upgrade method, so if you want to avoid all possible upgrade failures as much as possible, or if you want to upgrade from Windows Server 2012, then a fresh install may be better for you. Here's how to clean installing Windows Server 2019 step-by-step.

Step 1. Preparation before installing Windows Server 2019.

Download the Windows Server 2019 ISO file from Microsoft and burn Windows Server 2019 ISO to USB (over 8 GB) for installation.

Remember to backup files, or even operating system of Windows Server 2012 (r2)beforehand,this way you can prevent any accidents, and selectively restore the data you want onto the newly upgraded server.

Step 2. Boot from the installation media.

Insert the USB installation media and start your PC into BIOS, choose the USB as the first boot option to continue.

In the Windows Setup page, enter your language and other preferences, click Next -> Install Now to begin the Windows Server 2019 installation.

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 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 feature, etc.

With all these concerns, I prefer to use Qiling Disk Master 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.

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

2. Tap Folder or Files 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 Proceed.

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 - Qiling 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!

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• Windows 11/10/8.1/8/7 & Servers, 100% Secure

To make backups for client computers, just log in Qiling 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: Qiling Backup can not only help you backup physical machines but also virtual machines. It enables you to backup VMware and Hyper-V easily.

Conclusion

You can in-place 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.

Qiling Disk Master 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 cloud, bare metal restore Windows Server to different hardware, restore Windows Server to virtual machine and so on.

Windows Server 2019 Upgrading FAQ

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