Upgrading or Migrating to Windows Server 2019/2022 from 2016

This article will describe how to do an "in-place server upgrade" and how to migrate server data from an old computer to a new one. First, establish your goal:

If you want to upgrade in place from Windows Server 2016 to Server 2019 or 2022 and keep all your existing apps and files, see Part 1.

If you are changing codecs and plan to migrate your application, database, domain accounts, and user profiles from one server to another, see Part 2.

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Should you upgrade or migrate to Windows Server 2019/2022?

According to Microsoft, Windows Server 2016 will be supported until January 12, 2027. Windows Server 2019 will reach its end of life on January 9, 2029. Windows Server 2022 was released in September 2021.

While Windows Server 2016 still plays a significant role in many organizations, we recommend upgrading to the latest version, which offers enhanced security features and improved performance.

Comparison between Windows Server 2016 and 2019

Windows Server 2019 includes updates to Storage Migration Service, Kubernetes platform support, unified management, virtual network peering, and an enhanced version of Windows Defender ATP. However, Windows Server 2016 has removed iSNS, Business Scanning, Remote Desktop Connection Broker, Remote Desktop Virtualization Host, and Print Components, among others.

Read Microsoft's guide on the Windows Server 2019 edition comparison.

Comparing Windows Server 2019 and 2022

Server 2022 demonstrates four advanced security improvements: hypervisor-based code integrity, Secure Core Server, hardware-enforced stack protection, and Transport Layer Security (TLS) 1.3 enabled by default.

It also offers better platform flexibility, a new Windows Admin Center, an updated Hyper-V Manager, hybrid-cloud support, and an enhanced Kubernetes experience.

Learn more: See the Windows Server 2022 edition comparison.

Part 1: How to Upgrade Windows Server to 2019/2022

Incremental upgrade guide for in-place server:

Phase 1: Set up the server.

Step 1. Go to the Windows Server 2019 installation media and click setup.exe.

Step 2: Click "Yes" to proceed with the installation.

Step 3: You will see the “Get updates, drivers, and optional features” window. Select “Download updates, drivers, and optional features (recommended)” and click “Next.”

Step 4: Wait for the installer to check your device configuration. When it's done, select Next.

Step 5. Enter your server license key to proceed. (Find your Windows Server product key if you're not sure where to look.)

Step 6: Choose the Windows Server 2019 image you need, and then select **Next**.

Step 7: Click Accept to agree to the applicable notifications and license terms.

Step 8. Select what you want to keep, and click “Next”:

Select “Keep personal files and apps” to keep your data.

"Factory data reset" deletes everything, including files, apps, and settings.

Step 9. When the scan is finished, click on the «Install» button to proceed with the repair process.

Phrase 2: Check if the system has been successfully upgraded.

Type “Registry Editor” in the search box and click to open it.

View along the path: ProductName: Computer\HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion

Your ProductName should be Windows Server 2019. Make sure all your applications are running smoothly. If you happen to lose any apps or files, the Todo PCTrans tool can assist in creating an image file to save everything.

If you experience issues with your Windows Server installation, locate the files under the C:\Windows\Panther path, compress them, and then reach out to Microsoft for assistance with troubleshooting.

Part 2: How to Migrate from Server 2016 to 2019 in 2022

If an in-place upgrade isn't an option for you, learn about server migration to move your data quickly. Server users in particular will appreciate an easy and cost-effective way to transfer files and data – not to mention user accounts and domain accounts – to a new PC.

This part will offer you another option to migrate all programs, files, and settings – download the Windows Server Migration Tool. The advanced PC transfer utility for Windows Server – Todo PCTrans Technician tool, provides a Windows Server migration solution among Server 2003/2008/2012/2016/2019/2022.

Still have doubts about using Todo PCTrans? Watch the video tutorial to learn more about this advanced Windows Server file and app transfer software.

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The steps to migrate to Windows Server 2019/2022 are as follows:

Step 1: Launch Todo PCTrans on both the source and target computers, and connect the two computers via the Internet.

1. Under "PC to PC," click PC to PC to continue.

2. Select the target computer by its device name, then enter your account password or verification code, and choose the transfer direction. Click "Connect" to proceed.

You can find the verification code at the upper-right corner of the main Computer-to-Computer screen on the remote computer.

Step 2: Choose the categories of apps, files, and accounts that you want to transfer over the Internet.

To transfer data selectively, click “Edit” under each category and select specific items.

Select applications, files or accounts

Step 3: Click on “Transfer” to start transferring your apps/files/accounts over the Internet from one computer to another.

Transfer apps, files, or accounts over the Internet

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Final Thoughts

This post offers two sections on server upgrade and server migration. If you're focusing on upgrading Windows Server 2016 to 2019 or 2022, the built-in method in Windows can suffice for the task. One important thing – there is a chance of in-place upgrade failure leading to data loss. Therefore, to protect your data, we recommend backing up with an image using the Todo PCTrans tool.

Furthermore, data transfer has become the client's purpose. Thus, you can migrate directly to Server 2019 or 2022.