Upgrade windows server 2016 to 2019

This article covers in-place server upgrade solutions and Server data migration from an old PC to a new PC. Figure out your target first:

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

If you want to change old devices and plans to migrate applications, databases, domain accounts, user profiles from one server to another, see Part 2. 

According to Microsoft, Windows Server 2016 will continue to update until Jan 12, 2027. And the end of life for Windows server 2019 is Jan 9, 2029. Windows Server 2022 has released in Sep 2021.

Even though Windows Server 2016 still acts as the main workhorse on many companies, we recommend upgrading to the latest version due to the new security function and better performance.

Comparison of Windows Server 2016 vs. 2019

Windows 2019 updates storage migration service, Kubernetes platform support, unified management, virtual network peering, enhanced Windows Defender ATP, etc. However, Window Server 2016 has removed iSNS, business scanning, remote desktop connection broker, remote desktop virtualization host, print components, and more.

Read Microsoft guide about editions comparison window server 2019.

Comparison of Windows Server 2019 vs. 2022

Server 2022 unveils four advanced functions of improved security: Hypervisor-based code integrity, secured-core server, hardware-enforced stack protection, and transport Layer Security (Enable TLS 1.3). 

It also provides better platform flexibility, a new Windows admin center, upgraded Hyper-V Manager, Hybrid Cloud Support, and Enhanced Kubernetes Experience. 

Learn more: check editions comparison server 2022.

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

A step-by-step guide to performing In-Place Server Upgrade:

Phase 1: Start Server setup.

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

Step 2. Click Yes to Confirm the setup process.

Step 3. Then you can see the windows of «Get updates, drives, and optional features.» Select «Download updates, drivers and optional features (recommend)» and then click «Next.»

Step 4. Wait for setup to check the device configuration. When it finishes, select «Next.»

Step 5. Enter the Server license key to continue. (If you are confused about finding the Windows server product key, you can check this guide.) 

Step 6. Select the wanted Windows Server 2019 image and then choose «Next.»

Step 7. Click «Accept» to agree with the Applicable notices and license terms.

Step 8. Choose what to keep and click Next:

Please choose «Keep personal files and apps» to keep data. 

«Nothing» will cause all data to be deleted, including files, apps, and settings.

Step 9. After analyzing finish, you can click «Install» to prompt.

Phrase 2: Check whether the system is successfully upgraded.

Type Registry Editor on the search box and click to open it:

Follow the path to see ProductName: ComputerHKEY_LOCAL_MACHINESOFTWAREMicrosoftWindows NTCurrentVersion

Your ProductName should be Windows Server 2019. Remember to check all applications are running well. If apps or files are lost, EaseUS Todo PCTrans can help you create image files to keep everything.

If you find Windows Server goes wrong, you can follow the path (C:WindowsPanther) and zip the files. Then, contact Microsoft to help you.

Part 2. How to Migrate Server 2016 to 2019 of 2022

If the in-place upgrade is not your option, please shed light on Server Migration to move data quickly. For Server users, it is a headache to find a cost-effective and flexible method to transfer files and data, even users’ accounts and domain accounts, to a new PC. 

This part will give you another choice to migrate all programs, files, and settings — Download the Windows Server migration tool. Advanced Windows Server PC transfer utility — EaseUS Todo PCTrans Technician is capable of Windows Server transfer solution between Server 2003/2008/2012/2016/2019/2022.

Still, hesitate to use EaseUS Todo PCTrans? Check the video guide. Get more info about this advanced Windows Server file & app transfer software.

Steps about migrating to Windows Server 2019/2022:

Step 1. Launch EaseUS Todo PCTrans on your source and target computers, connect both PCs via the internet.

1. At the «PC to PC» section, click «PC to PC» to continue. 

2. Select your target computer via its device name, then enter its account password or verification code and select the transfer direction. Then click «Connect» to continue.

You can check the verification code on the right top of «PC to PC» mainscreen on the target computer.

Step 2. Select the categories Applications, Files, and Accounts to transfer via the internet.

If you want to transfer data selectively, click «Edit» under each category, and choose the specific items.

Step 3. Click «Transfer» to start transferring your apps/files/accounts from one computer to another computer via the Internet.

Final Thoughts

This post provides two parts in Server upgrade and Server migration. If you focus on upgrading Windows Server 2016 to 2019 or 2022, a Windows built-in method is enough to complete the task. One more important thing — here is a case that in-place upgrade turns to wrong and your data lost. So, to protect your data, we recommend making a backup image by EaseUS Todo PCTrans.

In addition, data transfer also becomes the client’s purpose. Therefore, you can enjoy the direct migration to Server 2019 or 2022.

In this blog I am sharing how I upgraded my Windows Server 2016 Hyper-V host that been running an Intel NUC for a solid 3 years now to Windows Server 2019. Before anything else I’m taking my collecting my current server info (reference link: here)

• Open a command prompt and type systeminfo.exe.

• Copy, paste the info to a notepad or OneNote save to another device or storage other than the machine that will be upgrading.
• Type ipconfig /all and take note of the IP settings.
• Open the Registry Editor this this hive: HKLMSOFTWAREMicrosoftWindows NTCurrentVersion and take note the Windows Server BuildLabEx (version) and EditionID (edition).

It’s also worth the trouble to that we backup the operating system, apps, and virtual machines.

As you can see above, we can’t have any virtual machines running during the in-place upgrade process, so we have to make sure that they are turned off.

Now, after this checklist are met, it’s time to launch the Windows Server 2019 installer.

If you are prompted a UAC – click Yes.

The next screen will ask for either Download updates, drivers and optional features (recommended) or Not right now options, if your device is internet-connected you may select the first option and then select Next.

Enter your Windows Server 2019 Product, in this example I have a Standard License (you won’t see any Datacenter options here).

I selected the Windows Server 2019 Standard (Desktop Experience) then clicked Next.

Select Accept to accept the terms of your licensing agreement

On the next screen you may select to Keep your personal files and apps or just wipe everything, I have chosen the keep my files, then I clicked Next.

The setup will then analyzes the device and will call your attention if needed (same in the example above of the running VMs), once all is good to go it will prompt you to proceed with the Installation.

Click install to proceed.

After the upgrade is completed, verify that the upgrade to Windows Server 2019 was successful by going the the System Properties.

Now this Windows Server 2019 is ready.

It is always a good idea to start a new Windows Server 2016 / 2019 installation on a new slate. However, in some instances, you may be working on a site that will force you to upgrade from the current installation to the latest version.

The routines described here apply to the server versions of Windows 2016 and 2019. This article describes moving to Windows Server 2016 / 2019 from different lower server platforms.

The path to the new Operating System (OS) depends on the current system and configurations that you are running.

That being the case, the following terms define activities you are likely to encounter when deploying the 2016 Server.

Installation

The simplest way of installing a new OS to work on your hardware, and get a clean installation, demands that you delete the previous Operating System.

Migration

To move system settings to the new Windows Server using a virtual machine is what we call migration. The process also varies depending on the roles and system configurations already running.

Cluster OS Rolling Upgrade

This feature is new in Windows Server 2016, and its role is to make sure the Administrator can upgrade the Operating System of all nodes running Windows Server 2012 R2 to Windows Server 2016, without interfering with the Hyper-V or Scale-Out File Server workloads.

The feature also helps in reducing downtime, which may affect Service Level Agreements.

License Conversion

Some Operating Systems use releases that allow the conversion of one edition to another without so much struggling.

What you need is a simple command issued alongside a license key, and you end doing the license conversion.

Upgrade

When you want to use the latest software that comes with the newer versions, then you have to do an upgrade.

In-place upgrades mean using the same hardware for installing the new Operating System. For example, you can upgrade from evaluation to retail version or from a volume license to an ordinary retail edition.

NOTE 1: An upgrade will work well in virtual machines if you do not need specific OEM hardware drivers.

NOTE 2: Following the Windows Server 2016 release, you can only perform an upgrade on a version installed using the Desktop Experience (not a server core option).

NOTE 3: If you use NIC teaming, disable it before you perform an upgrade; and when the upgrade is complete, re-enable it.

Upgrade Retail Versions of Windows Server to Windows Server 2016 / 2019

Note the following general principles:

• Upgrading a 32-bit to 64-bit architectures is not possible. Note that all Windows Server 2016 versions are only available in 64-bit.
• You cannot upgrade from one language to another.
• If you are running a domain controller, make sure you can handle the task, or read the following article: Upgrade Domain Controllers to Windows Server 2012 R2 and Windows Server 2012.
• You cannot upgrade from a preview version.
• You cannot switch from Server Core installation to a Server with a Desktop installation.
• You cannot upgrade from a Previous Windows Server installation to an evaluation copy of Windows Server.

You can read from the table below that shows a summary of Windows Operating Systems available for upgrade. If you are unable to upgrade your current Windows version, then upgrading to Windows Server 2016 is impossible

Per-Server-Role Considerations for Upgrading

It’s important to consider server roles before performing an upgrade.

For example, some server roles are part of the newer Windows versions and may only need additional preparation or actions to get the desired intent.

Converting Current Evaluation Version to Current Retail Version

It is possible to convert the trial version of Windows Server 2016 Standard to a Data 2016 Standard Server or a Datacenter version. The two conversions can be retail versions. You can also convert Windows Server 2016 Datacenter to the retail version.

Before making any conversion attempts to the retail version, ensure that your server is running an evaluation version; you can confirm this by following these steps:

• From the administrator’s command prompt, run

slmgr.vbs /dlv;

• The evaluation versions will include “EVAL” as the output
• Open the control panel
• Then click on System and Security
• Click on System
• View the activation status found on the activation area of the System page
• Click view details, and you will see more information on your Windows Status
• If your Windows is activated, you will see information showing the remaining time for the evaluation period.

If you are running a retail version, you will see the “Upgrading previous retail versions of Windows Server 2016” message prompting you to upgrade to Windows Server 2016.

In Windows Server 2016 Essentials, the conversion to retail version is possible if you have a retail volume license or OEM key in the command slmgr.vbs

In case you are running an evaluation version of Windows Server 2016 Standard or Windows Server 2016 Datacenter, the following conversions can help you:

• If the server is a domain controller, it cannot change to the retail version. First, install another domain controller on a server that runs a retail version and remove the AD DS from the domain controller that has the evaluation version.
• Read the license terms
• From the administrator’s command prompt, enter this command to get the current edition:

DISM /online /Get-CurrentEdition

Note the edition ID, the abbreviation form of the edition name, and then run the following command:

DISM /online /Set-Edition:<edition ID> /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula

Once you get the ID and product key, the server should restart twice.

You can convert the evaluation version of Windows Server 2016 Standard to the retail version of Windows Server 2016 Datacenter using the same command and product key.

Converting Current Retail Edition to a Different Current Retail Edition

After successful installation of Windows Server 2016, you can run setup to repair the installation using a process called “repair in place” that converts it to a different edition.

In case of Windows Server 2016 Standard, you can convert the system to Windows Server 2016 Datacenter by:

• From the administrator’s command prompt, use the following command to determine the existing edition:

DISM /online /Get-CurrentEdition

• Run this command to get the ID of the edition you want to upgrade to:

DISM /online /Get-TargetEditions

• Note the ID edition, the name of the edition, and then run this command:

DISM /online /Set-Edition:<edition ID> /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula

• Once you get the ID and product key, the server should restart twice.

Converting Current Retail Version to Current Volume Licensed Version

Once you have Windows Server 2016 running, you can convert it to a retail version, an OEM version, or a volume-licensed version. The edition will not change.

If the starting point was an evaluation version, change it to retail version and then do as follows:

• From the administrator’s command, run this command:

slmgr /ipk <key>

• Insert the appropriate volume license, OEM or retail key instead of <key>

Conclusion

Upgrading Windows Server is a complicated process; therefore, Microsoft suggests that you migrate all roles and settings to Windows Server 2016 to avoid costly mistakes.