Upgrade and Conversion Options for Windows Server 2016 / 2019

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.