Overview of Windows Server upgrades
The process of upgrading to a newer version of Windows Server can vary greatly, depending on which operating system you are starting with and the pathway you take. We use the following terms to distinguish between different actions, any of which could be involved in a new Windows Server deployment.
Upgrade. Also known as an "in-place upgrade". You move from an older version of the operating system to a newer version, while staying on the same physical hardware. This is the method we will be covering in this section.
Important
In-place upgrades might also be supported by public or private cloud companies; however, you must check with your cloud provider for the details. Additionally, you'll be unable to perform an in-place upgrade on any Windows Server configured to Boot from VHD. An in-place upgrade from Windows Storage Server Editions is not supported. You can perform either a Migration or Installation instead.
Installation. Also known as a "clean installation". You move from an older version of the operating system to a newer version, deleting the older operating system.
Migration. You move from an older version of the operating system to a newer version of the operating system, by transferring to a different set of hardware or virtual machine.
Cluster OS Rolling Upgrade. You upgrade the operating system of your cluster nodes without stopping the Hyper-V or the Scale-Out File Server workloads. This feature allows you to avoid downtime which could impact Service Level Agreements. For more information, see Cluster OS Rolling Upgrade
License conversion. Convert a particular edition of the release to another edition of the same release in a single step with a simple command and the appropriate license key. We call this "license conversion". For example, if your server is running Standard edition, you can convert it to Datacenter.
Which version of Windows Server should I upgrade to?
We recommend upgrading to the latest version of Windows Server. Running the latest version of Windows Server allows you to use the latest features – including the latest security features – and delivers the best performance.
Beginning with Windows Server 2025, you can upgrade up to four versions at a time. Meaning you can upgrade directly to Windows Server 2025 from Windows Server 2012 R2 and later.
With Windows Server 2022 and earlier, you can upgrade to a newer version of Windows Server by up to two versions at a time. For example, Windows Server 2016 can be upgraded to Windows Server 2019 or Windows Server 2022. If you are using the Cluster OS Rolling Upgrade feature you can only one version at at time.
In this table you can see the supported upgrade paths, based on the version you're currently on.
| Upgrade from / to | Windows Server 2012 R2 | Windows Server 2016 | Windows Server 2019 | Windows Server 2022 | Windows Server 2025 |
|---|---|---|---|---|---|
| Windows Server 2012 | Yes | Yes | - | - | - |
| Windows Server 2012 R2 | - | Yes | Yes | - | Yes |
| Windows Server 2016 | - | - | Yes | Yes | Yes |
| Windows Server 2019 | - | - | - | Yes | Yes |
| Windows Server 2022 | - | - | - | - | Yes |
| Windows Server 2025 | - | - | - | - | Yes |
You can also upgrade from an evaluation version of the operating system to a retail version, from an older retail version to a newer version, or, in some cases, from a volume-licensed edition of the operating system to an ordinary retail edition. For more information about upgrade options other than in-place upgrade, see Upgrade and conversion options for Windows Server.
Important
Support for Windows Server 2008 and Windows Server 2008 R2 has ended. We recommend you update your version of Windows Server to a more recent version as soon as possible. Learn more about Extended Security Updates (ESU) as a last resort.
Next steps
Now that you've ready to upgrade Windows Server, here are some articles that might help you get started: