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.
Learn to migrate a workload running in Windows Server to an infrastructure as a service (IaaS) virtual machine (VM) and to Windows Server 2025 by using Windows Server migration tools or the Storage Migration Service.
As a Windows Server hybrid administrator, you integrate Windows Server environments with Azure services and manage Windows Server in on-premises networks.