Windows Server 2012 R2 Upgrade Path

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Matthew Pendergrass

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Jul 16, 2024, 10:05:24 PM7/16/24
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The process of upgrading to a newer version of Windows Server can vary greatly, depending on whichoperating system you are starting with and the pathway you take. We use the following terms todistinguish between different actions, any of which could be involved in a new Windows Serverdeployment.

windows server 2012 r2 upgrade path


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Upgrade. Also known as an "in-place upgrade". You move from an older version of the operatingsystem to a newer version, while staying on the same physical hardware. This is the method wewill be covering in this section.

In-place upgrades might also be supported by public or private cloud companies; however, youmust check with your cloud provider for the details. Additionally, you'll be unable to performan in-place upgrade on any Windows Server configured to Boot from VHD. An in-place upgradefrom Windows Storage Server Editions is not supported. You can perform either a Migrationor Installation instead.

Cluster OS Rolling Upgrade. You upgrade the operating system of your cluster nodes withoutstopping the Hyper-V or the Scale-Out File Server workloads. This feature allows you to avoiddowntime which could impact Service Level Agreements. For more information, seeCluster OS Rolling Upgrade

License conversion. Convert a particular edition of the release to another edition of the samerelease 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 itto Datacenter.

With Windows Server 2022 and earlier, you can upgrade to a newer version of Windows Server by upto two versions at a time. For example, Windows Server 2016 can be upgraded to Windows Server 2019or Windows Server 2022. If you are using theCluster OS Rolling Upgrade featureyou can only one version at at time.

You can also upgrade from an evaluation version of the operating system to a retail version, from anolder retail version to a newer version, or, in some cases, from a volume-licensed edition of theoperating system to an ordinary retail edition. For more information about upgrade options otherthan in-place upgrade, seeUpgrade and conversion options for Windows Server.

Windows Server 2025 is in PREVIEW. This information relates to a prerelease product that may be substantially modified before it's released. Microsoft makes no warranties, expressed or implied, with respect to the information provided here.

Support for Windows Server 2008 andWindows Server 2008 R2 has ended. We recommend youupdate your version of Windows Server to a more recent version as soon as possible. Learn moreabout Extended Security Updates (ESU) as a last resort.

Doing some searches on the web, it's not clear if there is an upgrade path from 2012R2 to 2022 Windows Server. From the link, I was wondering if there is an upgraded diagram, or if Microsoft has a recommendation on the path forward for this route? Is this upgrade not supported, and we should opt to then do a clean install?

@Harm_Veenstra I appreciate the responses. My concern is that is there a official recommendation from Microsoft? Does Microsoft 'standby' that this upgrade path should work, or what I'm reading from other responses is that, it's better to do a clean install, or perform both routes just in case...

Actually migrating to Windows 11 needs much planning and considerations due to heavy changes to the underlying hardware security stack (TPM 2.0, UEFI, Secure Boot, VBS etc.).
Same is true for Windows Server 2022.
Just because it "works" doesn't mean it is properly configured, secured and optimized.

You certainly doesn't want your brand new Windows Server 2022 relying BIOS/MBR model by example.

This is very difficult to do when the DC has hundreds of users and computers and other roles running, especially when you are a new sys admin with no connection to the prior sys admin of anything else the DC vm may be doing that is critical that you can't migrate by doing a fresh install.

@Chrisntpsfor new domain controllers it's better just to spin up a new server 2022 and join it to the domain then make it a domain controller (DNS Server) I've removed all other roles from my domain controllers such as (DHCP, CERT, KMS, other roles) this way it's easier to upgrade domain controllers by adding a new DC already running the latest OS. if you haven't move the roles out of your DC I recommend you to first work on moving DHCP, KMS, Certificate of Authority or any roles you may be running on that DC aside from (DNS only) this role must stay in the DC imho.

@cespiritu @Zach_B635 it depends on the workloads and antivirus apps.
If this is a correctly setup server like "no Domain Controller + Certificate Authority at the same Server or VM it is a simple as

Pardon me, I wasn't aware at the time of writing I am necroing a thread from 2021, yet as the topic is still hot and the guidance given can be used universally now, allow me to add the last one from my end.

One of the things that administrators need to know before they can upgrade servers is the supported Windows Server upgrade paths. I often get emails asking me if a specific version of Windows Server can be upgraded to the latest version. Or is the upgrade to Windows Server 2019 from Windows Server 2012 R2 supported?

Many of us are confused about this, and we are aware that Microsoft has released different versions of Windows Server. Upgrading a Windows server to a higher version is always confusing. So, I decided to help server administrators by putting all the information about all the ways to upgrade Windows Server in this article.

When you plan to upgrade the Windows Server, Microsoft recommends upgrading to the latest version of Windows Server. You can use the newest features, including the newest security features, and get the best performance by running the most recent version of Windows Server.

Note that 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. You must, however, be aware of the proper server upgrade paths when using older versions of Windows Server before carrying out in-place upgrades.

@Alban1999 I have a Server 2012 R2 Datacenter file server that I need to get to 2022. While in place upgrade may not be optimal, it would be easier in this case just because of the amount of data that is involved as well as the messy folder permissions that predate me (we have a single file server that hosts all personal drives as well as corporate shares). Is it possible to migrate this (the plan is to go to 2019 first then to 2022) going from 2012 R2 datacenter to a 2022 standard?

shutdown old FS
attach VHDX to the new VM, assign same drive letter and make the drives online
import registry from lanmanserver
set AD DNS entry to short update time like 30 min
rename old FS and assign different ip
rename new FS and assign same ip (or DHCP)

Hey everyone, so as the titles states we are running Commvault 11.20.82 on win 2012 R2. Right now we are just considering doing the OS upgrades as 11.20 is still LTS until 2025; but if there is simple way to do them both without breaking anything that would be great.

Hi @ComBak so you are considering an in-place upgrade of the OS to a newer version? Is it a psychical system or virtual? Because, although it is supported to perform an in-place OS upgrade you can never get the guarantee that it will not break anything. So, running it virtually at least allows you to create a snapshot of the VM before starting the upgrade so you have a way to go back easily.

Not sure how big you environment, but as for running the FR20 LTS release I would strongly consider moving to FR24 or even FR28, who are both LTS. By sticking to FR20 you miss a lot of enhancements and updates, especially when it comes to the support of newer application versions.

@Onno van den Berg Thanks for your response. It is a VM so we are planning to take a snapshot before the in place upgrade. I was just wondering other than killing all jobs is there anything else I'm missing?

I would also always go for an approach to build it up from scratch instead of performing an in-place upgrade of a Windows Server version that old and thanks to @Jos Meijer for giving a very detailed overview which steps it takes it also shouldn't be a very difficult task ;-)

Well in all honesty the upgrade path by performing an in-place upgrade does look like the easiest way and fastest way, but it can also lead to unpredictable issues even after some time. Also, if you are not so experienced with Commvault than I would definitely try to make some time/room for yourself to use this migration to become more familiar with it. Having to take over the work from someone else can be very challenging just because you miss all the history. This opportunity gives you the ability to start from scratch and also build the environment with todays threats in mind.

Our RHEL team has hardened the servers such that /tmp is mounted as non-executable, and there are no exceptions to the policy. What happens is the upgrade fails, and the upgrade needs to be done manually.

But... did want to share, just in case you are unaware, that linux-based MID's can't discovery Windows targets. Since you are moving from existing Windows-based MIDS I presume your company might already be scanning at least some windows-based targets. Just know those MID's being repositioned on RHEL/Linux won't be able to scan Windows machines via WMI. Just in case FYI....

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