Microsoft Recommendation on Upgrade Path from 2012R2 to 2022?

[Zach_B635]

Hello,

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?

https://docs.microsoft.com/en-us/windows-server/upgrade/upgrade-overview

Thank you

[#2]

It is possible to upgrade from Windows 2012r2 to 2022, nice article about it here https://www.virtualizationhowto.com/2021/06/in-place-upgrade-windows-server-2008-r2-to-windows-serve... It's about 2008 R2 to 2012r2 and then to 2022 in one jump

Edit : You have to take a break first on Windows Server 2019 in between, jump is too big otherwise from 2012R2 to 2022

[#3]

The official support aside, I've done this upgrade path twice with a 50% success rate. The first, was a quick test with an relatively unused VM, and the upgrade went well. The second, on a server that I didn't have physical access to, never came back onto the network, and a reboot didn't help. As the server was already slated to be repurposed, unfortunately I never got the chance to see what went wrong before someone clean installed it.

[#4]

Avoid in-place upgrade whenever you can, as it is very unreliable, and prone to keep non-desired settings. Even if it works, you may encounter later multiple bugs and issues, potentially difficult to troubleshoot and fix.
This is even more true when you try to fill a 10+ years gap.
Do yourself a favor and plan a side-by-side migration with a fresh install of Windows Server 2022.

[#5]

Is this enough information for you?

[#6]

@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...

Thank you

[#7 · Accepted solution]

Did a in-place upgrade from 2012 R2 to 2019 just last week for two servers, no issues.. It just depends on the installed software/drivers/anti-virus etc if it will work. But nobody thinks twice about upgrading Windows 7 tot 8 to 8.1 to 10 to 11 ;) Upgrading does work and having issues in the future because of it is something of the past in my experience. If you can migrate to a new server without a lot of work.. Please do so, but it is still an option (But keep your backup and snapshots close)

[#8]

We'll keep these options in mind. Thanks for all the helpful replies here!

[#9]

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.

[#10]

To sum it up : imho, in-place upgrade is a quick-and-dirty way of migrating something.
It trades reduced initial migration costs for increased operational risks.
It's up to you to select it or not as the preferred migration method.

[#11]

@Alban1999 

"Avoid in-place upgrade whenever you can"

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.

[#12]

@Chrisntps If is a Domain Controller the recomendation is to create a new Windows server 2022, add the roll of Domain Controller and move all the DC rolls to this new one, then "demote" the old one. 

[#13]

@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.

[#14]

Hi @Harm_Veenstra

May I ask for the detailed procedure on how did you done the in-place upgrade?

[#15]

@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

some general guidelines from my numerous migration projects:

• Check compatiblity with software and vendors and dependencies such as .net., does your backup software, security solution, monitoring support the OS etc.
  Do vendors expressively not allow IPU, such as Citrix (workaround uninstall software, upgrade, install software such as Citrix VAD)
  
  
• Check your licensing eligibility! Are you licensed? How, which contract, do you introduce an OEM / CSP VL Server to your Enterprise Agreement environment. 
  Do you have SA or CSP Subscription or VL with obligatory SA like OVS, MPSA or EA?
  And do you need other licenses (still) like (RDS) CALs and are they covered under SA or licensed for the future version?
  
  
• Avoid (final) upgrades to OS that are not in Mainstream Support such as WS 2016 or WS 2019. Exception: interim version needed for the upgrade path.
  There will be literally no help, but self-help resources and you don't want to pay extended support fees.
  
  
• Have a recent and working full backup. A VM snapshot is nice but do not consider it a backup equivalency. 
  
  
• Always download the LASTEST Windows (Server) ISO in your OS language or at best en-us language, see below. There is NO patched ISO for Windows Server 2016. Avoid this OS at all cost on your path (and in general, too).
  Updated ISO is also true when using one OS as bridge like 2012R2 > 2019 > 2022 / 2022 Azure Edition in eligible systems.
  
  The upgrade path supported is always your base version + 2 (so 2016 > 2022, 2012R2 > 2019)
  This is most crucial for successful upgrades as the PG is also fixing issues in the upgrade and setup procedure
  
  
• Even though the ISO contains the latest CUs, do allow dynamic upgrades in the setup wizard. Without this .net or other components like language packs won't be upgraded properly. Caveat this may update drivers. Citrix VAD masters don't like updading NICs.
  
  
•  If the OS Language is not en-us consider side by side migration instead o in-place upgrade in this language and use language packs (thank me later) you can find out the language by Win + X > PowerShell (Admin) > Get-Computerinfo
  
  The important thing on the why en-us:
• Microsoft and even Microsoft PowerShell Scripts are rarely to none tested against other native languages of an OS such as security groups, account names (even though SID exist but rarely used in code)
• Windows Feature names are localized, too.
• Some ancient code Windows Roles and Features are language dependent when exporting the configuration and cannot then easily migrated such as DHCP (for sure), AD CS, eventually Print
• It is harder to find workarounds on the net in other language even more due to arbitrary translation.
• The MS Support with thank you, too, as only Evenlogs can be saved in other localization. 
  Error messages are harder to understand due localization.
• Windows Admin Center and extensions dislike non en-US language installation and greet you with random failures.
• You can find Group Policies in the Azure based search engine only in this language. Translation makes is pretty hard to find them.
• How to tame admins on changing the language:
  • apply language packs (fixed translation, little to no fixes / LIPs (language interface packs, these can be patched via updates)
  • use local keyboard and regional options in the setup (this does not change anything on the OS language for Windows Server)
    
    
    
• if the Server has a GUI check documentation if you really need it. Prefer Server Core option where possible. While possible do not bother with print server, some Version 3 drivers are horribly legacy coded and "require" GUI elements.
  
  Remote Management via Server Manager, DSAC and WAC is king using a special PAWS (privileged Admin Workstation / VM / Windows Server VM), incl. RDSH if licensed), for all tools needed. 

• Update the base system to the latest patch, including SSU if seperately available.
  
  
• is the Component Store (WinSXS) is broken? Good.
  Repair-WindowsHealth -Online (-scanhealth / -checkhealth) do not repair.
  In-place upgrade will fix this most of the times.
  
  
• If Windows Server 2012 (R2) or later run a chkdsk /f on C drive and restart.
  You'lll never now! (unexpected shutdowns, and other catastrophies.
  
  
• Spare enough free space usually 20 GB is enough.
  
  
• Use Microsoft Defender (free) or P1/ P2 if possible.
  Remove 3rd party "security" solutions before any upgrade, at best with the vendors removal tool. You can roll the 3rd party solution out after the upgrade.
  
  
• if you can afford use the rule one VM for one "task" especially if security related such as File, Print, AD DS (DC), AD CS (CA), DHCP. You can put them all together, but you will regret this. in the lastest MSFT finally forbid the installation of AD CS on AD DS
  
  
• when using ReFS mind there is no way back, IPU will upgrade all online mounted volumes (and should so). Mind there is no upgrade path from ReFS Windows Server 2012 (R2) to any later version. You need to start over to gain ReFS improvements.
  
  
• Do not upgrade the OS on Exchange Server, see above about vendor comments. It is NOT supported as per docs (too many dependencies on PowerShell / WMF and .net). this could become more relaxed starting with WS 2022 and later and Exchange vNext. 

• If you used Azure Arc e. g. for ESU, Defender, Monitoring etc, uninstall the agent and remove Azure references / resources. In-place upgrades are not supported by the otherwise modern connected machine agent, as per docs. 

Following this you will have a great success rate, better than other described. 

Hope this helped! Good luck on the tasks to come!

[#16]

Brief How-To:

- follow all guidance and details from this thread.
- Mount the ISO in File Explorer or provide it to the VM (Hyper-V, VMware etc)
- Start Setup (or automate using setup commandline arguments and PowerShell)

- Don't forget to optimize the VM post successful migration VM Generation for VMware and Hyper-V) etc.
- Convert Gen 1 VMs using Script from Altaro Hyper-V Dojo Post Migration (have a backup)
- Boot the ISO Convert from MBR to GPT using mbr2gpt tool (Gen 2 VM required for Hyper-V)
- do not delete the WinRE recovery at the end of the disk (right of the the OS partition)
- VMware: do not forget to change the "installed OS flag" in extended options)
- When on Windows Server 2022, consider VBS / Secured Core options via VMware + WAC security settings. GPT / UEFI is a requirement for this.
- Hyper-V Gen2, GPT and UEFI will become required with Windows Server vNext, as well as we can expect vTPM, equivalent to Windows 11 security requirements. You won't pay twice if your WS 2019 and later are already using GPT and UEFI + Secure Boot as a base.

[#17]

Hi @Harm_Veenstra there is a small oversight in your otherwise correct statement. 2012R2 to 2022 is not possible (or supported).
https://learn.microsoft.com/en-us/windows-server/get-started/upgrade-overview

[#18]

Ah, yes.. I see the upgrade table and you have to do 2019 in between!

[#19]

No problem Harm.

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.

Which is 

1. A great explaination of ESU if an upgrade isn't technical possible

2. The one the OP @Zach_B635 asked for which is today available, in form of an official recommendation , but maybe less complete. 

[#20]

Thank you so much for your assistance. But may I verify if I should follow the upgrade path provided on Microsoft Site if I will be doing migration and not in-place upgrade or I can directly migrate from 2012R2 to 2022?

For example,
In-place upgrade: Windows Server 2008 R2> 2012 R2 > 2016> 2022 version
Migration: Windows Server 2008 R2> 2022 version