SharePoint on premise 2019 Farm OS Upgrade (Windows Server 2016 to Windows Server 2019/2022) Assessment

Question

SharePoint on premise 2019 Farm OS Upgrade (Windows Server 2016 to Windows Server 2019/2022) Assessment

Praveen Kumar, Qatar Rail 0

We are planning to upgrade the operating system of the existing SharePoint Server 2019 on-premises farm from Windows Server 2016 to Windows Server 2019 or Windows Server 2022.

The farm currently hosts:

SharePoint Server 2019
Nintex Workflow & Forms 2019 (Version 5.2.0.0)

As building a new SharePoint farm and performing a full migration would be time-consuming and resource-intensive, we would like to assess the feasibility of performing an in-place OS upgrade of the existing servers.

Requested Action:

Review and confirm the feasibility of the in-place upgrade approach.
Identify any risks, prerequisites, dependencies, or rollback requirements.
Provide recommendations and implementation steps for upgrading the SharePoint farm servers from Windows Server 2016 to Windows Server 2019/2022.
Review any impact on SharePoint services, integrations, and third-party products such as Nintex.We are planning to upgrade the operating system of the existing SharePoint Server 2019 on-premises farm from Windows Server 2016 to Windows Server 2019 or Windows Server 2022. The farm currently hosts:
- SharePoint Server 2019
- Nintex Workflow & Forms 2019 (Version 5.2.0.0)
As building a new SharePoint farm and performing a full migration would be time-consuming and resource-intensive, we would like to assess the feasibility of performing an in-place OS upgrade of the existing servers. Requested Action:
- Review and confirm the feasibility of the in-place upgrade approach.
- Identify any risks, prerequisites, dependencies, or rollback requirements.
- Provide recommendations and implementation steps for upgrading the SharePoint farm servers from Windows Server 2016 to Windows Server 2019/2022.
- Review any impact on SharePoint services, integrations, and third-party products such as Nintex.

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1 answer

Your answer

Answer 1

Hello,

an in‑place OS upgrade of SharePoint Server 2019 farm servers from Windows Server 2016 to Windows Server 2019 or 2022 is technically possible but not recommended as a best practice. Microsoft’s official guidance is that SharePoint should always run on a cleanly installed supported OS, because the upgrade process can leave behind legacy binaries, registry entries, and driver states that interfere with farm stability. SharePoint Server 2019 is supported on Windows Server 2019 and Windows Server 2022, but the supported path is to build new servers on the target OS and join them to the farm, not to upgrade the existing OS in place.

The risks of an in‑place upgrade are significant. The farm services may fail to start after the upgrade because IIS bindings, .NET Framework versions, or SQL client libraries are altered. Nintex Workflow and Forms is particularly sensitive to OS changes, and vendor support may be voided if the underlying OS was upgraded in place rather than deployed fresh. Rollback is also problematic: once the OS upgrade is committed, you cannot revert without restoring the entire VM or server from backup.

If you want to minimize downtime without a full rebuild, the supported approach is a gradual node replacement. Provision new Windows Server 2019 or 2022 machines, install SharePoint Server 2019 with the same patch level, join them to the farm, and move service applications and roles over. Once validated, decommission the old Windows Server 2016 nodes. This ensures the farm remains supported and avoids the instability of an in‑place upgrade.

Implementation steps should include: verifying SharePoint 2019 patch level is current, confirming Nintex 5.2.0.0 compatibility with Windows Server 2019/2022 (via Nintex release notes), building new servers with identical farm configuration, and testing workflows and forms before cutover. Dependencies such as SQL connectivity, custom solutions, and certificates must be validated. For rollback, maintain full farm backups and SQL backups prior to introducing new nodes.

In short, while you can technically run setup.exe to upgrade the OS in place, it is not a supported or reliable method for production SharePoint farms. The recommended path is to build new servers on the target OS and migrate roles, ensuring both Microsoft and Nintex supportability.

I hope you've found something useful here. If it helps you get more insight into the issue, it's appreciated to accept the answer. Should you have more questions, feel free to leave a message. Have a nice day!

Domic Vo.