RDS Servers upgrade query (upgrade more than 2 server versions? e.g2016 to 2025)

Question

Hello,

Microsoft documentation states that RDS servers can only be upgraded by up to two Windows Server versions at a time (for example, 2016 to 2022). However, we’ve recently run into a situation where we may need to move to Windows Server 2025, due to Microsoft 365 Apps support ending for Windows Server 2022 later this year.

Our scenario:

• We currently still have some RDS servers on Windows Server 2016.
• Our original plan was to upgrade them to Windows Server 2022.
• Now, because of Microsoft 365 App support requirements, we need to go to Windows Server 2025 instead.
• This raises the question: Do RDS role servers still have the strict “maximum 2-version in‑place upgrade” limitation, or has this changed for Windows Server 2025?
• Has anyone tried to go from 2016 to 2025?

I’ve seen that general Windows Server OS upgrade rules allow much larger version jumps when moving to Server 2025, but it’s unclear whether this applies to RDS environments as well.

Thanks,

Sekela

Answer 1

Hello Sekela,

This issue is indeed related to Windows Server for business environments, specifically Remote Desktop Services (RDS) role servers. It is not related to Windows 365 Enterprise, which is a cloud service.

According to Microsoft’s current documentation for upgrading RDS deployments, the limitation of “two-version in-place upgrades” still applies when the RDS role is installed. That means you can upgrade from Windows Server 2016 to Windows Server 2019, and from 2019 to 2025, but not directly from 2016 to 2025. The supported upgrade path for RDS role servers is explicitly capped at two versions at a time, and this has not changed with Windows Server 2025.

For general Windows Server installations without the RDS role, Microsoft has indeed broadened the supported in-place upgrade paths with Server 2025, allowing larger jumps. However, RDS is a special case because of the dependencies between RD Connection Broker, RD Session Host, and RD Licensing roles. These components require a controlled upgrade sequence to maintain compatibility and avoid corruption of the deployment.

In practice, if you are running RDS on 2016 and need to move to 2025, you will need to first upgrade to 2019, validate the environment, and then proceed to 2025. Skipping directly from 2016 to 2025 with the RDS role installed is not supported and risks leaving the deployment in an unsupported state.

Given your dependency on Microsoft 365 Apps, the best approach is to plan a staged migration: upgrade the RDS servers from 2016 to 2019, stabilize the environment, and then move to 2025 before the support cutoff for Server 2022. If downtime is a concern, consider building new 2025 RDS servers in parallel and migrating user sessions, rather than relying solely on in-place upgrades.

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.

Answer 2

The upgrade limitation for Remote Desktop Services (RDS) role servers remains the same, even for Windows Server 2025. You can only upgrade RDS servers by up to two versions at a time. Therefore, if you are currently on Windows Server 2016, you would need to first upgrade to Windows Server 2022 before moving to Windows Server 2025.

The general Windows Server OS upgrade rules do allow for larger version jumps when moving to Windows Server 2025, but this does not apply to RDS environments. The RDS components must still adhere to the two-version upgrade limitation.

In summary, you will need to follow the upgrade path from 2016 to 2022, and then from 2022 to 2025 for your RDS role servers.