upgrade windows server essentials?

Question

Hi I have an older server that is still very capable for our small business but our OS is soon to come out of extended support.

I wish to update our server 2012 r2 to something supported.

I have looked at buying server standard and device / user cals and it would be price prohibitive for 13 users.

Is there some sort of upgrade path to upgrade to a newer version of essentials?
I talked to HPE and they said I can only buy the retail option kit bundled with a new server which is a shame as the software is relatively cheap.

I could buy a new server bundled with software but that is also expensive and unnecessary.

Is there some way to migrate or upgrade the OS to something newer or software assurance path I can go down to update to server essentials 2019 2022 or 2025? so i dont need to buy user and device cals?

Originally, we purchased essentials via VL from MS along with windows for our client computers.

Answer 1

Hello

Thank you for posting in Q&A forum.

Upgrading your Windows Server 2012 R2 to a newer version can be done, but there are a few considerations, especially when it comes to maintaining compatibility with your existing setup (like CALs and licensing). Here's an overview of your options:

1. Direct Upgrade Path

Unfortunately, there is no direct upgrade path from Windows Server 2012 R2 to Windows Server 2019 or 2022, as Microsoft generally requires a clean install for these versions. The upgrade path is only supported from specific earlier versions (like 2016 to 2019), so you'd have to perform a clean installation, which may involve data migration and reconfiguration.

2. Windows Server Essentials (2019, 2022, 2025)

Windows Server Essentials editions are specifically designed for smaller organizations (up to 25 users and 50 devices), and they come with a different licensing model than the standard editions (Standard, Datacenter). This could be an attractive option if you want to avoid purchasing new user/device CALs, as the Essentials version includes access for a set number of users/devices without requiring additional CALs.

3. Licensing and CALs

Windows Server Essentials editions (2019/2022) do not require separate user/device CALs for the first 25 users and 50 devices, so this could help you avoid additional licensing costs if your setup fits within those limits.

4. Migration to Newer OS Versions

If you're aiming to migrate to a supported version but want to avoid the reinstallation hassle, consider using the Windows Server Migration Tools (available in the 2016 and newer versions). These tools help transfer data, roles, and configurations from the old server to the new one, but again, this typically applies when upgrading from compatible versions.

5. Possible Path with Software Assurance

If you have Software Assurance (SA) on your existing Server 2012 R2 licenses, you may be eligible for free upgrades to newer versions of Windows Server as part of your SA benefits. It’s a good idea to check your current licensing agreement with Microsoft or your vendor to see if you can take advantage of this for a smoother transition.

I hope the information above is helpful.

If you have any questions or concerns, please feel free to let us know.

Best Regards,

Daisy Zhou

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