Is it still worth buying Windows Server 2022 or 2019 today? For a new server without constraints, Windows Server 2025 is the better choice because it receives security updates until 2034. Windows Server 2022 makes sense if your software does not yet support 2025, if the hardware cannot run 2025 or if you are extending an environment with existing 2022 CALs. Windows Server 2019 only has support until January 9, 2029 and only comes into question if an application requires exactly this version.
Quick decision
| Your situation | Recommendation |
|---|---|
| New server, no constraints from the software | Windows Server 2025 |
| Software vendor certifies only 2022 | Windows Server 2022 |
| Software vendor certifies only 2019 | Windows Server 2019, plan the replacement by 2028 |
| Additional server in an environment with 2022 CALs | Windows Server 2022 |
| Older CPU without SSE4.2 and POPCNT | Windows Server 2022 or 2019 |
| Replacement for a failed server of the same version | the same version as before |
| Server should run for eight years | Windows Server 2025 |
Remaining lifetime: what you get for your money
The dates come from Microsoft’s lifecycle pages. The remaining lifetime is calculated from November 10, 2026.
| Version | End of mainstream support | End of extended support | Remaining lifetime with security updates |
|---|---|---|---|
| Windows Server 2019 | January 9, 2024 | January 9, 2029 | about 2 years and 2 months |
| Windows Server 2022 | October 13, 2026 | October 14, 2031 | about 4 years and 11 months |
| Windows Server 2025 | November 13, 2029 | November 14, 2034 | about 8 years |
Both earlier versions are out of mainstream support: 2019 since January 2024, 2022 since October 13, 2026. They continue to receive security updates but no new features. The dates of all versions are in
Windows Server end of support: all versions.
The lifetime is a cost factor. If you buy 2019 today, you will be planning the next replacement in a good two years, including a new server license and new CALs. Microsoft points out that every new Windows Server version requires its own license.
Reasons for an earlier version
1. The software requires it. The most common reason. Inventory management, practice or industry software and some machine control systems are only certified for specific server versions. What counts is the vendor’s current compatibility list, not the packaging from three years ago.
2. The hardware requires it. Windows Server 2025 requires processors with SSE4.2 and POPCNT. For 2022 and 2019, Microsoft does not name this requirement. If an older server continues to be used, this can tip the balance.
3. Existing CALs. CALs are valid for their version and for earlier ones. If you have 40 CALs 2022 and add another server, they remain valid for a server with 2022 but not for one with 2025.
4. Uniform environment. If you run several identical servers, you like to keep version, updates and procedures the same. That is an argument for 2022 as an addition, hardly any longer for 2019.
Reasons against
- Shorter lifetime with the same licensing model and the same way of counting.
- CALs age too. If you buy 2019 or 2022 CALs now, you cannot use them on a later server with 2025. Conversely, 2025 CALs are also valid for 2022 and 2019.
- Missing features. SMB over QUIC and hotpatching are available in 2022 only in the Datacenter: Azure Edition, in 2025 also in Standard and Datacenter. Details in Windows Server 2025 or 2022.
- An upgrade is a new purchase. The in-place upgrade from 2019 or 2022 to 2025 is technically supported but requires licenses and CALs of the new version.
The middle way: old server version, new CALs
If the software requires 2022, buy the server license in version 2022 and the CALs in version 2025. The 2025 CALs entitle access to Windows Server 2022 and remain valid when the server later moves to 2025. The same applies to RDS CALs: RDS CALs 2025 work with session hosts running 2022 and 2019. The license server must then run Windows Server 2025, however. The tables for this are in Which CAL version fits which server.
Quantities: the same calculation in all versions
Windows Server 2019, 2022 and 2025 are counted in the same way: all physical cores, at least 8 per processor and 16 per server, two virtual machines per round of licensing with Standard.
| Server | 2019 Standard | 2022 Standard | 2025 Standard |
|---|---|---|---|
| 1 processor, 8 cores, 2 VMs | 16 core licenses | 16 core licenses | 16 core licenses |
| 2 processors, 10 cores each, 2 VMs | 20 core licenses | 20 core licenses | 20 core licenses |
| 2 processors, 8 cores each, 4 VMs | 32 core licenses | 32 core licenses | 32 core licenses |
The quantity therefore does not depend on the version, only the price per license. In the
license calculator you select the server version and see the total for 2019, 2022 or 2025 with the same entries. It suggests the CALs in the version of the server or a newer one. The counting rules are explained in
Licensing Windows Server: cores, VMs, CALs.
Typical cases
Practice software certified for 2022 only. Server with one processor and 8 cores, 9 users. 16 core licenses of Windows Server 2022 Standard and 9 user CALs, preferably in version 2025.
Second host for an environment with 2022. Two processors of 8 cores each, four VMs, 2022 CALs for 35 employees are available. 32 core licenses of Windows Server 2022 Standard or 16 core licenses of Datacenter. New CALs are not needed.
Machine control system requires 2019. It stays with 2019. Make a note that security updates end on January 9, 2029, and clarify the certification of a newer version with the vendor in good time.
New server without constraints, 2022 is offered at a lower price. Factor in the lifetime: with 2022, the replacement is due three years earlier, with a new server license and new CALs. A price advantage at purchase rarely makes up for that.
At VivaKeys
Windows Server 2022:
Standard, 16 Core,
Standard Core Add-on,
Datacenter, 16 Core,
User CAL,
Device CAL
Windows Server 2019:
Standard, 16 Core,
Standard Core Add-on,
Datacenter, 16 Core,
User CAL,
Device CAL
All versions are in the categories
Windows Server and
CALs. We deliver digitally: you receive the product key by email and download the software via the link in the delivery email or from the publisher. The delivery time is shown on the respective product.
Frequently asked questions
Can you still buy Windows Server 2022? Yes. The current offers for Windows Server 2022 and the matching CALs are in the categories
Windows Server and
CALs. The purchase makes sense above all if software, hardware or existing CALs speak for 2022.
How long will Windows Server 2022 still be supported? Mainstream support ended on October 13, 2026. Security updates are available in extended support until October 14, 2031.
Is Windows Server 2019 still worth it? Only if an application requires this version. Extended support ends on January 9, 2029, i.e. in a good two years.
What does Windows Server 2022 Standard 16 Core mean? It is the base license with 16 core licenses, the minimum quantity per server. If the server has more than 16 physical cores, additional licenses for 2 cores each are added.
Can I upgrade Windows Server 2022 to 2025 later? Technically yes, Microsoft supports the in-place upgrade. You need a license for Windows Server 2025 and 2025 CALs for it.
Are Windows Server 2025 CALs valid for a server with 2022 or 2019? Yes. CALs entitle access to the same and to earlier versions.
Sources
Checked on 2026-11-10 against the publisher’s information:
- learn.microsoft.com/en-us/lifecycle/products/windows-server-2019
- learn.microsoft.com/en-us/lifecycle/products/windows-server-2022
- learn.microsoft.com/en-us/lifecycle/products/windows-server-2025
- learn.microsoft.com/en-us/windows-server/get-started/hardware-requirements
- www.microsoft.com/licensing/terms/productoffering/WindowsServerStandardDatacenterEssentials/EAEAS
- learn.microsoft.com/en-us/windows-server/get-started/upgrade-overview
- learn.microsoft.com/en-us/windows-server/remote/remote-desktop-services/rds-client-access-license