I have recently set up several Windows management jump-server VMs, both temporary and permanent. A Windows Server evaluation installation must be converted to the correct edition before you can apply a permanent key.

This is what worked for me:

Windows Eval reg

Each Windows Server Evaluation edition requires the matching public setup key. These are the public keys for Windows Server Evaluation 2019–2022, Standard and Datacenter.

Windows Server Evaluation 2019 Activation Key

Windows Server201**9* Essentials ***JCKRF-N37P4-C2D82–9YXRT-4M63B

***Windows Server 2019 Standard ***N69G4-B89J2–4G8F4-WWYCC-J464C

***Windows Server 2019 ******Datacenter ***WMDGN-G9PQG-XVVXX-R3X43–63DFG

Windows Server Evaluation 2022 Activation Key

Windows Server***2022 Standard ***VDYBN-27WPP-V4HQT-9VMD4-VMK7H

Windows Server 2022 Azure Edition* NTBV8–9K7Q8-V27C6-M2BTV-KHMXV*

***Windows Server 2022 Datacenter ***WX4NM-KYWYW-QJJR4-XV3QB-6VM33

Choose the command for your installed edition. Open PowerShell as administrator, paste the command with the matching public key, and press Enter.

DISM /online /Set-Edition:ServerStandard /ProductKey:N69G4-B89J2–4G8F4-WWYCC-J464C /AcceptEula

DISM /online /Set-Edition:ServerDatacenter /ProductKey:WMDGN-G9PQG-XVVXX-R3X43–63DFG /AcceptEula

Use the matching public key in the DISM command. When DISM asks to restart, press Y and Enter.