When administrators install Windows Server from an evaluation ISO, the license expires after 180 days. Trying to activate this evaluation build by simply typing a product key into the GUI will result in error: "This edition cannot be upgraded."
You can seamlessly convert your server into production mode using Microsoft's DISM command line utility without reinstalling.
Step 1: Check Current Server Edition
Open an administrative PowerShell or Command Prompt and run:
DISM /online /Get-CurrentEdition
If it returns ServerStandardEval or ServerDatacenterEval, you are in evaluation mode.
Step 2: Run the DISM Edition Conversion Command
Execute the following command, inserting your genuine 25-digit WindowsKey license key:
DISM /online /Set-Edition:ServerStandard /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula
(Note: If you have a Datacenter key, replace ServerStandard with ServerDatacenter).
Step 3: Reboot and Verify Activation
The DISM tool will replace the evaluation binaries and prompt you to reboot. Type Y to restart. Once restarted, verify activation by executing:
slmgr.vbs /xpr
The dialog will report: "The machine is permanently activated."
