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Windows Server evaluation images are for evaluation, not a substitute for a production license. Check the terms and supported conversion path for your exact Windows Server release and edition before extending or activating it.

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Check the installed evaluation

Open PowerShell as Administrator:
Review the edition, evaluation expiry and remaining rearm count. Do not assume every image has the same count or that every rearm grants the same extension.

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Rearm when permitted

If the installed evaluation and Microsoft’s terms permit another rearm, save work, schedule a restart and run:
After restarting, run slmgr /dlv again and confirm the resulting expiry. If no rearms remain or the command fails, check the release-specific Microsoft guidance rather than repeatedly reinstalling to bypass licensing. For production, obtain a license valid for the edition and hosting arrangement and follow Microsoft’s supported activation/conversion procedure. Do not assume an Azure-specific licensing benefit applies to an EDBB VPS. See Microsoft Windows Server deployment guidance.