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r/WindowsServer • … • u/Carel_The_Man

Will an in-place upgrade from 2012 R2 to 2025 keep its license server ID?

I have a virtual machine which runs Windows Server 2012 R2, and it has a remote desktop license server, which holds the RDS user CAL/license.

I am planning on doing an in-place upgrade to Windows Server 2025. I already purchased the 2025 RDS user CAL, and I am aware of the activation steps, where I will give the seller my license server ID, and they will provide the activation codes.

I already did an in-place upgrade on an offline copy of the VM to test the process (offline because other services could conflict if both VM's would be running on the same IP). After it the license server does indeed keep its ID, but says it needs reactivation, which makes sense because the old 2012 R2 licenses won't cover 2025.

My question is, since I cannot test it online, will reactivating the license server with Clearinghouse possibly change its ID? Or is there any other trap that could change its ID?

I am planning on doing the upgrade in the weekend, so it's safe to stop the production server, but then I won't be able to reach the seller. So is it safe to already request the activation codes with my current ID before the upgrade?

Edit: I contacted the CAL seller and was told that the ID will likely change when reactivating, and that I should wait until after the upgrade to contact them. They also told me Microsoft gives a 120 day grace period to activate the RDS CALs, so I can already use the system before it is activated.

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