Invalid License Key Error When Performing Windows Edition Upgrade

Last week, I decided to perform the in-place edition upgrade from Windows Server 2012 R2 Essentials to Windows Server 2012 R2 Standard on my home server as part of a multitude of things I’m working on at home right now. Following the TechNet article for the command to run and the impact and implications of doing the edition upgrade at I ran the command as instructed in the article but I kept getting a license key error stating that my license key was not valid.

As my server was originally licensed under a TechNet key, I wondered if the problem could be down to different licensing channels preventing me from installing the key. On the server, I ran the command cscript slmgr.vbs /dlv to display the detailed license information and the channel was reported as Retail as I expected for a TechNet key. The key I am trying to use is an MSDN key which also should be reported as part of the Retail channel but to verify that, I downloaded the Ultimate PID Checker from and my Windows Server 2012 R2 Standard license key, sure enough is good, valid and just as importantly, from the Retail channel.

So my existing and new keys are from the same licensing channel and the new key checks out as being valid so what is the problem? Well it turns out, PowerShell was the problem.

Typically I launch a PowerShell prompt and then I enter cmd.exe if I need to run a something which explicitly requires a Command Prompt. This makes it easy for me to jump back and forth between PowerShell and Command Prompt within a single window hence the reason for doing it. I decided to try it differently so I opened a new Administrative Command Prompt standalone, without using PowerShell as my entry point and the key was accepted and everything worked as planned.

The lesson here is this: If you are entering a command into a PowerShell prompt and it’s not working, try it natively within a Command Prompt as that just maybe is your problem.


Richard works as a Cloud Consultant for Fordway Solution where his primary focus is to help customers understand, adopt and develop with Microsoft Azure, Office 365 and System Center. Richard Green is an IT Pro with over 15 years' of experience in all things Microsoft including System Center and Office 365. He has previously worked as a System Center consultant and as an internal solutions architect across many verticals. Outside of work, he loves motorbikes and is part of the orange army, marshaling for NGRRC, British Superbikes and MotoGP. He is also an Assistant Cub Scout Leader.