In place upgrade of Windows Server 2016 to 2019 on a laptop fails during SET_PRODUCT_KEY

Question

I have an older laptop serving as the primary domain controller.
I am trying to perform an in-place upgrade from 2016 to 2019

The install almost fully completes, then rolls back and the error message says it cant set the product key

I suspected I know why - this laptop originally came with a Windows Home license
When I installed Server 2016 on it, I had to use the workaround of putting the key in the PID.txt file in the sources directory
So I did that, and retried the upgrade (executing from the USB stick in the server)

Same result

Is the in place upgrade not going to work?
I hate having to switch over to the backup domain controller, do a fresh install of 2019 server, then switch the DC back to it
I was able to do the in place upgrade of the backup, but it is a Hyper-V client - maybe thats why it worked

Answer 1

In place upgrades are never recommended especially for a domain controller. The laptop hardware may also be problematic for two reason; a server operating system and the hardware in general may not meet the requirements. This doesn't mean it can't or won't work but does mean the vetting of all components is left to the end user to do.

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Answer 2

Hi,
Please make sure you have met the system requirements here
https://learn.microsoft.com/en-us/windows-server/get-started-19/sys-reqs-19

And there‘s always a risk of failure with in-place upgrade. Is there any issue when you perform a clean installation?

Best Regards,
Ian

Answer 3

If you have a second domain controller, moving the FSMO roles to that DC is a trivial task to perform before building a new DC from scratch.

However, you say you are running on an 'older laptop' for your current 'primary DC'. It is highly unlikely that the hardware on that laptop is supported by Windows Server 2019. Running a critical service like a DC on unsupported hardware is risky at best. You may want to consider building your new 2019 server on supported hardware.