Server 2016 to 2019 In-Place Upgrade Error

K

Kyleblitz

I have tried an in-place upgrade from Server 2016(v1608 Build xxx xx xxxx) Standard(Desktop Edition) to 2019 Standard(Desktop Edition) and I keep getting the following error:
We couldn't install Windows Server 2019
0x80070490 - 0x2000E
The Installation failed in the SAFE_OS phase with an error during SET_PRODUCT_KEY operation.

This is a VM inside VMWare with plenty of resources.
I have at least 20GBs of free space during the install.

I have tried many methods online from confirming the product key and even making sure some services were set to automatic. I haven't gone down the path of any registry edits just yet. But I'm willing to try it if that's the last resort.

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