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I don't think it is a 2019 issue specifically to be honest. I had a similar experience after upgrading from 2012 to 2016 years ago. Unfortunately it persisted until I wiped the box clean and installed the OS fresh. I am very much hoping it doesn't come to that this time. I actually wiped my install ...

This is literally the exact same situation I am in, minus the VM. Stand alone Windows 2016 installation, running great for years. Upgraded to Windows 2019 and I have the exact same experience. Reinstalling or rebooting makes it go away (with successful downloads) and then 12-24 hours later I start g...