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Version 5 since there are 4 other answers.

Windows Server 2008 R2 (Pretty much Win7) needed to be upgraded to 2012 R2 prior to upgrade to 2019. I've done this a number of times without any problem.

Installation would near finish then end with this: Windows could not prepare the computer to boot into the next phase of installation.  To install Windows, restart the installation.

System is a VMware ESXi virtual machine. Looked for ideas but could find nothing that applied. I tried with 2012 and tried with vCD vs install on local OS from extracted ISO (usually the way I go). Checked system files. No strange hardware installed that I don't always use.

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I found this in the Application Event log:

Mitigation: WipeGuard part of Sophos Endpoint Security (HitManPro)

Disabled Sophos Endpoint Security Tamper Protection, stopped all services, now Windows Server 2012 R2 installs just fine and so much faster.