Workstation Pro 16: Unable to Boot W10 ISO to Upgrade W7 VM

[MVCobb]

Using VMware Workstation 16 Pro. I'm unable to upgrade a Windows 7 VM to Windows 10. When I start the update from Windows, it gets stuck after the reboot. After hours of waiting, turning the VM off and on again will make it go back to Windows 7. Then an error message appears saying "Installation failed during SAFE_OS phase".

When booting from the Windows 10 ISO, it shows the logo and spinner wheel for a second and then goes into a blank dark-blue screen forever (waited overnight and nothing). The mouse cursor moves, but there's nothing else happening (see attachment).

The C: drive has 150GB free, so that's not the problem. I also disconnected all non-essential devices.

Tried setting the disk from SCSI to IDE and then to SATA, as described in this article (to no avail):
https://communities.vmware.com/t5/VMware-Fusion-Discussions/Solved-Have-been-unable-to-upgrade-Win-1...

Tried upgrading and downgrading the hardware (versions 12 through 16). Didn't work.

Also tried changing to BIOS and EFI. Didn't work.

However, if I replace the VMDK disk file (containing W7) with a blank/brand new one, then the ISO boots fine. So clearly the issue is with the VMDK file that has the Windows 7 guest client. This VMDK file was created from a hardware drive using the Converter years ago.

I've used VMware Workstation 16 Player, as well as VMware Workstation 16 Pro but I still can't boot the Windows 10 ISO if this particular VMDK disk is connected to the VM. Is there anything else that can be done?

[louyo]

About the only other thing I can think of is perhaps using diskpart to examine disks, volumes and filesystems to see if anything seems out of order. 

[wila]

Right... the reason I asked for the partition layout is because I had similar troubles when I wanted to switch a VM from BIOS to UEFI and thus the disk layout from MBR to GPT.

I had 2 recovery partitions (only one is used) and they were not in the correct spot and alignment.

Because of that I got similar messages about "windows not found". At least there I could get reasonable troubleshooting info from the logs (once I figured out how-to find & create those logs)

I used the steps from MS documentation:

https://docs.microsoft.com/en-us/windows/deployment/mbr-to-gpt

and in particular the /logs option was what helped in me figuring out why it could not find the Windows install.

You don't need to run the /convert option itself, you can run the /validate one and /allowFullOS option along with the logs and see if that gives you a tip.

--
Wil