Hi Bill,
This error is occurring during the second boot phase (SYSPREP/re-specialization), which indicates the VM is failing while attempting to reconfigure system settings post-upgrade. Since other VMs are upgrading successfully, the issue is likely related to this particular VM’s configuration or environment.
Here are some recommended steps to diagnose and resolve the issue:
- Reset Windows Update Components
Corrupted update components can trigger SYSPREP failures. Open PowerShell as Administrator and run the following commands:
net stop wuauserv
net stop cryptSvc
net stop bits
net stop msiserver
net start wuauserv
net start cryptSvc
net start bits
net start msiserver
- Check the disk and repair any system-level issues:
Open Powershell with Admin mode:
chkdsk /f /r
You may be prompted to reboot. After that, run:
DISM /Online /Cleanup-Image /RestoreHealth
sfc /scannow
- If the system still fails during re-specialization, you can try running SYSPREP manually:
C:\Windows\System32\Sysprep\sysprep.exe /generalize /oobe /reboot
Please make sure to back up the VM before performing this step.
- In some cases, disabling certain integration services helps complete the upgrade:
Shut down the VM.
Open Hyper-V Manager → Right-click the VM → Settings → Integration Services.
Uncheck:
"Operating system shutdown"
"Time synchronization"
Restart the upgrade process.
Should you have any questions, feel free to let me know.