That rollback error 0xC1900101 - 0x4000D means the upgrade tripped over a driver or data migration issue during the SECOND_BOOT phase. In plain terms, Windows tried to carry over some system data or drivers from your 2016 setup, but something didn’t play nice. First thing I’d do is disconnect any non‑essential hardware (USB drives, external NICs, etc.) and temporarily disable antivirus or endpoint protection. Then run Windows Update Troubleshooter and check that all drivers are up to date especially storage and network ones.
Next, clear out old upgrade files with Disk Cleanup (select “Windows upgrade log files”) and reboot before retrying. If it still fails, try the upgrade using the Media Creation Tool instead of Windows Update it’s more reliable for major version jumps. Also, make sure you’ve got enough free space (at least 20 GB) and that BitLocker is turned off during the process.
If you’re running any third‑party RAID or backup software, uninstall it temporarily those are common culprits for MIGRATE_DATA errors. Once the upgrade completes, you can reinstall them safely.
Give these steps a go and you should be able to get past that rollback loop. If this helps you get your server up and running, please hit “accept answer” it lets me know the fix worked and others in community with similar issues can benefit from the guidance. Thank you!