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If Windows Server won’t boot, shows “Preparing Automatic Repair” or ends on “Automatic Repair couldn’t repair your PC”, open the server’s console to see the exact message, then boot the Windows Recovery Environment (from Advanced options or a Windows Server ISO). From there, run Startup Repair, undo a failed update with DISM /Image:C:\ /Cleanup-Image /RevertPendingActions, and rebuild the boot configuration with bootrec /rebuildbcd. Restore a backup if none of these work.

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Before you start

  • VPS: open the VNC console. RDP doesn’t work until Windows has started.
  • Dedicated server: you need KVM or IPMI access to see the screen. Open a ticket and tell us the message you see.
  • Windows starts the recovery environment (WinRE) by itself after two failed starts in a row; that is the “Preparing Automatic Repair” screen.
Write down the exact message. Common ones are:

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How to reach the recovery tools

On the Automatic Repair screen, click Advanced options. You reach Troubleshoot > Advanced options, with Startup Repair, Command Prompt and System Image Recovery.

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Cause 1: an update or role change failed during the restart

Check: the problem started after Windows Update or after adding a role, often after a long “Working on updates” screen. Fix: undo the pending changes. In Command Prompt from the recovery tools, first find the Windows drive (it is not always C: here):
If that fails, try D:\Windows. Then, using the drive you found:
Close the prompt and restart the server to start Windows. The update will try to install again later; if it fails again, see Windows Update stuck or failing.

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Cause 2: damaged boot files or startup configuration

Check: messages about the BCD, Bootmgr or a missing operating system. Fix: first run Troubleshoot > Advanced options > Startup Repair. If it fails, open Command Prompt and run:
If rebuildbcd finds no installation, back up and rebuild the BCD store as Microsoft describes:
Startup Repair writes its findings to C:\Windows\System32\LogFiles\Srt\SrtTrail.txt.

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Cause 3: corrupted system files or disk errors

Check: Startup Repair runs but reports it couldn’t fix the problem, or the server crashed or lost power before it stopped booting. Fix: in Command Prompt, check the file system, then repair system files offline:
chkdsk /r reads the whole disk and can take a long time on large drives.

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Cause 4: a new driver, service or program

Check: the problem started after installing software, a driver or security tools, or Windows shows a stop code after the logo. Fix: start in Safe Mode: Troubleshoot > Advanced options > Startup Settings > Restart, then press 4 (or F4). Press 5 for Safe Mode with Networking. If Windows starts, uninstall the new software or roll back the driver, then restart normally. Check Event Viewer for event 7045 (new service) and 1001 (bugcheck) to find what changed.

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Cause 5: the boot type was changed

Check: on a VPS, the boot type (BIOS or UEFI) was changed after Windows was installed. Fix: set it back to the mode Windows was installed with and restart.

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Last resort: restore or reinstall

If nothing works, restore the latest backup. To save files first, boot the VPS into rescue mode and copy your data off. As a final step, reinstall the VPS, which erases the disk.
Rebuilding or reinstalling deletes everything on the server. Copy your data off first.

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How to check it worked

Windows reaches the sign-in screen in the console and you can connect with Remote Desktop again. Remove the ISO and set the disk first in the boot order again.

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Frequently asked questions

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How do I stop the Automatic Repair loop?

Fix the cause with the steps above. Microsoft also documents bcdedit /set {default} recoveryenabled no to stop Windows from entering recovery automatically, but that only hides the loop.

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Will Startup Repair delete my files?

No. Startup Repair and the commands above don’t remove your data. Reinstalling or rebuilding the server would.

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Which ISO do I need?

The installation ISO for the same Windows Server version (2019, 2022 or 2025) that is installed.

VPS and dedicated server guides

Every guide in this section.

Repair with SFC and DISM

Repair once Windows starts.

Windows Update stuck or failing

Updates that break restarts.

Back up a Windows server

Be ready next time.

Mount a custom ISO

Boot the VPS from an ISO.

Rescue mode

Copy data off a broken VPS.
Checked against Microsoft Learn: Windows startup issues troubleshooting , Windows Recovery Environment technical reference and Microsoft Support: Start in Safe Mode on 4 November 2026. Steps were not tested on a live Windows server for this page; recovery menus can differ slightly between Windows Server versions.

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Need Extra Help?

If you encounter any issues, our support team is ready to assist:

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Last Updated: November 2026