Windows 11 Upgrade and Installation Errors: The Cryptic Messages and How to Overcome Them

Since the original version of Windows 11 (21H2) first became available in late 2021, and especially since my post on how to do that on unsupported hardware, I've gotten so many requests on overcoming a myriad of Windows 11 upgrade errors, especially those with cryptic messages.

This post will offer some easy-to-follow tips that help you deal with those annoying situations.

Dong's note: I first published this piece on August 13, 2024, and updated it on August 26 with additional tips.

Upgrading to Windows 11 fails: The cryptic error messages and possible solutions

Some of the error messages you might run into when upgrading your computer to Windows 11—from Windows 10 or a previous release of the OS, such as from build 21H2 to 23H2—can be frustratingly vague. Here are some notorious examples:

• "Sorry, we're having trouble determining if your PC can run Windows 11. Please close the setup and try again."
• "We can't tell if your PC is ready to continue installing Windows 11. Try restarting Setup."
• We can't tell if your PC has enough space to continue installing Windows 11. Try restarting Setup.

Sometimes, these messages are accompanied by an error code; other times, they are not. In most cases, none of them give you an idea of what to do, and you might blame the Setup program itself or think that the ISO image you've downloaded is faulty or corrupted.

Rest assured, more often than not, though, it's your computer that has unknown software issues that prevent the Windows 11 upgrade process from functioning as intended.

Below are some common solutions I've used, including the simple (A) and advanced (B) tricks. They will highly likely rectify the situation.

"Highly likely" because there's a chance none of them will work. In that case, your only option is to go nuclear, which is the last resort option (C) mentioned below.

Before we continue, make sure you back up your computer. I'd recommend creating an image of the entire system, but the rule is any backup is better than no backup at all, and it never hurts to make multiple backups of different types.

A. Windows 11 Upgrade fails: The simple housekeeping tips

These are tips you can do without making intrusive changes to your computer.

I. Ensure the drive that holds the Windows operating system has enough free space

This generally is the C: drive as it should be. (If you have used another drive letter, that itself can be an issue. Go nuclear—below—instead.) This drive needs to have at least 30GB of free space. If it has less, clean up your drive or move your data to another place first. Or, if you need a new larger drive, here's the guide on how to upgrade it.

II. Remove specific third-party software

Here are the following software you should remove/disable:

Third-party VPN or Security software, such as North VPN, Norton Security, McAfee, etc. You can choose to install them later, but in my book, a VPN is generally unnecessary, and you don't need more security than the OS's built-in Windows Security, which is free.

Third-party ZIP and ISO handler—you should use Windows Explorer as the default for both. Sometimes, this third-party software changes the way the system accesses compressed files and causes unknown errors.

Once you've removed these software applications, restart the computer and try the Windows 11 upgrade again.

III. Turn off non-Microsoft services

Some third-party services may prevent the upgrade from running successfully. To eliminate that possibility, you can boot the system using only Microsoft services during the Windows 11 upgrade process. Here are the steps:

1. Hit Windows + S and type in the search field:

msconfig

2. As the "System Configuration" appears in the result, hit Enter.
3. On the System Configuration window that appears, pick the Services tab.
4. Click the box that reads "Hide all Microsoft services", then click on the "Disable all" button.
5. Click on the Apply (or OK) button.

Now restart your computer and try the Windows 11 upgrade process again. You can repeat the steps above, but use the "Enable all" button at step #4 to restore all these services after the Windows 11 upgrade process or whenever you want.

IV. Make your Windows update to date

Run Windows Update and update the system to the latest patches, including all optional updates, which are accessible in the "Advanced options".

Additionally, run Windows Update troubleshooters to make sure there are no issues. Here's how:

1. Hit Windows + S (that's when you press and hold the Windows key and then press the S key on the keyboard) and type in the search field:

Troubleshot settings

2. As "Troubleshoot settings" appears in the result, hit Enter.
3. On the Troubleshoot window that appears, pick "Other troubleshooters".
4. On the next window, click on the Run button by "Windows Update".

After that, run Windows Update one more time. Once there are no more updates, it's time to try the Windows 11 upgrade process again.

B. Windows 11 Upgrade fails: The advanced tips

These tips require you to remove data or make significant changes to the system. Most of these changes are safe to do. Still, note that you're here because you have already made backups of your computer, as mentioned above.

V. Completely remove Windows Update’s existing data

Often, the computer has erroneous update information that prevents the upgrade from working correctly. In this case, removing all existing Windows Update-related data will fix the issue. To do that, you need to remove the content of the two following folders on the computer:

• C:\Windows\SoftwareDistribution
• C:\Windows\System32\catroot2

Unfortunately, that's not as easy as removing any other folder since these two are protected system folders.

Here's how:

1. Open an elevated Command Prompt window—if you don't know how to do that, the cabinet below contains detailed steps.

2. Enter the following comments, one line at a time, hitting Enter after each (you can copy and paste):

net stop bits
net stop wuauserv
net stop appidsvc
net stop cryptsvc
rmdir C:\Windows\SoftwareDistribution /s /q
rmdir C:\Windows\System32\catroot2 /s /q
net start bits
net start wuauserv
net start appidsvc

If you do that correctly, you'll see what's shown in the screenshot below.

That's it. You can start the Windows 11 upgrade process now, even without restarting the computer.

VI. Remove or repair problematic registry settings and files

These are additional items that can be removed or repaired to make sure the computer is free of errors.

Run the following command using an elevated command prompt window (mentioned above). You can copy and paste each command into the window and press Enter after each:

reg delete "HKLM\SOFTWARE\Microsoft\Windows NT\CurrentVersion\Image File Execution Options\vdsldr.exe" /f

This command removes an entry in Windows's registry to reset the state of Windows' virtual disk service loader (the vdsldr.exe file) in case it blocks the Setup process.

reg delete "HKLM\SOFTWARE\Microsoft\Windows NT\CurrentVersion\Image File Execution Options\setuphost.exe" /f

This command removes another entry from the registry to make sure the Setuphost.exe module is not blocked.

sfc /scanfile=C:\Windows\System32\vdsldr.exe

This command checks the integrity of the virtual disk service loader and restores it if need be.

reg delete "HKLM\SOFTWARE\Policies\Microsoft\Windows\WindowsUpdate" /v "DisableWUfBSafeguards" /f

This command removes another problematic entry in the registry if the system's GPO setting blocks the upgrade process.

rmdir C:\$WINDOWS.~BT /s /q

This command removes the temp folder of the previous (and failed) upgrade attempt if it's still there.

And that's sit. Now restart your computer and try the upgrade process again. It should work.

C. Going nuclear: Remove everything

This last-resort option should be done only if, again, you have already made backups. It will bring your computer back to its brand-new state by removing all software and user data and, with that, the possible errors that prevent the upgrade from working correctly. This option also helps the machine run at its best afterward:

Here's how:

1. Hit Windows + S, then type the following phrase in the search area:

reset this PC

2. As "Reset this PC" appears in the result, hit Enter to open the Recovery dialog.
3. Click on the "Reset PC" button.
4. Choose the "Remove everything" option.

Wait for the process to finish, which takes from a few minutes to half an hour, depending on the computer. After that, you can set up the computer with the first user account and start the Windows 11 upgrade process before installing anything else. It'll work now.

The final thoughts

Clearly, the final method is the last resort when all of the previous ones don't work. I'll update this post with more easily executed tips before this nuclear option is needed when applicable. In the meantime, good luck! You'll need it.