Why keep files and apps option greyed out when upgrading to Windows 11

Use the correct Windows 11 ISO. This is the most common reason why the keep personal files and apps is greyed out during Windows 10 upgrade.

When Windows 11 Setup detects corrupted or missing system files, it assumes your current installation is unstable and may block the in-place upgrade path. That’s when you see "Keep files and apps" greyed out when upgrading Windows because Windows 11 Setup won't risk carrying over broken components.

By running SFC and DISM commands before upgrading, you repair or replace damaged Windows files, allowing the installer to recognize the system as healthy and eligible for an in-place upgrade.

Run System File Checker (SFC)

This scans for corrupted or modified Windows system files and restores them using cached copies.

sfc /scannow

Wait for it to reach 100%. If it says “Windows Resource Protection found corrupt files and successfully repaired them," that's good. If it says "could not repair some files," proceed to the next step.

Use DISM to Restore Health

DISM (Deployment Image Servicing and Management) repairs deeper corruption in the Windows 11 image that SFC cannot fix.

DISM /Online /Cleanup-Image /RestoreHealth

This step connects to Windows 11 Update or local sources to replace damaged components in the system image. It can take 10–20 minutes, depending on your system and internet speed.

That “Keep personal files and apps” option usually gets greyed out during a Windows 11 upgrade for one of a few technical reasons. The most popular one is using the wrong Windows Editions or Languages.

If you’re upgrading from, say, Windows 10 Home (English) to Windows 11 Pro (French) or vice versa, setup won’t allow keeping apps/files. You must match edition, language, and architecture (x64/ARM64) exactly.

(1) Check Your Current Edition

Press Windows + R, type winver, and hit Enter.

A small window appears showing something like:
Windows 10 Pro, Windows 11 Home, etc.

Or go to:
Settings > System > About → look under Windows specifications → check the Edition field.
Example: “Windows 10 Pro” or “Windows 11 Home Single Language.”

(2) Check the System Language

Go to Settings > Time & Language > Language & region.

Look under Windows display language — that’s the language of your system (e.g., English (United States), French (France)).

Note this exact language — it must match the ISO language you use to upgrade.

If All else fails or your computer still keep files and apps option greyed out when upgrading - Alternative approach:
Since you're working with a preview build (25H2), consider this workflow:

• Backup your current system using System Image Backup
• Upgrade to the latest stable Windows 11 version (23H2) first
• Then upgrade from 23H2 to 25H2 through Windows Update
• This step-by-step approach often resolves compatibility issues that occur when jumping directly from Windows 10 to a preview build.

This step-by-step approach often resolves compatibility issues that occur when jumping directly from Windows 10 to a preview build.

Check setup logs: Look in C:\$WINDOWS.~BT\Sources\Panther for setuperr.log and setupact.log. Run the PC Health Check app to see if it reports any specific blockers. Check Event Viewer for system logs around the time you tried to upgrade

The fact that you're going directly to 25H2 is the most likely culprit here. Preview builds often have stricter compatibility requirements and more potential blocking issues.

This is a specific and frustrating issue, especially since you've already checked the common culprits like disk space and edition matching. The keep files and apps option greyed out when upgrading typically indicates the installer has detected a blocking incompatibility that prevents an in-place upgrade..

Solution 1: Remove Blocking Software

• Uninstall third-party antivirus completely (use the vendor's removal tool if necessary)
• Temporarily uninstall virtualization software
• Disable any security/encryption software temporarily
• Check for recently installed software that might be causing conflicts

Solution 2: Update All Drivers

• Update your BIOS/UEFI to the latest version from your motherboard manufacturer
• Update chipset drivers from your motherboard/PC manufacturer
• Update storage controllers and graphics drivers
• Use Windows Update to get the latest driver updates

Solution 3: Run Compatibility Checks

• Open Command Prompt as Administrator
• Run the Windows 11 Compatibility Checker:
  cmd
  setup.exe /Auto Upgrade /Compat ScanOnly

Solution 4: Use Windows Update Instead

• Try upgrading through Windows Update instead of the installer:
• Go to Settings > Windows Update > Check for updates
• If Windows 11 is offered, use this method instead

Solution 5: Check System Requirements Manually

• Verify TPM 2.0: Press Win + R, type tpm.msc
• Verify Secure Boot: Press Win + R, type msinfo32, check "Secure Boot State"
• Check CPU compatibility: Ensure your processor is on Microsoft's supported list

Keeping files and apps option greyed out when upgrading? Since you're already on Windows 10 Pro, using the latest Windows 11 (25H2), and have verified disk space and edition matching, here are some common causes and troubleshooting steps:

Possible Causes:
1. Presence of Incompatible or Unrecognized Software/Drivers
  Certain security software, third-party drivers, or system modifications can block in-place upgrades.
2. Corrupted System Files or Upgrade Components
  Corruption in system files or Windows update components may cause the setup to restrict options.
3. Pending Updates or System Changes
  Pending Windows updates or system changes might interfere with the upgrade process.
4. Custom or Non-Standard Partition Layout
  Partitions, especially recovery or OEM partitions, can sometimes cause restrictions.

Troubleshooting Steps:
1. Run the Compatibility Troubleshooter
   Open Settings > Update & Security > Troubleshoot > Additional troubleshooters.
   Run Program Compatibility Troubleshooter and Windows Update Troubleshooter.
2. Check for Pending Updates and Install Them
  Make sure Windows 10 is fully updated before upgrading.
  Go to Settings > Update & Security > Windows Update and install all pending updates.
3. Run System File Checker and DISM
  Open Command Prompt as administrator.
  Run: sfc /scannow
  Then: DISM /Online /Cleanup-Image /RestoreHealth
  Restart and try again.
4. Disable Security Software Temporarily
  Temporarily disable any third-party antivirus or security tools, as they can block upgrade components.
5. Check Disk and Partition Layout
  Use Disk Management (diskmgmt.msc) to verify that your partitions are healthy and properly configured.
  Avoid upgrading over encrypted or heavily customized partitions.