Windows 11 Upgrade Keep Files: What Stays, What to Back Up

The most common worry before moving to Windows 11 is simple: will my photos and documents still be there afterwards? For a normal Windows 11 upgrade, keep files is the default, and Microsoft’s tools are designed to carry your files, apps and settings across. There are, however, a couple of ways to accidentally choose a clean install, and a handful of situations where files look missing afterwards. This guide shows which routes keep everything, how to back up in a few minutes anyway, and where to look if something seems to have vanished.

Which upgrade routes keep your files

Microsoft’s Ways to install Windows 11 page describes the options setup offers when you run it from inside Windows:

Choice	Personal files	Apps	Windows settings
Keep everything	Kept	Kept	Kept
Keep personal files only	Kept	Removed	Removed
Nothing	Removed	Removed	Removed

The everyday routes all use Keep everything:

• Windows Update, when Windows 11 is offered on a Windows 10 PC.
• The Windows 11 Installation Assistant (guide).
• setup.exe from a mounted ISO or USB, run from inside Windows, with Keep personal files and apps selected (in-place upgrade guide).

The route that erases everything is booting the PC from a USB drive or DVD and installing from there. Microsoft warns that this method completely wipes the contents of the drive. Only use it for a deliberate clean install.

Why back up anyway

Upgrades almost always go fine, but “almost” is not good enough for ten years of family photos. A failed disk, a power cut at the wrong moment or simply choosing the wrong option can cost data. A backup takes far less time than recovery.

Option 1: External drive. Copy C:\Users\YourName\Documents, Pictures, Videos, Music, Desktop and Downloads to an external drive. Simple, no account needed.

Option 2: Windows Backup. Open Windows Backup from Start, sign in with your Microsoft account and back up your folders, apps list and settings to OneDrive. Microsoft notes a free account includes 5 GB of OneDrive storage, so large photo libraries need an external drive or more storage.

Also export browser bookmarks and saved passwords if you do not use browser sync, and have your BitLocker recovery key to hand (BitLocker recovery).

There is no rush that justifies skipping this step: Windows 10 consumer Extended Security Updates run until 12 October 2027, according to Microsoft’s ESU page as checked on 14 October 2026.

Before you start the upgrade

• Check eligibility with the compatibility check.
• Free some disk space. Microsoft’s Installation Assistant page asks for 9 GB free just for the download.
• Disconnect external drives you do not need, including your backup drive, so setup cannot touch it.
• Plug a laptop into power.

What setup may not carry over

Keep everything is thorough, but a few items need attention:

• Incompatible apps: setup may show a What needs your attention screen listing programs that must be removed or updated before it continues. Uninstall them, upgrade, then reinstall a compatible version.
• Drivers: Windows 11 may replace older drivers. Check printers, scanners and audio devices afterwards and install current drivers from their makers if needed.
• Some settings: a few personalisation choices, default apps or the taskbar layout can reset to Windows 11 defaults. Our default apps and taskbar left guides help put things back.
• Encrypted files: files encrypted with third-party tools stay encrypted; make sure you still have the passwords.

None of these touch your documents, but knowing about them avoids surprises on the first day. If an app you rely on is flagged, check the maker’s website for a Windows 11 version before you upgrade, so you are not left without it.

After the upgrade: check your files

1. Sign in with the same account you used on Windows 10.
2. Open File Explorer and check Desktop, Documents and Pictures.
3. Open a few files from different years to be sure they are intact.

Only then delete or reuse your backup drive.

Files look missing? Where to look

Microsoft’s Find lost files after upgrading Windows page lists the usual causes. Work through them:

1. Temporary profile. If your desktop looks like a brand-new account, you may be signed in to a temporary profile. Restart and sign in again; check Settings > Accounts > Your info shows your usual account.
2. Search for a file you know. Use the search box in File Explorer or on the taskbar with a filename.
3. OneDrive. If OneDrive backed up your Desktop and Documents, files may be shown as online-only. Open the OneDrive folder and check.
4. Windows.old. After an upgrade, the previous installation is kept for a while in C:\Windows.old. Look in C:\Windows.old\Users\YourName. Copy anything you need back out; Windows removes this folder automatically after the go-back period.
5. Another account. If the PC had several user accounts, check under C:\Users for the other profile folders.

Going back if something is wrong

In most cases you can return to Windows 10 within 10 days: open Settings > System > Recovery and select Go back. Microsoft’s go-back page says your personal files are kept, but apps and settings changes made after the upgrade are removed. See roll back to Windows 10. For the overall process, start with upgrade Windows 10 to Windows 11.