Recover personal files from the Windows.old Folder such as Documents Pictures and Windows Live Mail Emails in Windows 10

Technical Level : Intermediate


If you performed a custom install of Windows 10 intentionally or not and you are looking for your personal files after Windows is installed, then you might need to recover them manually. A custom install is similar to a clean install, but instead of wiping the hard disk clean, your previous Windows installation is moved to a folder called Windows.old. Windows.old is an archive of your old Windows installation. It is created by setup for a number of reasons depending on how the upgrade was initiated, including recovery of personal data or to facilitate the rollback to that previous version of Windows if you performed an in place upgrade. A custom install is sometimes initiated by booting from the Windows 10 install media (DVD or USB thumbdrive) or if you start the installation from within a previous running version of Windows at the desktop then select the option ‘Keep Nothing’. In this article, we take a look at how to recover your files if they are still there.


To recover your personal files, click Start > File Explorer

Click This PC

Open the system drive where Windows 10 is installed represented by the Windows logo.

Open the folder Windows.old

Open the Users folder

Open your old account folder which should contain your files. In my case, its Andre.

Open each personal folder which will contain your files.

Press Control + A or click Select All then click Copy or Cut

Launch a new File Explorer window (press Windows key + E or click Start > File Explorer) then navigate to the respective personal folder (Documents, Pictures, Music, Videos) then paste the files there.

Repeat the same steps for other folders containing files such as Music, Pictures, Videos and Downloads.

Import your Windows Live Mail messages from the Windows.old folder

Windows 10 comes built in with a new Mail app which is incompatible with older mail desktop apps such as Windows Live Mail and Outlook Express. This means, you won't be able to import email messages into it from other mail programs. If you were previously running one of those mail programs, you will need to download then install the latest version which is Windows Live Mail 2012. It is included with the Windows Essentials 2012 suite which you can download for free at the following link.

Download Windows Essentials 2012 (Offline installer)

Once you have downloaded Windows Essentials 2012, proceed to install it. You will need to ensure the .NET Framework 3.5 is installed, the Windows Essentials 2012 setup program will guide you through the installation.

Enable Show Hidden Files and Folders

Click Start > File Explorer > This PC > click the View tab then click Options

Click View tab again then select the Show hidden files, folders and drives radio box. Click Apply then OK

Launch Windows Live Mail 2012

Once Windows Live Mail 2012 is installed, launch the program from Start > All Apps > Windows Live Mail

Resources: Quick Tip: Find and launch programs quickly using All Apps in Windows 10

You will be prompted to add an email account, click Cancel.

Click the File menu then click Import messages

Select the appropriate email program you were previously running. In this case, we will use Windows Live Mail. Click Next.

Click Browse

Expand This PC > Local Disk (where Windows 10 is installed) > Windows.old > Users > Your Old Account Folder (represented by the username) > expand AppData

Expand Local > Microsoft then select Windows Live Mail then click OK

Click Next

Make sure All folders is selected then click Next

Wait while your emails are imported.

Click Finish

Expand Storage folders > Imported folders > then click Inbox

Should you did delete the Windows.old folder?

It depends, I would wait 30 days before deleting it unless you are pressed for disk space. In which case you can do so. If an issue occurs where you might need to rollback to your previous version of Windows, you will have to do so using reinstall media.

Applications will need to be reinstalled for certain programs.

You will notice that application files are blank; you will need to reinstall the appropriate applications in order to view and edit them, examples include Microsoft Office. If you copied over your iTunes folder from the Music folder under your old account in Windows.old, simply reinstall iTunes and it should automatically import your audio files and playlist.

What about Microsoft Outlook?

Your old mail data is stored in C:\Windows.old\Users\AccountName\AppData\Local\Microsoft\Outlook

Copy the Outlook folder to Documents, launch Outlook then perform the import.


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The files located on C drive would move to Windows.old folder! Then what about the files located on D,E, F drives?
I have tried the steps you mentioned, should i wait 30 days to delete Windows.old folder or how else? Thiru
Files would not be affected on those drives. 
Windows Insider MVP
MVP-Windows and Devices for IT

You can wait or run Disk Cleanup to remove the Windows.old folder.

Learn more:

Windows Insider MVP
MVP-Windows and Devices for IT

did you notice any files gone missing without manually deleting during that 30 days?

my situation

The problem of this installation for me is not the data, but rather the apps or programs that are lost while this new installation is executed.

What does "Applications will need to be reinstalled for certain programs" mean?

Can there be found any more information, what apps, if any, will remain? Or does this new installation wipe the program-folders clean entirely, except for Windows?

The data I have secured on external harddrives almost to the latest stage, but the program installations are the real important part for me I would like to keep intact.

Is there a way to do that without going into this renewed installation blindly?

Thank you !

I would like to know exactly what needs to be installed and what should not be touched. I have Win 10 pro that I did a Recovery, after doing a roll back and an unistall of updates (which neither fixed the problem). I am missing the network adapter. My pc is WIFI and is never used with a wired connection. How do I know what or where to look? 
Pls help i downgraded to windows xp from 10 then upgraded to 7 but my windows 10 is in windows.old000 and i need to restor it now pls tell me 
All of my saved email folders were imported but not the contents of the folders!!!  I assumed the folders and contents would import together...where do I find all the saved emails?!?!


What happens on a custom install if space on original c drive was almost full? Will it use spare space from another partition drive?

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Last updated October 19, 2020 Views 64,771 Applies to: