W10 Anniversary Update - delete windows.old directory?

If I were you I would not do anything to the windows old folder. I had one pc that when I removed it, the pc then completely refused to boot.

Make a backup first...
Then try this script.
Copy it and save it into a notepad file.
Rename it to whatever_you_like.bat
Run it and press yes.

It will remove the windows.old folder.

Tell me if this worked ...

Code:

@echo off

:: BatchGotAdmin
:-------------------------------------
REM  --> Check for permissions
>nul 2>&1 "%SYSTEMROOT%\system32\cacls.exe" "%SYSTEMROOT%\system32\config\system"

REM --> If error flag set, we do not have admin.
if '%errorlevel%' NEQ '0' (
    echo Requesting administrative privileges...
    goto UACPrompt
) else ( goto gotAdmin )

:UACPrompt
    echo Set UAC = CreateObject^("Shell.Application"^) > "%temp%\getadmin.vbs"
    echo UAC.ShellExecute "%~s0", "", "", "runas", 1 >> "%temp%\getadmin.vbs"

    "%temp%\getadmin.vbs"
    exit /B

:gotAdmin
    if exist "%temp%\getadmin.vbs" ( del "%temp%\getadmin.vbs" )
    pushd "%CD%"
    CD /D "%~dp0"
:--------------------------------------

rem pause

takeown /f "C:\Windows.old" /r

icacls "C:\Windows.old" /reset /T

attrib -r -a -s -h C:\Windows.old /S /D

RD /S /Q %SystemDrive%\windows.old

gvp9000 said:

Make a backup first...
Then try this script.
Copy it and save it into a notepad file.
Rename it to whatever_you_like.bat
Run it and press yes.

It will remove the windows.old folder.

Tell me if this worked ...

Code:

@echo off

:: BatchGotAdmin
:-------------------------------------
REM  --> Check for permissions
>nul 2>&1 "%SYSTEMROOT%\system32\cacls.exe" "%SYSTEMROOT%\system32\config\system"

REM --> If error flag set, we do not have admin.
if '%errorlevel%' NEQ '0' (
    echo Requesting administrative privileges...
    goto UACPrompt
) else ( goto gotAdmin )

:UACPrompt
    echo Set UAC = CreateObject^("Shell.Application"^) > "%temp%\getadmin.vbs"
    echo UAC.ShellExecute "%~s0", "", "", "runas", 1 >> "%temp%\getadmin.vbs"

    "%temp%\getadmin.vbs"
    exit /B

:gotAdmin
    if exist "%temp%\getadmin.vbs" ( del "%temp%\getadmin.vbs" )
    pushd "%CD%"
    CD /D "%~dp0"
:--------------------------------------

rem pause

takeown /f "C:\Windows.old" /r

icacls "C:\Windows.old" /reset /T

attrib -r -a -s -h C:\Windows.old /S /D

RD /S /Q %SystemDrive%\windows.old

I had the same problem as the OP did, and your script worked like a charm. I had to run it twice to complete the entire process. I did it with Build 14971.

Interesting. What does one do to run it? It seems removing the Windows.old Folder even after Windows has automatically removed the contents, can cause the computer not to reboot. Why does Microsoft have it this way. This Windows.old file should simply be able to be removed and no problems. But others have had grief where their computers will not reboot after removing Windows.old.
And what about this Folder called Windows10Upgrade? Is it safe to remove this one or will this cause the computer to suddenly burst into a ball of flame?

I've had some trouble in the past removing the Windows.old folder, but I have never had a computer fail to boot after removing it. For really stubborn folders that don't want to delete, I boot into either Kyhi's recovery tools or a Linux USB flash drive and delete them from there. Windows 10 Upgrade folder can definitely be removed, that is just the upgrade assistant program.

Microsoft just cleaned up my Windows.old Folder which left me with with 15 Gigs of free space. Before Windows automatically cleaned it up, it was showing 32 plus Gigs of space in that folder. After the automatic cleanup in, not 10 days or 30 days but 14 days, the Folders are still there. I just got off the phone with Microsoft Support and they're telling me not to remove either of those Folders (Windows.old / Windows10Upgrade). They're saying because of previous problems with removing that, Microsoft has changed the rules and advising people (and aliens) not to remove it now.
I'm one of the ones who did indeed have serious problems after removing it last time with the Anniversary Update. My computer simply wouldn't reboot.
So I am going to take the advice of Microsoft and leave them there folders right where they are. I'll still be interested to hear the reaction to this.