Ok, nothing worked from this thread.

I'm trying to just delete this Windows.old folder now and I keep getting the message "You need permission from SYSTEM" to make changes to this folder (see screenshot).

This is a stand alone laptop, ALWAYS HAS BEEN, WTF is that talking about?

Goddmammit I'm getting so tired of Microsoft's SHIT.

Deep Dungeon's of Doom: XEXBC-Z45ZD-YM3I0

This Steam game is yours if you're interested and you change the X's to J's and the Z's to R's... I hope that's it. LOL

THe game is gone. What a doofus I am. I couldn't remember if I had changed the letters as I had described so i checked it out..... and now the game is in my library. No chance to turn it down like with GOG gift codes.
I'm such a moron. I am so sorry.

SYSTEM is a built-in special account that runs stuff at a very elevated permission level. Even a program that has been executed with administrator privileges may have issues modifying SYSTEM files, and with good reason.
If this is from the anniversary update, you could either wait about a month, after which it should be deleted on its own, or see how you can get ownership of a folder which should allow you to delete said folder.

Stil a very important message:
http://41.media.tumblr.com/82a6db68c42c84baa40d6b06fb90ab87/tumblr_mm8v44Fqa71rnft6so1_400.jpg

Thanks. THe date of the Windows.old folder is 10.09.16, so it's already been over a month. It's been two. So it apparently isn't going to delete itself. And I don't know how to 'get ownership" of a folder but will do a google search to see if I can figure it out.

THanks again.

No worries, feel free to ask if you need more info.

You mean to say that there are such folders that immune to administrator privileges on my computer that has no other admin or owner but me? Or am I mistaken?

From within the OS some are immune. But if you were to mount the drive on a different system, or, better yet, run something like Linux from a USB drive, you could delete them at will.

Yes. TrustedInstaller is another such user, who is used for specific installations which a user (any user) shouldn't be able to modify them.
That of course applies to newer Windows system, though both OSX and the various Linux distros should have similar users.
An administrator (elevated one) should be able to modify said folders, but the need to do so usually signifies that something has gone wrong.

Doh, so I took ownership of iit (put my name that I'm signed in as) and now it says I need permission from THAT name (MY NAME) to delete.

fuck you Microsoft..

Goddamit it.

Any other suggestions?

See my previous post. That is how you can delete it with ease and without having to tinker with your installed OS's settings.

Thank you for clearing that up. How do you elevate your admin privileges?