From research it seems to be when you delete the Windows.old folder that bad things can happen. I just can't trust it anymore as when it does happen it means I have to reinstall the entire system. Thankfully I keep important stuff backed up else I'd be extremely annoyed!
The CCleaner options I use, are the same I've used since day 1 and they worked fine up until a few months ago.
Windows 10 is the latest build, most recently had this problem on a new Dell Laptop, which came preinstalled with Windows 10 although I've had it on my PC a few times too.
Current PC install is a fresh install from a Windows 10 USB stick and CCleaner appears to work fine. Laptop is also now using a USB stick install because I had no other option as it failed to boot after running CCleaner.
What could be causing this? I've been speaking to a friend who experienced this before me, he did a fresh Windows 10 install, ran updates, rebooted, ran CCleaner and couldn't reboot.
@mta I format regularly, after updating Windows and installing all apps I tend to run CCleaner to clean out the crud left behind then reboot. This works most of the time, only when it doesn't work it can kill my system. All I get is a spinning icon on reboot. I've even attempted to run Windows Repair in order to fix whatever is broken and it won't work. So I'm not sure how making a backup would help if I can't even access Windows to roll back.
@hazelnut That explains it, although giving prior warning of this somewhere would be cool... CCleaner seems to be updated regularly, it wouldn't hurt to include a warning if you check Windows.old deletion.