A lot of times with Windows if I had to run it I often would have installations that were past their service life. I ran Windows 2000 for a long time and then held out with Windows XP for a long time in one situation. That was mainly on my parents machines.
I somewhat do that with Linux in certain situations which usually isn't as big of an issue but lately I have these new installs of Ubuntu 18.04 which is new so I'm kind of current as far as that goes.