My father did this.

I was giving him a PC tutorial and I asked him to turn off the PC and he turned off the monitor.

One of my users locked her Windows session and then signed in again, there, I rebooted.

Literally every single time!

At a previous job, I was not doing IT support but another role and I noticed a coworker had a red dot on the Windows Update status bar icon.

Told him I don't think I have seen that before, normally it is orange.

So he tells me that he is trying to see how long he can keep it going before something happens. I recommended against this, and also I normally recommend against using the desktop to store files. The laptop goes up in flames, so do your files. We have OneDrive for business, I know people hate it, but at least your stuff is... relatively safe. Backed up at least with version history.

A few weeks later I was chatting to someone else who sometimes shared my desk, and somehow I mentioned this encounter. A while later, his manager sitting ahead of us is on a phone call and we hear he is getting upset. He hangs up and turns around, tells us.

Him and one sales guy had spent hours on some proposals, worked out all the values and timings and it's gone. All that work gone. His laptop rebooted because Windows updates.

He mentions who... it is the same guy. I tell him I was just telling my desk buddy about him and how he intentionally left his laptop running for months to see what Windows Update would do and clearly he did not take my advice about rebooting and using OneDrive.

The rest of the day... this guy did not stop. Every 30 minutes or so he'd just go "All that work, gone. Why?"

We'd be walking to get lunch, talking about other things and again he'd just switch back to that and turn gloomy again.