First it was done the really dumb way, like you are in the middle of something, with lots of unsaved work, and suddenly you will have your computer shutting down on you (with 14 minutes count down that doesn't allow you to access and save your work). I mean that was really really dumb.

Then it got worse, same minus the 14 minutes count down

Then came the 12 hours out of hours update gap - they, coming from a very low ebb, I would say was an improvement but could have been better

Now we've gone backwards again. On installing the most recent windows upgrade, there was an update alert while I was in the middle of some work. The options were only restart now or Not now. I choose Not now otherwise I would loose tons of work. Its been days now since that first alert and I've not had another one since.

How about alternative options like "restart now" Or "arrange/select update time range" Yes this is similar to the previous way except that an update could be done within the next 1 to 3 hours of the first alert. You would just about have the time to get things to an organised state and save. Now this has not been the case

Considering this seems to be a very necessary security patch update

I want the updates ASAP but don't make me loose my work in doing so OR be left vulnerable if I don't, so give me a better alternative if I don't update now.

Ok maybe I should be humble and ask - is it just me Or maybe the patch isn't that important after all?

Considering this seems to be a very necessary security patch update
I want the updates ASAP

On Windows 10, Settings app, Update & Security, Update Settings you will have the following options:

• Change active hours: "Set active hours to let us know when you typically use this device. We won’t automatically restart it during active hours and we won’t restart without checking if you’re using it."
• Restart options: "We'll finish installing updates when you tell us to."

These aren't exactly hidden and can be used to prevent issues such as those described in the OP. Even if the defaults may be dumb, it doesn't require a huge amount of work to change them.

It is bad, but not as bad as the discovery that time was kept in 32-bit milliseconds and none of their machines could have lasted to 50 day uptime without crashing.

It's necesary to clarify that this only affected the Windows 9x line and was patched in Windows 98 SE. It's never been a problem for servers.

I set the settings and I've never had an issue. I've never, ever, with any software worth having installed lost any work even when forced to reset with little warning and it always remained interactive. I'm not sure what you're using Grumpy but you might want to get software written after 2000 or something. Heck, even my games detect and handle notifications of pending shutdown and will pop up a warning and save data.

Microsoft is far from great software, but honestly I've preferred 10 far better than 8 or Vista (both of which I refused to use after testing them).

Regardless of when the OS decides to install the updates and reboot (which is a problem, as Frob mentions above), there's also the problem of when it decides to download them. On my home PC, I don't notice the downloads on my cable connection, but I do notice the reboots when I've left work open overnight and it's all closed the next morning...

At work though, I've currently got 6 PC's sharing a 10mbps 4G LTE modem... When windows decides to start downloading files on its own, it completely saturates the link at the full 10mbps and everyone else's internet becomes incredibly slow... which is an impediment to office productivity. While the data transfer itself doesn't cost me money, having slow internet speeds does cost me a lot of money.
I had to go around to each Win10 PC and tell Windows that my Ethernet connection was metered (i.e. costs money to use), which tricks it into not auto downloading updates without asking first... most of the time... If it really feels like it, it still fucks you over and silently starts performing huge downloads without asking first :unsure:

@frob and @Hodgman but what does it really impact when it reboots overnight? You shouldn't have lost any work. Now you might have gotten security updates too. So you login, and < 1 minute later you're back up in your code. I actually just did that now. Came in, logged in, started up visual studios as my PC had updated. And I was right back where I had left off. Now my browser with it's 4000+ tabs (kidding, most like 25) took a few seconds to load.

Now, it should download large updates one night off hours and apply it another night. But I've had option windows popping up letting me delay a restart on both my Windows 10 desktop and my new laptop. I then went and set the time to like 3am to apply the patches.

I just don't see the issue honestly. No OS will ever be perfect or flawless and I rather security issues are pushed out right away and applied the same night in my off hours. I guess if you have a PC from 2002 and your IDE takes a few minutes to boot up once a month that can be annoying? *shrugs*.