Out of space? Out of inodes? Permissions or mount changed to read-only? I/O operations throwing errors? Crap antivirus interfering with I/O? No permissions?

I know with dark reign, the game didn't identify the CD image, simply reloading the game a time or two got it working due to whatever timing issue it had. Permissions, ejected drive where files are stored or other seems more likely.

But in reality, we don't know the OS so...

Windows 10 update screwed your game up? A fault in RAM or storage space (HDD/SSD) detroyed part of something hindering you from playing?

THIS!

I dread those moments i see a windows update happening, i will be wondering what f---ups are coming this time?

Even disabling the windows update service wont stop it these days, you just have to suffer.

Your dog ate the disk?

Your cat ate the disk?

YOU ate the disk?!?

Windows 10 setting allow you delay... for a little while the updates.. not stop...

Perhaps there's a way to fully make it a better OS, but i don't trust it.

These days the windows updates are nothing about making the OS better, they are all about market manipulation and making sure the third party software and hardware that are not part of the 'in' crowd happen to become incompatible. And the third party mates that are part of the 'in' crowd, have their shit rammed down your throat weather you like it or not.
(we are not stupid Microsoft, we see whats going on)

Once I was forced to update to Win10 (from win8.1) due to new hardware (ryzen3700x, etc) I blocked my Windows for this very reason on my firewall.
I'm using a VirtualBox with Ubuntu, if I need Internet access. Files are downloaded in the "Shared folder", so they are instant accessable once the download is finished.

VirtualBox gets another IP/MAC, so you can filter the traffic quite easy by source IP.
Every traffic from, that gets blocked, will be reported in a daily mail (with a lot of other stuff happening on my firewall).
By far the most "new connection"-attempts are to the following IP:
5589x 13.78.168.230 (United States, Microsoft Corporation) I check my harddrives on a regular basis with "HD Tune Pro" to minimize the risk of data loss due to hardware faults. Might give it a try

You managed to block windows 10?? NICE!!!
I bet all those connection attempts are Microsofts market research, trying to see what hardware and software products you are using, and to see if your serial key/keys are valid.... Big Brother is watching you.