What are your most memorable experiences of a PC game breaking in some way after upgrading your Operating System?

My two picks would be trying to Play the original Diablo on anything newer than Windows 98, or the original Far Cry on anything above Windows XP. Both games can be installed and run on newer operating systems, but Diablo is practically unplayable with numerous bugs and timing errors that weren't present on earlier versions of Windows, and Far Cry has several visual bugs - useless draw distance/fog glitch, holes in water reflections, inability to enable Very High Lighting Quality, inability to uninstall the game if you install it to your Program Files folder, and several AI changes the more patches you apply that, somewhere along the way, turn them into god-like aimbots.

What about you?

Windows 98 and XP are fundamentally different OS'.

98 was the last version of DOS-based Windows.

Windows XP (aka Windows NT 5.1) is a pure 32-bit OS.

So I'm sure that's part of the janky Diablo stuff.

I can't think of any, but I don't play legacy games very often. Most of the popular old games are on GOG. They fix the issues if there are any.

I think it was dreamfall the longest journey but i can't be sure. anyway it used a DRM designed for Windows XP. when i tried to run it on windows 7 my computer froze and restarted. Windows 7 popped up with a message saying it recovered from a major disaster basically.

yeah...noped out of that one pretty quickly. an OS breaking game bug :P. gotta love that invasive DRM.

@pyro1245: I think Windows ME is the last dos based windows.

Yeah Win 98 with a face lift. Fair enough

Kotor is pretty bust on modern OS.

@Random_Matt: How so? I played it in my Vista/Win7 days perfectly fine, although I used the Star Wars: Best of PC Collection to install it. Did something break since those days?

Buffer effects has to be switched off to avoid crashes, grass has to be turned off to avoid transparency. My recent save crashed during the lift movie into the shadowlands, it corrupted it and gave up on the piece of shit. Best played on IOS/Android.

@osan0: Yeah, Starforce is the worst. Unfortunately, I never got those bypass programs to properly crack it, so I just have to live with it whenever I play Pac-Man World 2.