> There are a lot of games from the 90s and even the 00s that require jumping through a lot of hoops to run on Windows

What are some examples?

ntoskrnl_exe 21 hours ago | parent | next [-]

Pretty much all the Renderware based GTAs have issues these days that only community made patches can mitigate.

A recent example is that in San Andreas, the seaplane never spawns if you're running Windows 11 24H2 or newer. All of it due to a bug that's always been in the game, but only the recent changes in Windows caused it to show up. If anybody's interested, you can read the investigation on it here: https://cookieplmonster.github.io/2025/04/23/gta-san-andreas...

	▲	robotnikman 16 hours ago \| parent [-]
		I remember seeing a thread about that bug here on HN a while ago, that was a fun read.

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sgarland 21 hours ago | parent | prev | next [-]

The last time I tried to run Tachyon: The Fringe was Windows 10, and it failed. IIRC I could launch it and play, but there was a non-zero chance that a FMV cutscene would cause it to freeze.

I see there are guides on Steam forums on how to get it to run under Windows 11 [0], and they are quite involved for someone not overly familiar with computers outside of gaming.

0: https://steamcommunity.com/sharedfiles/filedetails/?id=29344...

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xtracto 20 hours ago | parent | prev | next [-]

Lemmings Revolutions. Apparently to run in something else that is not Windows 95/98/Me requires some unofficial .EXE patch that you could download from some shady website. The file is now nowehre to be found.

It's a great game, unfortunately right now I am not able to play it anymore :( even though I have the original CD.

Unfortunately, Wine is of no help here :(

Also original Commandos games.

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forgotusername6 3 hours ago | parent | prev | next [-]

Anything written with SafeDisk DRM e.g. medal of honor allied assault.

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shakna 21 hours ago | parent | prev [-]

Anything around DirectX 10 and older has issues with Windows, these days.

One more popular example is Grid 2, another is Morrowind. Both crash on launch, unless you tweak a lot of things, and even then it won't always succeed.

Need for Speed II: SE is "platinum" on Wine, and pretty much unable to be run at all on Windows 11.

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tubs 21 hours ago | parent [-]

Isn’t this because the wine db has those tweaks pre configured?

	▲	Xirdus 21 hours ago \| parent \| next [-]
		Windows used to be half operating system, half preconfigured compatibility tweaks for all kinds of applications. That's how it kept its backwards compatibility.
	▲	shakna 21 hours ago \| parent \| prev \| next [-]
		More a case of DirectX radically changing how it worked [0]. [0] https://learn.microsoft.com/en-us/windows/win32/direct3darti...
	▲	realusername 18 hours ago \| parent \| prev [-]
		It's because wine OS selector actually tries to match bug for bug the OS version you set but Window's one gave up after Windows 7.