Do you have any examples that aren't because of the OS (as in, not trying to run a 90's game on Windows 11) or specialized hardware (like an old Voodoo GPU or something)?
The program may work fine on its original OS, and the OS may work fine on its original hardware, but for someone trying to actually run their business or what have you on the software these facts are often not particularly helpful.
Backwards-compatibility in OSes is the exception, not the rule. IBM does pretty well here. Microsoft does okay. Linux is either fine or a disaster depending on who you ask. MacOS, iOS, and Android laugh at the idea. And even the OSes most dedicated to compatibility devote a ton of effort to ensuring it on new hardware.