I've recounted a similar story to this in the past: Basically some custom DOS app being used at a small chain of quick oil change places wouldn't run on Windows 7+ anymore, regardless of compatibility settings but worked fine on Linux under wine. This was done as a stopgap until they could redevelop the application. Because of the experience they had with their console app, they kept it a console app and just had its replacement modernized and written to run in a linux shell (saved all their licensing costs too). They seemed pretty happy in the end.
Microsoft moved away from the core tenet of backwards compatibility at all costs more than a decade ago seemingly across the entire company all at once.
Sincere question: Did that core tenet become incompatible with security against malware? Were the attack surfaces too big when supporting the old stuff?
It is infeasible and unmaintainable for them to be compatible with everything they have ever released since the 1980s. 16-bit DOS and Windows applications don't run on 64-bit versions of Windows.
Microsoft moved away from the core tenet of backwards compatibility at all costs more than a decade ago seemingly across the entire company all at once.