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

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.