[dagw]

Windows is, for better or worse, fiercely proud of its backwards compatibility. So it's not so much a stupid Windows design choice as a 'stupid' DOS 1.0 design choice (and not even so much a choice as simply a quirk of how the DOS 1.0 file system worked) that Windows doesn't want to break backwards comparability with.

[wand3r]

I agree with parent that it's a bit crazy; but I wouldn't be as critical. to your point; presumably even if they dropped DOS support something between DOS and now likely relies on that. It's a fine line.

[rodorgas]

Stupid design choices on Windows are always justified by "backwards compatibility". What I don't understand is why an app for DOS doesn't work on Windows 10. Or a lot of Windows XP software that doesn't work anymore. Heck, anyone remember of Windows Vista and all the mess with "Compatibility Mode" that never worked?