A developer traced how Windows handles clicking an unassociated file across versions. Windows 386/2.11 (1989) simply displayed a "not executable" message. Windows 3.0 added a dialog to configure file type associations. Windows 95 introduced a direct program selection dialog, a pattern that continued through Windows 2000.
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Summary by ByteBrief
Linux 7.2 Improves File-System Casefolding