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After 30 Years, We Finally Know Why Windows 95's Installer Juggled Three Operating Systems


In a technical blog post, Microsoft veteran Raymond Chen has explained why Windows 95's installation process required users to pass through three different operating systems -- MS-DOS, Windows 3.1, and Windows 95. The design choice stemmed from the need to support upgrades from multiple starting poi...

The design choice stemmed from the need to support upgrades from multiple starting points while maintaining a graphical user interface throughout the process. Rather than creating separate installers for MS-DOS, Windows 3.1, and Windows 95 users, developers opted for a unified approach using three chained setup programs. The process began with installing a minimal version of Windows 3.1 when starting from MS-DOS, followed by a 16-bit Windows application that handled core installation tasks, and concluded with a 32-bit Windows 95 program for final configuration steps.

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