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Microsoft's worst software flop was secretly packed with Windows for years

May 2025

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PCWorld

A former Windows developer revealed why the OS was uselessly dragging around Microsoft Bob for many years.

- BY HANS-CHRISTIAN DIRSCHERL & JOEL LEE

Microsoft's worst software flop was secretly packed with Windows for years

In the mid-1990s, Microsoft DOS dominated most PCs. Those who were a step ahead might've been using Windows 3.1, but even that was a superimposed user interface on top of MS-DOS (fave.co/4lq9Gla). Windows was still pretty darn unfamiliar to people back then, so in 1995, Microsoft came up with a more user-friendly interface called Microsoft Bob (fave.co/3RdCTSO, code name Utopia).

Bob was a complete replacement for Windows 3.1, changing the way users interacted with their PCs. Instead of “windows,” you interfaced with a digital house with all files, folders, and features represented as parts of the house. For example, there was a room for mail and one for the calendar, plus furniture and animated characters (like the dog Rover), all in a welcoming cartoony look (fave. co/4j6mAU6). The intent was to lower the usability barriers for PC beginners and make computers easier to navigate.

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