Microsoft’s worst software flop was secretly packed with Windows for years
by #AI [2.0] April 8, 2025 · Automatic / Editor's Picks [News]
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. 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 (codename 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. The intent was to lower the usability barriers for PC beginners and make computers easier to navigate.
However, user enthusiasm was limited and critical reception was poor. Hardly anyone bought Bob—only about 30,000 copies were sold—and it made high demands on the hardware, requiring 8MB of RAM, which was a lot in 1995. Microsoft discontinued Bob about a year later, around the time Windows 95 came out, but that wasn’t the end for Bob.
Microsoft Bob makes a comeback… sort of
With Windows XP’s release in 2001, the failed Microsoft Bob made a curious comeback. When Microsoft put Windows XP on installation CDs, they discovered that there were still 30 MB free on those discs—so Microsoft decided to fill up that space. With what, you ask? With an encrypted form of Bob, of course!
Former Microsoft employee and Windows developer Raymond Chen explained the reasoning in a 2008 issue of TechNet Magazine:
“The result was a rather feeble attempt to slow down the people who like to make illegal copies of Windows. Somebody decided to fill that extra capacity on the CD with dummy data and to have the Windows Setup program verify that the dummy data was still there. This, the logic went, would force people downloading a copy of the CD image to download an additional thirty or so megabytes of data. Remember, this was back in the day when ‘broadband’ hadn’t yet become a household word and mainstream users were using dial-up connections. Having to transfer an additional thirty megabytes of data over a 56Kb modem was a bit of an obstacle to slow users down—not that it would slow them down much by today’s standards.”
But why Bob’s code of all things? Chen continues:
“The person who was asked to implement this check needed a source for the dummy data. Now, he could have just called the CryptGenRandom function to generate 30 megabytes of cryptographically random bytes, but where’s the fun in that? Instead, he dug through the archives and found a copy of Microsoft Bob. He took all the floppy disk images and combined them into one big file. The contents of the Microsoft Bob floppy disk images are not particularly random, so he decided to scramble up the data by encrypting it. When it came time to enter the encryption key, he just smashed his hand haphazardly across the keyboard and out came an encrypted copy of Microsoft Bob. That’s what went into the unused space as ballast data on the Windows XP CD.”
And so, everyone who bought Windows XP also (unknowingly) received a copy of the totally flopped Microsoft Bob.
It’s kind of funny in the grand scheme, considering we once named Microsoft Bob as one of the worst tech products of all time. Still, little Easter eggs like this are expected and unavoidable when you have a history as extensively storied as Microsoft does.
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