Microsoft Bob was a peculiar attempt to make a PC more user friendly. The idea was to make an abstract set of rooms that represented different functions on a PC.

While Windows 3.1 is fine on a 80486, few have such a CPU available due to the cost. With a 80386 or better and at least 4MB of memory the 386 protected mode was more suitable for Windows 3.1. Most with the 32-bit setup also had win32s installed.

In late 1993 the advertising showed: One company was advertising 9,600-baud modems for as low as $500. Dell was selling a top-of-the-line 486 with a 66MHz processor, eight megabytes of RAM and a 320-megabyte hard drive for $4,400. A monitor was extra cost as was a keyboard and mouse.

Windows 3.1 is a comparatively crude user interface which is the main motivation for Bob. Many home users found the UI to be clumsy and lethargic. Part of the problem for Windows 3.1 was that most home users had machines that were far too underpowered.

Bob wanted a more powerful PC with an 80486SX or better and a whopping 8MB of memory. In 1995 this much hardware does not come cheap. 4096 KB memory was $159 per SIMM and a machine needs four of them to make up the 32-bit memory width.

A cartoon dog named Rover and other cartoon characters provided guidance using speech balloons. Actual speech for computers was limited to canned audio which tended to use more space than most could afford.

Bob included various office suite programs such as a finance application and a word processor. The user interface was designed to simplify the navigational experience for novice computer users.

The applications built into Bob are represented by matching decorations – for example, clicking on a clock opens the calendar, while a pen and paper represent the word processor. The user can also add shortcuts to applications on their computer. These shortcuts display the icon inside various styles of decorations such as boxes and picture frames.

Bob offered an email client with which a user could subscribe to MCI Mail, a dial-up email account. The price was $5.00 per month to send up to 15 emails per month. Each email was limited to 5000 characters, and each additional email after the limit was reached was an additional 45 cents. A toll-free phone number had to be called to set up the account.

Microsoft had just the one 210 page book available for Bob. Most made do without it and it did not take time before the product was abandoned.