Microsoft Bob presented screens showing a house, with rooms that the user could visit containing familiar objects corresponding to computer applications, such as a desk with pen and paper and a checkbook.

[10] Bob features "Assistants", cartoon characters intended to help the user navigate the virtual house or perform tasks in the main interface or within the built-in applications.

[12] The New York Times found the characters irritating and the home design apparently the work of an "esthetically challenged sixth-grader," criticized the hardware requirements and storage file formats and concluded that the program was not as simple to use as Microsoft had advertised.

[13] The Washington Post called the home environment "sterile" and "lifeless," wrote that the characters' cuteness wore thin quickly and criticized the scarce customization and access to Windows components.

[5] Despite being discontinued just one year after launch, Microsoft Bob continued to be sharply criticized in reviews and popular media.

[17] It was also listed among the 50 worst inventions in Time magazine, which called Bob "overly cutesy" and an "operating system designed around Clippy.

"[19] Microsoft employee Raymond Chen disclosed that an encrypted copy of Bob was included on Windows XP installation CDs in order to consume space to prevent piracy.

[12] It was thought that by consuming an additional 30 megabytes on the disc (in the era of dial-up internet access), users with 56 kbit/s modems would be dissuaded from attempting to download the software illegally.

[21][22] Tech journalist Harry McCracken called the story "a delightfully urban legend-y tale" and noted its similarities to an April Fools' Day joke claiming that Bob was hidden in Windows Vista.

Rover, the dog mascot character introduced with Bob, became a "search companion" for Windows XP's file-search function.