After years of highly publicized product demonstrations that haven't quite gone as planned - including the infamous unveiling of Windows 98 when founder Bill Gates wound up with the so-called blue screen of death - the world's biggest computer maker had yet another red faced moment last week as it tried to show off its new Windows Vista voice recognition software.
Vista is the new operating system that will replace XP, and is touted as being more stable, more functional and more secure than anything currently available.
That was enough to bring an auditorium full of financial analysts to the monolith's Redmond, Washington headquarters to see the very latest technology that promised to make the firm even more money.
But in what critics are calling one of the worst embarrassment in Microsoft history, things didn't exactly go as planned.
The trouble began when Vista product manager Shanen Boettcher attempted to show off the program by dictating a letter to his mother.
"Dear mom," he began, fully expecting to see those words automatically typed on the screen.
Instead, the computer read out "Dear Aunt", and stubbornly refused all attempts at correction.
Boettcher then tried to repair it by telling the software to "fix aunt".
The computer took the words off and replaced them with "let's set".
"Delete that", barked Boettcher, who by this time was beginning to see things were falling apart. He repeated the phrase three times, only to see the cursor sit there blinking back at him with no response.
Waves of uncomfortable giggles from the crowd turned into huge guffaws when the programmer gave it one last try.
After telling the machine to "select all" as a means to wipe the offending message off the screen for good, the computer left the "let's set" intact but added the following message: "so double the killer delete select all."
Many tried to downplay the incident afterwards. "I think they took a risk by demo-ing that on stage," figures analyst Jim Rosoff. "Voice recognition is historically fraught with danger. It's really difficult to get right."
But the latest glitch has some wondering if the highly touted Windows Vista is ready for prime time.
Microsoft has repeatedly been forced to advance the release date and the product is now years overdue. The company still won't say for sure exactly when it will hit the market, although January appears to be the most likely date.
But the software maker vows it won't be unveiled until it's working perfectly.
Still, if you want to let mom know about it in an email, for now you may want to use a keyboard to write it.