Since joining the stock market in 1986, Microsoft has never reported a quarterly loss: until now.
Announcing the results for the fourth quarter of its financial year which runs July – June, Microsoft said it made a $492 million (about £313.2m) loss in the three months ending on June 30.
By contrast, it made $5.9 billion (£3.8bn) in the same period last year.
The giant dip in money-making came as Microsoft wrote off its acquisition of Aquantive, an internet advertising firm that the Redmond company bought in 2007 for $6 billion (about £4bn), hoping to take Google on.
But looking beyond the mega write-off, Microsoft is in rude health. Its revenue is actually up $18 billion compared to the same quarter in 2011, a rise of 4%.
Microsoft attributes the healthy figures to several areas of its business, particularly the entertainment and devices division which grew by 20 per cent thanks to a healthy boost from Skype.
But Windows and Windows Live saw a decline of 13 per cent because of the imminent release of Windows 8 and the company's attractive $15/£15 upgrade offer.
CEO Steve Ballmer, for one, is optimistic: "We delivered record fourth quarter and annual revenue, and we're fast approaching the most exciting launch season in Microsoft history.
"Over the coming year, we'll release the next versions of Windows, Office, Windows Server, Windows Phone, and many other products and services that will drive our business forward and provide unprecedented opportunity to our customers and partners."