Amazon.com reported weak quarterly results on Thursday as the world's largest Internet retailer spent heavily and suffered from an economic slowdown in Europe.
Amazon shares fell more than 5 percent to $211 in after-hours trading following the results.
The company said its third-quarter net loss was $274 million, or 60 cents a share, versus net income of $63 million, or 14 cents a share, in the third quarter of 2011. Part of the loss was related to an impairment charge from Amazon's investment in daily deal company LivingSocial.
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Third-quarter revenue was $13.81 billion, up 27 percent from a year earlier, Amazon also said.
Amazon was expected to lose 8 cents a share in the third quarter on revenue of $13.9 billion, according to Thomson Reuters.
Before Thursday's report, Amazon had generated 18 straight quarters of net income, according to BGC Partners.
For the crucial fourth-quarter holiday shopping period, Amazon forecast revenue that missed analysts' expectations.
Amazon is spending heavily on new distribution warehouses and technology to support its cloud-computing businesses, Amazon Web Services. It is also investing hundreds of millions of dollars a year on digital content to sell through its Kindle tablets and e-readers.
Those Kindle gadgets are being sold at cost, pressuring earnings in the short term. Amazon hopes to make money when customers use them to buy more physical and digital products from the company.
Europe's sovereign debt crisis and recession is reducing consumer demand, sparking concern that even fast-growing Internet companies may be affected.
EBay Inc Chief Financial Officer Bob Swan said last week that the company expected an "OK" holiday season, partly because of macro pressure in Europe.
Amazon said on Thursday that revenue from North America was $7.88 billion, up 25 percent from a year earlier. International sales, including Europe, totaled $5.92 billion, up 17 percent from the same period in 2011.