Media giant News Corp has reported a net loss of $149m (£102.6m) for the three months to March. That compares with a profit of $23m in the same quarter last year.
The group suffered as a result of a one off legal charge of $280m at its News America Marketing business.
Revenue also fell - by 7.3% to $1.89bn.
News Corp, controlled by Rupert Murdoch, gets over half its revenue from outside the US and it blamed "currency headwinds" for the drop.
The one off charge at News America, an in-store advertising and grocery coupon business, was flagged up earlier this year. At that time, News Corp said it had agreed to pay $280m to resolve claims that News America had monopolised the market for in-store promotions at more than 50,000 retail outlets across the US.
News Corp's businesses include news and information services, book publishing, real estate services and cable network programming as well as pay-TV distribution in Australia.
In a statement released with the earnings, the media firm said: "While we believe in the strength of our print properties, we are also investing energetically in the rapid pursuit of digital which is clearly evident in the transition at Dow Jones.
"At Dow Jones this quarter, digital accounted for more than 50% of total revenues for the first time, and digital-only subscribers at the Wall Street Journal grew to 893,000, representing nearly 45% of the base."
Revenue at News Corp's online real estate services business which includes website realtor.com jumped 14% in the quarter to $194m.
Meanwhile revenue from the book publishing business, which includes HarperCollins Publishers fell 11% to $358m.
News Corp's Chief Executive Robert Thomson said the company's third quarter performance was "disappointing".
However, he added, the company believes it is "on track to see improvements in the fourth quarter, with the expansion of our digital real estate business, foreign currency comparisons hopefully beginning to ease, and cost saving initiatives taking firmer root."